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Journal articles on the topic 'Aromatic abietane diterpenoid'

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Published: 22 February 2025

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1

Martin, Vincent J. J., and William W. Mohn. "Genetic Investigation of the Catabolic Pathway for Degradation of Abietane Diterpenoids by Pseudomonas abietaniphilaBKME-9." Journal of Bacteriology 182, no. 13 (July 1, 2000): 3784–93. http://dx.doi.org/10.1128/jb.182.13.3784-3793.2000.

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ABSTRACT We have cloned and sequenced the dit gene cluster encoding enzymes of the catabolic pathway for abietane diterpenoid degradation by Pseudomonas abietaniphila BKME-9. Thedit gene cluster is located on a 16.7-kb DNA fragment containing 13 complete open reading frames (ORFs) and 1 partial ORF. The genes ditA1A2A3 encode the α and β subunits and the ferredoxin of the dioxygenase which hydroxylates 7-oxodehydroabietic acid to 7-oxo-11,12-dihydroxy-8,13-abietadien acid. The dioxygenase mutant strain BKME-941 (ditA1::Tn5) did not grow on nonaromatic abietanes, and transformed palustric and abietic acids to 7-oxodehydroabietic acid in cell suspension assays. Thus, nonaromatic abietanes are aromatized prior to further degradation. Catechol 2,3-dioxygenase activity of xylEtranscriptional fusion strains showed induction of ditA1and ditA3 by abietic, dehydroabietic, and 7-oxodehydroabietic acids, which support the growth of strain BKME-9, as well as by isopimaric and 12,14-dichlorodehydroabietic acids, which are diterpenoids that do not support the growth of strain BKME-9. In addition to the aromatic-ring-hydroxylating dioxygenase genes, thedit cluster includes ditC, encoding an extradiol ring cleavage dioxygenase, and ditR, encoding an IclR-type transcriptional regulator. Although ditR is not strictly required for the growth of strain BKME-9 on abietanes, aditR::Kmr mutation in aditA3::xylE reporter strain demonstrated that it encodes an inducer-dependent transcriptional activator of ditA3. An ORF with sequence similarity to genes encoding permeases (ditE) is linked with genes involved in abietane degradation.
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2

González, Miguel A. "Aromatic abietane diterpenoids: their biological activity and synthesis." Natural Product Reports 32, no. 5 (2015): 684–704. http://dx.doi.org/10.1039/c4np00110a.

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3

González, Miguel A. "Aromatic abietane diterpenoids: total syntheses and synthetic studies." Tetrahedron 71, no. 13 (April 2015): 1883–908. http://dx.doi.org/10.1016/j.tet.2015.01.058.

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4

Gonzalez, Miguel A. "ChemInform Abstract: Aromatic Abietane Diterpenoids: Total Syntheses and Synthetic Studies." ChemInform 46, no. 19 (April 23, 2015): no. http://dx.doi.org/10.1002/chin.201519313.

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5

González, Miguel A. "Synthetic derivatives of aromatic abietane diterpenoids and their biological activities." European Journal of Medicinal Chemistry 87 (November 2014): 834–42. http://dx.doi.org/10.1016/j.ejmech.2014.10.023.

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6

Li, Xin, and Rich G. Carter. "Total Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement." Organic Letters 20, no. 18 (September 10, 2018): 5546–49. http://dx.doi.org/10.1021/acs.orglett.8b02060.

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7

Gonzalez, Miguel A. "ChemInform Abstract: Synthetic Derivatives of Aromatic Abietane Diterpenoids and Their Biological Activities." ChemInform 46, no. 2 (December 19, 2014): no. http://dx.doi.org/10.1002/chin.201502275.

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8

Salamatin, Arthur A., Alyona S. Khaliullina, and Ramil Sh Khaziev. "Extraction of aromatic abietane diterpenoids from Salvia officinalis leaves by petroleum ether: Data resolution analysis." Industrial Crops and Products 143 (January 2020): 111909. http://dx.doi.org/10.1016/j.indcrop.2019.111909.

