4651-48-3Relevant articles and documents
Synthesis of 7-oxo- and 7-hydroxy-derivatives of stigmasterol
Kovganko, N. V.,Chernov, Yu. G.
, p. 183 - 186 (1996)
The phytosteroids 3β-hydroxy-(24S)-stigmast-5,22E-dien-7-one and (24S)-stigmasta-5,22E-diene-3β,7β-diol have been synthesized from stigmasterol.
COMPARATIVE STUDY OF IN VIVO STIGMASTEROL BIOSYNTHESIS IN NICOTIANA TABACUM AND HORDEUM VULGARE
Huang, Li-Shar,Grunwald, Claus
, p. 2779 - 2782 (1986)
Key Word Index - Nicotiana tabacum; Solanaceae; tobacco; Hordeum vulgare; Gramineae; barley; phytosterols; stigmasterol; sitosterol.Six-day-old tobacco (Nicotiana tabacum) and barley (Hordeum vulgare) seedlings rapidly incorporated and metabolized exogenously supplied sitosterol but neither plant was able to convert it into stigmasterol.However, a sterol metabolite was isolated from both species and the acetate derivative was slightly more polar, on AgNO3-silica gel TLC, than stigmasteryl acetate.A similar metabolite was also obtained with cholesterol, indicating a general metabolic reaction of plants to exogenous sterols.Both species incorporated mevalonic acid into sitosterol and stigmasterol.We suggest that in vascular plants, whether monocotyledons or dicotyledons, the pathway of stigmasterol biosynthesis is not via sitosterol but through a common precursor which is derived from mevalonic acid.
Absolute configuration assignment of stigmasterol oxiranes
Burgue?o-Tapia, Eleuterio,Fuentes-Figueroa, Miguel á.,Joseph-Nathan, Pedro
, (2021/11/20)
Diastereoisomeric stigmasterol oxiranes 4, 5, 8, and 9 are known phytosterol oxidation products (POPs) that have been evaluated for their cytotoxicity, although the results are of limited significance since, in most cases, they were evaluated as mixtures. Consequently, to establish biological activity hierarchy of these oxides, it is critical to evaluate individual pure POPs. Therefore, we now describe the obtention of individual molecules and their absolute configuration (AC) determination. The two acetylated C-5?C-6 oxiranes 6 and 7; the two acetylated C-22?C-23 oxides 10 and 11, obtained by means of Δ5 double bond protection-deprotection; and the four C-5?C-6, C-22?C-23 diepoxystigmasteryl acetates 19–22 were now individually gained and their AC determined by vibrational circular dichroism. Vibrational modes associated with the C-5?C-6 and the C-22?C-23 bonds were identified in dioxiranes 19–22 and used to assign the AC of monoepoxides 6, 7, 10, and 11. The AC of biological active non-acetylated molecules follows immediately. Due to the scarce spectroscopic information available for these POPs, the 1H and 13C NMR chemical shifts of 3–22 were assigned using 1D- and 2D-NMR experiments.
Synthesis and cytotoxicity of new stigmasterol derivatives
Lu, Yu,Hu, Jizhi,Wu, Zibin,Zeng, Li,Yu, Bo
, p. 715 - 721 (2018/07/15)
This study identifies potential antitumor compounds from a series of new stigmasterol derivatives. Eleven stigmasterol derivatives were synthesized and their structures were confirmed by 1H NMR, MS, and elemental analyses. Their cytotoxicity in vitro against three human cancer cell lines (MCF-7, A549 and HepG2) were evaluated by the MTT assay. Among these compounds, AB-5 and AB-11 shows much better cytotoxicity against MCF-7, A549, and HepG2 cells, and AB-10 exhibits selective cytotoxicity against MCF-7. Their structure-activity relationships were also investigated. In conclusion, AB-5, AB-10 and AB-11 serve as potential compounds for the new generation of anticancer drugs.
