Diterpenes from the roots of Salvia canariensis

Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses

“…All the spectroscopic data gave good agreement with those reported for the natural sample. [21] Experimental evidence for abiotic benzo [1,3] [23] Salvicanol (12)w as acetylated in high yield (90 %) to afford salvicanol acetate (13), whichw as used later on for the subsequentoxidationr eaction.…”

Two New Icetexane Diterpenoids from Salvia przewalskii

“…[15][16][17][18] Carefully analysis of the 1D-NMR spectra indicated that compound 1 could be ascribed to be an icetexane diterpenoid by the absence of the characteristic quaternary carbon (C-10) and methyl group (Me-20) for abietane diterpenoids. 8,[16][17][18] A comparison of the 1 H-and 13 C-NMR spectral data of 1 with those of barbatusol (3) indicated that they were strikingly similar except for the presence of a methoxyl group in 1.8) The methoxyl group was located at C-7 on the basis of the heteronuclear multiple bond correlation (HMBC) correlations of d (Fig. 1).…”

“…Considering the structures of the compounds previously isolated from this genus and the formula of 1, along with the characteristic methine signals at d C 27.3 and 43.7 due to C-15 and C-5, respectively, a noticeable quaternary carbon signals at d C 31.7 (C-4), and four characteristic methyl signals at d C 22.6 (C-16, C-17), 27.6 (C-18), and 26.6 (C-19), compound 1 could be ascribed to be an icetexane or abietane diterpenoid. [15][16][17][18] Carefully analysis of the 1D-NMR spectra indicated that compound 1 could be ascribed to be an icetexane diterpenoid by the absence of the characteristic quaternary carbon (C-10) and methyl group (Me-20) for abietane diterpenoids. 8,[16][17][18] A comparison of the 1 H-and 13 C-NMR spectral data of 1 with those of barbatusol (3) indicated that they were strikingly similar except for the presence of a methoxyl group in 1.…”

“…The Me 2 CO fraction of S. przewalskii (whole parts) was subjected to silica gel chromatography to afford two new icetexane diterpenoids trivially named as przewalskin C, D (1, 2) along with sixteen known ones: barbatusol (3), 8) tanshinone I (4), 9) crypotanshinone (5), 10) tanshinone IIA (6), 11) ferruginol (7), 12) sugiol (8), 13) carnosol (9), 14) przewalskin (10), 5) 1,2-dihydrotanshinone (11), 15) salvicanol (12), 16) rosmadial (13), 10) pisiferin (14), 17) pisiferanol (15), 17) 8,11,13-icetexantrien-10,11,12-triol (16), 18) danshenspiroketallactone (17), 19) and epi-danshenspiroketallactone (18). 19) The identification and structural elucidation of these compounds were based on 1D-and 2D-NMR spectral data analysis.…”

Norditerpenoids from Salvia castanea Diels f. pubescens

“…The structures of other known compounds (4−21) were identified to be 6,7,8,9-tetrahydro-1,6,6-trimethylfuro [3,2-c] naphth-[2,1-e]oxepine-10,12-dione (4) [7], ferruginol (5) [10], przewalskin (6) [12], methylenetanshinquinone (7) [13], 1,2-dihydrotanshinone I (8) [13], danshenspiroketallactone (9) [14], epi-danshenspiroketallactone (10) [14], sibiriquinone B (11) [15], neo-tanshinlactone (12) [16], tanshinone I (13) [17], methylenedihydrotanshinquinone (14) [18], trijuganone B (15) [19], dihydrotanshinone I (16) [20], methyltanshinoate (17) [21], salvicanol (18) [22], tanshinone IIB (19) [23], tanshinone IIA (20) [17], and crypotanshinone (21) [20], respectively, by comparison of their spectroscopic data with those reported in the literature.…”