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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

Abrahanr, Wolf-Rainer, and Dawit Abate. "Chromanones from Lentinus crinitus (Basidiomycetes)." Zeitschrift für Naturforschung C 50, no. 11-12 (December 1, 1995): 748–50. http://dx.doi.org/10.1515/znc-1995-11-1202.

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The fungus Lentinus crinitus DR-5 (Basidiomycotina) produces in submerse culture the new natural products 2,2-dimethyl-6-methoxy-4-chromanone 1, its alcohol 3 and (S)-2,2-di-methyl-3-hydroxy-6-methoxy-4-chromanone 2. Beside these merohemiterpenes the antibioti-cally active hirsutane sesquiterpenes 5 -8 were isolated. The formation of these metabolites displayed strong dependence from the carbon source in the medium. While lactose favoured the formation of the antibiotic sesquiterpene ketones 5 and 6, they were suppressed with mannose where the hemiterpenes 1 and 4 and the hirsutane-diol 8 were the dominating metabolites.

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2

Yadav, Indrajeet, Akhil Rautela, Agendra Gangwar, Vigya Kesari, Aditya K. Padhi, and Sanjay Kumar. "Geranyl Diphosphate Synthase (CrtE) Inhibition Using Alendronate Enhances Isoprene Production in Recombinant Synechococcus elongatus UTEX 2973: A Step towards Isoprene Biorefinery." Fermentation 9, no. 3 (February 24, 2023): 217. http://dx.doi.org/10.3390/fermentation9030217.

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A hemiterpene, isoprene, is commercially produced from crude oil refining processes. As a result of fossil fuel depletion, isoprene production process development is gaining attention from recombinant cyanobacteria and other microbial systems for its industrial and biofuel applications. In the present study, a fast-growing and CO2-tolerant cyanobacteria, Synechococcus elongatus UTEX 2973, is engineered with Pueraria montana isoprene synthase (IspS) at neutral site I (NSI) in the genome of S. elongatus UTEX 2973. Furthermore, to enhance isoprene production a key enzyme (isopentenyl diphosphate isomerase, IDI) of the methyl-D-erythritol 4-phosphate (MEP) pathway is also overexpressed at neutral site III (NSIII). Wild-type and recombinant strains of S. elongatus UTEX 2973 (UTEX IspS and UTEX IspS.IDI) are studied for growth and isoprene production in the presence of an inducer (IPTG) and/or inhibitor (alendronate). Alendronate is used for the inhibition of geranyl diphosphate synthase (CrtE), downstream of the MEP pathway that catalyzes dimethylallyl diphosphate/isopentenyl pyrophosphate (DMAPP/IPP) condensation in the recombinant UTEX 2973 strains. The docking studies on SeCrtE (CrtE of Synechcoccus elongatus PCC 7942) and alendronate as an inhibitor have revealed that alendronate binds more tightly than IPP in the cavity of SeCrtE, with a higher number of intermolecular interactions and energy. The UTEX IspS strain has shown isoprene production below the limit of detection in the presence of an inducer and/or inhibitor; however, production studies using UTEX IspS.IDI showed a maximum production of 79.97 and 411.51 µg/g dry cell weight (DCW) in a single day in the presence of an inducer only and an inducer along with an inhibitor, respectively. The UTEX IspS.IDI strain produced 0.41 mg/g DCW of cumulative isoprene in the presence of an inducer and 1.92 mg/g DCW in the presence of an inducer as well as an inhibitor during six days of production. The yield improvement of isoprene is observed as being 4.7-fold by using the inhibition strategy, which is used for the first time in the recombinant cyanobacterial system. The average productivities of isoprene obtained from UTEX IspS.IDI are observed to be 2.8 μg/g DCW/h in the presence of an inducer and 13.35 μg/g DCW/h in the presence of an inducer as well as an inhibitor. This study provides a basis for the process development and yield improvement in isoprene production using a novel inhibition strategy in fast-growing recombinant cyanobacteria. Recombinant strains and metabolic pathway inhibition studies can be used in future attempts to photosynthetically produce hemiterpenes.

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3

Liu, Hong-Xin, Hai-Bo Tan, Kai Chen, Li-Yun Zhao, Yu-Chan Chen, Sai-Ni Li, Hao-Hua Li, and Wei-Min Zhang. "Cytosporins A–D, novel benzophenone derivatives from the endophytic fungus Cytospora rhizophorae A761." Organic & Biomolecular Chemistry 17, no. 9 (2019): 2346–50. http://dx.doi.org/10.1039/c8ob03223h.

