Literature DB >> 17190449

Bioactive compounds from the gorgonian Briareum polyanthes. Correction of the structures of four asbestinane-type diterpenes.

Claudia A Ospina1, Abimael D Rodríguez.   

Abstract

Our extended chemical investigation of the crude MeOH-CHCl3 extract of the gorgonian octocoral Briareum polyanthes from Puerto Rico has led to the isolation of three eunicellin-type diterpenoids, 1-3, along with five (4-8) diterpenoids of the asbestinane-type and one (9) of the briarane-type of polycyclized diterpenes. The structures and relative stereochemistry of the new compounds 1-9 were established on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY). The biological activity of these compounds against pathogenic microbes responsible for various human infectious diseases was investigated. In addition, new data recorded for four known asbestinin diterpenes also isolated during this investigation and further analysis through chemical reactions have prompted us to revise our original structural assignments for these compounds.

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Year:  2006        PMID: 17190449     DOI: 10.1021/np060317y

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


  11 in total

Review 1.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

2.  Synthesis of silyloxy dienes by silylene transfer to divinyl ketones: application to the asymmetric synthesis of substituted cyclohexanes.

Authors:  Christian C Ventocilla; K A Woerpel
Journal:  J Org Chem       Date:  2012-03-16       Impact factor: 4.354

3.  A unified strategy for enantioselective total synthesis of cladiellin and briarellin diterpenes: total synthesis of briarellins E and F and the putative structure of alcyonin and revision of its structure assignment.

Authors:  Olivier Corminboeuf; Larry E Overman; Lewis D Pennington
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

4.  Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

Authors:  T David Bateman; Aarti L Joshi; Kwangyul Moon; Elena N Galitovskaya; Meenakshi Upreti; Timothy C Chambers; Matthias C McIntosh
Journal:  Bioorg Med Chem Lett       Date:  2009-10-22       Impact factor: 2.823

5.  Briarenolides F and G, new briarane diterpenoids from a Briareum sp. octocoral.

Authors:  Pei-Han Hong; Yin-Di Su; Jui-Hsin Su; Yung-Husan Chen; Tsong-Long Hwang; Ching-Feng Weng; Chia-Hung Lee; Zhi-Hong Wen; Jyh-Horng Sheu; Nai-Cheng Lin; Yueh-Hsiung Kuo; Ping-Jyun Sung
Journal:  Mar Drugs       Date:  2012-05-23       Impact factor: 6.085

6.  Absolute configuration by vibrational circular dichroism of anti-inflammatory macrolide briarane diterpenoids from the Gorgonian Briareum asbestinum.

Authors:  Dawrin Pech-Puch; Pedro Joseph-Nathan; Eleuterio Burgueño-Tapia; Carlos González-Salas; Diana Martínez-Matamoros; David M Pereira; Renato B Pereira; Carlos Jiménez; Jaime Rodríguez
Journal:  Sci Rep       Date:  2021-01-12       Impact factor: 4.379

7.  seco-Briarellinone and briarellin S, two new eunicellin-based diterpenoids from the Panamanian octocoral Briareum asbestinum.

Authors:  José Félix Gómez-Reyes; Ana Salazar; Héctor M Guzmán; Yisett González; Patricia L Fernández; Armando Ariza-Castolo; Marcelino Gutiérrez
Journal:  Mar Drugs       Date:  2012-11-21       Impact factor: 5.118

8.  Orthogonal Method for Double-Bond Placement via Ozone-Induced Dissociation Mass Spectrometry (OzID-MS).

Authors:  Sonja L Knowles; Ngoc Vu; Daniel A Todd; Huzefa A Raja; Antonis Rokas; Qibin Zhang; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2019-12-11       Impact factor: 4.803

9.  Krempfielins J-M, new eunicellin-based diterpenoids from the soft coral Cladiella krempfi.

Authors:  Yan-Ning Lee; Chi-Jen Tai; Tsong-Long Hwang; Jyh-Horng Sheu
Journal:  Mar Drugs       Date:  2013-08-02       Impact factor: 5.118

10.  Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D, 4-Deoxyasbestinin C, Asbestinin-10, -20, -21 and -23.

Authors:  Angus Campbell; Ian Mat Som; Claire Wilson; J Stephen Clark
Journal:  Chemistry       Date:  2020-01-16       Impact factor: 5.236

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