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维基百科

α-葎草烯

十月 07, 2023

α-葎草烯（英语：Humulene）[註 1]，又名蛇麻烯或α-石竹烯，是天然存在的单环倍半萜，分子式C15H24，可看作三个异戊二烯单元构成，分子有三个非共轭双键。

葎草烯
IUPAC名
(1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4-8-triene
别名 蛇麻烯、α-石竹烯
识别
CAS号 6753-98-6  
PubChem 5281520
ChemSpider 4444853
SMILES
 
  • C\1=C/C(C)(C)C/C=C(/CC/C=C(/C/1)C)C
InChI
 
  • 1/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+
InChIKey FAMPSKZZVDUYOS-HRGUGZIWBF
ChEBI 5768
性质
化学式 C15H24
摩尔质量 204.35 g·mol−1
外观 淡黄绿色的透明液体
密度 0.886 g/cm3
熔点 25 °C（298 K）
沸点 106 - 107 °C（272 K）
危险性
致死量或浓度：
LD50（中位剂量）
 >48 mg/kg
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

葎草烯最早从啤酒花（葎草属，学名：Humulus）精油发现，因此得名[1]。葎草烯有个双环的同分异构体β-石竹烯，在很多有香气植物中，都能提取出兩者的混合物。

发现 编辑

 
蛇麻

葎草烯是蛇麻花精油成分之一，其浓度根据品种不同而变，最高可占精油40%[2]。酿啤酒过程中会产生多种葎草烯的环氧化物，根据GC-MS及气味分析研究，葎草烯环氧衍生物水解会散发出啤酒花香气[3][4]。

分布 编辑

葎草烯与β-石竹烯在各大洲的许多植物中都能找到，能釋放葎草烯的植物有松树[5]、橘园[6]、烟草 [7]和向日葵[8]。在芳香气氛的植物精油中也能找到葎草烯，如药用鼠尾草 [9]、乌药、人参属的三七、花旗参 [10]、留兰香（可占精油29.9 %）[11]、姜科植物[12]、雾社木姜子（一种中国月桂树）[13]、erva baleeira（马鞭草科一种灌木，位于南美洲沿海）的叶片提取物中可達4 %，另有25%反式石竹烯[14]是越南香菜和大麻属植物的香气成分[15]。

合成 编辑

葎草烯衍生自法尼基焦磷酸（FPP），FPP合成葎草烯过程由倍半萜合成酶催化[16]，FPP脫焦磷酸基团後产生烯丙基阳离子[16]。

 


实验室合成葎草烯的方法有很多，如模拟生物合成从法尼醇（英语：Farnesol）合成葎草烯（Corey合成）；闭合大环化合物不同位置的碳－碳键；钛催化羰基偶联反应（McMurry合成）；烯丙基卤化物和受保护羟腈阴离子内烷基化（Takahashi合成）等[17]。有研究报道了更简单构建碳－碳键和环结构的方法，用四部份组装和钯介导环化两步合成[18]。

 

