Literature DB >> 12502319

Semisynthesis of new sarcophine derivatives with chemopreventive activity.

Isamu Katsuyama1, Hesham Fahmy, Jordan K Zjawiony, Sherief I Khalifa, Raouf W Kilada, Takao Konoshima, Midori Takasaki, Harakuni Tokuda.   

Abstract

The natural cembranolide sarcophine (3) and its lactone ring-opened analogue (10) were oxidized using selenium dioxide under different reaction temperatures to prepare hydroxylated derivatives. Nine new compounds were obtained, six of them targeted hydroxylated derivatives. The determination of regio- and stereochemistry as well as the mechanistic considerations on the selectivity observed in these reactions are discussed on the basis of 2D NMR and molecular modeling. In preliminary in vitro tests on inhibition of EBV-EA activation, compounds 10 and 12-15 have shown higher activity than the known chemopreventive agent sarcophytol A.

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Year:  2002        PMID: 12502319     DOI: 10.1021/np020221d

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


  10 in total

1.  Chemopreventive effects of sarcophine-diol on ultraviolet B-induced skin tumor development in SKH-1 hairless mice.

Authors:  Xiaoying Zhang; Ajay Bommareddy; Wei Chen; Michael B Hildreth; Radhey S Kaushik; David Zeman; Sherief Khalifa; Hesham Fahmy; Chandradhar Dwivedi
Journal:  Mar Drugs       Date:  2009-04-30       Impact factor: 5.118

2.  Sarcophine-diol, a Chemopreventive Agent of Skin Cancer, Inhibits Cell Growth and Induces Apoptosis through Extrinsic Pathway in Human Epidermoid Carcinoma A431 Cells.

Authors:  Xiaoying Zhang; Ajay Bommareddy; Wei Chen; Sherief Khalifa; Radhey S Kaushik; Hesham Fahmy; Chandradhar Dwivedi
Journal:  Transl Oncol       Date:  2009-03       Impact factor: 4.243

3.  Sarcophine-diol, a skin cancer chemopreventive agent, inhibits proliferation and stimulates apoptosis in mouse melanoma B₁₆F₁₀ cell line.

Authors:  Pawel T Szymanski; Bhimanna Kuppast; Safwat A Ahmed; Sherief Khalifa; Hesham Fahmy
Journal:  Mar Drugs       Date:  2011-12-22       Impact factor: 6.085

4.  Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum.

Authors:  Mohamed-Elamir F Hegazy; Amira M Gamal Eldeen; Abdelaaty A Shahat; Fathy F Abdel-Latif; Tarik A Mohamed; Bruce R Whittlesey; Paul W Paré
Journal:  Mar Drugs       Date:  2012-01-18       Impact factor: 6.085

5.  New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral Sarcophyton tenuispiculatum.

Authors:  Tzu-Yin Huang; Chiung-Yao Huang; Shu-Rong Chen; Jing-Ru Weng; Tzu-Hsuan Tu; Yuan-Bin Cheng; Shih-Hsiung Wu; Jyh-Horng Sheu
Journal:  Mar Drugs       Date:  2020-12-27       Impact factor: 5.118

6.  Dose-response on the chemopreventive effects of sarcophine-diol on UVB-induced skin tumor development in SKH-1 hairless mice.

Authors:  Ruth F Guillermo; Xiaoying Zhang; Radhey S Kaushik; David Zeman; Safwat A Ahmed; Sherief Khalifa; Hesham Fahmy; Chandradhar Dwivedi
Journal:  Mar Drugs       Date:  2012-09-24       Impact factor: 6.085

7.  Chemopreventive effects of sarcotriol on ultraviolet B-induced skin tumor development in SKH-1 hairless mice.

Authors:  Vipra Kundoor; Xiaoying Zhang; Ajay Bommareddy; Sherief Khalifa; Hesham Fahmy; Chandradhar Dwivedi
Journal:  Mar Drugs       Date:  2007-12-12       Impact factor: 5.118

8.  Stereoselective chemo-enzymatic oxidation routes for (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene.

Authors:  Christian Görner; Max Hirte; Stephanie Huber; Patrick Schrepfer; Thomas Brück
Journal:  Front Microbiol       Date:  2015-10-13       Impact factor: 5.640

9.  A High-Content Screening Assay for the Discovery of Novel Proteasome Inhibitors from Formosan Soft Corals.

Authors:  Xue-Hua Ling; Shang-Kwei Wang; Yun-Hsuan Huang; Min-Jay Huang; Chang-Yih Duh
Journal:  Mar Drugs       Date:  2018-10-21       Impact factor: 5.118

10.  New Biscembranoids Sardigitolides A-D and Known Cembranoid-Related Compounds from Sarcophyton digitatum: Isolation, Structure Elucidation, and Bioactivities.

Authors:  Tzu-Yin Huang; Chiung-Yao Huang; Chih-Hua Chao; Chi-Chien Lin; Chang-Feng Dai; Jui-Hsin Su; Ping-Jyun Sung; Shih-Hsiung Wu; Jyh-Horng Sheu
Journal:  Mar Drugs       Date:  2020-08-29       Impact factor: 5.118

  10 in total

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