ゲルマクレン

Germacrene A
IUPAC名 (1E,5E,8S)-1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene
別称 (-)-Germacrene A Germacra-3,9,11-triene, (E,E)- 1,5-cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (1E,5E,8S)- 1,5-cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (S-(E,E))-
識別情報
CAS登録番号	28387-44-2
ChemSpider	29776407
SMILES C/C/1=C\CC/C(=C/C[C@H](CC1)C(C)C)/C
InChI InChI=1S/C15H26/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,12,15H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+/t15-/m0/s1  Key: YDLBHMSVYMFOMI-SDFJSLCBSA-N  InChI=1/C15H26/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,12,15H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+/t15-/m0/s1 Key: YDLBHMSVYMFOMI-SDFJSLCBBV
特性
化学式	C15H24
モル質量	204.35 g/mol
密度	0.793 g/mL
沸点	236.4 °C, 510 K, 458 °F
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

Germacrene D
IUPAC名 (S,1Z,6Z)-8-isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene
別称 1-methyl-5-methylene-8-(1-methylethyl)-1,6-cyclodecadiene 1,6-cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-
識別情報
CAS登録番号	37839-63-7
ChemSpider	28288426
SMILES C/C/1=C/CCC(=C)/C=C\[C@@H](CC1)C(C)C
InChI InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-/t15-/m0/s1 Key: GAIBLDCXCZKKJE-ACWLMNNXSA-N InChI=1/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-/t15-/m0/s1 Key: GAIBLDCXCZKKJE-ACWLMNNXBY
特性
化学式	C15H24
モル質量	204.35 g/mol
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

ゲルマクレン(Germacrene)は、セスキテルペンの1群である。抗細菌活性や殺菌成分として多くの植物が生産するが、昆虫フェロモンとしても働く。重要な分子としてゲルマクレンAとゲルマクレンDがある。

構造

ゲルマクレンは、5つの異性体を持つ。

ゲルマクレンの異性体

A	B	C	D	E

天然の存在

ヒメオドリコソウの精油には、ゲルマクレンDが高濃度で含まれる。

出典

一般

• Adio AM (2009). “Germacrenes A-E and related compounds: thermal, photochemical and acid induced transannular cyclizations”. Tetrahedron 65 (8): 1533-1552. doi:10.1016/j.tet.2008.11.050. 

ゲルマクレンA

• Deguerry F, Pastore L, Wu S, Clark A, Chappell J, Schalk M. The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases. Arch Biochem Biophys. 2006 Oct 15;454(2):123-36.
• Omura H, Honda K, Feeny P. From terpenoids to aliphatic acids: further evidence for late-instar switch in osmeterial defense as a characteristic trait of swallowtail butterflies in the tribe papilionini. J Chem Ecol. 2006 Sep;32(9):1999-2012.
• Forcat S, Allemann RK. Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase. Org Biomol Chem. 2006 Jul 7;4(13):2563-7.
• Bertea CM, Voster A, Verstappen FW, Maffei M, Beekwilder J, Bouwmeester HJ. Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Arch Biochem Biophys. 2006 Apr 15;448(1-2):3-12.
• Lou Y, Baldwin IT. Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores. Plant Physiol. 2006 Mar;140(3):1126-36.
• Chang YJ, Jin J, Nam HY, Kim SU. Point mutation of (+)-germacrene A synthase from Ixeris dentata. Biotechnol Lett. 2005 Mar;27(5):285-8.

ゲルマクレンD

• Rivero-Cruz B, Rivero-Cruz I, Rodriguez JM, Cerda-Garcia-Rojas CM, Mata R. Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy. J Nat Prod. 2006 Aug;69(8):1172-6.
• Yang FQ, Li SP, Chen Y, Lao SC, Wang YT, Dong TT, Tsim KW. Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):552-8.
• Umlauf D, Zapp J, Becker H, Adam KP. Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). Phytochemistry. 2004 Sep;65(17):2463-70.
• Agnihotri VK, Thappa RK, Meena B, Kapahi BK, Saxena RK, Qazi GN, Agarwal SG. Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India). Phytochemistry. 2004 Aug;65(16):2411-3.
• Raal A, Paaver U, Arak E, Orav A. Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia. Medicina (Kaunas). 2004;40(8):795-800.
• He X, Cane DE. Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2). J Am Chem Soc. 2004 Mar 10;126(9):2678-9.
• Arimura, G-I., Huber, DPW, Bohlmann, J. Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar (Populus trichocarpa x deltoides): cDNA cloning, functional characterization, and patterns of gene expression of (-)-germacrene D synthase, PtdTPS1. The Plant Journal 2004 37: 603-616.