猕猴桃碱

猕猴桃碱
	IUPAC名; (7S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine
识别
CAS号	524-03-8
PubChem	68231
ChemSpider	61533
SMILES	C[C@@H](CC1)C2=C1C(C)=CN=C2;
InChI	1/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1;
InChIKey	ZHQQRIUYLMXDPP-ZETCQYMHBZ
Beilstein	81308
ChEBI	2443
KEGG	C09910
性质
化学式	C10H13N
摩尔质量	147.22 g·mol−1
熔点	25 °C（298 K）
沸点	100 - 103 °C（270 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

猕猴桃碱（英語：Actinidine）是一种环烯醚萜化合物，由多种植物和动物在自然界中产生。它是第一个被发现的环戊单萜生物碱。^[1]它是可从缬草（Valeriana officinalis）根^[2]和葛枣猕猴桃（Actinidia polygama）以及几种处于幼虫和成虫阶段的昆虫中提取的化合物之一。^[3]猕猴桃碱是一种猫引诱剂，其作用类似于猫薄荷中的活性化合物荆芥内酯。^[4]

某些竹节虫物种，包括Megacrania batesii和津田氏大头䗛（Megacrania tsudai），具有化学防御机制，当受到捕食者威胁时，其前胸腺会分泌含猕猴桃碱的物质。^[5]

生物合成

下图显示了从L-香茅醛中生物合成猕猴桃碱的潜在方法。^[6]

参考资料

^ Tsutsui, Minoru; Tsutsui, Ethel Ashworth. Diterpenoids. Chemical Reviews. 1959, 59 (6): 1031–1075 [2024-03-15]. doi:10.1021/cr50030a003. （原始内容存档于2022-06-17）.
^ Janot MM, Guilhem J, Contz O, Venera G, Cionga E. Contribution to the study of valerian alcaloids (Valeriana officinalis L.): actinidine and naphthyridylmethylketone, a new alkaloid. Ann. Pharm. Fr. 1979, 37 (9–10): 413–20. PMID 547813 （法语）.
^ Weibel DB, Oldham NJ, Feld B, Glombitza G, Dettner K, Boland W. Iridoid biosynthesis in staphylinid rove beetles (Coleoptera: Staphylinidae, Philonthinae). Insect Biochemistry and Molecular Biology. 2001, 31 (6–7): 583–591. PMID 11267897. doi:10.1016/s0965-1748(00)00163-6.
^ Lichman, Benjamin R.; Godden, Grant T.; Hamilton, John P.; Palmer, Lira; Kamileen, Mohamed O.; Zhao, Dongyan; Vaillancourt, Brieanne; Wood, Joshua C.; Sun, Miao; Kinser, Taliesin J.; Henry, Laura K. The evolutionary origins of the cat attractant nepetalactone in catnip. Science Advances. 2020-05-01, 6 (20): eaba0721. Bibcode:2020SciA....6..721L. ISSN 2375-2548. PMC 7220310  . PMID 32426505. doi:10.1126/sciadv.aba0721  （英语）.
^ Wu, I-Hsin; Liu, Hsui-Huei; Chen, Yu-Yen; Tsai, Cheng-Lung; Yu, Yi-Ching; Hsiao, Chung-Yi; Yeh, Wen-Bin. Life cycles, phenology and genetic structure of endangered Megacrania tsudai Shiraki (Phasmatodea: Phasmatidae): Male individuals from a geographic parthenogenesis species. Entomological Science. 2020, 23 (2): 183–192. S2CID 216322536. doi:10.1111/ens.12410.
^ Funayama, Shinji; Cordell, Geoffrey A. (编). 14: Alkaloids Derived from Terpenoids. Alkaloids. Academic Press. 2015: 233–255.

这是一篇杂环化合物小作品。您可以通过编辑或修订扩充其内容。

[Tsutsui1959-1] Tsutsui, Minoru; Tsutsui, Ethel Ashworth. Diterpenoids. Chemical Reviews. 1959, 59 (6): 1031–1075 [2024-03-15]. doi:10.1021/cr50030a003. （原始内容存档于2022-06-17）.

[2] Janot MM, Guilhem J, Contz O, Venera G, Cionga E. Contribution to the study of valerian alcaloids (Valeriana officinalis L.): actinidine and naphthyridylmethylketone, a new alkaloid. Ann. Pharm. Fr. 1979, 37 (9–10): 413–20. PMID 547813 （法语）.

[3] Weibel DB, Oldham NJ, Feld B, Glombitza G, Dettner K, Boland W. Iridoid biosynthesis in staphylinid rove beetles (Coleoptera: Staphylinidae, Philonthinae). Insect Biochemistry and Molecular Biology. 2001, 31 (6–7): 583–591. PMID 11267897. doi:10.1016/s0965-1748(00)00163-6.

[4] Lichman, Benjamin R.; Godden, Grant T.; Hamilton, John P.; Palmer, Lira; Kamileen, Mohamed O.; Zhao, Dongyan; Vaillancourt, Brieanne; Wood, Joshua C.; Sun, Miao; Kinser, Taliesin J.; Henry, Laura K. The evolutionary origins of the cat attractant nepetalactone in catnip. Science Advances. 2020-05-01, 6 (20): eaba0721. Bibcode:2020SciA....6..721L. ISSN 2375-2548. PMC 7220310  . PMID 32426505. doi:10.1126/sciadv.aba0721  （英语）.

[Wu2020-5] Wu, I-Hsin; Liu, Hsui-Huei; Chen, Yu-Yen; Tsai, Cheng-Lung; Yu, Yi-Ching; Hsiao, Chung-Yi; Yeh, Wen-Bin. Life cycles, phenology and genetic structure of endangered Megacrania tsudai Shiraki (Phasmatodea: Phasmatidae): Male individuals from a geographic parthenogenesis species. Entomological Science. 2020, 23 (2): 183–192. S2CID 216322536. doi:10.1111/ens.12410.

[6] Funayama, Shinji; Cordell, Geoffrey A. (编). 14: Alkaloids Derived from Terpenoids. Alkaloids. Academic Press. 2015: 233–255.

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猕猴桃碱


IUPAC名 (7S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine
识别
CAS号	524-03-8 ^Y
PubChem	68231
ChemSpider	61533
SMILES	C[C@@H](CC1)C2=C1C(C)=CN=C2
InChI	1/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1
InChIKey	ZHQQRIUYLMXDPP-ZETCQYMHBZ
Beilstein	81308
ChEBI	2443
KEGG	C09910
性质
化学式	C₁₀H₁₃N
摩尔质量	147.22 g·mol⁻¹
熔点	25 °C（298 K）
沸点	100 - 103 °C（270 K）
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。