75082-06-3Relevant articles and documents
STEROLS OF THE UNICELLULAR ALGAE NEMATOCHRYSOPSIS ROSCOFFENSIS AND CHRYSOTILA LAMELLOSA: ISOLATION OF (24E)-24-n-PROPYLIDENECHOLESTEROL AND 24-n-PROPYLCHOLESTEROL
Raederstorff, Daniel,Rohmer, Michel
, p. 2835 - 2838 (1984)
Key Word Index-Nematochrysopsis roscoffensis; Chrysotila lamellosa; Chrysophyceae; Prymnesiophyceae; unicellular algae; sterols; (24E)-24-n-propylidenecholesterol; 24-n-propylcholesterol.Two rare C30-sterols, (24E)-24-n-propylidenecholest-5-en-3β-ol and 24-n-propylcholest-5-en-3β-ol, and (24S)-24-ethylcholesta-5,22-dien-3β-ol (stigmasterol) are the major sterols of Nematochrysopsis roscoffensis, a Chrysophyte of the Sarcinochrysidales order.This unique sterol composition is different from the sterol contents of other Chrysophytes and justifies the peculiar position of the Sarcinochrysidales, which are by some characteristics morphologically and biologically related to the Phaeophyceae.The presence of (24S)-24-methylcholesta-5,22-dien-3β-ol (24-epibrassicasterol) as a major sterol in Chrysotila lamellosa is in accordance with the few previous results obtained from other Prymnesiophyceae, although the presence of the other major sterol, (24R)-24-ethylcholesta-5,22-dien-3β-ol (poriferasterol), has never been reported in these algae.
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.
