Premium
Novel Rearranged Abietane Diterpenoids from the Roots of Salvia sahendica
Author(s) -
Jassbi Amir Reza,
Mehrdad Morteza,
Eghtesadi Farrokh,
Ebrahimi Samad Nejad,
Baldwin Ian T.
Publication year - 2006
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200690093
Subject(s) - abietane , chemistry , heteronuclear molecule , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , terpenoid , terpene , diterpene , carbon 13 nmr , nuclear magnetic resonance spectroscopy
Two naphthoquinone diterpenoids, 1 and 2 , one tricyclic, and one tetracyclic rearranged abietane (‘4,5‐seco‐10,5‐friedo‐abietane’) diterpenoids, 3 and 4 , respectively, together with horminone ( 5 ) have been isolated from the roots of Salvia sahendica. Compounds 2 and 3 are new, and the 13 C‐NMR assignment for compound 4 was modified using ‘ Heteronuclear Multiple‐Bond Correlation’ (HMBC) spectroscopic data. The structures of the compounds have been established by using different spectral data including 1D‐ and 2D‐NMR, IR, UV, and MS. The elemental composition for the major peaks of 3 and 4 were determined by ‘ High‐Resolution Electron Impact Mass Spectrometry’ (HR‐EI‐MS). The relative configurations of the new compounds were determined by 1 H‐NMR and ‘Rotating‐Frame NOES’ (ROESY) spectroscopy. Compounds 1, 2 , and 5 showed antifungal activities when tested on Blakeslea trispora. Lapachol, a prelynated naphthoquinone, was used as a positive control. The biological activities of the related naphthoquinones and abietane diterpenoids were discussed.