Cannabis Ruderalis

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{{Short description|Compound isolated from long pepper and black pepper}}
{{Chembox
{{Infobox drug
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<!-- Images -->
| drug_name =
| ImageFile = Guineesine skeletal.svg
| image = Guineesine skeletal.svg
| ImageSize = 200px
| ImageAlt = Chemical structure of guineesine
| width = 240
| caption = Chemical structure of guineesine

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<!-- Names -->
<!-- Clinical data -->
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| IUPACName = (2''E'',4''E'',12''E'')-13-(1,3-Benzodioxol-5-yl)-''N''-(2-methylpropyl)trideca-2,4,12-trienamide
| pronounce =
| OtherNames = Guineensine
| tradename =
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<!-- Sections -->
| Drugs.com =
| Section1 = {{Chembox Identifiers
| MedlinePlus =
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| CASNo = 55038-30-7
| ChEMBL = 404184
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration =
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| class =
| ATC_prefix =
| ATC_suffix =

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<!-- Legal status -->
| legal_status =

<!-- Pharmacokinetic data -->
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =

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<!-- Identifiers -->
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| CAS_number = 55038-30-7
| CAS_supplemental =
| PubChem = 6442405
| PubChem = 6442405
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 4946489
| ChemSpiderID = 4946489
| UNII = 7DK8DMU9JX
| KEGG =
| ChEBI = 181825
| ChEMBL = 404184
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = Guineensine; UNII-7DK8DMU9JX

<!-- Chemical data -->
⚫
| 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
| SMILES = 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+
| 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+
| InChIKey = FPMPOFBEYSSYDQ-AUVZEZIHSA-N
| StdInChIKey = FPMPOFBEYSSYDQ-AUVZEZIHSA-N
}}
| Section2 = {{Chembox Properties
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| C=24|H=33|N=1|O=3
| Appearance =
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| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
}}


'''Guineesine''' (or '''guineensine''') is an [[alkaloid]] isolated from [[long pepper]] (''Piper longum'')<ref>{{cite journal | vauthors = Liu W, Jiang Z, Chen J, Zhang X, Ma Y | title = 荜茇三氯甲烷部位化学成分研究 | language = Chinese | journal = Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica | volume = 34 | issue = 9 | pages = 1101–3 | date = May 2009 | pmid = 19685743 | url = http://www.cnki.com.cn.dincheng.cn/Article/CJFDTOTAL-ZGZY200909012.htm | trans-title = Chemical constituents from air-dried Piper longum }}</ref> and [[black pepper]] (''Piper nigrum'').<ref>{{cite journal | vauthors = Park IK | title = Insecticidal activity of isobutylamides derived from Piper nigrum against adult of two mosquito species, Culex pipiens pallens and Aedes aegypti | journal = Natural Product Research | volume = 26 | issue = 22 | pages = 2129–31 | year = 2011 | pmid = 22010905 | doi = 10.1080/14786419.2011.628178 }}</ref>
'''Guineesine''' (or '''guineensine''') is a compound isolated from [[long pepper]] (''Piper longum'')<ref>{{cite journal | vauthors = Liu W, Jiang Z, Chen J, Zhang X, Ma Y | title = 荜茇三氯甲烷部位化学成分研究 | language = Chinese | journal = Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica | volume = 34 | issue = 9 | pages = 1101–3 | date = May 2009 | pmid = 19685743 | url = http://www.cnki.com.cn.dincheng.cn/Article/CJFDTOTAL-ZGZY200909012.htm | trans-title = Chemical constituents from air-dried Piper longum }}</ref> and [[black pepper]] (''Piper nigrum'').<ref>{{cite journal | vauthors = Park IK | title = Insecticidal activity of isobutylamides derived from Piper nigrum against adult of two mosquito species, Culex pipiens pallens and Aedes aegypti | journal = Natural Product Research | volume = 26 | issue = 22 | pages = 2129–31 | year = 2011 | pmid = 22010905 | doi = 10.1080/14786419.2011.628178 | s2cid = 34316867 }}</ref>

It was first isolated, studied and named from ''[[Piper guineense]]''.<ref>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.</ref><ref>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.</ref>


