Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii.
The absolute stereostructure of a novel skeletal diterpene, standishinal (1), from the bark of Thuja standishii was confirmed by X-ray crystallographic analyses of 1 and its p-bromobenzoate derivative. Aromatase inhibitory activities of standishinal, eight known diterpenes, totarol, 12-methoxyabieta-8,11,13-trien-11-ol, 12-hydroxy-6,7-seco-abieta-8,11,13-triene-6,7-dial, trans-communic acid, labda-8(17),13-dien-12 R,15-olid-19-oic acid, 12 S-hydroxylabda-8(17),13(16),14-trien-19-oic acid, 13-oxo-15,16-dinorlabda-8(17),11 E-dien-19-oic acid and 14-oxo-15-norlabda-8 (17),12 E-dien-19-oic acid from the plant, and four synthetic analogs were evaluated using a recombinant human aromatase. Among them, standishinal and its diacetate derivative had significant inhibitory activities.
Minami
Toshifumi
T
Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, Osaka, Japan.
Iwamoto
Manabu
M
Ohtsu
Hironori
H
Ohishi
Hirofumi
H
Tanaka
Reiko
R
Yoshitake
Akira
A
D045784:Abietanes; D001141:Aromatase / Q000378:metabolism; D047072:Aromatase Inhibitors; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D013329:Structure-Activity Relationship; D029783:Thuja / Q000737:chemistry*
C467919:3,11-dihydroxy-12-methoxyabieta-8,11,13-triene-7-one; D045784:Abietanes; D047072:Aromatase Inhibitors; D004224:Diterpenes; D004791:Enzyme Inhibitors; D001141:Aromatase