Journal articles: 'Sesquiterpenes'

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Coca-Ruíz, Víctor, Ivonne Suárez, Josefina Aleu, and Isidro G. Collado. "Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites." Plants 11, no. 6 (March 14, 2022): 769. http://dx.doi.org/10.3390/plants11060769.

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The compounds 11,12,13-tri-nor-sesquiterpenes are degraded sesquiterpenoids which have lost the C3 unit of isopropyl or isopropenyl at C-7 of the sesquiterpene skeleton. The irregular C-backbone originates from the oxidative removal of a C3 side chain from the C15 sesquiterpene, which arises from farnesyl diphosphate (FDP). The C12-framework is generated, generally, in all families of sesquiterpenes by oxidative cleavage of the C3 substituent, with the simultaneous introduction of a double bond. This article reviews the isolation, biosynthesis and biological activity of this special class of sesquiterpenes, the 11,12,13-tri-nor-sesquiterpenes.

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Silva, Waldeyr M. C. da, Jakob L. Andersen, Maristela T. Holanda, Maria Emília M. T. Walter, Marcelo M. Brigido, Peter F. Stadler, and Christoph Flamm. "Exploring Plant Sesquiterpene Diversity by Generating Chemical Networks." Processes 7, no. 4 (April 25, 2019): 240. http://dx.doi.org/10.3390/pr7040240.

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Plants produce a diverse portfolio of sesquiterpenes that are important in their response to herbivores and the interaction with other plants. Their biosynthesis from farnesyl diphosphate depends on the sesquiterpene synthases that admit different cyclizations and rearrangements to yield a blend of sesquiterpenes. Here, we investigate to what extent sesquiterpene biosynthesis metabolic pathways can be reconstructed just from the knowledge of the final product and the reaction mechanisms catalyzed by sesquiterpene synthases. We use the software package MedØlDatschgerl (MØD) to generate chemical networks and to elucidate pathways contained in them. As examples, we successfully consider the reachability of the important plant sesquiterpenes β -caryophyllene, α -humulene, and β -farnesene. We also introduce a graph database to integrate the simulation results with experimental biological evidence for the selected predicted sesquiterpenes biosynthesis.

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Wang, Junchi, Qi Zheng, Huaxiang Wang, Leiling Shi, Guoping Wang, Yaqin Zhao, Congzhao Fan, and Jianyong Si. "Sesquiterpenes and Sesquiterpene Derivatives from Ferula: Their Chemical Structures, Biosynthetic Pathways, and Biological Properties." Antioxidants 13, no. 1 (December 19, 2023): 7. http://dx.doi.org/10.3390/antiox13010007.

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Ferula is a genus of flowering plants known for its edible and medicinal properties. Since ancient times, many species of Ferula have been used in traditional medicine to treat various health issues across countries, such as digestive disorders, respiratory problems, and even as a remedy for headaches and toothaches. In addition, they are also used as a flavoring agent in various cuisines. As the main active ingredients in Ferula, sesquiterpenes and their derivatives, especially sesquiterpene coumarins, sesquiterpene phenylpropanoids, and sesquiterpene chromones, have attracted the attention of scientists due to the diversity of their chemical structures, as well as their extensive and promising biological properties, such as antioxidative, anti-inflammatory, antibacterial properties. However, there has not been a comprehensive review of sesquiterpenes and their derivatives from this plant. This review aims to provide an overview of the chemical structures, biosynthetic pathways, and biological properties of sesquiterpenes and sesquiterpene derivatives from Ferula, which may help guide future research directions and possible application methods for this valuable edible and medicinal plant.

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Saifudin, Azis, Ken Tanaka, Shigetoshi Kadota, and Yasuhiro Tezuka. "Chemical Constituents of Blumea balsamifera of Indonesia and Their Protein Tyrosine Phosphatase 1B Inhibitory Activity." Natural Product Communications 7, no. 7 (July 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700701.

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A methanol extract of the leaves of Blumea balsamifera (L.) DC. (Asteraceae) afforded a new guaian-type sesquiterpene, epiblumeaene K (1), together with four known guaian-type sesquiterpenes (2–5), three known sesquiterpenes (6–8), and nine known flavonoids (9–17) by a combination of chromatography and preparative TLC techniques. Their structures were elucidated by extensive spectroscopic methods and comparison with the literature data. Among the isolated compounds, a known sesquiterpene, β-caryophyllene 8 R,9 R-oxide (6), exhibited a significant PTP1B inhibitory activity in a dose-dependent manner, with an IC50 value of 25.8μM (5.62μg/mL).

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Ayer, William A., and Peter Craw. "Metabolites of the fairy ring fungus, Marasmiusoreades. Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin." Canadian Journal of Chemistry 67, no. 9 (September 1, 1989): 1371–80. http://dx.doi.org/10.1139/v89-210.

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The fungus Marasmiusoreades has previously been reported to produce the sesquiterpenes marasmone (1), anhydromarasmone (2), isomarasmone (3), and dihydromarasmone (4) when grown in liquid culture. We report herein several other sesquiterpene metabolites of the same skeleton but with differing oxidation patterns. The norsesquiterpenes O-formyloreadone (15a), 3α-hydroxyoreadone (15c), and dehydrooreadone (17b) are also reported. It is suggested that the formyl group in 15a is derived biogenetically from C-15 of a precursor sesquiterpene. Oxidation of 1α, 15-dihydroxymarasmene (13a), one of the new sesquiterpenes reported, with one equivalent of pyridinium dichromate gives O-formyloreadone (15a) as one of the products. Agrocybin (5), a polyacetylene amide previously isolated from the fungus Agrocybedura, has also been isolated from the cultures of M. oreades. It is suggested that agrocybin (5) is the phytotoxic compound responsible for the killing of grass caused by the fairy ring mushroom fungus. Keywords: sesquiterpenes, fungal metabolites, drimanes, fairy ring mushroom, agrocybin.

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Li, Li, Shenghui Yang, Dilu Chen, Zhihuang Wu, Meijun Zhang, Fang Yang, Li Qin, and Xiaojiang Zhou. "In Vitro Anti-Influenza A Virus H1N1 Effect of Sesquiterpene-Rich Extracts of Carpesium abrotanoides." Molecules 27, no. 23 (November 29, 2022): 8313. http://dx.doi.org/10.3390/molecules27238313.

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Due to a high content of sesquiterpenes, Carpesium abrotanoides has been investigated to fully explore its health-promoting properties. Therefore, this work aimed to assess, for the first time, the anti-influenza A virus H1N1 potential of sesquiterpene-targeted fractions of the herb derived from C. abrotanoides. Five compounds, including four sesquiterpenes and one aldehyde, were isolated and identified from the sesquiterpene-rich extracts of C. abrotanoides (SECA), and the contents of three main sesquiterpenes in the SECA were determined. Furthermore, SECA showed a significant protective effect in the MDCK cells infected with influenza A virus (H1N1) in three different conditions: premixed administration, prophylactic administration, and therapeutic administration. SECA can significantly decrease the mRNA expressions of TLR4, MyD88, NF-κB, TNF-α, and IL-6, as well as the protein expressions of TLR4, MyD88, and NF-κB. This result suggests that SECA can resist the influenza A virus H1N1 through the TLR4/MyD88/NF-κB signal pathway.

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Yan, Xiaoguang, Yukun Li, Weiguo Li, Dongmei Liang, Shengxin Nie, Ruiqi Chen, Jianjun Qiao, Mingzhang Wen, and Qinggele Caiyin. "Transcriptome Analysis and Identification of Sesquiterpene Synthases in Liverwort Jungermannia exsertifolia." Bioengineering 10, no. 5 (May 9, 2023): 569. http://dx.doi.org/10.3390/bioengineering10050569.