葎草烯上两个已取代双键更活潑，计算结果顯示有四种不同构象[19]。

应用 编辑

有研究报道植物精油的葎草烯有潜在抗炎作用[20][21]。2015年，巴西研究员用气相色谱法证明鼠尾草叶油的葎草烯可抑制埃及伊蚊繁殖[22][23]。

备注 编辑

  1. ^ 下文中如无说明，皆以葎草烯指代α-葎草烯。

参考文献 编辑

  1. ^ Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html （页面存档备份，存于互联网档案馆）> Accessed July 21, 2010
  2. ^ Katsiotis, S. T.; Langezaal, C. R.; Scheffe, J. J. C. Analysis of the Volatile Compounds from Cones of Ten Humulus lupulus Cultivars. Planta Med. 1989, 55 (7): 634. doi:10.1055/s-2006-962205. 
  3. ^ Yange, Xiaogen; Lederer, Cindy; McDaniel, Mina; Deinzer, Max. Evaluation of hydrolysis products of humulene epoxides II and III. Journal of Agricultural and Food Chemistry. 1993, 41 (8): 1300–1304. doi:10.1021/jf00032a026. 
  4. ^ Peackock, Val; Deinzer, Max. . Journal of the American Society of Brewing Chemists. 1981, 39. （原始内容存档于2013-12-30）. 
  5. ^ D. Helmig; J. Ortega; T. Duhl; D. Tanner; A. Guenther; P. Harley; C. Wiedinmyer; J. Milford; T. Sakulyanontvittaya. Sesquiterpene emissions from pine trees--identifications, emission rates and flux estimates for the contiguous United States. Environ. Sci. Technol. 2007, 41 (5): 1545–1553 [2022-07-11]. Bibcode:2007EnST...41.1545H. PMID 17396639. doi:10.1021/es0618907. （原始内容于2022-07-11）. 
  6. ^ P. Ciccioli; E. Brancaleoni; M. Frattoni; V. Di Palo; R. Valentini; G. Tirone; G. Seufert; N. Bertin; U. Hansen; O. Csiky; R. Lenz; M. Sharma. Emission of reactive terpene compounds from orange orchards and their removal by within-canopy processes. J. Geophys. Res. 1999, 104 (D7): 8077–8094. Bibcode:1999JGR...104.8077C. doi:10.1029/1998JD100026  . 
  7. ^ C. De Moraes; M. Mescher; J. Tumlinson. Caterpillar-induced nocturnal plant volatiles repel conspecific females. Nature. 2001, 410 (6828): 577–580. Bibcode:2001Natur.410..577D. PMID 11279494. S2CID 4408480. doi:10.1038/35069058. 
  8. ^ G. Schuh; A. Heiden; T. Hoffmann; J. Kahl; P. Rockel; J. Rudolph; J. Wildt. Emissions of Volatile Organic Compounds from Sunflower and Beech: Dependence on Temperature and Light Intensity. J. Atmos. Chem. 1997, 27 (3): 291–318. Bibcode:1997JAtC...27..291S. S2CID 94314856. doi:10.1023/A:1005850710257. 
  9. ^ Bouajaj, S; Benyamna, A; Bouamama, H; Romane, A; Falconieri, D; Piras, A; Marongiu, B. Antibacterial, allelopathic and antioxidant activities of essential oil of Salvia officinalis L. growing wild in the Atlas Mountains of Morocco. Nat Prod Res. 2013, 27 (18): 1673–6. PMID 23240623. S2CID 29522122. doi:10.1080/14786419.2012.751600. 
  10. ^ Cho, IH; Lee, HJ; Kim, YS. Differences in the volatile compositions of ginseng species (Panax sp.). J Agric Food Chem. Aug 2012, 60 (31): 7616–22. PMID 22804575. doi:10.1021/jf301835v. 
  11. ^ Chauhan, SS; Prakash, O; Padalia, RC; Vivekanand, Pant AK; Mathela, CS. Chemical diversity in Mentha spicata: antioxidant and potato sprout inhibition activity of its essential oils. Nat Prod Commun. 2011, 6 (9): 1373–8. PMID 21941918. 
