Literature DB >> 21999614

Cannabinomimetic lipid from a marine cyanobacterium.

Marcelino Gutiérrez1, Alban R Pereira, Hosana M Debonsi, Alessia Ligresti, Vincenzo Di Marzo, William H Gerwick.   

Abstract

NMR-guided fractionation of two independent collections of the marine cyanobacteria Lyngbya majuscula obtained from Papua New Guinea and Oscillatoria sp. collected in Panama led to the isolation of the new lipids serinolamide A (3) and propenediester (4). Their structures were determined by NMR and MS data analysis. Serinolamide A (3) exhibited a moderate agonist effect and selectivity for the CB1 cannabinoid receptor (Ki=1.3 μM, >5-fold) and represents the newest addition to the known cannabinomimetic natural products of marine origin.

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Year:  2011        PMID： 21999614      PMCID： PMC3325759          DOI： 10.1021/np200610t

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  21 in total

Review 1.  The unique mechanistic transformations involved in the biosynthesis of modular natural products from marine cyanobacteria.

Authors:  Adam C Jones; Emily A Monroe; Eli B Eisman; Lena Gerwick; David H Sherman; William H Gerwick
Journal:  Nat Prod Rep       Date:  2010-05-04       Impact factor: 13.423

Review 2.  The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

Authors:  Didier M Lambert; Christopher J Fowler
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

3.  Discovery of novel cannabinoid receptor ligands from diverse marine organisms.

Authors:  K Soderstrom; T F Murray; H D Yoo; S Ketchum; K Milligan; W Gerwick; M J Ortega; J Salva
Journal:  Adv Exp Med Biol       Date:  1997       Impact factor: 2.622

4.  Challenging the absence of observable hydrogens in the assignment of absolute configurations by NMR: application to chiral primary alcohols.

Authors:  Félix Freire; José Manuel Seco; Emilio Quiñoá; Ricardo Riguera
Journal:  Chem Commun (Camb)       Date:  2007-01-30       Impact factor: 6.222

Review 5.  Plant, synthetic, and endogenous cannabinoids in medicine.

Authors:  Vincenzo Di Marzo; Luciano De Petrocellis
Journal:  Annu Rev Med       Date:  2006       Impact factor: 13.739

Review 6.  Update on the endocannabinoid system as an anticancer target.

Authors:  Anna Maria Malfitano; Elena Ciaglia; Giuseppina Gangemi; Patrizia Gazzerro; Chiara Laezza; Maurizio Bifulco
Journal:  Expert Opin Ther Targets       Date:  2011-01-19       Impact factor: 6.902

7.  Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase.

Authors:  T Bisogno; D Melck; L De Petrocellis; N M Gretskaya; V V Bezuglov; N Sitachitta; W H Gerwick; V Di Marzo
Journal:  Biochem Biophys Res Commun       Date:  1998-07-30       Impact factor: 3.575

8.  Crystal structure of the ECH2 catalytic domain of CurF from Lyngbya majuscula. Insights into a decarboxylase involved in polyketide chain beta-branching.

Authors:  Todd W Geders; Liangcai Gu; Jonathan C Mowers; Haichuan Liu; William H Gerwick; Kristina Håkansson; David H Sherman; Janet L Smith
Journal:  J Biol Chem       Date:  2007-10-10       Impact factor: 5.157

9.  Semiplenamides A-G, fatty acid amides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena.

Authors:  Bingnan Han; Kerry L McPhail; Alessia Ligresti; Vincenzo Di Marzo; William H Gerwick
Journal:  J Nat Prod       Date:  2003-10       Impact factor: 4.050

10.  N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties.

Authors:  Garry Milman; Yehoshua Maor; Saleh Abu-Lafi; Michal Horowitz; Ruth Gallily; Sandor Batkai; Fong-Ming Mo; Laszlo Offertaler; Pal Pacher; George Kunos; Raphael Mechoulam
Journal:  Proc Natl Acad Sci U S A       Date:  2006-02-07       Impact factor: 11.205
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  14 in total

1.  Marine cyanobacterial fatty acid amides acting on cannabinoid receptors.

Authors:  Rana Montaser; Valerie J Paul; Hendrik Luesch
Journal:  Chembiochem       Date:  2012-11-09       Impact factor: 3.164

2.  Phylogenetic inferences reveal a large extent of novel biodiversity in chemically rich tropical marine cyanobacteria.

Authors:  Niclas Engene; Sarath P Gunasekera; William H Gerwick; Valerie J Paul
Journal:  Appl Environ Microbiol       Date:  2013-01-11       Impact factor: 4.792

3.  Combining Mass Spectrometric Metabolic Profiling with Genomic Analysis: A Powerful Approach for Discovering Natural Products from Cyanobacteria.

Authors:  Karin Kleigrewe; Jehad Almaliti; Isaac Yuheng Tian; Robin B Kinnel; Anton Korobeynikov; Emily A Monroe; Brendan M Duggan; Vincenzo Di Marzo; David H Sherman; Pieter C Dorrestein; Lena Gerwick; William H Gerwick
Journal:  J Nat Prod       Date:  2015-07-07       Impact factor: 4.050

Review 4.  Recent progress in neuroactive marine natural products.

Authors:  Ryuichi Sakai; Geoffrey T Swanson
Journal:  Nat Prod Rep       Date:  2014-01-17       Impact factor: 13.423

5.  Marine cyanobacteria-derived serotonin receptor 2C active fraction induces psychoactive behavioral effects in mice.

Authors:  Neil C Lax; Kh Tanvir Ahmed; Christopher M Ignatz; Carmenza Spadafora; Benedict J Kolber; Kevin J Tidgewell
Journal:  Pharm Biol       Date:  2016-05-14       Impact factor: 3.503

6.  Mooreamide A: a cannabinomimetic lipid from the marine cyanobacterium Moorea bouillonii.

Authors:  Emily Mevers; Teatulohi Matainaho; Marco Allara'; Vincenzo Di Marzo; William H Gerwick
Journal:  Lipids       Date:  2014-09-10       Impact factor: 1.880

Review 7.  Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review.

Authors:  Sayed Asmat Ali Shah; Najeeb Akhter; Bibi Nazia Auckloo; Ishrat Khan; Yanbin Lu; Kuiwu Wang; Bin Wu; Yue-Wei Guo
Journal:  Mar Drugs       Date:  2017-11-10       Impact factor: 5.118

8.  Trichophycin A, a Cytotoxic Linear Polyketide Isolated from a Trichodesmium thiebautii Bloom.

Authors:  Matthew J Bertin; Paul G Wahome; Paul V Zimba; Haiyin He; Peter D R Moeller
Journal:  Mar Drugs       Date:  2017-01-06       Impact factor: 5.118

Review 9.  Care and feeding of the endocannabinoid system: a systematic review of potential clinical interventions that upregulate the endocannabinoid system.

Authors:  John M McPartland; Geoffrey W Guy; Vincenzo Di Marzo
Journal:  PLoS One       Date:  2014-03-12       Impact factor: 3.240

Review 10.  Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development.

Authors:  Charu Sharma; Bassem Sadek; Sameer N Goyal; Satyesh Sinha; Mohammad Amjad Kamal; Shreesh Ojha
Journal:  Evid Based Complement Alternat Med       Date:  2015-11-17       Impact factor: 2.629
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