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The liverwort Jungermannia exsertifolia is one of the oldest terrestrial plants and rich in structurally specific sesquiterpenes. There are several sesquiterpene synthases (STSs) with non-classical conserved motifs that have been discovered in recent studies on liverworts; these motifs are rich in aspartate and bind with cofactors. However, more detailed sequence information is needed to clarify the biochemical diversity of these atypical STSs. This study mined J. exsertifolia sesquiterpene synthases (JeSTSs) through transcriptome analysis using BGISEQ-500 sequencing technology. A total of 257,133 unigenes was obtained, and the average length was 933 bp. Among them, a total of 36 unigenes participated in the biosynthesis of sesquiterpenes. In addition, the in vitro enzymatic characterization and heterologous expression in Saccharomyces cerevisiae showed that JeSTS1 and JeSTS2 produced nerolidol as the major product, while JeSTS4 could produce bicyclogermacrene and viridiflorol, suggesting a specificity of J. exsertifolia sesquiterpene profiles. Furthermore, the identified JeSTSs had a phylogenetic relationship with a new branch of plant terpene synthases, the microbial terpene synthase-like (MTPSL) STSs. This work contributes to the understanding of the metabolic mechanism for MTPSL-STSs in J. exsertifolia and could provide an efficient alternative to microbial synthesis of these bioactive sesquiterpenes.

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Zhang, Xu-Feng, Jie Ren, Xiang-Rong Cheng, Hui-Zi Jin, and Wei-Dong Zhang. "One new unusual sesterterpenoid and four new sesquiterpene dimers from Inula britannica." RSC Advances 5, no. 3 (2015): 1979–82. http://dx.doi.org/10.1039/c4ra11171k.

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Jerković, Igor, Željan Maleš, and Maja Friščić. "Actualities in the phytochemical research on selected terpenes." Acta Pharmaceutica 69, no. 4 (December 1, 2019): 533–40. http://dx.doi.org/10.2478/acph-2019-0036.

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Abstract A short review of our recent research on the essential oil phytochemical composition of Petasites albus (L.) Gaertn. and Petasites hybridus (L.) G. Gaertn., B. Mey. & Scherb. (Asteraceae) as well as on the oils of Globularia cordifolia L., Globularia meridionalis (Podp.) O. Schwarz and Globularia punctata Lapeyr. (Plantaginaceae) is presented. All essential oils contained a variety of oxygenated sesquiterpenes among their major constituents, including a bakkane type sesquiterpene fukinanolid (bakkenolide A). The paper is focused on: i) a short overview of the abundance of major terpenes in the essential oils of Petasites and Globularia species from Croatia; ii) possible biosynthetic pathways of major identified sesquiterpenes; and iii) biological activities (literature data) of major sesquiterpenes from Petasites and Globularia species.

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Liang, Yi, Xiao-Ming Li, Chun-Shun Li, Hong Sun, and Bin-Gui Wang. "Laurane-, Cyclolaurane-, and Cuparane-type Sesquiterpenes from the Marine Red Alga Laurencia okamurai." Natural Product Communications 9, no. 3 (March 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900310.

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Chemical investigation of the secondary metabolites extracted from the marine red alga Laurencia okamurai has resulted in the isolation of one new (lauramurin, 1) and six known (2–7) sesquiterpenes. On the basis of the data obtained by our detailed spectroscopic analysis as well as by comparison with those reported, the structures of these compounds were elucidated as four laurane sesquiterpenes including lauramurin (1), laur-11-en-10-ol (2), aplysinol (3), and debromoaplysinol (4), two cyclolaurane sesquiterpenes laurequinone (5) and laurentristich-4-ol (6), and one cuparane ether sesquiterpene (7). The antibacterial activity against Staphylococcus aureus and brine shrimp ( Artemia salina) lethality for the isolated compounds were evaluated. Compounds 2 and 5–7 displayed moderate lethality against brine shrimp.

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Martin, Aurelio San, Juana Rovinosa, Alvaro Carrasco, Silvia Orejarena, Jorge Soto-Delgado, Renato Contreras, and M. Cristina Chamy. "Microbial Transformation of Marine Halogenated Sesquiterpenes." Natural Product Communications 5, no. 12 (December 2010): 1934578X1000501. http://dx.doi.org/10.1177/1934578x1000501203.

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The sesquiterpene pacifenol is one of the main constituents of the red alga Laurencia claviformis. Earlier work on the semisynthetic derivatives of pacifenol afforded a series of halogenated sesquiterpenes. The aim of the present work was to obtain new hydroxylated derivatives of halogenated sesquiterpenes by means of microbial transformation using Aspergillus níger, Gibberella fujikuroi and Mucor plumbeus. The best results were obtained with M. plumbeus. The microbiological transformation by M. plumbeus of pacifenol, and two semisynthetic derivatives, is described. The structures of the new compounds obtained were determined by spectroscopic means.

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Bouvier-Brown, N. C., A. H. Goldstein, J. B. Gilman, W. C. Kuster, and J. A. de Gouw. "In-situ ambient quantification of monoterpenes, sesquiterpenes, and related oxygenated compounds during BEARPEX 2007 – implications for gas- and particle-phase chemistry." Atmospheric Chemistry and Physics Discussions 9, no. 2 (April 23, 2009): 10235–69. http://dx.doi.org/10.5194/acpd-9-10235-2009.

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Abstract. We quantified ambient mixing ratios of 9 monoterpenes, 6 sesquiterpenes, methyl chavicol, the oxygenated terpene linalool, and nopinone using an in-situ gas chromatograph with a quadrupole mass spectrometer (GC-MS). These measurements were a part of the 2007 Biosphere Effects on AeRosols and Photochemistry EXperiment (BEARPEX) at Blodgett Forest, a ponderosa pine forest in the Sierra Nevada Mountains of California. To our knowledge, these observations represent the first direct in-situ ambient quantification of the sesquiterpenes α-bergamotene, longifolene, α-farnesene, and β-farnesene. From average diurnal mixing ratio profiles, we show that α-farnesene emissions are dependent mainly on temperature whereas α-bergamotene and β-farnesene emissions are temperature- and light-dependent. The amount of sesquiterpene mass quantified above the canopy was small (averaging a total of 3.3 ppt during the day), but nevertheless these compounds contributed 8.5% to the overall ozone reactivity above the canopy. Assuming that the monoterpene-to-sesquiterpene emission rate in the canopy is similar to that observed in branch enclosure studies at the site during comparable weather conditions, and the average yield of aerosol mass from these sesquiterpenes is 10–50%, the amount of sesquiterpene mass reacted within the Blodgett Forest canopy alone accounts for 8–38% of the total organic aerosol mass measured during BEARPEX. The oxygenated monoterpene linalool was also quantified for the first time at Blodgett Forest. The linalool mass contribution was small (9.9 ppt and 0.74 ppt within and above the canopy, respectively), but it contributed 1.2% to the total ozone reactivity above the canopy. Reactive and semi-volatile compounds, especially sesquiterpenes, significantly impact the gas- and particle-phase chemistry of the atmosphere at Blodgett Forest and should be included in both biogenic volatile organic carbon emission and atmospheric chemistry models.

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Bouvier-Brown, N. C., A. H. Goldstein, J. B. Gilman, W. C. Kuster, and J. A. de Gouw. "In-situ ambient quantification of monoterpenes, sesquiterpenes, and related oxygenated compounds during BEARPEX 2007: implications for gas- and particle-phase chemistry." Atmospheric Chemistry and Physics 9, no. 15 (August 5, 2009): 5505–18. http://dx.doi.org/10.5194/acp-9-5505-2009.

