The chemical constituents of Australian Flindersia species. XIX. Triterpenoids from the leaves of F. bourjotiana F. Muell

Abstract

From the leaves of Flindersia bourjotinna F. Muell. there were isolated sitosterol, triacontanol, lupeol, germanicol, germanicone, and four new triterpenoids, the bourjotinolones A, B, and C, and bourjotone. By chemical degradation and spectroscopic methods, the structures of these substances were shown to be 21,24-epoxy-23,25-dihydroxytirucall-7-en-3one, 23,24-dihydroxytirucalla-7,25-dien- 3-one, 25-chloro-23,24-dihydroxytirucall-7-en-3-one, and 25,26,27-trisnortirucall-7- ene-3,23-dione, respectively. Bourjotinolone C is almost certainly an artefact but bourjotinolone B and bourjotone are less likely to be. From biogenetic and N.M.R. spectral considerations, the absolute stereochemistry of the new triterpenes may be deduced.

Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

“…It was noted that compound 3 has been synthesized previously, 16 however, it was isolated from natural sources for the first time. In addition, the NMR data of 3 were firstly assigned in this study (Table 1).…”

“…Known compounds were identified as (4,4,14-trimethyl-3-oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic acid) (3), 16 hydroxydammarenone I (4), 17 ocotillone (5), 18 stigmasta-4-ene-3-one (6), 19 stigmasta-4,6,8(14),22-tetraen-3-one (7), 20 artelin (8), 21 polystachyol (9), 22 coniferyl alcohol (10), ferulic acid (11), 2,6-dimethoxyhydroquinone (12), antiarol (13), and 4-hydroxybenzaldehyde (14) by comparison with published literature data or direct identification by spectroscopic evidences. It was noted that compound 3 has been synthesized previously, 16 however, it was isolated from natural sources for the first time.…”

Complete 1H and 13C NMR data assignment of protolimonoids from the stem barks of Aphanamixis grandifolia

“…Similar to 4, protons of the terminal dimethyl group at δ 1.02 (H 3 -26) and 1.27 (H 3 -27) showed correlations with one oxygenated tertiary carbon signal at δ 77.7 (C-25) and one oxygenated methine carbon signal at δ 81.7 (C-24). The methoxyl group was assigned to be at C-25 by the observed HMBC correlation of its proton signal [19] which was also supported by comparison of its NMR data with those of similar compounds with vicinal dihydroxyl groups at C-23 and C-24, e.g. phellochin [20] and piscidinol A, its structure had been determined by the X-ray crystallographic analysis.…”

Sterol Metabolism X: Epimeric 23-Hydroxycholesterols

“…23-Hydroxysterols have limited representation in nature in the fungal metabolite 23s-hydroxylanosterol (lanosta-8,24-dien-3/3,23S-diol)( I), the chiograsterols (2), the plant hormone antheridiol (3), and possibly a 23-hydroxycholesterol (cholest-5-ene-3P,23-diol) sulfate in human infant meconium (4). Other 23-hydroxylated steroids include several bile acids (3, the jervine and veratramine classes of steroidal alkaloids (6), and a variety of triterpenoid compounds (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). In view of a continuing interest in the autoxidation of cholesterol in the side chain (19,20) and in the occurrence of side-chainoxidized cholesterol derivatives in human tissues (21)(22)(23), the authors sought to prepare the as yet undescribed epimeric 23-hydroxycholesteroIs for record purposes.…”

“…for C27H4602: C, 80.53; H, 11.52. Found: C, 80.25; H,11.82.Cholest-5-ene-3~,23aF(23S)-diol 3&23-Diacetate-A solution of 55 mg. of the more mobile 3P,2301~-diOI in 5 ml. of dry pyridineacetic anhydride (2 : 1) was held overnight at room temperature and worked up by precipitation with 10 ml.…”