34427-61-7Relevant academic research and scientific papers
Oxyphytosterols as active ingredients in wheat bran suppress human colon cancer cell growth: Identification, chemical synthesis, and biological evaluation
Zhu, Yingdong,Soroka, Dominique,Sang, Shengmin
, p. 2267 - 2276 (2015/03/14)
Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 2-3) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 1-8 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.
Sterols as anticancer agents: Synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis
Carvalho, Jo?o F. S.,Silva, M. Manuel Cruz,Moreira, Jo?o N.,Sim?es, Sérgio,Sá E Melo, M. Luisa
supporting information; experimental part, p. 7632 - 7638 (2011/02/21)
The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6β-hemiphthalates directly from Δ5-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 5.6 μM). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.
Non-cannabinoid constituents from a high potency Cannabis sativa variety
Radwan, Mohamed M.,ElSohly, Mahmoud A.,Slade, Desmond,Ahmed, Safwat A.,Wilson, Lisa,El-Alfy, Abir T.,Khan, Ikhlas A.,Ross, Samir A.
experimental part, p. 2627 - 2633 (2009/04/06)
Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L. variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and β-sitosteryl-3-O-β-d-glucopyranoside-2′-O-palmitate (6). In addition, five known compounds, α-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and β-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and anti-oxidant activities. Compounds 2-4 were inactive as analgesics.
Gram-scale chromatographic purification of β-sitosterol: Synthesis and characterization of β-sitosterol oxides
Zhang, Xin,Geoffroy, Philippe,Miesch, Michel,Julien-David, Diane,Raul, Francis,Aoude-Werner, Dalal,Marchioni, Eric
, p. 886 - 895 (2007/10/03)
An effective purification method for β-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. β-Sitosterol (≥95% purity) was obtained on a gram-scale. Thus, the synthesis of six β-sitosterol oxides, including 7α-hydroxy, 7β-hydroxy, 5,6α-epoxy, 5,6β-epoxy, 7-keto, and 5α,6β-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (～95% purity) were well-documented.
Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
McCarthy, Florence O.,Chopra, Jay,Ford, Alan,Hogan, Sean A.,Kerry, Joe P.,O'Brien, Nora M.,Ryan, Eileen,Maguire, Anita R.
, p. 3059 - 3065 (2007/10/03)
β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides. The Royal Society of Chemistry 2005.
Mass spectrometry characterization of the 5α-, 7α-, and 7β-hydroxy derivatives of β-sitosterol, campesterol, stigmasterol, and brassicasterol
Bortolomeazzi, Renzo,De Zan, Michela,Pizzale, Lorena,Conte, Lanfranco S.
, p. 3069 - 3074 (2007/10/03)
The 5α-hydroperoxides of β-sitosterol, campesterol, stigmasterol, and brassicasterol were obtained by photooxidation of the respective sterols in pyridine in the presence of hematoporphyrine as sensitizer. The reduction of the hydroperoxides gives the corresponding 5α-hydroxy derivatives. The 7α- and 7β-hydroperoxides of the sterols were obtained by allowing an aliquot of the 5α-hydroperoxides to isomerize to 7α-hydroperoxides, which in turn epimerize to 7β-hydroperoxides. The reduction gave the corresponding 7α- and 7β-hydroxy derivatives. The 5α-, 7α-, and 7β-hydroxy derivatives of β-sitosterol, campesterol, stigmasterol, and brassicasterol were identified by comparing thin-layer chromatography mobilities, specific color reactions, and mass spectral data with those of the corresponding hydroxy derivatives of cholesterol, which were synthesized in the same manner. The phytosterols had the same behavior to photooxidation as cholesterol and, moreover, the different phytosterols photooxidized at about the same rate. The mass spectra of the trimethylsilyl ethers of the hydroxy derivatives of the phytosterols investigated and of the corresponding hydroxy derivatives of cholesterol have the same fragmentation patterns and similar relative ion abundances.
Inhibitory effect of some oxygenated stigmastane-type sterols on 12-O- tetradecanoylphorbol-13-acetate-induced inflammation in mice
Kimura,Yasukawa,Takido,Akihisa,Tamura
, p. 1617 - 1619 (2007/10/03)
The oxygenated stigmastane-type sterols stigmastane-3β,6α-diol, stigmastane-3β,6α-diol, 7α-hydroxysitosterol and its diacetyl derivative, 7β-hydroxysitosterol and its diacetyl derivative, 7-oxositosterol, 4β- hydroxysitosterol, and stigmast-4-ene-3β,6β-diol were evaluated with respect to their anti-inflammatory activity against 12-O- tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the sterols, with the exception of 7α-hydroxysitosterol and its diacetyl derivative, were found to possess marked inhibitory activity. The 50% inhibitory dose of these compounds for TPA-inflammation (1 μg) was 0.5-1.0 mg/ear.