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Abstract. We quantified ambient mixing ratios of 9 monoterpenes, 6 sesquiterpenes, methyl chavicol, the oxygenated terpene linalool, and nopinone using an in-situ gas chromatograph with a quadrupole mass spectrometer (GC-MS). These measurements were a part of the 2007 Biosphere Effects on AeRosols and Photochemistry EXperiment (BEARPEX) at Blodgett Forest, a ponderosa pine forest in the Sierra Nevada Mountains of California. To our knowledge, these observations represent the first direct in-situ ambient quantification of the sesquiterpenes α-bergamotene, longifolene, α-farnesene, and β-farnesene. From average diurnal mixing ratio profiles, we show that α-farnesene emissions are dependent mainly on temperature whereas α-bergamotene and β-farnesene emissions are temperature- and light-dependent. The amount of sesquiterpene mass quantified above the canopy was small (averaging a total of 3.3 ppt during the day), but nevertheless these compounds contributed 7.6% to the overall ozone-olefin loss rate above the canopy. Assuming that the monoterpene-to-sesquiterpene emission rate in the canopy is similar to that observed in branch enclosure studies at the site during comparable weather conditions, and the average yield of aerosol mass from these sesquiterpenes is 10–50%, the amount of sesquiterpene mass reacted within the Blodgett Forest canopy alone accounts for 6–32% of the total organic aerosol mass measured during BEARPEX. The oxygenated monoterpene linalool was also quantified for the first time at Blodgett Forest. The linalool mass contribution was small (9.9 ppt and 0.74 ppt within and above the canopy, respectively), but it contributed 1.1% to the total ozone-olefin loss rate above the canopy. Reactive and semi-volatile compounds, especially sesquiterpenes, significantly impact the gas- and particle-phase chemistry of the atmosphere at Blodgett Forest and should be included in both biogenic volatile organic carbon emission and atmospheric chemistry models.

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Sut, Stefania, Filippo Maggi, Marcello Nicoletti, Valeria Baldan, and Stefano Dall`Acqua. "New Drugs from Old Natural Compounds: Scarcely Investigated Sesquiterpenes as New Possible Therapeutic Agents." Current Medicinal Chemistry 25, no. 10 (April 9, 2018): 1241–58. http://dx.doi.org/10.2174/0929867324666170404150351.

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Sesquiterpenes are natural products that have been extensively studied for their bioactivities, evidencing their potentiality as useful scaffolds for the development of drugs. Considering the different derivatives, the sesquiterpene lactones have been evaluated, especially on cancer cell and antineoplastic efficacy in in vivo studies. Their bioactivity is strictly related to the presence of the reactive α-methylene-γ-lactone group (αMγL). Nevertheless, several other sesquiterpenes lacking αMγL are known and have been studied for their biological effects and potential usefulness in the development of new drugs. In this review, we focused on several sesquiterpenes that are not presenting the αMγL moiety and may have future potential as scaffold for the development of new drugs, namely the bicyclic compounds belonging to the carotane type (daucanes) that present significant effects as antiproliferative and estrogenic agents. The monocyclic humulane derivatives correlated to zerumbone, and the bicyclic compound beta-caryophyllene and its derivatives that have been considered in the field of cancer and inflammation. It is noteworthy that published studies on sesquiterpenes, reported in this review, focus on pathologies of increasing importance, like estrogen, anti-proliferative, bone loss, immunity deficiency and anti-tumour activities. Some of the natural “old” sesquiterpenes can be considered for their possible role in drug discovery and in counteracting these “new” challenges.

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Guella, Graziano, Danielle Skropeta, Ines Mancini, and Francesco Pietra. "The First 6,8-Cycloeudesmane Sesquiterpene from a Marine Organism: The Red Seaweed Laurencia microcladia from the Baia di Calenzana, Elba Island." Zeitschrift für Naturforschung B 57, no. 10 (October 1, 2002): 1147–51. http://dx.doi.org/10.1515/znb-2002-1012.

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Reported here is the isolation and structural elucidation of a new 6,8-cycloeudesmane sesquiterpene, 5-bromo-1-isopropyl-2,5a-dimethyl-decahydro-cyclopropa[a]inden-2-ol (5), alongside the known sesquiterpenes (-)-δ-cadinene (7) and (+)-α-cadinol (8), from the red seaweed Laurencia microcladia Kützing of the Baia di Calenzana, Elba Island. Other than belonging to a rare sesquiterpene class, 5 is the first 6,8-cycloeudesmane sesquiterpene of marine origin.

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Könen, Philipp P., Ines Stötzel, Wilfried Schwab, and Matthias Wüst. "Qualitative profiling of mono- and sesquiterpenols in aglycon libraries from Vitis vinifera L. Gewürztraminer using multidimensional gas chromatography–mass spectrometry." European Food Research and Technology 247, no. 5 (February 10, 2021): 1117–24. http://dx.doi.org/10.1007/s00217-021-03692-3.

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AbstractIn grape berries (Vitis vinifera L.), sesquiterpenes are mainly accumulated as hydrocarbons in the epicuticular wax layer of grapes, whereas monoterpenes, which are predominantly present as alcohols, are glycosylated and are stored as glycosides in the vacuoles of grape berry cells. In this study, extensive analysis of grape berry hydrolysates by means of comprehensive two-dimensional gas chromatography–time-of-flight–mass spectrometry demonstrated that glycosylated sesquiterpene alcohols show very little structural diversity when compared to the sesquiterpene hydrocarbon fraction in the cuticle and are glycosylated to a rather low extent when compared to monoterpenols. Twenty-four enzymatically released terpenols were found in hydrolysates of the aromatic white wine variety Gewürztraminer (V. vinifera subsp. vinifera) after previous solid-phase extraction and headspace solid-phase microextraction. The detection of only three sesquiterpene alcohols, namely farnesol, nerolidol and drimenol, shows that most sesquiterpene hydrocarbons do not have a related hydroxylated structure in grapes. Nevertheless, the presence of the acyclic aglycone farnesol and nerolidol may be of importance for the wine aroma, since these structural isomers can be converted into numerous sesquiterpenes by nonenzymatic acid-catalyzed reactions during wine production. Grape-derived glycosidically bound sesquiterpene alcohols, therefore, represent, in addition to free sesquiterpene hydrocarbons, another pool of compounds that may influence the aroma profile of wines.

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Ahmed, Ahmed A. "Sesquiterpene coumarins and sesquiterpenes from Ferula sinaica." Phytochemistry 50, no. 1 (January 1999): 109–12. http://dx.doi.org/10.1016/s0031-9422(98)00489-0.

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Aati, Hanan Y., Shagufta Perveen, Raha Orfali, Areej M. Al-Taweel, Jiangnan Peng, Sobia Tabassum, Maged S. Abdel-Kader, Hasan Soliman Yusufoglu, and Orazio Taglialatela-Scafati. "Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities." Plants 10, no. 6 (June 2, 2021): 1130. http://dx.doi.org/10.3390/plants10061130.

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Anvillea garcinii is a medicinal plant used in the Arab region for intestinal diseases, lung and liver diseases, digestive problems, and as an antidiabetic agent. Repeated chromatographic purifications of A. garcinii leaves led to the isolation of three undescribed guaiane sesquiterpene derivatives, named garcinamines F–H, characterized by the presence of an amino acid unit, along with five known sesquiterpene lactones (garcinamines B–E and 9β-hydroxyparthenolide). The structures of the new compounds were established using spectroscopic (1D and 2D NMR) and spectrometric methods (ESIMS). Garcinamine H possesses a double bond at the Δ1,10 position, a structural feature rarely reported in guaianolide-type sesquiterpenes. The antiproliferative activity of the isolated sesquiterpenes was screened against three different cancer cell lines, and 9β-hydroxyparthenolide and garcinamines C and D displayed significant effects against lung carcinoma (A549), colon carcinoma (LoVo), and breast carcinoma (MCF7) cell lines.

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Barreto, Ighor C., Anderson S. de Almeida, and José G. Sena Filho. "Taxonomic Insights and Its Type Cyclization Correlation of Volatile Sesquiterpenes in Vitex Species and Potential Source Insecticidal Compounds: A Review." Molecules 26, no. 21 (October 23, 2021): 6405. http://dx.doi.org/10.3390/molecules26216405.