==Research==
==Biological activities==
Guineensine [[Reuptake inhibitor|inhibits the cellular reuptake]] of [[anandamide]] and [[2-arachidonoylglycerol]] in a [[mouse model]] ([[EC50|EC<sub>50</sub>]] = 290 nM).<ref name="Nicolussi et al 2014">{{cite journal | vauthors = Nicolussi S, Viveros-Paredes JM, Gachet MS, Rau M, Flores-Soto ME, Blunder M, Gertsch J | title = Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice | journal = Pharmacological Research | volume = 80 | pages = 52–65 | date = February 2014 | pmid = 24412246 | doi = 10.1016/j.phrs.2013.12.010 }}</ref> <ref>{{cite journal | vauthors = Sharma C, Sadek B, Goyal SN, Sinha S, Kamal MA, Ojha S | title = Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development | journal = Evidence-Based Complementary and Alternative Medicine | volume = 2015 | pages = 238482 | year = 2015 | pmid = 26664449 | doi = 10.1155/2015/238482 | pmc=4664820| doi-access = free }}</ref> This causes an increase in the activity of the two [[neurotransmitter]]s which are classified as [[Endogeny (biology)|endogenous]] [[cannabinoids]].
===Reuptake inhibition===
Guineenine seems to potently [[Reuptake inhibitor|inhibit the cellular reuptake]] of [[anandamide]] and [[2-arachidonoylglycerol]] ([[EC50|EC<sub>50</sub>]] = 290 nM).<ref>{{cite journal | vauthors = Sharma C, Sadek B, Goyal SN, Sinha S, Kamal MA, Ojha S | title = Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development | journal = Evidence-Based Complementary and Alternative Medicine | volume = 2015 | pages = 238482 | year = 2015 | pmid = 26664449 | doi = 10.1155/2015/238482 | pmc=4664820}}</ref><ref name="Nicolussi et al 2014">{{cite journal | vauthors = Nicolussi S, Viveros-Paredes JM, Gachet MS, Rau M, Flores-Soto ME, Blunder M, Gertsch J | title = Guineensine is a novel inhibitor of endocannabinoid uptake showing cannabimimetic behavioral effects in BALB/c mice | journal = Pharmacological Research | volume = 80 | pages = 52–65 | date = February 2014 | pmid = 24412246 | doi = 10.1016/j.phrs.2013.12.010 }}</ref>
This causes an increase in the activity of the two [[neurotransmitter]]s which are classified as [[Endogeny (biology)|endogenous]] [[cannabinoids]].


⚫
Guineesine can dose-dependently produce [[Cannabinoidergic|cannabimimetic]] effects in a mouse model<ref name="Nicolussi et al 2014" /> which are indicated by potent [[Catatonia|catatonic]], [[analgesic]], [[Hypolocomotion|hypo-locomotive]] and [[Hypothermia|hypo-thermic]] effects. In addition, the analgesic and catatonic effects were reversed by the [[cannabinoid receptor type 1]] (CB1) [[inverse agonist]] [[rimonabant]].<ref name="Nicolussi et al 2014"/>
===Cannabimimetic effects===
⚫
Guineesine can dose-dependently produce [[Cannabinoidergic|cannabimimetic]] effects<ref>{{cite journal | vauthors = Nicolussi S, Chicca A, Rau M, Rihs S, Soeberdt M, Abels C, Gertsch J | title = Correlating FAAH and anandamide cellular uptake inhibition using N-alkylcarbamate inhibitors: from ultrapotent to hyperpotent | journal = Biochemical Pharmacology | volume = 92 | issue = 4 | pages = 669–89 | date = December 2014 | pmid = 25283614 | doi = 10.1016/j.bcp.2014.09.020 }}</ref> which are indicated by potent [[Catatonia|catatonic]], [[analgesic]], [[Hypolocomotion|hypo-locomotive]] and [[Hypothermia|hypo-thermic]] effects. In addition, the analgesic and catatonic effects were reversed by the [[cannabinoid receptor type 1]] (CB1) [[inverse agonist]] [[rimonabant]].<ref name="Nicolussi et al 2014"/>


⚫
Guineesine is also a [[monoamine oxidase inhibitor]] (MAOI) ''[[in vitro]]'' ([[IC50|IC<sub>50</sub>]] = 139.2 μM).<ref>{{cite journal | vauthors = Lee SA, Hwang JS, Han XH, Lee C, Lee MH, Choe SG, Hong SS, Lee D, Lee MK, Hwang BY | title = Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase | journal = Archives of Pharmacal Research | volume = 31 | issue = 6 | pages = 679–83 | date = June 2008 | pmid = 18563347 | doi = 10.1007/s12272-001-1212-7 | s2cid = 45675434 }}</ref>
===Enzyme activities===
⚫
Guineesine also appears to possess significant [[Monoamine oxidase inhibitor|monoamine oxidase inhibitory]] (MAOI) effects ([[IC50|IC<sub>50</sub>]] = 139.2 μM).<ref>{{cite journal | vauthors = Lee SA, Hwang JS, Han XH, Lee C, Lee MH, Choe SG, Hong SS, Lee D, Lee MK, Hwang BY | title = Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase | journal = Archives of Pharmacal Research | volume = 31 | issue = 6 | pages = 679–83 | date = June 2008 | pmid = 18563347 | doi = 10.1007/s12272-001-1212-7 }}</ref>


== References ==
== References ==
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[[Category:Monoamine oxidase inhibitors]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Reuptake inhibitors]]
[[Category:Endocannabinoid reuptake inhibitors]]
[[Category:Analgesics]]

Latest revision as of 04:52, 12 February 2024

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
PubChem CID
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 (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[edit]

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[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. ^ 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.
  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.
source: https://en.wikipedia.org/w/index.php?title=Guineesine&diff=1206443165&oldid=767898896

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