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9

Ramírez, Jorge, Gianluca Gilardoni, Matteo Radice, and Vladimir Morocho. "Phytochemistry, Bioactivity, and Ethnopharmacology of the Genus Lepechinia Willd. (Lamiaceae): A Review." Plants 13, no. 4 (February 8, 2024): 481. http://dx.doi.org/10.3390/plants13040481.

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The genus Lepechinia (Lamiaceae) involves several aromatic shrubs that are distributed only in the American continent, inhabiting mountain areas, mainly in the Andean region of South America. Based on the PRISMA approach, we selected and critically analyzed 48 research articles. From a phytochemical point of view, most of the secondary metabolites reported in Lepechinia spp. are terpenes and terpenoids, with a few exceptions comprising flavonoids and other shikimic acid derivatives. On the one hand, sesquiterpenoids of the guajane, aromadendrane, eudesmane, and cadinane groups are characteristic of essential oils, together with (E)-β-caryophyllene as the main representative of its chemical family. On the other hand, abietane diterpenoids are the prevalent compounds described in non-volatile fractions. Many biological activities and traditional medical uses have been reported for both pure metabolites and complex mixtures (e.g., essential oils). Regarding ethno-medical uses, the treatment of muscle pain, headache, toothache, diabetes mellitus, uterine tumors, uterine infections, and diarrhea has been reported. Concerning their verified biological activities, insecticidal, antifungal, antioxidant, and anticholinesterase properties have been described. Furthermore, some data concerning anti-herpetic activity have been reported.
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10

Yoshikawa, Kazuko, Naoki Kokudo, Masami Tanaka, Tatsuro Nakano, Hirofumi Shibata, Naokatsu Aragaki, Tomihiko Higuchi, and Toshihiro Hashimoto. "Novel Abietane Diterpenoids and Aromatic Compounds from Cladonia rangiferina and Their Antimicrobial Activity against Antibiotics Resistant Bacteria." CHEMICAL & PHARMACEUTICAL BULLETIN 56, no. 1 (2008): 89–92. http://dx.doi.org/10.1248/cpb.56.89.

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11

Yu, Zhongtang, Gordon R. Stewart, and William W. Mohn. "Apparent Contradiction: Psychrotolerant Bacteria from Hydrocarbon-Contaminated Arctic Tundra Soils That Degrade Diterpenoids Synthesized by Trees." Applied and Environmental Microbiology 66, no. 12 (December 1, 2000): 5148–54. http://dx.doi.org/10.1128/aem.66.12.5148-5154.2000.

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ABSTRACT Resin acids are tricyclic terpenoids occurring naturally in trees. We investigated the occurrence of resin acid-degrading bacteria on the Arctic tundra near the northern coast of Ellesmere Island (82�N, 62�W). According to most-probable-number assays, resin acid degraders were abundant (103 to 104propagules/g of soil) in hydrocarbon-contaminated soils, but they were undetectable (<3 propagules/g of soil) in pristine soils from the nearby tundra. Plate counts indicated that the contaminated and the pristine soils had similar populations of heterotrophs (106to 107 propagules/g of soil). Eleven resin acid-degrading bacteria belonging to four phylogenetically distinct groups were enriched and isolated from the contaminated soils, and representative isolates of each group were further characterized. Strains DhA-91, IpA-92, and IpA-93 are members of the genusPseudomonas. Strain DhA-95 is a member of the genusSphingomonas. All four strains are psychrotolerant, with growth temperature ranges of 4�C to 30�C (DhA-91 and DhA-95) or 4�C to 22�C (IpA-92 and IpA-93) and with optimum temperatures of 15 to 22�C. Strains DhA-91 and DhA-95 grew on the abietanes, dehydroabietic and abietic acids, but not on the pimaranes, isopimaric and pimaric acids. Strains IpA-92 and IpA-93 grew on the pimaranes but not the abietanes. All four strains grew on either aliphatic or aromatic hydrocarbons, which is unusual for described resin acid degraders. Eleven mesophilic resin acid degraders did not use hydrocarbons, with the exception of two Mycobacterium sp. strains that used aliphatic hydrocarbons. We conclude that hydrocarbon contamination in Arctic tundra soil indirectly selected for resin acid degraders, selecting for hydrocarbon degraders that coincidentally use resin acids. Psychrotolerant resin acid degraders are likely important in the global carbon cycle and may have applications in biotreatment of pulp and paper mill effluents.
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12