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4

Liu, Hongxin, Haibo Tan, Wenxuan Wang, Wenge Zhang, Yuchan Chen, Saini Li, Zhaoming Liu, Haohua Li, and Weimin Zhang. "Cytorhizophins A and B, benzophenone-hemiterpene adducts from the endophytic fungus Cytospora rhizophorae." Organic Chemistry Frontiers 6, no. 5 (2019): 591–96. http://dx.doi.org/10.1039/c8qo01306c.

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5

Baltenweck-Guyot, R., J. M. Trendel, P. Albrecht, and A. Schaeffer. "New Hemiterpene Glycosides inVitis viniferaWine." Journal of Natural Products 60, no. 12 (December 1997): 1326–27. http://dx.doi.org/10.1021/np970281x.

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6

Szabó, Géza, Harald Greger, and Otmar Hofer. "Coumarin-hemiterpene ethers from Artemisia species." Phytochemistry 24, no. 3 (1985): 537–41. http://dx.doi.org/10.1016/s0031-9422(00)80763-3.

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7

Nicoletti, Marcella, Lamberto Tomassini, and Sebastiano Foddai. "A New Hemiterpene Glucoside fromOrnithogalum montanum." Planta Medica 58, no. 05 (October 1992): 472. http://dx.doi.org/10.1055/s-2006-961519.

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8

FUCHINO, Hiroyuki, Hironori TACHIBANA, and Nobutoshi TANAKA. "Three New Hemiterpene Glycosides from Ilex macropoda." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 9 (1997): 1533–35. http://dx.doi.org/10.1248/cpb.45.1533.

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9

Damtoft, Søren, and Søren Rosendal Jensen. "Hemialboside, a hemiterpene glucoside from Lamium album." Phytochemistry 39, no. 4 (July 1995): 923–24. http://dx.doi.org/10.1016/0031-9422(95)00085-l.

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10

Choudhary, M. Iqbal, Nadra Naheed, Ahmed Abbaskhan, Sajjad Ali, and Atta-ur-Rahman. "Hemiterpene glucosides and other constituents from Spiraea canescens." Phytochemistry 70, no. 11-12 (July 2009): 1467–73. http://dx.doi.org/10.1016/j.phytochem.2009.07.013.

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11

Ono, Masateru, Shin Yasuda, Yuki Shiono, Chisato Furusawa, Shinya Inaba, Takayuki Tanaka, Tsuyoshi Ikeda, and Toshihiro Nohara. "A new hemiterpene glycoside from the ripe tomatoes." Natural Product Research 29, no. 3 (November 25, 2014): 262–67. http://dx.doi.org/10.1080/14786419.2014.974053.

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12

Jiang, Zhi-Hong, Jing-Rong Wang, Min Li, Zhong-Qiu Liu, Ka-Yee Chau, Chi Zhao, and Liang Liu. "Hemiterpene Glucosides with Anti-Platelet Aggregation Activities fromIlexpubescens." Journal of Natural Products 68, no. 3 (March 2005): 397–99. http://dx.doi.org/10.1021/np049735y.

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13

Hano, Y., A. Ayukawa, T. Nomura, and S. Ueda. "A chimeric hemiterpene biosynthesis inMorus alba cell cultures." Naturwissenschaften 81, no. 6 (June 1994): 260–62. http://dx.doi.org/10.1007/bf01131577.

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14

Zhang, Qing-He, Fredrik Schlyter, and Göran Birgersson. "2-methyl-3-buten-2-ol: A Pheromone Component of Conifer Bark Beetles Found in the Bark of Nonhost Deciduous Trees." Psyche: A Journal of Entomology 2012 (2012): 1–7. http://dx.doi.org/10.1155/2012/414508.

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Анотація:

Volatiles from bark of aspen,Populus tremulaL. and two species of birch: silver birch (Betula pendulaRoth.) and common birch (B. pubescensEhrh.), were collected by direct solvent extraction and aeration of both newly cut bark chips and undamaged stems in June 1998 and subjected to GC-MS analysis. The results showed the presence of 2-methyl-3-buten-2-ol (MB), one of the two principal aggregation pheromone components of the spruce bark beetle,Ips typographus, in bark extraction samples of all the three deciduous tree species tested. In addition, one more oxygenated hemiterpene, 3-methyl-3-buten-2-one, and (E)-3-penten-2-ol were also found in the bark extracts. Only trace amounts of MB were detected in some aeration samples of the fresh bark chips, and no MB was found from the aeration samples of undamaged stems at detectable levels. The occurrence of this compound was also confirmed in the bark of four exotic birch species:B. albosinensisSchneid.,B. ermaniiCham.,B. jacquemontiiSpach, andB. maximowiczianaRegel, but not yet in the European pines/spruces and the common yeasts. Our results raise major questions regarding the evolution, the tropospheric chemistry, and the ecological role of this hemiterpene alcohol. They also suggest that comparative studies on the biosynthetic pathways for MB in different sources would be of considerably evolutionary interest.

