Biology:Guineesine
| Error creating thumbnail: Unable to save thumbnail to destination Chemical structure of guineesine | |
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| Other names | Guineensine; UNII-7DK8DMU9JX |
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| Formula | C24H33NO3 |
| Molar mass | 383.532 g·mol−1 |
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Guineesine (or guineensine) is a compound isolated from long pepper (Piper longum)[1] and black pepper (Piper nigrum).[2]
Research
Guineensine inhibits the cellular reuptake of anandamide and 2-arachidonoylglycerol in a mouse model (EC50 = 290 nM).[3] [4] This causes an increase in the activity of the two neurotransmitters which are classified as endogenous cannabinoids.
Guineesine can dose-dependently produce cannabimimetic effects in a mouse model[3] which are indicated by potent catatonic, analgesic, hypo-locomotive and hypo-thermic effects. In addition, the analgesic and catatonic effects were reversed by the cannabinoid receptor type 1 (CB1) inverse agonist rimonabant.[3]
Guineesine is also a monoamine oxidase inhibitor (MAOI) in vitro (IC50 = 139.2 μM).[5]
References
- ↑ "荜茇三氯甲烷部位化学成分研究" (in Chinese). Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica 34 (9): 1101–3. May 2009. PMID 19685743. http://www.cnki.com.cn.dincheng.cn/Article/CJFDTOTAL-ZGZY200909012.htm.
- ↑ "Insecticidal activity of isobutylamides derived from Piper nigrum against adult of two mosquito species, Culex pipiens pallens and Aedes aegypti". Natural Product Research 26 (22): 2129–31. 2011. doi:10.1080/14786419.2011.628178. PMID 22010905.
- ↑ 3.0 3.1 3.2 "Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice". Pharmacological Research 80: 52–65. February 2014. doi:10.1016/j.phrs.2013.12.010. PMID 24412246.
- ↑ "Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development". Evidence-Based Complementary and Alternative Medicine 2015: 238482. 2015. doi:10.1155/2015/238482. PMID 26664449.
- ↑ "Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase". Archives of Pharmacal Research 31 (6): 679–83. June 2008. doi:10.1007/s12272-001-1212-7. PMID 18563347.
Guineesine(Guineensine) was first isolated,studied and named from Piper guineense Schum and Thonn.[1,2] 1. OKOGUN, J.I. and Ekong, D.E.U. 1974 Extracts from the Fruits of the Piper guineense. Schum and Thonn. J. Chem. Soc. Perkin Transactions I, 1974, 2195-2198. 2. Okwute, S.K. OKOGUN, J.I. and Okorie, D.A. 1984 Revised Structure and Synthesis of Piperolein acids; Guineensine and Wisanine from Piper guineense, TETRAHEDRON, 40, 2541-2545.
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