Structure and stereochemistry of epoxyserratanes from the cuticle of Piceajezoensis var. jezoensis.
Three new epoxytriterpenes, 14 beta,15 beta-epoxy-21 beta-hydroxyserratan-3-one (1), 13 alpha,14 alpha-epoxy-21 alpha-methoxyserratan-3-one (2), and 13 alpha,14 alpha-epoxy-3 beta-methoxyserratan-21 beta-ol (3), were isolated together with two known triterpenoids, 21 alpha-methoxyserrat-13-en-3-one (4) and 21 beta-hydroxyserrat-14-en-3-one (5), from the cuticle of Picea jezoensis var. jezoensis. The structures of these new compounds were established on the basis of spectral data (NMR, MS) and single-crystal X-ray analyses (1 and 2) and partial synthesis (2 and 3).
Tanaka
R
R
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@oysun01.oups.ac.jp
Tsujimoto
K
K
In
Y
Y
Ishida
T
T
Matsunaga
S
S
Terada
Y
Y
D002855:Chromatography, Thin Layer; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification*; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
C436350:13alpha,14alpha-epoxy-21alpha-methoxyserratan-3-one; C436351:13alpha,14alpha-epoxy-3beta-methoxyserratan-21beta-ol; C436349:14beta,15beta-epoxy-21beta-hydroxyserratan-3-one; D004852:Epoxy Compounds; D014315:Triterpenes