Incarvillateine

Incarvillateine is a complex monoterpene alkaloid that is a derivative of α-truxillic acid. It can be isolated from the plant genus Incarvillea.

Incarvillateine
Names
Preferred IUPAC name
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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C42H58N2O8/c1-21-17-43(5)19-29-23(3)33(15-27(21)29)51-41(47)39-37(25-9-11-31(45)35(13-25)49-7)40(38(39)26-10-12-32(46)36(14-26)50-8)42(48)52-34-16-28-22(2)18-44(6)20-30(28)24(34)4/h9-14,21-24,27-30,33-34,37-40,45-46H,15-20H2,1-8H3/t21-,22-,23-,24-,27-,28-,29-,30-,33+,34+,37-,38-,39-,40-/m0/s1
    Key: VQKTZIKAARDZIA-FYBVMHBNSA-N
  • 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
Properties
C42H58N2O8
Molar mass 718.932 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Biological activity

Opioidergic

Incarvillateine isolated from Incarvillea sinensis has demonstrated significant analgesic activity when compared to the opiate alkaloid morphine.[1]

Incarvillateine's pain-killing effect was partially blocked by administration of naloxone,[2] norbinaltorphimine and beta-funaltrexamine,[3] which are receptor antagonists with varying selectivity for mu and kappa opioid receptors. Naltrindole, a delta opioid receptor antagonist, did not counteract the analgesic activity of incarvillateine.[3]

These findings indicate that incarvillateine may possess opioidergic receptor activity, but it is worthy to note that some studies indicate that naloxone was ineffective at countering incarvillateine's analgesic activity.[4]

Adenosinergic

Incarvillateine's antinociceptive effect was blocked by the administration of adenosine receptor antagonists such as theophylline. This suggests that incarvillateine's main mechanism of action is mediated through the adenosine receptor.[4]

References
  1. Nakamura, M.; Chi, Y. M.; Yan, W. M.; Nakasugi, Y.; Yoshizawa, T.; Irino, N.; Hashimoto, F.; Kinjo, J.; Nohara, T. (1999-09-01). "Strong antinociceptive effect of incarvillateine, a novel monoterpene alkaloid from Incarvillea sinensis". Journal of Natural Products. 62 (9): 1293–1294. doi:10.1021/np990041c. ISSN 0163-3864. PMID 10514316.
  2. Ichikawa, Masaya; Takahashi, Masaki; Aoyagi, Sakae; Kibayashi, Chihiro (2004). "Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine". Journal of the American Chemical Society. 126 (50): 16553–16558. doi:10.1021/ja0401702. PMID 15600360.
  3. Chi, Yu-Ming; Nakamura, Motoyuki; Yoshizawa, Toyokichi; Zhao, Xi-Ying; Yan, Wen-Mei; Hashimoto, Fumio; Kinjo, Junei; Nohara, Toshihiro; Sakurada, Shinobu (2005-10-01). "Pharmacological study on the novel antinociceptive agent, a novel monoterpene alkaloid from Incarvillea sinensis". Biological & Pharmaceutical Bulletin. 28 (10): 1989–1991. doi:10.1248/bpb.28.1989. ISSN 0918-6158. PMID 16204962.
  4. 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 (2015-11-03). "Antinociceptive effects of incarvillateine, a monoterpene alkaloid from Incarvillea sinensis, and possible involvement of the adenosine system". Scientific Reports. 5: 16107. Bibcode:2015NatSR...516107W. doi:10.1038/srep16107. ISSN 2045-2322. PMC 4630779. PMID 26527075.
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