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15

FUCHINO, H., H. TACHIBANA, and N. TANAKA. "ChemInform Abstract: Three New Hemiterpene Glycosides from Ilex macropoda." ChemInform 29, no. 7 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199807201.

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16

Hano, Y., A. Ayukawa, T. Nomura, and S. Ueda. "A Chimeric Hemiterpene Biosynthesis in Morus alba Cell Cultures." Naturwissenschaften 81, no. 6 (June 1, 1994): 260–62. http://dx.doi.org/10.1007/s001140050067.

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17

Mojarrab, Mahdi, Abbas Delazar, Matthias Hamburger, and Olivier Potterat. "New Coumarin-Hemiterpene Ether Glucosides and a Structurally Related Phenylpropanoic Acid Derivative from Artemisia Armeniaca." Natural Product Communications 5, no. 10 (October 2010): 1934578X1000501. http://dx.doi.org/10.1177/1934578x1000501021.

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Анотація:

Two new coumarin-hemiterpene ether glucosides, 4’- O-(β-D-glucopyranosyl) desoxylacarol (1), and 5- O-(β-D-glucopyranosyl) lacarol (2), were isolated from the methanolic extract of the aerial parts of Artemisia armeniaca Lam. Their structures were established by means of spectroscopic analysis including 1H- and 2D-NMR, HRESIMS, and acid hydrolysis. In addition, a structurally related phenylpropanoic acid derivative (3) was obtained in small amounts, and its structure tentatively assigned as 3-(4-hydroxy–3-methylbutoxy)-4-methoxy melilotic acid.

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18

Lund, Sean, Rachael Hall, and Gavin J. Williams. "An Artificial Pathway for Isoprenoid Biosynthesis Decoupled from Native Hemiterpene Metabolism." ACS Synthetic Biology 8, no. 2 (January 16, 2019): 232–38. http://dx.doi.org/10.1021/acssynbio.8b00383.

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19

Cardona, Luz, Begoña García, Pedro José R., and José Pérez. "6-Prenyloxy-7-methoxycoumarin, a coumarin-hemiterpene ether from Carduus tenuiflorus." Phytochemistry 31, no. 11 (January 1992): 3989–91. http://dx.doi.org/10.1016/s0031-9422(00)97569-1.

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20

Yang, Can, Zhi Wang, Yan Qiu, Haiyan Zha, and Xuedong Yang. "New hemiterpene and furolactone-type lignan glycosides from Securidaca inappendiculata Hassk." Phytochemistry Letters 37 (June 2020): 42–46. http://dx.doi.org/10.1016/j.phytol.2020.04.001.

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21

Lopes, Edizon Veiga, Hercules Bezerra Dias, Zelina Estevam dos Santos Torres, Francisco Célio Maia Chaves, Antonio Carlos Siani, and Adrian Martin Pohlit. "Coumarins, triterpenes and a hemiterpene from Bonamia ferruginea (Choisy) Hallier f." Biochemical Systematics and Ecology 61 (August 2015): 67–69. http://dx.doi.org/10.1016/j.bse.2015.04.034.

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22

TOYOTA, Masao, Yasushi OISO, and Yoshinori ASAKAWA. "New Bitter-Tasting Hemiterpene Glycosides from the Japanese Fern Hymenophyllum barbatum." CHEMICAL & PHARMACEUTICAL BULLETIN 49, no. 12 (2001): 1567–72. http://dx.doi.org/10.1248/cpb.49.1567.

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23

Kim, Manh Heun, Kwan Hee Park, Myeong Hwan Oh, Han Hyuk Kim, Kang In Choe, Sang Hee Park, and Min Won Lee. "Two new hemiterpene glycosides from the leaves of Ilex rotunda. thunb." Archives of Pharmacal Research 35, no. 10 (October 2012): 1779–84. http://dx.doi.org/10.1007/s12272-012-1010-1.

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24

Xie, Mei-Ping, Lan Li, Hua Sun, An-Qi Lu, Bo Zhang, Jian-Gong Shi, Dan Zhang, and Su-Juan Wang. "Hepatoprotective hemiterpene glycosides from the rhizome of Cibotium barometz (L.) J. Sm." Phytochemistry 138 (June 2017): 128–33. http://dx.doi.org/10.1016/j.phytochem.2017.02.023.

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25

Park, Sang Hee, Kwan Hee Park, Myeong Hwan Oh, Han Hyuk Kim, Kang In Choe, So Ra Kim, Kwang Jun Park, and Min Won Lee. "Anti-oxidative and anti-inflammatory activities of caffeoyl hemiterpene glycosides from Spiraea prunifolia." Phytochemistry 96 (December 2013): 430–36. http://dx.doi.org/10.1016/j.phytochem.2013.09.017.

