Guineesine

Guineesine
	Chemical structure of guineesine
Clinical data
Other names	Guineensine; UNII-7DK8DMU9JX
Identifiers
	IUPAC name (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide;
CAS Number	55038-30-7;
PubChem CID	6442405;
ChemSpider	4946489;
UNII	7DK8DMU9JX;
ChEBI	CHEBI:181825;
ChEMBL	ChEMBL404184;
CompTox Dashboard (EPA)	DTXSID801336042 ;
Chemical and physical data
Formula	C24H33NO3
Molar mass	383.532 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/C1=CC2=C(C=C1)OCO2;
	InChI 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 (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^[5] 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]

References

^ 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.
^ 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.
^ 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.
^ ^a ^b ^c Nicolussi 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.
^ 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.
^ 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.

[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.

[Nicolussi_et_al_2014-5] Nicolussi 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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