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Sesquiterpenes (SS) are secondary metabolites formed by the bonding of 3 isoprene (C5) units. They play an important role in the defense and signaling of plants to adapt to the environment, face stress, and communicate with the outside world, and their evolutionary history is closely related to their physiological functions. This review considers their presence and extensively summarizes the 156 sesquiterpenes identified in Vitextaxa, emphasizing those with higher concentrations and frequency among species and correlating with the insecticidal activities and defensive responses reported in the literature. In addition, we classify the SS based on their chemical structures and addresses cyclization in biosynthetic origin. Most relevant sesquiterpenes of the Vitex genus are derived from the germacredienyl cation mainly via bicyclogermacrene and germacrene C, giving rise to aromadrendanes, a skeleton with the highest number of representative compounds in this genus, and 6,9-guaiadiene, respectively, indicating the production of 1.10-cyclizing sesquiterpene synthases. These enzymes can play an important role in the chemosystematics of the genus from their corresponding routes and cyclizations, constituting a new approach to chemotaxonomy. In conclusion, this review is a compilation of detailed information on the profile of sesquiterpene in the Vitex genus and, thus, points to new unexplored horizons for future research.

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Cong, Zhanren, Qiang Yin, Kunhong Tian, Njeru Joe Mukoma, Liming Ouyang, Tom Hsiang, Lixin Zhang, Lan Jiang, and Xueting Liu. "Genome Mining of Fungal Unique Trichodiene Synthase-like Sesquiterpene Synthases." Journal of Fungi 10, no. 5 (May 13, 2024): 350. http://dx.doi.org/10.3390/jof10050350.

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Sesquiterpenoids served as an important source for natural product drug discovery. Although genome mining approaches have revealed numerous novel sesquiterpenoids and biosynthetic enzymes, the comprehensive landscape of fungal sesquiterpene synthases (STSs) remains elusive. In this study, 123 previously reported fungal STSs were subjected to phylogenetic analysis, resulting in the identification of a fungi-specific STS family known as trichodiene synthase-like sesquiterpene synthases (TDTSs). Subsequently, the application of hidden Markov models allowed the discovery of 517 TDTSs from our in-house fungi genome library of over 400 sequenced genomes, and these TDTSs were defined into 79 families based on a sequence similarity network. Based on the novelty of protein sequences and the completeness of their biosynthetic gene clusters, 23 TDTS genes were selected for heterologous expression in Aspergillus oryzae. In total, 10 TDTSs were active and collectively produced 12 mono- and sesquiterpenes, resulting in the identification of the first chamipinene synthase, as well as the first fungi-derived cedrene, sabinene, and camphene synthases. Additionally, with the guidance of functionally characterized TDTSs, we found that TDTSs in Family 1 could produce bridged-cyclic sesquiterpenes, while those in Family 2 could synthesize spiro- and bridged-cyclic sesquiterpenes. Our research presents a new avenue for the genome mining of fungal sesquiterpenoids.

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Yaosanit, Wiriya, Vatcharin Rukachaisirikul, Souwalak Phongpaichit, Sita Preedanon, and Jariya Sakayaroj. "Sesquiterpenes from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346." Beilstein Journal of Organic Chemistry 18 (April 29, 2022): 479–85. http://dx.doi.org/10.3762/bjoc.18.50.

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Two new sesquiterpenes, trichocitrinovirenes A (1) and B (2), and five known compounds including four structurally related sesquiterpenes and one γ-lactone were isolated from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346. The structures were identified by analysis of their spectroscopic data. The relative configuration was assigned based on NOEDIFF data. The absolute configuration of compound 1 was established according to specific rotations and ECD data while that of compound 2 was proposed based on biosynthetic considerations. Compound 2 possesses a rare bicyclic sesquiterpene skeleton. The antimicrobial and cytotoxic activities of the isolated compounds were evaluated.

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Arya, Ashwani, Rubal Chahal, Rekha Rao, Md Habibur Rahman, Deepak Kaushik, Muhammad Furqan Akhtar, Ammara Saleem, et al. "Acetylcholinesterase Inhibitory Potential of Various Sesquiterpene Analogues for Alzheimer’s Disease Therapy." Biomolecules 11, no. 3 (February 25, 2021): 350. http://dx.doi.org/10.3390/biom11030350.

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Alzheimer’s disease (AD) is a gradually growing irreversible illness of the brain that almost affects every fifth person (aged > 80 years) in the world. World Health Organization (WHO) also revealed that the prevalence of this disease will enhance (upto double) significantly upto 2030. The poor cholinergic transmission at the synapse is considered to be one of the main reasons behind the progression and occurrence of this disorder. Natural inhibitors of acetylcholine (ACh) such as galanthamine and rivastigmine are used commercially in the treatmentof AD. The biomolecules such assesquiterpenes, possess a great structural diversity and are responsible for a plethora of pharmacological properties. The potential of various sesquiterpenes as anticholinesterase has been reviewed in this article. For this purpose, the various databases, mainly PubMed, Scopus, and Web of Science were investigatedwith different keywords such as “sesquiterpenes+acetylcholinesterase” and “sesquiterpenes+cholinesterase+inhibitors” in the surveyed time frame (2010–2020). A vast literature was evident in the last decade, which affirms the potential of various sesquiterpenes in the improvement of cholinergic transmission by inhibiting the AChE. After data analysis, it was found that 12 compounds out of a total of 58 sesquiterpenes were reported to possess IC50 < 9 μM and can be considered as potential candidates for the improvement of learning and memory. Sesquiterpene is an important category of terpenoids, found to possess a large spectrum of biological activities. The outcome of the review clearly states that sesquiterpenes (such as amberboin, lipidiol, etc.) from herbs could offer fresh, functional compounds for possible prevention and treatment of AD.

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Yee, Lindsay D., Gabriel Isaacman-VanWertz, Rebecca A. Wernis, Meng Meng, Ventura Rivera, Nathan M. Kreisberg, Susanne V. Hering, et al. "Observations of sesquiterpenes and their oxidation products in central Amazonia during the wet and dry seasons." Atmospheric Chemistry and Physics 18, no. 14 (July 23, 2018): 10433–57. http://dx.doi.org/10.5194/acp-18-10433-2018.

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Abstract. Biogenic volatile organic compounds (BVOCs) from the Amazon forest region represent the largest source of organic carbon emissions to the atmosphere globally. These BVOC emissions dominantly consist of volatile and intermediate-volatility terpenoid compounds that undergo chemical transformations in the atmosphere to form oxygenated condensable gases and secondary organic aerosol (SOA). We collected quartz filter samples with 12 h time resolution and performed hourly in situ measurements with a semi-volatile thermal desorption aerosol gas chromatograph (SV-TAG) at a rural site (T3) located to the west of the urban center of Manaus, Brazil as part of the Green Ocean Amazon (GoAmazon2014/5) field campaign to measure intermediate-volatility and semi-volatile BVOCs and their oxidation products during the wet and dry seasons. We speciated and quantified 30 sesquiterpenes and 4 diterpenes with mean concentrations in the range 0.01–6.04 ng m−3 (1–670 ppqv). We estimate that sesquiterpenes contribute approximately 14 and 12 % to the total reactive loss of O3 via reaction with isoprene or terpenes during the wet and dry seasons, respectively. This is reduced from ∼ 50–70 % for within-canopy reactive O3 loss attributed to the ozonolysis of highly reactive sesquiterpenes (e.g., β-caryophyllene) that are reacted away before reaching our measurement site. We further identify a suite of their oxidation products in the gas and particle phases and explore their role in biogenic SOA formation in the central Amazon region. Synthesized authentic standards were also used to quantify gas- and particle-phase oxidation products derived from β-caryophyllene. Using tracer-based scaling methods for these products, we roughly estimate that sesquiterpene oxidation contributes at least 0.4–5 % (median 1 %) of total submicron OA mass. However, this is likely a low-end estimate, as evidence for additional unaccounted sesquiterpenes and their oxidation products clearly exists. By comparing our field data to laboratory-based sesquiterpene oxidation experiments we confirm that more than 40 additional observed compounds produced through sesquiterpene oxidation are present in Amazonian SOA, warranting further efforts towards more complete quantification.

