Three abietane diterpenes and two diterpenes incorporated sesquiterpenes from the bark of Cryptomeria japonica

Chemical & Pharmaceutical Bulletin
Kazuko YoshikawaShigenobu Arihara

Abstract

Three new abietane diterpenes, sugikurojins D (1), E (2), and F (3), and two new abietanes which incorporate cadinane, sugikurojins G (4) and H (5) were isolated from the bark of Cryptomeria japonica. These structures were elucidated primarily by extensive NMR experiments. The structure of sugikurojin D (1) was deduced to be 6alpha-acetoxy-7beta,11-dihydroxy-12-methoxy-8,11,13-abietatriene. Sugikurojin E (2) was deduced to be 6alpha-acetoxy-7beta,12-dihydroxy-8,11,13-abietatriene. Sugikurojin F (3) was 7alpha-methoxy-8,13-abietadien-11,12-dione. Sugikurojins G (4) and H (5) had a unique skeleton incorporating an alpha-cadinol or a 1alpha-hydroxy-T-cadinol in ferruginol, respectively. Also obtained in this investigation were the known diterpenes (6-14). An antibacterial activity of ten among these against Staphylococcus aureus and Escherichia coli was inactive at the (MIC: 125 microg/ml) level. Meanwhile, in the cytotoxic activity against HL-60, compounds 4, 8, and 11 showed moderate (IC50: 4, 35.4; 8, 28.0; 11, 52.4 microM) though weak (IC50: 4, 100; 8, 80.8; 11, 100 microM) activity against HCT-15.

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Citations

Sep 10, 2008·Natural Product Research·Wen-Hsin LiHui-Ting Chang
Apr 6, 2006·Chemical & Pharmaceutical Bulletin·Kazuko YoshikawaShigenobu Arihara
Apr 2, 2008·Biological & Pharmaceutical Bulletin·Yumiko FujiwaraTetsuro Shinada
Oct 31, 2014·Integrative Cancer Therapies·Shang-Tse HoJyh-Horng Wu
Feb 3, 2015·Natural Product Reports·Miguel A González
Nov 23, 2007·Natural Product Reports·James R Hanson
Nov 23, 2007·Natural Product Reports·Braulio M Fraga
Jun 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chi-I ChangYueh-Hsiung Kuo
Jun 14, 2008·Journal of Natural Products·Sheng YaoYang Ye
May 21, 2010·Organic Letters·Cheng-Chi ChenYueh-Hsiung Kuo
Nov 30, 2018·Journal of Natural Products·Lu FengYang Ye

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