Guineesine Explained
| Width: | 240 |
| Cas Number: | 55038-30-7 |
| Pubchem: | 6442405 |
| Chemspiderid: | 4946489 |
| Unii: | 7DK8DMU9JX |
| Chebi: | 181825 |
| Chembl: | 404184 |
| Synonyms: | Guineensine; UNII-7DK8DMU9JX |
| Iupac Name: | (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide |
| C: | 24 |
| H: | 33 |
| N: | 1 |
| O: | 3 |
| Smiles: | CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/C1=CC2=C(C=C1)OCO2 |
| Stdinchi: | 1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+ |
| Stdinchikey: | FPMPOFBEYSSYDQ-AUVZEZIHSA-N |
Guineesine (or guineensine) is a compound isolated from long pepper (Piper longum)[1] and black pepper (Piper nigrum).[2]
It was first isolated, studied and named from Piper guineense.[3] [4]
Research
Guineensine inhibits the cellular reuptake of anandamide and 2-arachidonoylglycerol in a mouse model (EC50 = 290 nM).[5] [6] 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 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.[5]
Guineesine is also a monoamine oxidase inhibitor (MAOI) in vitro (IC50 = 139.2 μM).[7]
Notes and References
- Liu W, Jiang Z, Chen J, Zhang X, Ma Y . 荜茇三氯甲烷部位化学成分研究 . Chinese . Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica . 34 . 9 . 1101–3 . May 2009 . 19685743 . Chemical constituents from air-dried Piper longum .
- Park IK . 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 . 22010905 . 10.1080/14786419.2011.628178 . 34316867 .
- 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.
- 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.
- Nicolussi S, Viveros-Paredes JM, Gachet MS, Rau M, Flores-Soto ME, Blunder M, Gertsch J . Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice . Pharmacological Research . 80 . 52–65 . February 2014 . 24412246 . 10.1016/j.phrs.2013.12.010 .
- Sharma C, Sadek B, Goyal SN, Sinha S, Kamal MA, Ojha S . 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 . 26664449 . 10.1155/2015/238482 . 4664820. free .
- Lee SA, Hwang JS, Han XH, Lee C, Lee MH, Choe SG, Hong SS, Lee D, Lee MK, Hwang BY . Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase . Archives of Pharmacal Research . 31 . 6 . 679–83 . June 2008 . 18563347 . 10.1007/s12272-001-1212-7 . 45675434 .