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26

Nahrstedt, Adolf, Dimitrios Economou та Victor Wray. "2-Methylbutan-l-yl-β/-D-glucoside, a Hemiterpene Glucoside from Bystropogon plumosus". Journal of Natural Products 53, № 5 (вересень 1990): 1387–89. http://dx.doi.org/10.1021/np50071a045.

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27

OISO, Yasushi, Masao TOYOTA, and Yoshinori ASAKAWA. "Hymenosides A-F, Six New Hemiterpene Glucosides from the Japanese Fern Hymenophyllum barbatum." CHEMICAL & PHARMACEUTICAL BULLETIN 49, no. 1 (2001): 126–28. http://dx.doi.org/10.1248/cpb.49.126.

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28

Toyota, Masao, Yasushi Oiso, and Yoshinori Asakawa. "ChemInform Abstract: New Bitter-Tasting Hemiterpene Glycosides from the Japanese Fern Hymenophyllum barbatum." ChemInform 33, no. 17 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200217201.

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29

Zhao, Mei-Li, Wen-Sheng Cai, Si-Qi Zheng, Jia-Lin Zhao, Jun-Liang Zhang, Ying Huang, Zhang-Li Hu, and Bin Jia. "Metabolic Engineering of the Isopentenol Utilization Pathway Enhanced the Production of Terpenoids in Chlamydomonas reinhardtii." Marine Drugs 20, no. 9 (September 15, 2022): 577. http://dx.doi.org/10.3390/md20090577.

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Анотація:

Eukaryotic green microalgae show considerable promise for the sustainable light-driven biosynthesis of high-value fine chemicals, especially terpenoids because of their fast and inexpensive phototrophic growth. Here, the novel isopentenol utilization pathway (IUP) was introduced into Chlamydomonas reinhardtii to enhance the hemiterpene (isopentenyl pyrophosphate, IPP) titers. Then, diphosphate isomerase (IDI) and limonene synthase (MsLS) were further inserted for limonene production. Transgenic algae showed 8.6-fold increase in IPP compared with the wild type, and 23-fold increase in limonene production compared with a single MsLS expressing strain. Following the culture optimization, the highest limonene production reached 117 µg/L, when the strain was cultured in a opt2 medium supplemented with 10 mM isoprenol under a light: dark regimen. This demonstrates that transgenic algae expressing the IUP represent an ideal chassis for the high-value terpenoid production. The IUP will facilitate further the metabolic and enzyme engineering to enhance the terpenoid titers by significantly reducing the number of enzyme steps required for an optimal biosynthesis.

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30

Kaser, L., T. Karl, R. Schnitzhofer, M. Graus, I. S. Herdlinger-Blatt, J. P. DiGangi, B. Sive, et al. "Comparison of different real time VOC measurement techniques in a ponderosa pine forest." Atmospheric Chemistry and Physics Discussions 12, no. 10 (October 24, 2012): 27955–88. http://dx.doi.org/10.5194/acpd-12-27955-2012.

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Abstract. Volatile organic compound (VOC) mixing ratios measured by five independent instruments are compared at a forested site dominated by ponderosa pine (Pinus Ponderosa) during the BEACHON-ROCS field study in summer 2010. The instruments included a Proton Transfer Reaction Time of Flight Mass Spectrometer (PTR-TOF-MS), a Proton Transfer Reaction Quadrupole Mass Spectrometer (PTR-MS), a Fast Online Gas-Chromatograph coupled to a Mass Spectrometer (GC/MS; TOGA), a Thermal Dissociation Chemical Ionization Mass Spectrometer (PAN-CIMS) and a Fiber Laser-Induced Fluorescence Instrument (FILIF). The species discussed in this comparison include the most important biogenic VOCs and a selected suite of oxygenated VOCs that are thought to dominate the VOC reactivity at this particular site as well as typical anthropogenic VOCs that showed low mixing ratios at this site. Good agreement was observed for methanol, the sum of the oxygenated hemiterpene 2-methyl-3-buten-2-ol (MBO) and the hemiterpene isoprene, acetaldehyde, the sum of acetone and propanal, benzene and the sum of methyl ethyl ketone (MEK) and butanal. Measurements of the above VOCs conducted by different instruments agree within 20%. The ability to differentiate the presence of toluene and cymene by PTR-TOF-MS is tested based on a comparison with GC-MS measurements, suggesting a study-average relative contribution of 74% for toluene and 26% for cymene. Similarly, 2-hydroxy-2-methylpropanal (HMPR) is found to interfere with the sum of methyl vinyl ketone and methacrolein (MVK+MAC) using PTR-(TOF)-MS at this site. A study-average relative contribution of 85% for MVK+MAC and 15% for HMPR was determined. The sum of monoterpenes measured by PTR-MS and PTR-TOF-MS was generally 20–25% higher than the sum of speciated monoterpenes measured by TOGA, which included α-pinene, β-pinene, camphene, carene, myrcene, limonene, cineole as well as other terpenes. However, this difference is consistent throughout the study, and likely points to an offset in calibration, rather than a difference in the ability to measure the sum of terpenes. The contribution of isoprene relative to MBO inferred from PTR-MS and PTR-TOF-MS was smaller than 12% while GC-MS data suggested an average of 21% of isoprene relative to MBO. This comparison demonstrates that the current capability of VOC measurements to account for OH reactivity associated with the measured VOCs is within 20%.