Badalamenti, Natale, Giovanna Salbitani, Piergiorgio Cianciullo, Rosanna Bossa, Francesca De Ruberto, Valeria Greco, Adriana Basile, Viviana Maresca, Maurizio Bruno, and Simona Carfagna. "Chemical Composition of Salvia fruticosa Mill. Essential Oil and Its Protective Effects on Both Photosynthetic Damage and Oxidative Stress in Conocephalum conicum L. Induced by Environmental Heavy Metal Concentrations." Antioxidants 12, no. 11 (November 11, 2023): 1990. http://dx.doi.org/10.3390/antiox12111990.

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The genus Salvia L., belonging to the Lamiaceae family, contains more than 900 species distributed in various parts of the world. It is a genus containing aromatic plants used both in the culinary field and above all in the cosmetic area to produce several perfumes. Salvia fruticosa Mill., notoriously known as Greek Salvia, is a plant used since ancient times in traditional medicine, but today cultivated and used in various parts of Europe and Africa. Polar and apolar extracts of this plant confirmed the presence of several metabolites such as abietane and labdane diterpenoids, triterpenoids, steroids, and some flavonoids, causing interesting properties such as sedative, carminative, and antiseptic, while its essential oils (EOs) are mainly characterized by compounds such as 1,8-cineole and camphor. The aim of this work concerns the chemical analysis by GC and GC-MS, and the investigation of the biological properties, of the EO of S. fruticosa plants collected in eastern Sicily. The gas-chromatographic analysis confirmed the presence of 1,8-cineole (17.38%) and camphor (12.81%), but at the same time, also moderate amounts of α-terpineol (6.74%), β-myrcene (9.07%), camphene (8.66%), β-pinene (6.55%), and α-pinene (6.45%). To study the protective effect of EOs from S. fruticosa (both the total mixture and the individual compounds) on possible damage induced by heavy metals, an in vitro system was used in which a model organism, the liverwort Conocephalum conicum, was subjected to the effect of a mix of heavy metals (HM) prepared using values of concentrations actually measured in one of the most polluted watercourses of the Campania region, the Regi Lagni. Finally, the antioxidant response and the photosynthetic damage were examined. The exogenous application of the EO yields a resumption of the oxidative stress induced by HM, as demonstrated by the reduction in the Reactive Oxygen Species (ROS) content and by the increased activity of antioxidant enzyme catalase (CAT) and glutathione-S-transferase (GST). Furthermore, plants treated with HMs and EO showed a higher Fv/Fm (maximal quantum efficiency of PSII in the dark) with respect to HMs-only treated ones. These results clearly indicate the protective capacity of the EO of S. fruticosa against oxidative stress, which is achieved at least in part by modulating the redox state through the antioxidant pathway and on photosynthetic damage.
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13

Li, Mengran, Peng Chen, Haoqi Liu, Jian Huang, and Yang Chen. "Review of total synthesis of aromatic abietane diterpenoid: Ferruginol." Synthesis, October 5, 2023. http://dx.doi.org/10.1055/a-2186-7983.

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The biologic properties and synthetic effort of ferruginol as a classical abietane-type diterpenoid with an aromatic C ring are reviewed. A strategy overview from 1954 to 2023 toward the total synthesis of ferruginol may provide some references for future design and synthesis of new diterpenoids natural products.
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14

Mitaka, Yuki, Kenji Matsuura, and Toshiharu Akino. "Dehydroabietic acid, an aromatic abietane diterpenoid, attracts termite workers." Applied Entomology and Zoology, March 23, 2024. http://dx.doi.org/10.1007/s13355-024-00869-6.

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15

R.S., Reyno, Sravya Surendran, Glory James, and Rajendar Goreti. "A Biomimetic Stereoselective Approach to Euolutchuol C and Its Structural Assignment." European Journal of Organic Chemistry, September 4, 2023. http://dx.doi.org/10.1002/ejoc.202300748.