  12. ^ Suthisut, D; Fields, PG; Chandrapatya, A. Contact toxicity, feeding reduction, and repellency of essential oils from three plants from the ginger family (Zingiberaceae) and their major components against Sitophilus zeamais and Tribolium castaneum. J Econ Entomol. 2011, 104 (4): 1445–54. PMID 21882715. S2CID 45872520. doi:10.1603/ec11050. 
  13. ^ Ho, CL; Wang, EI; Tseng, YH; Liao, PC; Lin, CN; Chou, JC; Su, YC. Composition and antimicrobial activity of the leaf and twig oils of Litsea mushaensis and L. linii from Taiwan. Nat Prod Commun. 2010, 5 (11): 1823–8. PMID 21213991. 
  14. ^ de Carvalho, Jr.; Rodrigues, R.F.; Sawaya, A.C.; Marques, M.O.; Shimizu, M.T. Chemical composition and antimicrobial activity of the essential oil of Cordia verbenacea D.C. Journal of Ethnopharmacology. 2004, 95 (2–3): 297–301. PMID 15507352. doi:10.1016/j.jep.2004.07.028. 
  15. ^ Hillig, Karl W. A chemotaxonomic analysis of terpenoid variation in Cannabis. Biochemical Systematics and Ecology. October 2004, 32 (10): 875–891. ISSN 0305-1978. doi:10.1016/j.bse.2004.04.004. 
  16. ^ 16.0 16.1 Moss, G.P., "Humulene derived sesquiterpenoid biosynthesis." International Union of Biochemistry and Molecular Biology Enzyme Nomenclature. Accessed April 10, 2011. http://www.enzyme-database.org/reaction/terp/humul.html （页面存档备份，存于互联网档案馆）
  17. ^ Goldsmith, David. "The total synthesis of natural products". Canada: John Wiley & Sons. 1997 pp 129-133
  18. ^ Hu, Tao & Corey, E.J. Short Syntheses of (±)-δ-Araneosene and Humulene Utilizing a Combination of Four-Component Assembly and Palladium-Mediated Cyclization. Organic Letters. 2002, 4 (14): 2441–2443. PMID 12098267. doi:10.1021/ol026205p. 
  19. ^ Neuenschwander, U; et al. Origin of Regioselectivity in α-Humulene Functionalization. J. Org. Chem. 2012, 77 (6): 2865–2869. PMID 22332847. doi:10.1021/jo3000942. 
  20. ^ Passosa, G.F.; Fernandesa, ES.; et al. Anti-inflammatory and anti-allergic properties of the essential oil and active compounds from Cordia verbenacea. Journal of Ethnopharmacology. 2007, 110 (2): 323–333. PMID 17084568. doi:10.1016/j.jep.2006.09.032. 
  21. ^ Fernandes E.S.; Passos G.F.; Medeiros R.; da Cunha F.M.; Ferreira J.; Campos M.M.; Pianowski L.F.; Calixto J.B. Anti-inflammatory effects of compounds alpha-humulene and (−)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea. European Journal of Pharmacology. 2007, 569 (3): 228–236. PMID 17559833. doi:10.1016/j.ejphar.2007.04.059. 
  22. ^ Janelle Lassalle. Humulene. The Cannigma. 2020-09-19 [2021-01-27]. （原始内容于2022-07-11）. 
  23. ^ Santos da Silva, R.C.; Milet-Pinheiro, P.; Bezerra da Silva, P.C.; Gomes da Silva, A.; Vanusa da Silva, M.; Amaral Ferraz Navarro, D.M.; da Silva, N.H.; et al. Boudko, Dmitri , 编. (E)-Caryophyllene and α-Humulene: Aedes aegypti Oviposition Deterrents Elucidated by Gas Chromatography-Electrophysiological Assay of Commiphora leptophloeos Leaf Oil. PLOS ONE. 2015-12-19, 10 (12): e0144586. Bibcode:2015PLoSO..1044586D. PMC 4674132  . PMID 26650757. doi:10.1371/journal.pone.0144586  . 