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31

Kaser, L., T. Karl, R. Schnitzhofer, M. Graus, I. S. Herdlinger-Blatt, J. P. DiGangi, B. Sive, et al. "Comparison of different real time VOC measurement techniques in a ponderosa pine forest." Atmospheric Chemistry and Physics 13, no. 5 (March 11, 2013): 2893–906. http://dx.doi.org/10.5194/acp-13-2893-2013.

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Анотація:

Abstract. Volatile organic compound (VOC) mixing ratios measured by five independent instruments are compared at a forested site dominated by ponderosa pine (Pinus Ponderosa) during the BEACHON-ROCS field study in summer 2010. The instruments included a Proton Transfer Reaction Time of Flight Mass Spectrometer (PTR-TOF-MS), a Proton Transfer Reaction Quadrupole Mass Spectrometer (PTR-MS), a Fast Online Gas-Chromatograph coupled to a Mass Spectrometer (GC/MS; TOGA), a Thermal Dissociation Chemical Ionization Mass Spectrometer (PAN-CIMS) and a Fiber Laser-Induced Fluorescence Instrument (FILIF). The species discussed in this comparison include the most important biogenic VOCs and a selected suite of oxygenated VOCs that are thought to dominate the VOC reactivity at this particular site as well as typical anthropogenic VOCs that showed low mixing ratios at this site. Good agreement was observed for methanol, the sum of the oxygenated hemiterpene 2-methyl-3-buten-2-ol (MBO) and the hemiterpene isoprene, acetaldehyde, the sum of acetone and propanal, benzene and the sum of methyl ethyl ketone (MEK) and butanal. Measurements of the above VOCs conducted by different instruments agree within 20%. The ability to differentiate the presence of toluene and cymene by PTR-TOF-MS is tested based on a comparison with GC-MS measurements, suggesting a study-average relative contribution of 74% for toluene and 26% for cymene. Similarly, 2-hydroxy-2-methylpropanal (HMPR) is found to interfere with the sum of methyl vinyl ketone and methacrolein (MVK + MAC) using PTR-(TOF)-MS at this site. A study-average relative contribution of 85% for MVK + MAC and 15% for HMPR was determined. The sum of monoterpenes measured by PTR-MS and PTR-TOF-MS was generally 20–25% higher than the sum of speciated monoterpenes measured by TOGA, which included α-pinene, β-pinene, camphene, carene, myrcene, limonene, cineole as well as other terpenes. However, this difference is consistent throughout the study, and likely points to an offset in calibration, rather than a difference in the ability to measure the sum of terpenes. The contribution of isoprene relative to MBO inferred from PTR-MS and PTR-TOF-MS was smaller than 12% while GC-MS data suggested an average of 21% of isoprene relative to MBO. This comparison demonstrates that the current capability of VOC measurements to account for OH reactivity associated with the measured VOCs is within 20%.

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32

Lund, Sean, Taylor Courtney, and Gavin J. Williams. "Probing the Substrate Promiscuity of Isopentenyl Phosphate Kinase as a Platform for Hemiterpene Analogue Production." ChemBioChem 20, no. 17 (July 22, 2019): 2217–21. http://dx.doi.org/10.1002/cbic.201900135.

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33

Oiso, Yasushi, Masao Toyota, and Yoshinori Asakawa. "ChemInform Abstract: Hymenosides A-F, Six New Hemiterpene Glucosides from the Japanese Fern Hymenophyllum barbatum." ChemInform 32, no. 31 (May 25, 2010): no. http://dx.doi.org/10.1002/chin.200131187.

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34

Khosnutdinova, T. S., N. G. Gemejiyeva, Zh Zh Karzhaubekova, and N. A. Sultanova. "Coumarins of genus Ferula L. (Apiaceae Lindl.)." Eurasian Chemico-Technological Journal 25, no. 1 (March 20, 2023): 39–56. http://dx.doi.org/10.18321/ectj1494.

