Three abietane diterpenes and two diterpenes incorporated sesquiterpenes from the bark of Cryptomeria japonica.
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.
Yoshikawa
Kazuko
K
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Tanaka
Toshinori
T
Umeyama
Akemi
A
Arihara
Shigenobu
S
D045784:Abietanes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D032485:Cryptomeria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D024301:Plant Bark / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet; D013211:Staphylococcus aureus / Q000187:drug effects; D013778:Tetrazolium Salts; D013844:Thiazoles
D045784:Abietanes; D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes; D013778:Tetrazolium Salts; D013844:Thiazoles; C510518:sugikurojin D; C510519:sugikurojin E; C510520:sugikurojin F; C022616:thiazolyl blue