十月 07, 2023
葎草烯, 英语, humulene, 又名蛇麻烯或α, 石竹烯, 是天然存在的单环倍半萜, 分子式c15h24, 可看作三个异戊二烯单元构成, 分子有三个非共轭双键, 葎草烯iupac名, tetramethylcycloundeca, triene别名, 蛇麻烯, 石竹烯识别cas号, 6753, pubchem, 5281520chemspider, 4444853smiles, cinchi, c15h24, 12h2, inchikey, fampskzzvduyos, hrgugziwbfchebi, 5. a 葎草烯 英语 Humulene 註 1 又名蛇麻烯或a 石竹烯 是天然存在的单环倍半萜 分子式C15H24 可看作三个异戊二烯单元构成 分子有三个非共轭双键 葎草烯IUPAC名 1E 4E 8E 2 6 6 9 Tetramethylcycloundeca 1 4 8 triene别名 蛇麻烯 a 石竹烯识别CAS号 6753 98 6 PubChem 5281520ChemSpider 4444853SMILES C 1 C C C C C C C CC C C C 1 C CInChI 1 C15H24 c1 13 7 5 8 14 2 10 12 15 3 4 11 6 9 13 h6 7 10 11H 5 8 9 12H2 1 4H3 b11 6 13 7 14 10 InChIKey FAMPSKZZVDUYOS HRGUGZIWBFChEBI 5768性质化学式 C15H24摩尔质量 204 35 g mol 1外观 淡黄绿色的透明液体密度 0 886 g cm3熔点 25 C 298 K 沸点 106 107 C 272 K 危险性致死量或浓度 LD50 中位剂量 gt 48 mg kg若非注明 所有数据均出自标准状态 25 100 kPa 下 葎草烯最早从啤酒花 葎草属 学名 Humulus 精油发现 因此得名 1 葎草烯有个双环的同分异构体b 石竹烯 在很多有香气植物中 都能提取出兩者的混合物 目录 1 发现 2 分布 3 合成 4 应用 5 备注 6 参考文献发现 编辑 nbsp 蛇麻葎草烯是蛇麻花精油成分之一 其浓度根据品种不同而变 最高可占精油40 2 酿啤酒过程中会产生多种葎草烯的环氧化物 根据GC MS及气味分析研究 葎草烯环氧衍生物水解会散发出啤酒花香气 3 4 分布 编辑葎草烯与b 石竹烯在各大洲的许多植物中都能找到 能釋放葎草烯的植物有松树 5 橘园 6 烟草 7 和向日葵 8 在芳香气氛的植物精油中也能找到葎草烯 如药用鼠尾草 9 乌药 人参属的三七 花旗参 10 留兰香 可占精油29 9 11 姜科植物 12 雾社木姜子 一种中国月桂树 13 erva baleeira 马鞭草科一种灌木 位于南美洲沿海 的叶片提取物中可達4 另有25 反式石竹烯 14 是越南香菜和大麻属植物的香气成分 15 合成 编辑葎草烯衍生自法尼基焦磷酸 FPP FPP合成葎草烯过程由倍半萜合成酶催化 16 FPP脫焦磷酸基团後产生烯丙基阳离子 16 nbsp 实验室合成葎草烯的方法有很多 如模拟生物合成从法尼醇 英语 Farnesol 合成葎草烯 Corey合成 闭合大环化合物不同位置的碳 碳键 钛催化羰基偶联反应 McMurry合成 烯丙基卤化物和受保护羟腈阴离子内烷基化 Takahashi合成 等 17 有研究报道了更简单构建碳 碳键和环结构的方法 用四部份组装和钯介导环化两步合成 18 nbsp 葎草烯上两个已取代双键更活潑 计算结果顯示有四种不同构象 19 应用 编辑有研究报道植物精油的葎草烯有潜在抗炎作用 20 21 2015年 巴西研究员用气相色谱法证明鼠尾草叶油的葎草烯可抑制埃及伊蚊繁殖 22 23 备注 编辑 下文中如无说明 皆以葎草烯指代a 葎草烯 参考文献 编辑 Glenn Tinseth Hop Aroma and Flavor January February 1993 Brewing Techniques lt http realbeer com hops aroma html 页面存档备份 存于互联网档案馆 gt Accessed July 21 2010 Katsiotis S T Langezaal C R Scheffe J J C Analysis of the Volatile Compounds from Cones of Ten Humulus lupulus Cultivars Planta Med 1989 55 7 634 doi 10 1055 s 2006 962205 Yange Xiaogen Lederer Cindy McDaniel Mina Deinzer Max Evaluation of hydrolysis products of humulene epoxides II and III Journal of Agricultural and Food Chemistry 1993 41 8 1300 1304 doi 10 1021 jf00032a026 Peackock Val Deinzer Max Chemistry of hop aroma in beer Journal of the American Society of Brewing Chemists 1981 39 原始内容存档于2013 12 30 D Helmig J Ortega T Duhl D Tanner A Guenther P Harley C Wiedinmyer J Milford T Sakulyanontvittaya Sesquiterpene emissions from pine trees identifications emission rates and flux estimates for the contiguous United States Environ Sci Technol 2007 41 5 1545 1553 2022 07 11 Bibcode 2007EnST 41 1545H PMID 17396639 doi 10 1021 es0618907 原始内容存档于2022 07 11 P Ciccioli E Brancaleoni M Frattoni V Di Palo R Valentini G Tirone G Seufert N Bertin U Hansen O Csiky R Lenz M Sharma Emission of reactive terpene compounds from orange orchards and their removal by within canopy processes J Geophys Res 1999 104 D7 8077 8094 Bibcode 1999JGR 104 8077C doi 10 1029 1998JD100026 nbsp C De Moraes M Mescher J Tumlinson Caterpillar induced nocturnal plant volatiles repel conspecific females Nature 2001 410 6828 577 580 Bibcode 2001Natur 410 577D PMID 11279494 S2CID 4408480 doi 10 1038 35069058 G Schuh A Heiden T Hoffmann J Kahl P Rockel J Rudolph J Wildt Emissions of Volatile Organic Compounds from Sunflower and Beech Dependence on Temperature and Light Intensity J Atmos Chem 1997 27 3 291 318 Bibcode 1997JAtC 27 291S S2CID 94314856 doi 10 1023 A 1005850710257 Bouajaj S Benyamna A Bouamama H Romane A Falconieri D