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Guineesine

From Wikipedia, the free encyclopedia
Compound isolated from long pepper and black pepper
Pharmaceutical compound
Guineesine
Chemical structure of guineesine
Clinical data
Other namesGuineensine; UNII-7DK8DMU9JX
Identifiers
  • (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H33NO3
Molar mass383.532 g·mol−1
3D model (JSmol)
  • CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/C1=CC2=C(C=C1)OCO2
  • InChI=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+
  • Key:FPMPOFBEYSSYDQ-AUVZEZIHSA-N

Guineesine (orguineensine) is a compound isolated fromlong pepper (Piper longum)[1] andblack pepper (Piper nigrum).[2]

It was first isolated, studied and named fromPiper guineense.[3][4]

Research

[edit]

Guineensineinhibits the cellular reuptake ofanandamide and2-arachidonoylglycerol in amouse model (EC50 = 290 nM).[5][6] This causes an increase in the activity of the twoneurotransmitters which are classified asendogenouscannabinoids.

Guineesine can dose-dependently producecannabimimetic effects in a mouse model[5] which are indicated by potentcatatonic,analgesic,hypo-locomotive andhypo-thermic effects. In addition, the analgesic and catatonic effects were reversed by thecannabinoid receptor type 1 (CB1)inverse agonistrimonabant.[5]

Guineesine is also amonoamine oxidase inhibitor (MAOI)in vitro (IC50 = 139.2 μM).[7]

References

[edit]
  1. ^Liu W, Jiang Z, Chen J, Zhang X, Ma Y (May 2009)."荜茇三氯甲烷部位化学成分研究" [Chemical constituents from air-dried Piper longum].Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica (in Chinese).34 (9):1101–3.PMID 19685743.
  2. ^Park IK (2011). "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.doi:10.1080/14786419.2011.628178.PMID 22010905.S2CID 34316867.
  3. ^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.
  4. ^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.
  5. ^abcNicolussi S, Viveros-Paredes JM, Gachet MS, Rau M, Flores-Soto ME, Blunder M, Gertsch J (February 2014). "Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice".Pharmacological Research.80:52–65.doi:10.1016/j.phrs.2013.12.010.PMID 24412246.
  6. ^Sharma C, Sadek B, Goyal SN, Sinha S, Kamal MA, Ojha S (2015)."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.doi:10.1155/2015/238482.PMC 4664820.PMID 26664449.
  7. ^Lee SA, Hwang JS, Han XH, Lee C, Lee MH, Choe SG, Hong SS, Lee D, Lee MK, Hwang BY (June 2008). "Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase".Archives of Pharmacal Research.31 (6):679–83.doi:10.1007/s12272-001-1212-7.PMID 18563347.S2CID 45675434.
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