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The first stereoselective total synthesis of euolutchuol C using a biomimetic cationic polyene cyclization is demonstrated, and its absolute structure was established. Four potential stereoisomers of euolutchuol C were synthesized, to confirm the structure as aromatic abietane diterpenoid consisting of 15(S)‐stereogenic center. Asymmetric Sharpless dihydroxylation was used to build chiral epoxide, while CBS‐reduction was utilized for enantiomerically pure benzylic alcohols. A convergent approach used to synthesize euolutchuol C in seven longest linear steps to give an overall yield of 23%.
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16

Kundu, Sourav, Debgopal Jana, Nilangshu Mandal, Ayan Mondal, Ranjit Murmu, Nanda Kishore Roy, Ayan Datta, and Alakesh Bisai. "Biomimetic total synthesis of the reported structure of (+)-selaginedorffone B." Chemical Science, 2024. http://dx.doi.org/10.1039/d4sc04103h.

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The first enantioselective total synthesis of the reported structure of the structurally unique aromatic tetraterpenoid of anti-cancer potential, (+)-selaginedorffone B (2) has been accomplished from two modified abietane diterpenoids through...
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17

López‐Cabeza, Rocío, Samuel Rodríguez‐Sabina, Carolina P. Reyes, Daniela G. Expósito, Cristina Giménez, Ignacio A. Jiménez, Raimundo Cabrera, and Isabel L. Bazzocchi. "Bio‐guided isolation of aromatic abietane diterpenoids from Salvia canariensis as biopesticides in the control of phytopathogenic fungi." Pest Management Science, January 23, 2024. http://dx.doi.org/10.1002/ps.7958.

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AbstractBackgroundBiofungicides arise as a promising alternative to the indiscriminate use of harmful synthetic fungicides in crop management.ResultsThe present study reports the bio‐guided fractionation of an endemic plant from the Canary Islands, Salvia canariensis against the phytopathogens, Alternaria alternata, Botrytis cinerea, and Fusarium oxysporum. This procedure allowed identifying a series of diterpenoids with an abietane skeleton (1–5), which exhibited remarkable activity against the phytopathogenic fungi assayed. Their structures were established by means of spectroscopic and spectrometric methods, as well as comparison with reported data. Compounds 2 (carnosic acid), 4 (11‐acetoxy carnosic acid) and 5 (11,12‐diacetoxy carnosic acid) showed significant mycelium growth inhibition (%GI > 50 at 0.1 mg/mL concentration) on all the assayed fungi, and with a potency also higher than the positive control, Fosbel‐Plus, a fungicide commonly used in agriculture. A preliminary structure–activity relationship is also discussed.ConclusionsThese findings underline the aromatic abietane diterpenoids as promising eco‐friendly alternatives to conventional fungicides to use in integrated pest management. © 2024 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
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18

Peng, Xing, Qingyun Tan, Leiming Wu, Deyin Wu, Jun Xu, Huihao Zhou, and Qiong Gu. "Ferroptosis Inhibitory Aromatic Abietane Diterpenoids from Ajuga decumbens and Structural Revision of Two 3,4-Epoxy Group-Containing Abietanes." Journal of Natural Products, July 7, 2022. http://dx.doi.org/10.1021/acs.jnatprod.2c00352.

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19

Gonzalez, Miguel A. "ChemInform Abstract: Aromatic Abietane Diterpenoids: Their Biological Activity and Synthesis." ChemInform 47, no. 17 (April 2016). http://dx.doi.org/10.1002/chin.201617220.

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20

Kakde, Badrinath N., Amarchand Parida, Vipin R. Gavit, Rhituparna Nandi, Sourav Kundu, and Alakesh Bisai. "FeCl3-Catalyzed Highly Efficient Nazarov Type Cyclization of Arylvinyl Carbinols: Total Syntheses of Naturally Occurring Taiwaniaquinoids." Prayogik Rasayan 5, no. 2 (2021). http://dx.doi.org/10.53023/p.rasayan-20211115.