Piras A Marongiu B Antibacterial allelopathic and antioxidant activities of essential oil of Salvia officinalis L growing wild in the Atlas Mountains of Morocco Nat Prod Res 2013 27 18 1673 6 PMID 23240623 S2CID 29522122 doi 10 1080 14786419 2012 751600 Cho IH Lee HJ Kim YS Differences in the volatile compositions of ginseng species Panax sp J Agric Food Chem Aug 2012 60 31 7616 22 PMID 22804575 doi 10 1021 jf301835v Chauhan SS Prakash O Padalia RC Vivekanand Pant AK Mathela CS Chemical diversity in Mentha spicata antioxidant and potato sprout inhibition activity of its essential oils Nat Prod Commun 2011 6 9 1373 8 PMID 21941918 Suthisut D Fields PG Chandrapatya A Contact toxicity feeding reduction and repellency of essential oils from three plants from the ginger family Zingiberaceae and their major components against Sitophilus zeamais and Tribolium castaneum J Econ Entomol 2011 104 4 1445 54 PMID 21882715 S2CID 45872520 doi 10 1603 ec11050 Ho CL Wang EI Tseng YH Liao PC Lin CN Chou JC Su YC Composition and antimicrobial activity of the leaf and twig oils of Litsea mushaensis and L linii from Taiwan Nat Prod Commun 2010 5 11 1823 8 PMID 21213991 de Carvalho Jr Rodrigues R F Sawaya A C Marques M O Shimizu M T Chemical composition and antimicrobial activity of the essential oil of Cordia verbenacea D C Journal of Ethnopharmacology 2004 95 2 3 297 301 PMID 15507352 doi 10 1016 j jep 2004 07 028 Hillig Karl W A chemotaxonomic analysis of terpenoid variation in Cannabis Biochemical Systematics and Ecology October 2004 32 10 875 891 ISSN 0305 1978 doi 10 1016 j bse 2004 04 004 16 0 16 1 Moss G P Humulene derived sesquiterpenoid biosynthesis International Union of Biochemistry and Molecular Biology Enzyme Nomenclature Accessed April 10 2011 http www enzyme database org reaction terp humul html 页面存档备份 存于互联网档案馆 Goldsmith David The total synthesis of natural products Canada John Wiley amp Sons 1997 pp 129 133 Hu Tao amp Corey E J Short Syntheses of d Araneosene and Humulene Utilizing a Combination of Four Component Assembly and Palladium Mediated Cyclization Organic Letters 2002 4 14 2441 2443 PMID 12098267 doi 10 1021 ol026205p Neuenschwander U et al Origin of Regioselectivity in a Humulene Functionalization J Org Chem 2012 77 6 2865 2869 PMID 22332847 doi 10 1021 jo3000942 Passosa G F Fernandesa ES et al Anti inflammatory and anti allergic properties of the essential oil and active compounds from Cordia verbenacea Journal of Ethnopharmacology 2007 110 2 323 333 PMID 17084568 doi 10 1016 j jep 2006 09 032 Fernandes E S Passos G F Medeiros R da Cunha F M Ferreira J Campos M M Pianowski L F Calixto J B Anti inflammatory effects of compounds alpha humulene and trans caryophyllene isolated from the essential oil of Cordia verbenacea European Journal of Pharmacology 2007 569 3 228 236 PMID 17559833 doi 10 1016 j ejphar 2007 04 059 Janelle Lassalle Humulene The Cannigma 2020 09 19 2021 01 27 原始内容存档于2022 07 11 Santos da Silva R C Milet Pinheiro P Bezerra da Silva P C Gomes da Silva A Vanusa da Silva M Amaral Ferraz Navarro D M da Silva N H et al Boudko Dmitri 编 E Caryophyllene and a Humulene Aedes aegypti Oviposition Deterrents Elucidated by Gas Chromatography Electrophysiological Assay of Commiphora leptophloeos Leaf Oil PLOS ONE 2015 12 19 10 12 e0144586 Bibcode 2015PLoSO 1044586D PMC 4674132 nbsp PMID 26650757 doi 10 1371 journal pone 0144586 nbsp 取自 https zh wikipedia org w index php title A 葎草烯 amp oldid 76873898, 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