角蒿特灵酯碱[1](英语:Incarvillateine)是一种古柯间二酸衍生的单萜生物碱,可以从角蒿属植物中分离得到。
Quick Facts 角蒿特灵酯碱, 识别 ...
角蒿特灵酯碱
|
|
IUPAC名 Bis[(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl] (1R,2R,3S,4S)-2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate
|
识别
|
CAS号
|
129748-10-3 Y
|
PubChem
|
9875096
|
ChemSpider
|
24712075
|
SMILES
|
- C[C@@H]1[C@H]2[C@H]([C@@H]([C@@H](C2)OC(=O)[C@H]3[C@@H]([C@@H]([C@H]3c4cc(c(cc4)O)OC)C(=O)O[C@H]5[C@H]([C@H]6[C@@H](C5)[C@H](CN(C6)C)C)C)c7cc(c(cc7)O)OC)C)CN(C1)C
|
性质
|
化学式
|
C42H58N2O8
|
摩尔质量
|
718.92 g·mol−1
|
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。
|
Close
角蒿特灵酯碱是从角蒿(Incarvillea sinensis)分离得到,与阿片类生物碱吗啡相比具有更显著的镇痛效果[2]。角蒿特灵酯碱的止痛作用可被纳洛酮[3] 、nor-BNI和β-富纳曲胺[4]等阿片类药物的部分阻断。而且这些药物对μ-和κ-阿片受体激动选择性不同。对于δ-阿片受体药物纳曲吲哚,其不会抵消角蒿特灵酯碱的镇痛作用[4]。
这些发现表明角蒿特灵酯碱可能具有阿片类受体活性,但值得注意的是,一些研究表明纳洛酮无法抵消角蒿特灵酯碱的镇痛活性[5]。
诸如茶碱等腺苷受体拮抗剂可阻断蒿特灵酯碱的镇痛作用。这表明角蒿特灵酯碱的主要作用机制是通过腺苷受体介导的[5]。
苏子仁,赖小平 (编). 汉英、英汉中草药化学成分词汇. 北京: 中国中医药出版社. 2006: 562.
Nakamura, M.; Chi, Y. M.; Yan, W. M.; Nakasugi, Y.; Yoshizawa, T.; Irino, N.; Hashimoto, F.; Kinjo, J.; Nohara, T. Strong antinociceptive effect of incarvillateine, a novel monoterpene alkaloid from Incarvillea sinensis. Journal of Natural Products. 1999-09-01, 62 (9): 1293–1294. ISSN 0163-3864. PMID 10514316. doi:10.1021/np990041c.
Ichikawa, Masaya; Takahashi, Masaki; Aoyagi, Sakae; Kibayashi, Chihiro. Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine. Journal of the American Chemical Society. 2004, 126 (50): 16553–16558. PMID 15600360. doi:10.1021/ja0401702.
Chi, Yu-Ming; Nakamura, Motoyuki; Yoshizawa, Toyokichi; Zhao, Xi-Ying; Yan, Wen-Mei; Hashimoto, Fumio; Kinjo, Junei; Nohara, Toshihiro; Sakurada, Shinobu. Pharmacological study on the novel antinociceptive agent, a novel monoterpene alkaloid from Incarvillea sinensis. Biological & Pharmaceutical Bulletin. 2005-10-01, 28 (10): 1989–1991. ISSN 0918-6158. PMID 16204962. doi:10.1248/bpb.28.1989
.
Wang, Mei-Liang; Yu, Gang; Yi, Shou-Pu; Zhang, Feng-Ying; Wang, Zhi-Tong; Huang, Bin; Su, Rui-Bin; Jia, Yan-Xing; Gong, Ze-Hui. Antinociceptive effects of incarvillateine, a monoterpene alkaloid from Incarvillea sinensis, and possible involvement of the adenosine system. Scientific Reports. 2015-11-03, 5: 16107. Bibcode:2015NatSR...516107W. ISSN 2045-2322. PMC 4630779
. PMID 26527075. doi:10.1038/srep16107 (英语).