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FeCl3-catalyzed cyclization of arylvinylcarbinols for the synthesis of [6,5,6]-carbotricyclic core sharing an all-carbon quaternary center has been described in this full article. A careful mechanistic details suggest that the reaction follows a stepwise mechanism via the intermediacy of arylallyl carbocationic species. The carbocation subsequently reacts with an adjacent aromatic ring to form [6,5,6]-carbotricyclic scaffold of abeo-abietane diterpenoids. The methodology works under mild conditions to afford a variety of carbotricyclic core in good to excellent yields (up to 99% yield). Our strategy has been applied to a concise synthesis of a number of structurally intriguing naturally occurring taiwaniaquinoids, (±)-taiwaniaquinol F (1a), (±)-taiwaniaquinol B (1b), (±)-dichronanone (1c), (±)-taiwaniaquinone H (1d) and unnatural (±)-5-epi-taiwaniaquinone G (epi-1e).
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21

Zhang, Ming, Yi-Ran Yang, Yan-Fang Chen, Fu-Cai Ren, Xiang-Dong Pu, and Chuanpu Shen. "Aromatic Abietane‐Type Diterpenoids from the Roots of Salvia prattii and Their Protective Activity Against alcoholic liver disease." Chemistry & Biodiversity, September 25, 2024. http://dx.doi.org/10.1002/cbdv.202401339.

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Eighteen aromatic abietane‐type diterpenes, including three previously unreported compounds, Salkanoids A‐C (1‐3), were isolated from the roots of Salvia prattii. Their stuctures were extensively elucidated using 1D/2D NMR, high‐resolution electrospray ionization mass spectrometry (HRESIMS) data, and ECD calculation. Among these, compounds 1, 6 and 7 belong to a class of diterpenes featuring a [5, 5]‐oxaspirolactones moiety, a rare structure isolated from the Salvia plants. All the isolates were assessed for their protective effects against alcoholic liver disease using ethanol‐induced AML‐12 cell lines. The findings revealed that compounds 2, 5, 8 and 15 demonstrated potential protective activity.
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22

Feng, Yiling, Tristan Weers, and Reuben J. Peters. "Double-barreled defense: dual ent-miltiradiene synthases in most rice cultivars." aBIOTECH, May 20, 2024. http://dx.doi.org/10.1007/s42994-024-00167-3.

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AbstractRice (Oryza sativa) produces numerous diterpenoid phytoalexins that are important in defense against pathogens. Surprisingly, despite extensive previous investigations, a major group of such phytoalexins, the abietoryzins, were only recently reported. These aromatic abietanes are presumably derived from ent-miltiradiene, but such biosynthetic capacity has not yet been reported in O. sativa. While wild rice has been reported to contain such an enzyme, specifically ent-kaurene synthase-like 10 (KSL10), the only characterized ortholog from O. sativa (OsKSL10), specifically from the well-studied cultivar (cv.) Nipponbare, instead has been shown to make ent-sandaracopimaradiene, precursor to the oryzalexins. Notably, in many other cultivars, OsKSL10 is accompanied by a tandem duplicate, termed here OsKSL14. Biochemical characterization of OsKLS14 from cv. Kitaake demonstrates that this produces the expected abietoryzin precursor ent-miltiradiene. Strikingly, phylogenetic analysis of OsKSL10 across the rice pan-genome reveals that from cv. Nipponbare is an outlier, whereas the alleles from most other cultivars group with those from wild rice, suggesting that these also might produce ent-miltiradiene. Indeed, OsKSL10 from cv. Kitaake exhibits such activity as well, consistent with its production of abietoryzins but not oryzalexins. Similarly consistent with these results is the lack of abietoryzin production by cv. Nipponbare. Although their equivalent product outcome might suggest redundancy, OsKSL10 and OsKSL14 were observed to exhibit distinct expression patterns, indicating such differences may underlie retention of these duplicated genes. Regardless, the results reported here clarify abietoryzin biosynthesis and provide insight into the evolution of rice diterpenoid phytoalexins.
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23

Yoshikawa, Kazuko, Naoki Kokudo, Masami Tanaka, Tatsuro Nakano, Hirofumi Shibata, Naokatsu Aragaki, Tomihiko Higuchi, and Toshihiro Hashimoto. "ChemInform Abstract: Novel Abietane Diterpenoids and Aromatic Compounds from Cladonia rangiferina and Their Antimicrobial Activity Against Antibiotics Resistant Bacteria." ChemInform 39, no. 28 (July 8, 2008). http://dx.doi.org/10.1002/chin.200828177.

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