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The biologically active coumarins from Ferula L. species of the family Apiaceae Lindl. for the period 1970 to 2022 have been reviewed. The phytochemical investigation of different parts of Ferula L., including gum resin, leaves, fruits, seeds, roots, rhizomes, and resins led to the separation of different types of coumarins. Nearly 185 coumarins were isolated from 35 species of Ferula L. growing in different countries. Coumarins are represented mainly by umbelliferone (7-O-hydroxycoumarin) derivatives substituted in the C-7 position of aglycone, furanocoumarins and metabolites have terpene fragments, esters and glycosides. Umbelliferon is found as a taxon for the genus Ferula L. Some «unusual» metabolites have a furan fragment attached to the pyrone ring. Coumarins are of the psoralen type, containing a furan ring in the C-6 and C-7 positions of the primary skeleton. The rare coumarins with terpene fragments (hemiterpene, monoterpen, sesquiterpene) were reported. The biological activities of some extracts and individual metabolites such as antiinflammatory, cytotoxicity, antibacterial, antileishmanial, antiviral, antigenotoxic, antitumor, anticoagulant, antioxidant, antimycobacterial, inhibition a-glucosidase, antileishmanial were found.

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35

Hano, Yoshio, Akio Ayukawa, Taro Nomura, and Shinichi Ueda. "Origin of the Acetate Units Composing the Hemiterpene Moieties of Chalcomoracin in Morus alba Cell Cultures." Journal of the American Chemical Society 116, no. 10 (May 1994): 4189–93. http://dx.doi.org/10.1021/ja00089a007.

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36

Wang, Zhi, Haiyan Zha, Xuedong Yang, Licui Hu, Wenfeng Zheng, and Lizhen Xu. "Two new hemiterpene glycosides and one new phenolic glycoside from the roots of Securidaca inappendiculata Hassk." Phytochemistry Letters 21 (September 2017): 74–77. http://dx.doi.org/10.1016/j.phytol.2017.05.019.

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Tabata, Jun, Yutaka Narai, Nobuo Sawamura, Syuntaro Hiradate, and Hajime Sugie. "A new class of mealybug pheromones: a hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi." Naturwissenschaften 99, no. 7 (July 2012): 567–74. http://dx.doi.org/10.1007/s00114-012-0935-z.

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38

Akihisa, Toshihiro, Ken-ichi Seino, Etsuyo Kaneko, Kensuke Watanabe, Shun Tochizawa, Makoto Fukatsu, Norihiro Banno, Koichi Metori, and Yumiko Kimura. "Melanogenesis Inhibitory Activities of Iridoid-, Hemiterpene-, and Fatty Acid-glycosides from the Fruits of Morinda citrifolia (Noni)." Journal of Oleo Science 59, no. 1 (2010): 49–57. http://dx.doi.org/10.5650/jos.59.49.

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39

Gray, Dennis W., Steven R. Breneman, Lauren A. Topper, and Thomas D. Sharkey. "Biochemical Characterization and Homology Modeling of Methylbutenol Synthase and Implications for Understanding Hemiterpene Synthase Evolution in Plants." Journal of Biological Chemistry 286, no. 23 (April 19, 2011): 20582–90. http://dx.doi.org/10.1074/jbc.m111.237438.

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40

Carr, Sean, Jared Aldridge, and Nicole R. Buan. "Isoprene Production from Municipal Wastewater Biosolids by Engineered Archaeon Methanosarcina acetivorans." Applied Sciences 11, no. 8 (April 8, 2021): 3342. http://dx.doi.org/10.3390/app11083342.

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Wastewater biosolids are a promising feedstock for production of value-added renewable chemicals. Methane-producing archaea (methanogens) are already used to produce renewable biogas via the anaerobic treatment of wastewater. The ability of methanogens to efficiently convert dissolved organic carbon into methane makes them an appealing potential platform for biorefining using metabolic engineering. We have engineered a strain of the methanogen Methanosarcina acetivorans to produce the volatile hemiterpene isoprene in addition to methane. The engineered strain was adapted to grow in municipal wastewater through cultivation in a synthetic wastewater medium. When introduced to municipal wastewater the engineered methanogens were able to compete with the indigenous microorganisms and produce 0.97 mM of isoprene (65.9 ± 21.3 g per m3 of effluent). The production of isoprene in wastewater appears to be dependent on the quantity of available methanogenic substrate produced during upstream digestion by heterotrophic fermenters. This shows that with minimal adaptation it is possible to drop-in engineered methanogens to existing wastewater environments and attain value-added products in addition to the processing of wastewater. This shows the potential for utilizing methanogens as a platform for low-cost production of renewable materials without expensive feedstocks or the need to build or adapt existing facilities.