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24

Ali, Muhammad Shaiq, Waqar Ahmed, and Syed Amir Ibrahim. "Guaianolide and seco-Guaianolide from Salvia nubicola (Lamiaceae)." Zeitschrift für Naturforschung B 60, no. 9 (September 1, 2005): 1012–15. http://dx.doi.org/10.1515/znb-2005-0917.

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A sesquiterpene-lactone of the guaianolide class (nubenone) and a seco-guaianolide (nubenoic acid) have been isolated from Salvia nubicola collected in Quetta, Pakistan. Structures of both sesquiterpenes were elucidated with the aid of spectroscopic techniques including two dimensional NMR spectroscopy.

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Tran, NH, JNA Hooper, and RJ Capon. "New Oxygenated Sesquiterpenes From a Southern Australian Marine Sponge, Dictyodendrilla sp." Australian Journal of Chemistry 48, no. 10 (1995): 1757. http://dx.doi.org/10.1071/ch9951757.

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Chemical investigation of a Dictyodendrilla sp. from Port Phillip Bay, Victoria, yielded three new oxygenated sesquiterpenes, dictyodendrillin -A (6), -B (7) and -C (8), together with the known sesquiterpene dendrolasin (9). Structures for all these metabolites were established by spectroscopic analysis.

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Wu, Chia-Li, Wei-Yu Chen, and Chi-Sheng Chu. "Bisabolenes and Nor-Sesquiterpenes from Bazzania tridens." Natural Product Communications 2, no. 4 (April 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200403.

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Two bisabolene sesquiterpenes (1 and 2), two nor-sesquiterpene ketones (3 and 4) and one humulene epoxide (6) were identified from the Taiwanese liverwort Bazzania tridens. Among them, 3 was novel, and 2, 4 and 6 were reported for the first time from a natural source. Their structures were mainly elucidated by analysis of various NMR spectra.

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27

Farooq, Umar, Afsar Khan, Saleha Suleman Khan, Shazia Iqbal, Rizwana Sarwar, Sher Bahadar Khan, and Viqar Uddin Ahmad. "Isolation and Structure Determination of Three New Sesquiterpenoids from Achillea millefolium." Zeitschrift für Naturforschung B 67, no. 5 (May 1, 2012): 421–25. http://dx.doi.org/10.5560/znb.2011-0244.

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Phytochemical investigation of the whole plant of Achillea millefolium led to the isolation of three new sesquiterpenes which were trivially named as sesquiterpene lactone-esters A and B (1 and 2), and sesquiterpene lactone-diol (3). The structures of these compounds were determined with the help of one- and two-dimensional (1D and 2D) NMR techniques including 1H NMR, 13C NMR, HMQC, HMBC, COSY, and NOESY experiments.

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28

Fraga, Braulio M., Inmaculada Cabrera, Matías Reina, and David Terrero. "Two New Sesquiterpenes from Laurus azorica." Zeitschrift für Naturforschung C 56, no. 7-8 (August 1, 2001): 503–5. http://dx.doi.org/10.1515/znc-2001-7-805.

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The structures of a new eudesmane sesquiterpene, lauradiol, and a new secoeudesmane, azoridione, have been determined by spectroscopic methods. These compounds and the known sesquiterpenic alcohols, clovanediol and caryophyllenol II, have been isolated from the aerial parts of Laurus azorica

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29

Di Sotto, Irannejad, Eufemi, Mancinelli, Abete, Mammola, Altieri, Mazzanti, and Di Giacomo. "Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study." International Journal of Molecular Sciences 21, no. 2 (January 17, 2020): 633. http://dx.doi.org/10.3390/ijms21020633.

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Doxorubicin represents a valuable choice for different cancers, although the severe side effects occurring at the high effective dose limits its clinical use. In the present study, potential strategies to potentiate low-dose doxorubicin efficacy, including a metronomic schedule, characterized by a short and repeated exposure to the anticancer drug, and the combination with the natural chemosensitizing sesquiterpenes β-caryophyllene and β-caryophyllene oxide, were assessed in human hepatoma HepG2 cells. The involvement of P-glycoprotein (P-gp) in the HepG2–chemosensitization to doxorubicin was evaluated. Also, the direct interaction of caryophyllene sesquiterpenes with P-gp was characterized by molecular docking and dynamic simulation studies. A metronomic schedule allowed us to enhance the low-dose doxorubicin cytotoxicity and the combination with caryophyllane sesquiterpenes further potentiated this effect. Also, an increased intracellular accumulation of doxorubicin and rhodamine 123 induced by caryophyllane sesquiterpenes was found, thus suggesting their interference with P-gp function. A lowered expression of P-gp induced by the combinations, with respect to doxorubicin alone, was observed too. Docking studies found that the binding site of caryophyllane sesquiterpene was next to the ATP binding domain of P-gp and that β-caryophyllene possessed the stronger binding affinity and higher inhibition potential calculated by MM-PBSA. Present findings strengthen our hypothesis about the potential chemosensitizing power of caryophyllane sesquiterpenes and suggest that combining a chemosensitizer and a metronomic schedule can represent a suitable strategy to overcome drawbacks of doxorubicin chemotherapy while exploiting its powerful activity.

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30

Duong, Thuc-Huy, Mehdi A. Beniddir, Nguyen T. Trung, Cam-Tu D. Phan, Van Giau Vo, Van-Kieu Nguyen, Quynh-Loan Le, Hoang-Dung Nguyen, and Pierre Le Pogam. "Atypical Lindenane-Type Sesquiterpenes from Lindera myrrha." Molecules 25, no. 8 (April 16, 2020): 1830. http://dx.doi.org/10.3390/molecules25081830.

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Two new lindenane sesquiterpenes were obtained from the roots of Lindera myrrha. These compounds were structurally elucidated by HRMS data, extensive NMR analyses, and comparison between experimental and theoretical 13C-NMR data. Myrrhalindenane A is the first monomeric seco-d lindenane displaying a non-rearranged, cyclohexanic C-ring. Myrrhalindenane B is the second occurrence of an angular lindenane-sesquiterpene related to a C6-C7 lactonization.

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de Menezes, Jane Eire S. A., Francisca Elane A. Machado, Telma Leda G. Lemos, Edilberto R. Silveira, Raimundo Braz Filho, and Otília Deusdêni L. Pessoa. "Sesquiterpenes and a Phenylpropanoid from Cordia trichotoma." Zeitschrift für Naturforschung C 59, no. 1-2 (February 1, 2004): 19–22. http://dx.doi.org/10.1515/znc-2004-1-204.

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Two new secondary metabolites, the phenylpropanoid 3-(2′,4′,5′-trimethoxyphenyl)propanoic acid (1) and the sesquiterpene (+)-1β,4β,6α-trihydroxyeudesmane (2) were isolated from the heartwood of Cordia trichotoma Vell., along with the known sesquiterpenes (D)-1β,4β,7α- trihydroxyeudesmane (3) and (+)-1β,4β,11-trihydroxyoppositane (4). Their structures were elucidated by means of spectroscopic data interpretation, mainly 1D and 2D NMR and mass spectrometry.

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32

Ee, Su-Fang, Zeti-Azura Mohamed-Hussein, Roohaida Othman, Noor Azmi Shaharuddin, Ismanizan Ismail, and Zamri Zainal. "Functional Characterization of Sesquiterpene Synthase fromPolygonum minus." Scientific World Journal 2014 (2014): 1–11. http://dx.doi.org/10.1155/2014/840592.

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Polygonum minusis an aromatic plant, which contains high abundance of terpenoids, especially the sesquiterpenes C15H24. Sesquiterpenes were believed to contribute to the many useful biological properties in plants. This study aimed to functionally characterize a full length sesquiterpene synthase gene fromP. minus.P. minussesquiterpene synthase (PmSTS) has a complete open reading frame (ORF) of 1689 base pairs encoding a 562 amino acid protein. Similar to other sesquiterpene synthases, PmSTS has two large domains: the N-terminal domain and the C-terminal metal-binding domain. It also consists of three conserved motifs: the DDXXD, NSE/DTE, and RXR. A three-dimensional protein model for PmSTS built clearly distinguished the two main domains, where conserved motifs were highlighted. We also constructed a phylogenetic tree, which showed that PmSTS belongs to the angiosperm sesquiterpene synthase subfamily Tps-a. To examine the function ofPmSTS, we expressed this gene inArabidopsis thaliana. Two transgenic lines, designated asOE3andOE7, were further characterized, both molecularly and functionally. The transgenic plants demonstrated smaller basal rosette leaves, shorter and fewer flowering stems, and fewer seeds compared to wild type plants. Gas chromatography-mass spectrometry analysis of the transgenic plants showed that PmSTS was responsible for the production ofβ-sesquiphellandrene.

