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A total synthetic strategy of 20S-hydroxyvitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig–Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated vitamin D receptor (VDR) and initiated the expression of downstream genes...
Much attention has been paid to cholestane-type steroidal glycosides because of their importance from the perspectives of both chemical diversity and significant biological activities. A phytochemical investigation of the rhizomes of Polygonatum odoratum (Liliaceae) resulted in the isolation of three novel cholestane-type steroidal glycosides (1–3) with unique Δ 14,16 -unsaturated D-ring structures...
(20R)-25-Methoxyl-dammarane-3β,12β,20-triol (25-OCH 3 -PPD) is a dammarane-type sapogenin showing anti-proliferative potential. In our study, two series of analogs substituted at the C-3 or C-3 and C-12 positions with fatty acids were prepared conveniently. The cytotoxic activity of these compounds was evaluated using four different human tumor cell lines (A549, Hela, HT-29 and MCF-7) and...
Periodontitis is a complication of diabetes mellitus, and the two diseases are highly associated with the dysfunction of inflammatory mediators. 25-hydroxyvitamin D 3 (25(OH)D 3 ) plays a pivotal role in inflammatory modulation, but little is known about its effects on the progression of diabetic periodontitis and the underlying mechanism. In this paper, we showed that 25(OH)D ...
We have synthesized 3β,21-dihydroxypregna-5,7-dien-20-one (21(OH) 7DHP) and used UVB radiation to induce its photoconversion to analogues of vitamin D (pD), lumisterol (pL) and tachysterol (pT). The number and character of the products and the dynamics of the process were dependent on the UVB dose. The main products: pD and pT compounds were characterized by UV absorption, MS and NMR spectroscopy...
To identify small molecules that suppress the apoptosis of mesenchymal stem cells (MSCs) is promising for stem cell therapy. We recently showed that bone morphogenetic protein 4 (BMP4) signalling involves the effect of cholesterol myristate on the proliferation of MSCs. The present study evaluated the effects of cholesterol myristate on the apoptosis of MSCs and the inhibitor of differentiation (Id1),...
20S-hydroxyvitamin D3 (20S-(OH)D3), an in vitro product of vitamin D3 metabolism by the cytochrome P450scc, was recently isolated, identified and shown to possess antiproliferative activity without inducing hypercalcemia. The enzymatic production of 20S-(OH)D3 is tedious, expensive, and cannot meet the requirements for extensive chemical and biological studies. Here we report for the first time the...
The new steroidal 5,7-diene, 3β-hydroxyandrosta-5,7-diene-17β-carboxylic acid (17-COOH-7DA), was synthesized from 21-acetoxypregnenolone, with the oxidative cleavage of the side chain being dependent on the presence of oxygen. In human epidermal (HaCaT) keratinocytes, 17-COOH-7DA inhibited proliferation in a dose-dependent manner, starting at a dose as low as 10 −11 M. This inhibition was...
We recently identified that cholesterol myristate in traditional Chinese medicine (TCM) is the active compound that increases proliferation of mesenchymal stem cell (MSCs). The present study is further to determine what signal pathway involves in effect of cholesterol myristate. Reverse transcription-PCR, Western blot and ELISA analysis show that cholesterol myristate increases the release of bone...
Eleven new 14,15-seco-pregnane-type steroidal glycosides, cynanosides P 1 –P 5 , Q 1 –Q 3 , R 1 –R 3 , and a novel 12,13-seco-14,18-nor-pregnane-type steroidal glycoside, cynanoside S, were isolated from the roots of Cynanchum atratum, together with four known compounds, atratoside C, sublanceoside E 3 , chekiangensoside C and cynatroside B....
Pregna-5,7-dienes and their hydroxylated derivatives can be formed in vivo when there is a deficiency in 7-dehydrocholesterol (7-DHC) Δ-reductase function, e.g., Smith–Lemli–Opitz syndrome (SLOS). Ultraviolet B (UVB) radiation induces photoconversion of 7-DHC to vitamin D 3 , lumisterol 3 and tachysterol 3 . Two epimers (20R and 20S) of pregna-5,7-diene-3β,17α,20-triol (4R...
Five new pregnane glycosides, cynanosides K–O (1–5) with a 14,15-seco-pregnane-type skeleton as the aglycon, together with five known compounds, cynascyroside C, sublanceoside E 1 , sublanceoside I 1 , atratoside A and atratoside B, were isolated from the roots of Cynanchum atratum. Their structures were determined on the basis of spectroscopic analysis and chemical evidence.
Three new 4α-methyl steroids, 4α-methyl-ergost-7,24(28)-diene-3β-ol-23-one (1), 4α-methyl-ergost-8(14),24(28)-diene-3β-ol-23-one (2), 4α-methyl-ergost-24(28)-en-3β,11β-diol-23-one (3), and two new polyoxygenated steroids, ergost-5,25-diene-3β,24S,28-triol (4), ergost-5,24(28)-diene-3β,23S-diol (5), along with one known steroid 24-methylencholesterol (6) were isolated from the soft coral Nephthea sp...
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