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Ohta, Naohiro, Naoki Mori, Yasumasa Kuwahara, and Ritsuo Nishida. "A hemiterpene glucoside as a probing deterrent of the bean aphid, Megoura crassicauda, from a non-host vetch, Vicia hirsuta." Phytochemistry 67, no. 6 (March 2006): 584–88. http://dx.doi.org/10.1016/j.phytochem.2005.12.013.

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42

Lund, Sean, Taylor Courtney, and Gavin J. Williams. "Cover Feature: Probing the Substrate Promiscuity of Isopentenyl Phosphate Kinase as a Platform for Hemiterpene Analogue Production (ChemBioChem 17/2019)." ChemBioChem 20, no. 17 (August 21, 2019): 2162. http://dx.doi.org/10.1002/cbic.201900494.

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43

González-Cabanelas, Diego, Louwrance P. Wright, Christian Paetz, Nawaporn Onkokesung, Jonathan Gershenzon, Manuel Rodríguez-Concepción, and Michael A. Phillips. "The diversion of 2-C-methyl-d-erythritol-2,4-cyclodiphosphate from the 2-C-methyl-d-erythritol 4-phosphate pathway to hemiterpene glycosides mediates stress responses inArabidopsis thaliana." Plant Journal 82, no. 1 (March 24, 2015): 122–37. http://dx.doi.org/10.1111/tpj.12798.

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Schuster, J., F. Schafer, N. Hubler, A. Brandt, M. Rosell, C. Hartig, H. Harms, R. H. Muller, and T. Rohwerder. "Bacterial Degradation of tert-Amyl Alcohol Proceeds via Hemiterpene 2-Methyl-3-Buten-2-ol by Employing the Tertiary Alcohol Desaturase Function of the Rieske Nonheme Mononuclear Iron Oxygenase MdpJ." Journal of Bacteriology 194, no. 5 (December 22, 2011): 972–81. http://dx.doi.org/10.1128/jb.06384-11.

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45

Messerer, Monika, and Peter Winterhalter. "(2Z)-4-hydroxy-2-methyl-2-buten-1-yl-ß-D-glucoside and (2Z)-1-hydroxy-2-methyl-2-buten-4-yl-ß-D-glucoside: Two New Hemiterpene Glucosides fromVitis viniferaLeaves." Natural Product Letters 5, no. 4 (January 1995): 241–44. http://dx.doi.org/10.1080/10575639508044067.

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46

Lehnert, Ann-Sophie, Erica Perreca, Jonathan Gershenzon, Georg Pohnert, and Susan E. Trumbore. "Simultaneous Real-Time Measurement of Isoprene and 2-Methyl-3-Buten-2-ol Emissions From Trees Using SIFT-MS." Frontiers in Plant Science 11 (November 27, 2020). http://dx.doi.org/10.3389/fpls.2020.578204.

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The C5 hemiterpenes isoprene and 2-methyl-3-buten-2-ol (MBO) are important biogenic volatiles emitted from terrestrial vegetation. Isoprene is emitted from many plant groups, especially trees such as Populus, while emission of MBO is restricted to certain North American conifers, including species of Pinus. MBO is also a pheromone emitted by several conifer bark beetles. Both isoprene and MBO have typically been measured by proton-transfer reaction mass spectrometry (PTR-MS), but this method cannot accurately distinguish between them because of their signal overlap. Our study developed a method for using selective ion flow tube mass spectrometry (SIFT-MS) that allows simultaneous on-line measurement of isoprene and MBO by employing different reagent ions. The use of m/z(NO+) = 68 u for isoprene and m/z(O2+) = 71 u for MBO gave minimal interference between the compounds. We tested the suitability of the method by measuring the emission of young trees of Populus, Picea, and Pinus. Our results largely confirm previous findings that Populus nigra, Picea glauca, and Picea abies emit isoprene and Pinus ponderosa emits MBO, but we also found MBO to be emitted by Picea abies. Thus SIFT-MS provides a reliable, easy to use, on-line measuring tool to distinguish between isoprene and MBO. The method should be of use to atmospheric chemists, tree physiologists and forest entomologists, among others.

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Rana, Anup, Leandro Cid Gomes, João S. Rodrigues, Dalia M. M. Yacout, Hugo Arrou-Vignod, Johan Sjölander, Nathalie Proos Vedin, et al. "A combined photobiological-photochemical route to C10 cycloalkane jet fuels from carbon dioxide via isoprene." Green Chemistry, 2022. http://dx.doi.org/10.1039/d2gc03272d.

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The hemiterpene isoprene is a volatile C5 hydrocarbon with industrial applications. It is generated today from fossil resources, but can also be made in biological processes. We have utilized engineered...