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Liu, Juan, Yanhong Xu, Zheng Zhang, and Jianhe Wei. "Hydrogen peroxide promotes programmed cell death and salicylic acid accumulation during the induced production of sesquiterpenes in cultured cell suspensions of Aquilaria sinensis." Functional Plant Biology 42, no. 4 (2015): 337. http://dx.doi.org/10.1071/fp14189.

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Aquilaria sinensis (Lour.) Gilg produces a highly valuable agarwood characterised by a diverse array of sesquiterpenes and chromone derivatives that can protect wounded trees against potential herbivores and pathogens. A defensive reaction on the part of the plant has been proposed as the key reason for agarwood formation, but the issue of whether programmed cell death (PCD), an important process of plant immune responding, is involved in agarwood formation, still needs to be clarified. In this study, treatment of cultured cell suspensions with hydrogen peroxide (H2O2) induced the production of sesquiterpenes due to endogenous accumulation of salicylic acid (SA) and elevations in the expression of sesquiterpene biosynthetic genes. Moreover, PCD was stimulated by H2O2 in cultured cell suspensions of A. sinensis due to the induction of caspase activity, upregulated expression of metacaspases and cytochrome c, and SA accumulation. Our findings demonstrate for the first time that H2O2 stimulates PCD, SA accumulation and sesquiterpene production in cultured cell suspensions of A. sinensis. Furthermore, results from this study provide a valuable insight into investigations of the potential interactions between sesquiterpene synthesis and PCD during agarwood formation.

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Zhang, Mi, Jun-Song Wang, Masayoshi Oyama, Jun Luo, Chao Guo, Tetsuro Ito, Munekazu Iinuma, and Ling-Yi Kong. "Anti-inflammatory sesquiterpenes and sesquiterpene dimers fromChloranthus fortunei." Journal of Asian Natural Products Research 14, no. 7 (July 2012): 708–12. http://dx.doi.org/10.1080/10286020.2012.685724.

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35

Paknikar, Shashikumar K., Shahuraj H. Kadam, April L. Ehrlich, and Robert B. Bates. "Alternate Biosynthesis of Valerenadiene and Related Sesquiterpenes." Natural Product Communications 8, no. 9 (September 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800901.

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It is proposed that the biosynthesis of the sesquiterpene valerenadiene, a key intermediate in the biosynthesis of a sedative in valerian, involves cyclopropane and not cyclobutane intermediates and includes as a key step a cyclopropylcarbinylcation-cyclopropylcarbinylcation rearrangement analogous to the one observed in the conversion of presqualene to squalene in triterpene and steroid biosynthesis. Similar mechanisms are proposed for the biosynthesis of the related sesquiterpenes pacifigorgiol, tamariscene and (+)-pacifigorgia-1,10-diene.

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36

Luo, Xiangchao, Rongcui Wu, Xiao Han, Xuli Tang, Qi Wang, Pinglin Li, and Guoqiang Li. "Guaiane sesquiterpenes from the gorgonian Echinogorgia flora collected in the South China Sea." RSC Advances 12, no. 5 (2022): 2662–67. http://dx.doi.org/10.1039/d1ra08631f.

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Echinoflorine (1), a new dimethylamino-substituted guaipyridine alkaloid with a novel γ-lactone-cyclohepta[c]pyridine fused skeleton, and three new guaiane sesquiterpene lactones, echinofloranolides A–C (2–4), together with eight known guaiane sesquiterpenes were isolated from the gorgonian Echinogorgia flora collected in the South China Sea.

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37

Bhagavathy, Ganga V., Glory M. Velazquez Nieves, Meiling Z. Webb, and Kamlesh R. Chauhan. "Arthropod Deterrents from Artemisia Pallens (Davana Oil) Components." Natural Product Communications 10, no. 8 (August 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000802.

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Davanone, a key sesquiterpene component of davana oil, has been synthesized in five convenient steps. Oxygenated sesquiterpenes have been linked to insect deterrent properties. Based on initial screening of davana oil, davanone and its hydroxy precursors have been generated and are being evaluated as arthropod deterrents against disease vectors.

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Sánchez-Martínez, Raquel, Lucinda Villaescusa-Castillo, Manuel Bernabé, and Ana María Díaz-Lanza. "Two New Eudesmane Alcohols from Jasonia glutinosa." Zeitschrift für Naturforschung C 55, no. 9-10 (October 1, 2000): 693–96. http://dx.doi.org/10.1515/znc-2000-9-1004.

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Abstract Two new sesquiterpene alcohols have been isolated from the aerial parts of Jasonia glutinosa D. C. The structure of these sesquiterpenes were characterized by 1D and 2D NMR techniques (DQCOSY, TOCSY, NOESY, HMQC and HMBC) as (11R)-eudesm -4-en-11,12- diol and (11R)-eudesmane-5α,11,12-triol.

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Wu, Min, Kai-Long Ji, Peng Sun, Jian-Mei Lu, Jia-Rui Yue, Dong-Hua Cao, Chun-Fen Xiao, and You-Kai Xu. "Croargoids A–G, Eudesmane Sesquiterpenes from the Bark of Croton argyratus." Molecules 27, no. 19 (September 27, 2022): 6397. http://dx.doi.org/10.3390/molecules27196397.

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Seven new sesquiterpenes, named croargoid A–G (1–7), were isolated from the bark of Croton argyratus. Compounds 1–4 were the first examples of eudesmane sesquiterpene lactones containing C5-OH group. Compound 7 was a highly degraded eudesmane sesquiterpene possessing a rare eleven-carbon skeleton. Their structures with stereochemistry were mainly elucidated by NMR analyses in combination with MS and ECD data. Cytotoxicities and NO inhibitions of all isolates were evaluated and only compound 5 showed moderate NO inhibitory activity.

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Nagar, Shipra, Maria Pigott, Sophie Whyms, Apolline Berlemont, and Helen Sheridan. "Effect of Extraction Methods on Essential Oil Composition: A Case Study of Irish Bog Myrtle-Myrica gale L." Separations 10, no. 2 (February 14, 2023): 128. http://dx.doi.org/10.3390/separations10020128.

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Myrica gale is an aromatic peatland shrub that has reported traditional use as an insect repellent. Different extraction methodologies were used in this study to isolate the essential oil of Myrica gale L., including Clevenger hydrodistillation (CH) and microwave-assisted hydrodistillation (MAH). The oils, isolated from different plant parts (leaves, fruit and branches) collected in summer and autumn, were analysed by GC-MS and the volatiles from plant tissue were directly analysed by headspace-GC-MS. A total of 58 components were identified, including 15 monoterpene hydrocarbons (22.78–98.98%), 14 oxygenated monoterpenes (0.91–43.02%), 13 sesquiterpene hydrocarbons (0.05–24.98%), 3 oxygenated sesquiterpenes (0.07–13.16%) and 13 other compounds (0.05–5.21%). Headspace sampling furnished monoterpenes, while CH and MAH extracted monoterpenes and sesquiterpenes, with α-pinene (6.04–70.45%), eucalyptol (0.61–33.80%), limonene (2.27–20.73%) and α-phellandrene (2.33–15.61%) as major components in all plant parts. Quantitative differences occurred between extraction methodologies, with MAH yielding higher quantities of monoterpene and sesquiterpene hydrocarbons and CH targeting oxygenated counterparts. Leaves gave more complex chemical fingerprints than branches and fruit, and the summer collection yielded more components than the autumn collections. An OPLS-DA model was applied to the GC-MS data to compare the chemical profiles based on the extraction techniques and plant parts, and molecular networks were obtained for monoterpenes and sesquiterpenes connected via biosynthetic pathways. The essential oil profile of Myrica gale was influenced by the season of collection, plant part and extraction method.

