角蒿特靈酯鹼

角蒿特靈酯鹼
	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
識別
CAS號	129748-10-3
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;
性質
化學式	C42H58N2O8
摩爾質量	718.92 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

角蒿特靈酯鹼^[1]（英語：Incarvillateine）是一種古柯間二酸衍生的單萜生物鹼，可以從角蒿屬植物中分離得到。

生物活性

阿片劑

角蒿特靈酯鹼是從角蒿（Incarvillea sinensis）分離得到，與阿片類生物鹼嗎啡相比具有更顯著的鎮痛效果^[2]。角蒿特靈酯鹼的止痛作用可被納洛酮^[3] 、nor-BNI（英語：Norbinaltorphimine）和β-富納曲胺（英語：beta-Funaltrexamine）^[4]等阿片類藥物的部分阻斷。而且這些藥物對μ-和κ-阿片受體激動選擇性不同。對於δ-阿片受體藥物納曲吲哚（英語：Naltrindole），其不會抵消角蒿特靈酯鹼的鎮痛作用^[4]。

這些發現表明角蒿特靈酯鹼可能具有阿片類受體活性，但值得注意的是，一些研究表明納洛酮無法抵消角蒿特靈酯鹼的鎮痛活性^[5]。

作用於腺苷受體

諸如茶鹼等腺苷受體拮抗劑可阻斷蒿特靈酯鹼的鎮痛作用。這表明角蒿特靈酯鹼的主要作用機制是通過腺苷受體介導的^[5]。

參考文獻

^ 蘇子仁,賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 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.
^ ^4.0 ^4.1 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  .
^ ^5.0 ^5.1 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 （英語）.

[1] 蘇子仁,賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 2006: 562.

[2] 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.

[3] 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-4] 4.0 ^4.1 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-5] 5.0 ^5.1 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 （英語）.

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角蒿特靈酯鹼

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
識別
CAS號	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
性質
化學式	C₄₂H₅₈N₂O₈
摩爾質量	718.92 g·mol⁻¹
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。