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Phulara, Suresh Chandra, Swapnil Pandey, Anubhuti Jha, Puneet Singh Chauhan, Pratima Gupta, and Virendra Shukla. "Hemiterpene compound, 3,3-dimethylallyl alcohol promotes longevity and neuroprotection in Caenorhabditis elegans." GeroScience, July 28, 2020. http://dx.doi.org/10.1007/s11357-020-00241-w.

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49

Giordano, Deborah, Angelo Facchiano, Sabato D'Auria, and Francesco Loreto. "A hypothesis on the capacity of plant odorant-binding proteins to bind volatile isoprenoids based on in silico evidences." eLife 10 (June 23, 2021). http://dx.doi.org/10.7554/elife.66741.

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Volatile organic compounds (VOCs) from ‘emitting’ plants inform the ‘receiving’ (listening) plants of impending stresses or simply of their presence. However, the receptors that allow receivers to detect the volatile cue are elusive. Most likely, plants (as animals) have odorant-binding proteins (OBPs), and in fact, a few OBPs are known to bind ‘stress-induced’ plant VOCs. We investigated whether these and other putative OBPs may bind volatile constitutive and stress-induced isoprenoids, the most emitted plant VOCs, with well-established roles in plant communication and defense. Molecular docking simulation experiments suggest that structural features of a few plant proteins screened in databases could allow VOC binding. In particular, our results show that monoterpenes may bind the same plant proteins that were described to bind other stress-induced VOCs, while the constitutive hemiterpene isoprene is unlikely to bind any investigated putative OBP and may not have an info-chemical role. We conclude that, as for animal, there may be plant OBPs that bind multiple VOCs. Plant OBPs may play an important role in allowing plants to eavesdrop messages by neighboring plants, triggering defensive responses and communication with other organisms.

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Sukul, Pritam, Julia Bartels, Patricia Fuchs, Phillip Trefz, Rasmus Remy, Leo Rührmund, Svend Kamysek, Jochen K. Schubert, and Wolfram Miekisch. "Effects of COVID-19 protective face-masks and wearing durations onto respiratory-haemodynamic physiology and exhaled breath constituents." European Respiratory Journal, February 15, 2022, 2200009. http://dx.doi.org/10.1183/13993003.00009-2022.

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BackgroundWhile assumed to protect against coronavirus transmission, face-masks may have effects on respiratory-haemodynamic parameters. Within this pilot study, we investigated immediate and progressive effects of FFP2 and surgical masks on exhaled breath constituents and physiological attributes in 30 adults at rest.MethodsWe continuously monitored exhaled breath profiles within mask space in older (age: 60–80 years) and young to mid-aged (age: 20–60 years) adults over the period of 15 and 30 min, respectively by high-resolution real-time mass-spectrometry (PTR-ToF-MS). Peripheral oxygen saturation, respiratory- and haemodynamic parameters were measured (non-invasively) simultaneously.ResultsProfound, consistent and significant (p-value≤0.001) changes in SpO2 (Adults>60_FFP2-15 min: 5.8±1.3%↓, Adults>60_surgical-15 min: 3.6±0.9%↓, Adults<60_FFP2-30 min: 1.9±1.0%↓, Adults<60_surgical-30 min: 0.9±0.6%↓) and pET-CO2 (Adults>60_FFP2-15 min: 19.1±8.0%↑, Adults>60_surgical-15 min: 11.6±7.6%↑, Adults<60_FFP2- 30 min: 12.1±4.5%↑, Adults<60_surgical- 30 min: 9.3±4.1%↑) indicate ascending deoxygenation and hypercarbia. Secondary changes (p-value≤0.005) to hemodynamic parameters (e.g. MAP: Adults>60_FFP2-15 min: 9.8±10.4%↑) were found. Exhalation of blood-borne volatile metabolites e.g. aldehydes, hemiterpene, organosulfur, short-chain fatty acids, alcohols, ketone, aromatics, nitrile and monoterpene mirrored behaviour of cardiac output, MAP, SpO2, respiratory rate and pET-CO2. Exhaled humidity (e.g. Adults>60_FFP2-15 min: 7.1±5.8%↑) and exhaled oxygen (e.g. Adults>60_FFP2-15 min: 6.1±10.0%↓) changed significantly (p-value≤0.005) over time.ConclusionsBreathomics allows unique physio-metabolic insights into immediate and transient effects of face-mask wearing. Physiological parameters and breath profiles of endogenous and/or exogenous volatile metabolites indicated putative cross-talk between transient hypoxemia, oxidative stress, hypercarbia, vasoconstriction, altered systemic microbial activity, energy homeostasis, compartmental storage and washout. FFP2 masks affected more pronouncedly than surgical masks. Older adults were more vulnerable to FFP2 mask induced hypercarbia, arterial oxygen decline, blood pressure fluctuations and concomitant physiological and metabolic effects.

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