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Kuck, Katrin, Guido Jürgenliemk, Bartosz Lipowicz, and Jörg Heilmann. "Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro." Molecules 26, no. 1 (December 23, 2020): 42. http://dx.doi.org/10.3390/molecules26010042.

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By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC50: 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes.

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Hussain, Abid, Muhammad Rizwan-ul-haq, Ahmed Mohammed AlJabr, and Hassan Al-Ayedh. "Lethality of Sesquiterpenes Reprogramming Red Palm Weevil Detoxification Mechanism for Natural Novel Biopesticide Development." Molecules 24, no. 9 (April 26, 2019): 1648. http://dx.doi.org/10.3390/molecules24091648.

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Natural biopesticide development for invasive populations of red palm weevils is mainly responsible for the destruction of date palms and demands an extensive screening program of plant secondary metabolites. In the current study, the pesticidal potential of sesquiterpenes (C15 H24), an important class of plant secondary metabolites primarily composed of three isoprene units, was evaluated by laboratory toxicity, feeding performance bioassays, and host detoxification gene expression patterns. Dose-mortality response bioassays performed against mid-aged eighth-instar red palm weevil larvae revealed dose-dependent mortality. Only three sesquiterpenes, including Farnesol (LD50 = 6559 ppm) and Farnesyl acetate (LD50 = 7867 ppm), are considered to have significant toxicity, with Picrotoxin (LD50 = 317 ppm) being the most toxic. Furthermore, highly toxic sesquiterpene (Picrotoxin) established in the current study tremendously reduced the feeding performance indices, including the efficacy of conversion of digested food (ECD) (81.74%) and the efficacy of conversion of ingested food (ECI) (73.62%). The least toxic sesquiterpenes, including β-Caryophyllene, (+)-Cedrol, Nerolidol, (+)-Nootkatone, and Parthenolide, observed in the current study failed to impart significant reductions of ECI and ECD indices. Lethality of the least toxic sesquiterpenes was overcome by greatly inducing gene expressions of Glutathione S transferase (GST) and Cytochrome P450. These encouraging results enabled us to suggest Picrotoxin as a promising biopesticide for the control of red palm weevil infestations.

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Zárybnický, Tomáš, Petra Matoušková, Lenka Skálová, and Iva Boušová. "The Hepatotoxicity of Alantolactone and Germacrone: Their Influence on Cholesterol and Lipid Metabolism in Differentiated HepaRG Cells." Nutrients 12, no. 6 (June 8, 2020): 1720. http://dx.doi.org/10.3390/nu12061720.

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The sesquiterpenes alantolactone (ATL) and germacrone (GER) are potential anticancer agents of natural origin. Their toxicity and biological activity have been evaluated using the differentiated HepaRG (dHepaRG) cells, a hepatocyte-like model. The half-maximal inhibitory concentrations of cell viability after 24-h treatment of dHepaRG cells are approximately 60 M for ATL and 250 M for GER. However, both sesquiterpenes induce reactive oxygen species (ROS) formation in non-toxic concentrations and significantly dysregulate the mRNA expression of several functional markers of mature hepatocytes. They similarly decrease the protein level of signal transducer and activator of transcription 3 (STAT3), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-B) and their transcription target, intercellular adhesion molecule 1 (ICAM-1). Based on the results of a BATMAN-TCM analysis, the effects of sesquiterpenes on cholesterol and lipid metabolism were studied. Sesquiterpene-mediated dysregulation of both cholesterol and lipid metabolism was observed, during which these compounds influenced the protein expression of 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCR) and sterol regulatory element-binding protein 2 (SREBP-2), as well as the mRNA expression of HMGCR, CYP19A1, PLIN2, FASN, SCD, ACACB, and GPAM genes. In conclusion, the two sesquiterpenes caused ROS induction at non-toxic concentrations and alterations in cholesterol and lipid metabolism at slightly toxic and toxic concentrations, suggesting a risk of liver damage if administered to humans.

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Carvalho, Flavio Alexandre, Fernando Bombarda Oda, Ant�nio Eduardo Miller Crotti, Eduardo Jos� Crevelin, and Andr� Gonzaga Dos Santos. "Geographical chemical variability and processing oxidation of volatile compounds of Casearia sylvestris leaves." Ecl�tica Qu�mica Journal 46, no. 3 (July 1, 2021): 42–48. http://dx.doi.org/10.26850/1678-4618eqj.v46.3.2021.p42-48.

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The Casearia sylvestris Sw. dried leaf essential oil (EO) contains sesquiterpenes as the main components. However, the volatile components in the in natura leaves remain unknown. This study compares the volatile chemicals in the in natura leaves and dried leaf EO of two C. sylvestris populations from Atlantic Forest and Cerrado. The volatile compounds were directly analysed by thermal desorption (TD) coupled to gas chromatography mass spectrometry (GC-MS); the dried leaf EO composition was determined by GC-MS. All the identified compounds were sesquiterpenes, and the major components were (E)-caryophyllene, bicyclogermacrene, ?-elemene, spathulenol, and caryophyllene oxide. In both populations, the sesquiterpene hydrocarbon content and the oxygenated sesquiterpene content respectively decreased and increased on going from the in natura leaves to the dried leaf essential oil, indicating that drying and/or hydrodistillation modified the volatile chemical composition by generating oxidation artifacts. Results suggested that (E)-caryophyllene and bicyclogermacrene may be oxidized during the process to yield caryophyllene oxide and spathulenol, respectively. The two C. sylvestris populations also differed in terms of volatile chemical composition.

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Choodej, Siwattra, Khanitha Pudhom, and Tohru Mitsunaga. "Inhibition of TNF-α-Induced Inflammation by Sesquiterpene Lactones from Saussurea lappa and Semi-Synthetic Analogues." Planta Medica 84, no. 05 (September 29, 2017): 329–35. http://dx.doi.org/10.1055/s-0043-120115.

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We investigated the tumor necrosis factor-alpha (TNF-α) inhibitory activity of sesquiterpenes from Saussurea lappa root extracts. According to the hexane and EtOAc extracts showing significant activity with IC50 values of 0.5 and 1.0 µg/mL, respectively, chromatographic fractionation of the extracts was performed and led to the isolation of 10 sesquiterpenes (1–10). Costunolide (1), a major compound, and dehydrocostus lactone (4) exhibited high efficiency in decreasing TNF-α levels, with IC50 values of 2.05 and 2.06 µM, respectively. In addition, sesquiterpene analogues were synthesized to establish their structure-activity relationship (SAR) profile. Among the semi-synthetic analogues, compounds 6a and 16 showed the most potent activity with IC50 values of 1.84 and 1.97 µM, respectively. More importantly, compound 6a showed less toxicity than costunolide and 16. These results provided the first SAR profile of sesquiterpene lactones and indicated that the α-methylene-γ-lactone moiety plays a crucial role in TNF-α inhibition. Additionally, the epoxide derivative 6a might represent a lead compound for further anti-TNF-α therapies, owing to its potent activity and reduced toxicity.

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Arizmendi, Narcy, Hui Qian, Yiming Li, and Marianna Kulka. "Sesquiterpene-Loaded Co-Polymer Hybrid Nanoparticle Effects on Human Mast Cell Surface Receptor Expression, Granule Contents, and Degranulation." Nanomaterials 11, no. 4 (April 8, 2021): 953. http://dx.doi.org/10.3390/nano11040953.

