Literature DB >> 19783432

Puupehanol, a sesquiterpene-dihydroquinone derivative from the marine sponge Hyrtios sp.

Wen-Hui Xu1, Yuanqing Ding, Melissa R Jacob, Ameeta K Agarwal, Alice M Clark, Daneel Ferreira, Zong-Suo Liang, Xing-Cong Li.   

Abstract

Puupehanol (1), a new sesquiterpene-dihydroquinone derivative, was isolated from the marine sponge Hyrtios sp., along with the known compounds puupehenone (2) and chloropuupehenone (3) that are responsible for the antifungal activity observed in the extract. The structure of 1 was established as (20R,21R)-21-hydroxy-20,21-dihydropuupehenone by extensive spectroscopic and computational methods. Compound 2 exhibited potent activity against Cryptococcus neoformans and Candida krusei with MFCs of 1.25 and 2.50 microg/mL, respectively.

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Year:  2009        PMID: 19783432      PMCID: PMC2760646          DOI: 10.1016/j.bmcl.2009.09.015

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  17 in total

1.  Methanol adduct of puupehenone, a biologically active derivative from the marine sponge Hyrtios species.

Authors:  M L Bourguet-Kondracki; F Lacombe; M Guyot
Journal:  J Nat Prod       Date:  1999-09       Impact factor: 4.050

2.  Sorocenols G and H, anti-MRSA oxygen heterocyclic Diels-Alder-type adducts from Sorocea muriculata roots.

Authors:  Samir A Ross; Raquel Rodríguez-Guzmán; Mohamed M Radwan; Melissa Jacob; Yuanqing Ding; Xing-Cong Li; Daneel Ferreira; Susan P Manly
Journal:  J Nat Prod       Date:  2008-10-11       Impact factor: 4.050

3.  Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system.

Authors:  J K Zjawiony; P Bartyzel; M T Hamann
Journal:  J Nat Prod       Date:  1998-12       Impact factor: 4.050

4.  Exploring sponge-derived terpenoids for their potency and selectivity against 12-human, 15-human, and 15-soybean lipoxygenases.

Authors:  Taro Amagata; Stephanie Whitman; Tyler A Johnson; Chad C Stessman; Christopher P Loo; Emil Lobkovsky; Jon Clardy; Phillip Crews; Theodore R Holman
Journal:  J Nat Prod       Date:  2003-02       Impact factor: 4.050

5.  Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8''-biflavonoid morelloflavone.

Authors:  Yuanqing Ding; Xing-Cong Li; Daneel Ferreira
Journal:  J Org Chem       Date:  2007-10-24       Impact factor: 4.354

6.  Theoretical calculation of electronic circular dichroism of a hexahydroxydiphenoyl-containing flavanone glycoside.

Authors:  Yuanqing Ding; Xing-Cong Li; Daneel Ferreira
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

7.  Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.

Authors:  R E Longley; O J McConnell; E Essich; D Harmody
Journal:  J Nat Prod       Date:  1993-06       Impact factor: 4.050

8.  Determination of absolute configuration using concerted ab Initio DFT calculations of electronic circular dichroism and optical rotation: bicyclo[3.3.1]nonane diones.

Authors:  P J Stephens; D M McCann; E Butkus; S Stoncius; J R Cheeseman; M J Frisch
Journal:  J Org Chem       Date:  2004-03-19       Impact factor: 4.354

9.  Cycloabiesesquine A, a unique sesquiterpenoid from Abies delavayi.

Authors:  Xian-Wen Yang; Yuanqing Ding; Xing-Cong Li; Daneel Ferreira; Yun-Heng Shen; Su-Mei Li; Ning Wang; Wei-Dong Zhang
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

10.  Pregnane glycosides from Hoodia gordonii.

Authors:  Yatin J Shukla; Rahul S Pawar; Yuanqing Ding; Xing-Cong Li; Daneel Ferreira; Ikhlas A Khan
Journal:  Phytochemistry       Date:  2009-03-19       Impact factor: 4.072

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  6 in total

1.  Selective Killing of Dormant Mycobacterium tuberculosis by Marine Natural Products.

Authors:  Carolina Rodrigues Felix; Rashmi Gupta; Sandra Geden; Jill Roberts; Priscilla Winder; Shirley A Pomponi; Maria Cristina Diaz; John K Reed; Amy E Wright; Kyle H Rohde
Journal:  Antimicrob Agents Chemother       Date:  2017-07-25       Impact factor: 5.191

Review 2.  Secondary Metabolites from the Marine Sponge Genus Phyllospongia.

Authors:  Huawei Zhang; Menglian Dong; Hong Wang; Phillip Crews
Journal:  Mar Drugs       Date:  2017-01-06       Impact factor: 5.118

Review 3.  Pleiotropic Role of Puupehenones in Biomedical Research.

Authors:  Beatriz Martínez-Poveda; Ana R Quesada; Miguel Ángel Medina
Journal:  Mar Drugs       Date:  2017-10-21       Impact factor: 5.118

Review 4.  Bioactive Natural Products of Marine Sponges from the Genus Hyrtios.

Authors:  Nourhan Hisham Shady; Ebaa M El-Hossary; Mostafa A Fouad; Tobias A M Gulder; Mohamed Salah Kamel; Usama Ramadan Abdelmohsen
Journal:  Molecules       Date:  2017-05-11       Impact factor: 4.411

5.  Puupehenone, a Marine-Sponge-Derived Sesquiterpene Quinone, Potentiates the Antifungal Drug Caspofungin by Disrupting Hsp90 Activity and the Cell Wall Integrity Pathway.

Authors:  Siddharth K Tripathi; Qin Feng; Li Liu; David E Levin; Kuldeep K Roy; Robert J Doerksen; Scott R Baerson; Xiaomin Shi; Xuewen Pan; Wen-Hui Xu; Xing-Cong Li; Alice M Clark; Ameeta K Agarwal
Journal:  mSphere       Date:  2020-01-08       Impact factor: 4.389

Review 6.  Meroterpenes from marine invertebrates: structures, occurrence, and ecological implications.

Authors:  Marialuisa Menna; Concetta Imperatore; Filomena D'Aniello; Anna Aiello
Journal:  Mar Drugs       Date:  2013-05-17       Impact factor: 5.118

  6 in total

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