獼猴桃鹼

化合物

獼猴桃鹼(英語:Actinidine)是一種環烯醚萜化合物,由多種植物和動物在自然界中產生。它是第一個被發現的環戊單萜生物鹼。[1]它是可從纈草Valeriana officinalis)根[2]葛棗獼猴桃Actinidia polygama)以及幾種處於幼蟲和成蟲階段的昆蟲中提取的化合物之一。[3]獼猴桃鹼是一種貓引誘劑,其作用類似於貓薄荷中的活性化合物荊芥內酯[4]

獼猴桃鹼
IUPAC名
(7S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine
識別
CAS號 524-03-8  checkY
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
性質
化學式 C10H13N
摩爾質量 147.22 g·mol−1
熔點 25 °C(298 K)
沸點 100 - 103 °C(270 K)
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

某些竹節蟲物種,包括Megacrania batesii津田氏大頭䗛Megacrania tsudai),具有化學防禦機制,當受到捕食者威脅時,其前胸腺會分泌含獼猴桃鹼的物質。[5]

生物合成

下圖顯示了從L-香茅醛中生物合成獼猴桃鹼的潛在方法。[6]

 

參考資料

  1. ^ Tsutsui, Minoru; Tsutsui, Ethel Ashworth. Diterpenoids. Chemical Reviews. 1959, 59 (6): 1031–1075 [2024-03-15]. doi:10.1021/cr50030a003. (原始內容存檔於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 (法語). 
  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  (英語). 
  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. (編). 14: Alkaloids Derived from Terpenoids. Alkaloids. Academic Press. 2015: 233–255.