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Biodegradable polymeric nanoparticles (NPs) such as poly(lactic-co-glycolic acid) (PLGA) and polyvinyl alcohol (PVA) have been used as drug delivery systems for natural and synthetic compounds and are designed to control the loading and release of biodegradable materials to target cells, tissues, and organs. Eremophilane-type sesquiterpenes have anti-inflammatory properties but are lipophilic, cytotoxic, and not biocompatible with many cells. To determine whether biodegradable PLGA/PVA could improve the biocompatibility of sesquiterpenes, sesquiterpene-loaded NPs were synthesized and their effects on human mast cells (LAD2), the major effector cells of allergic inflammation, were determined. NPs composed of PLGA/PVA and two types of sesquiterpenes (fukinone, PLGA/PVA-21 and 10βH-8α,12-epidioxyeremophil-7(11)-en-8β-ol, PLGA/PVA-22) were produced using a microfluidic synthesis method. The NPs’ size distribution and morphology were evaluated by dynamic light scattering and cryogenic transmission electron microscopy (TEM). PLGA/PVA-21 and PLGA/PVA-22 were 60 to 70 nm and were readily internalized by LAD2 as shown by flow cytometry, fluorescence microscopy, and TEM. While unencapsulated sesquiterpenes decreased LAD2 cell viability by 20%, PLGA/PVA-21 and PLGA/PVA-22 did not alter LAD2 viability, showing that encapsulation improved the biocompatibility of the sesquiterpenes. PLGA/PVA-21 and PLGA/PVA-22 decreased the expression of genes encoding the subunits of the high affinity immunoglobulin E receptor (FcεR1α, FcεR1β, FcεR1γ) and the stem cell factor receptor (Kit,), suggesting that hybrid NPs could alter mast cell responses to antigens and shift their maturation. Similarly, PLGA/PVA-21 and PLGA/PVA-22 inhibited tryptase expression but had no effect on chymase expression, thereby promoting a shift to the tryptase-positive phenotype (MCT). Lastly, PLGA/PVA-21 and PLGA/PVA-22 inhibited mast cell degranulation when the LAD2 cells were activated by IgE crosslinking and FcεRI. Overall, our results suggest that PLGA/PVA-21 and PLGA/PVA-22 alter human mast cell phenotype and activation without modifying viability, making them a more biocompatible approach than treating cells with sesquiterpenes alone.

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Czechowski, Tomasz, Tony R. Larson, Theresa M. Catania, David Harvey, Geoffrey D. Brown, and Ian A. Graham. "Artemisia annua mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism." Proceedings of the National Academy of Sciences 113, no. 52 (December 7, 2016): 15150–55. http://dx.doi.org/10.1073/pnas.1611567113.

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Artemisinin, a sesquiterpene lactone produced by Artemisia annua glandular secretory trichomes, is the active ingredient in the most effective treatment for malaria currently available. We identified a mutation that disrupts the amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway. Detailed metabolic studies of cyp71av1-1 revealed that the consequence of blocking the artemisinin biosynthetic pathway is the redirection of sesquiterpene metabolism to a sesquiterpene epoxide, which we designate arteannuin X. This sesquiterpene approaches half the concentration observed for artemisinin in wild-type plants, demonstrating high-flux plasticity in A. annua glandular trichomes and their potential as factories for the production of novel alternate sesquiterpenes at commercially viable levels. Detailed metabolite profiling of leaf maturation time-series and precursor-feeding experiments revealed that nonenzymatic conversion steps are central to both artemisinin and arteannuin X biosynthesis. In particular, feeding studies using 13C-labeled dihydroartemisinic acid (DHAA) provided strong evidence that the final steps in the synthesis of artemisinin are nonenzymatic in vivo. Our findings also suggest that the specialized subapical cavity of glandular secretory trichomes functions as a location for both the chemical conversion and the storage of phytotoxic compounds, including artemisinin. We conclude that metabolic engineering to produce high yields of novel secondary compounds such as sesquiterpenes is feasible in complex glandular trichomes. Such systems offer advantages over single-cell microbial hosts for production of toxic natural products.

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48

Haapanala, S., A. Ekberg, H. Hakola, V. Tarvainen, J. Rinne, H. Hellén, and A. Arneth. "Mountain birch – potentially large source of sesquiterpenes into high latitude atmosphere." Biogeosciences Discussions 6, no. 3 (June 2, 2009): 5409–30. http://dx.doi.org/10.5194/bgd-6-5409-2009.

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Abstract. Emissions of volatile organic compounds (VOCs) from mountain birches were measured in Abisko, northern Sweden. Mountain birches make up majority of the tree biomass in Scandinavian high latitudes, area subject to significant climate warming. The measurements were carried out in two growing seasons. The emissions of a branch from four individual trees were measured in June–August 2006 and one of them again in July 2007. The measurements were conducted using a dynamic flow through chamber covered with Teflon film. The studied mountain birches were found to emit substantial amounts of linalool, monoterpenes and sesquiterpenes. The monoterpene emission was dominated by sabinene. The magnitude and composition of sesquiterpene emission changed dramatically between the years. For example, the average α-farnesene emission in 2006 was almost 2000 ng gdw−1 h−1 while in 2007 the emission of α-farnesene was negligible. Also the emissions of other sesquiterpenes decreased in 2007 to a fraction of that in 2006. One possible explanation for the change in emissions is the herbivory damage that occurred in the area in 2004. Herbivory is known to enhance the emissions of sesquiterpenes, especially those of α-farnesene, and the effect may last several years.

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Elhouiti, Fatiha, Djilali Tahri, Mohamed Ouinten, and Mohamed Yousfi. "In silico assessment of Rhanterium adpressum sesquiterpenes inhibitory effect on 3 and 15-O-trichothecene acetyltransferases." Nova Biotechnologica et chimica 19, no. 1 (June 30, 2020): 30–36. http://dx.doi.org/10.36547/nbc.v19i1.575.

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Essential oils (EO) from leaves and flowers of Rhanterium adpressum have shown to inhibit the mycelial growth and type B trichothecenes production. The four strains of Fusarium culmorum and Fusarium graminearum were inhibited with 0.25 μL.mL-1 of each oil. The inhibitory activity of 11 sesquiterpenes identified in these oils was here examined in silico against two key enzymes in the biosynthesis pathway of trichotecenes namely: 15-O-trichothecene acetyltransferase and 3-O-trichothecene acetyltransferase. In sesquiterpene composition, T-Muurolol and α-Eudesmol have the highest percentages ranging from 1.4 to 2.75 %. Three-dimensional structures of these two enzymes were modeled using SWISS-MODEL with GMQE = 0.93 and QMEAN = -0.45 for 3-O-trichothecene acetyltransferase and GMQE = 0.93, QMEAN = -0.58 for 15-O-trichothecene acetyltransferase. By the results of docking, T-Muurolol and α-Eudesmol showed high affinity compared to 15-Decalonectrin and Deoxynivalenol. These molecules are all sesquiterpenes with no major conformational difference with an RMSD of 3.7 Å and 3.5 Å between 15-decalonectrin and α-Eudesmol, T-Muurolol respectively. The results of docking prove the inhibitory effect of R. adpressum EO sesquiterpenes on the enzymes of mycotoxins biosynthesis pathway of F. culmorum and F. graminearum.

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Wu, Jiajun, Xiaoran Yang, Yingce Duan, Pengchao Wang, Jianzhao Qi, Jin-Ming Gao, and Chengwei Liu. "Biosynthesis of Sesquiterpenes in Basidiomycetes: A Review." Journal of Fungi 8, no. 9 (August 28, 2022): 913. http://dx.doi.org/10.3390/jof8090913.

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Sesquiterpenes are common small-molecule natural products with a wide range of promising applications and are biosynthesized by sesquiterpene synthase (STS). Basidiomycetes are valuable and important biological resources. To date, hundreds of related sesquiterpenoids have been discovered in basidiomycetes, and the biosynthetic pathways of some of these compounds have been elucidated. This review summarizes 122 STSs and 2 fusion enzymes STSs identified from 26 species of basidiomycetes over the past 20 years. The biological functions of enzymes and compound structures are described, and related research is discussed.

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Journal articles on the topic 'Sesquiterpenes'

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