Literature DB >> 17804167

Chemical transformation and biological studies of marine sesquiterpene (S)-(+)-curcuphenol and its analogs.

Waseem Gul1, Nicholas L Hammond, Muhammad Yousaf, Jiangnan Peng, Andy Holley, Mark T Hamann.   

Abstract

Chemical transformation studies of the marine sesquiterpene phenol (S)-(+)-curcuphenol (1), isolated from the Jamaican sponges Myrmekioderma styx, were accomplished. In order to optimize the activity and better understand the SAR of (S)-(+)-curcuphenol, nineteen semisynthetic analogs were prepared and evaluated for activity against infectious diseases. A number of analogs showed significant activity against Mtb and Leishmania donovani, while showed good to moderate activities in antibacterial and antifungal assays as well as against Plasmodium falciparium (D6 clone) and (W2 clone). The analogs a, c, h, and r exhibited Mtb activity with MICs of 24.6, 41.2, 6.90, and 50.5 microM, respectively. Analog f showed enhanced activity against L. donovani with an IC50 of 0.6 microM and IC90 of 40 microM respectively.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17804167      PMCID： PMC2266081          DOI： 10.1016/j.bbagen.2007.05.011

Source DB:  PubMed          Journal:  Biochim Biophys Acta        ISSN： 0006-3002


  14 in total

1.  Lipoxygenase-catalyzed polymerization of phenolic lipids suggests a new mechanism for allergic contact dermatitis induced by urushiol and its analogs.

Authors:  Zuyong Xia; Tetsuo Miyakoshi; Takashi Yoshida
Journal:  Biochem Biophys Res Commun       Date:  2004-03-12       Impact factor: 3.575

2.  (+)-Curcuphenol and dehydrocurcuphenol, novel sesquiterpenes which inhibit H,K-ATPase, from a marine sponge Epipolasis sp.

Authors:  N Fusetani; M Sugano; S Matsunaga; K Hashimoto
Journal:  Experientia       Date:  1987-12-01

3.  Synthesis and antimycobacterial activity of some indole derivatives of pyridine-2-carboxamidrazone and quinoline-2-carboxamidrazone.

Authors:  M G Mamolo; L Vio; E Banfi
Journal:  Farmaco       Date:  1996-01

4.  Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol.

Authors:  M Ono; Y Ogura; K Hatogai; H Akita
Journal:  Chem Pharm Bull (Tokyo)       Date:  2001-12       Impact factor: 1.645

5.  Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]piperazine monomethanesulfonate (U-90152S), a second-generation clinical candidate.

Authors:  D L Romero; R A Morge; M J Genin; C Biles; M Busso; L Resnick; I W Althaus; F Reusser; R C Thomas; W G Tarpley
Journal:  J Med Chem       Date:  1993-05-14       Impact factor: 7.446

6.  Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases.

Authors:  Karumanchi V Rao; Noer Kasanah; Subagus Wahyuono; Babu L Tekwani; Raymond F Schinazi; Mark T Hamann
Journal:  J Nat Prod       Date:  2004-08       Impact factor: 4.050

7.  Microbial and chemical transformation studies of the bioactive marine sesquiterpenes (S)-(+)-curcuphenol and -curcudiol isolated from a deep reef collection of the Jamaican sponge Didiscus oxeata.

Authors:  Khalid A El Sayed; Muhammad Yousaf; Mark T Hamann; Mitchell A Avery; Michelle Kelly; Peter Wipf
Journal:  J Nat Prod       Date:  2002-11       Impact factor: 4.050

8.  Abrogation of cisplatin-induced hepatotoxicity in mice by xanthorrhizol is related to its effect on the regulation of gene transcription.

Authors:  Seong Hwan Kim; Kyoung Ok Hong; Won-Yoon Chung; Jae Kwan Hwang; Kwang-Kyun Park
Journal:  Toxicol Appl Pharmacol       Date:  2004-05-01       Impact factor: 4.219

9.  Marine natural products as novel antioxidant prototypes.

Authors:  Satoshi Takamatsu; Tyler W Hodges; Ira Rajbhandari; William H Gerwick; Mark T Hamann; Dale G Nagle
Journal:  J Nat Prod       Date:  2003-05       Impact factor: 4.050

10.  [Antimycobacterial indole derivatives].

Authors:  S Mahboobi; G Grothus; W Meindl
Journal:  Arch Pharm (Weinheim)       Date:  1994-02       Impact factor: 3.751
View more
  4 in total

Review 1.  Role of Marine Natural Products in the Genesis of Antiviral Agents.

Authors:  Vedanjali Gogineni; Raymond F Schinazi; Mark T Hamann
Journal:  Chem Rev       Date:  2015-08-28       Impact factor: 60.622

2.  An entry to curcuphenol/elvirol core structures via a retro-Aldol reaction.

Authors:  María F Plano; Guillermo R Labadie; Melissa R Jacob; Babu L Tekwani; Raquel M Cravero
Journal:  Chem Biodivers       Date:  2011-06       Impact factor: 2.408

Review 3.  Marine pharmacology in 2007-8: Marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous system, and other miscellaneous mechanisms of action.

Authors:  Alejandro M S Mayer; Abimael D Rodríguez; Roberto G S Berlinck; Nobuhiro Fusetani
Journal:  Comp Biochem Physiol C Toxicol Pharmacol       Date:  2010-09-15       Impact factor: 3.228

Review 4.  A look around the West Indies: The spices of life are secondary metabolites.

Authors:  Adrian Demeritte; William M Wuest
Journal:  Bioorg Med Chem       Date:  2020-10-01       Impact factor: 3.641
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.