- 7-DEHYDROSITOSTEROL FROM RAUWOLFIA SERPENTINA
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7-Dehydrositosterol has been isolated from the roots of Rauwolfia serpentina. Key Word Index - Rauwolfia serpentina; Apocynaceae; 7-dehydrositosterol.
- Karmakar, Tapan,Chakraborty, D. P.
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- Novel approach to determining the absolute configurations at the C3-positions of various types of sterols based on an induced circular dichroism
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Circular dichroism (CD) spectra of the 2,2′-binaphthyl ester derived from Δ5-sterols showed not bisignate CD but diagnostic CD bands at around 210 and 240 nm. These bands might be attributable to an interaction between an olefinic chromophore and a binaphthyl one. Various types of unsaturated sterols were thus derivatized followed by complete hydrogenation, to give saturated sterols. As a result, CD spectra of the binaphthyl derivatives of the saturated sterols showed bisignate curves centered at 240 nm (3S(β): positive chirality; 3R(α): negative one). This suggested a straightforward and practical method for discriminating the absolute stereogenic center at the C-3 positions of sterols based on an induced CD. This finding should contribute significantly to the analysis of metabolites of various types of sterols.
- Fujiwara, Toshio,Taniguchi, Yuka,Katsumoto, Yukiteru,Tanaka, Takeyuki,Ozeki, Minoru,Iwasaki, Hiroki,Node, Manabu,Yamashita, Masayuki,Hosoi, Shinzo
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p. 1198 - 1204
(2012/11/07)
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- Novel human umbilical vein endothelial cells (HUVEC)-apoptosis inhibitory phytosterol analogues: Insight into their structure-activity relationships
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Design, synthesis and insight into the structure-activity relationships (SAR) of phytosterol analogues as novel antiapoptotic agents are described. In particular, the non-branched alkyl chain at C24 and the pseudosugar moiety at C3 hydroxyl group turned out crucial for the inhibition of human umbilical vein endothelial cells (HUVEC) apoptosis.
- Lee, Sujin,Marharjan, Sony,Jung, Jong-Wha,Kim, Nam-Jung,Kim, Kyeojin,Han, Young Taek,Lim, Changjin,Choi, Hyun-Jung,Kwon, Young-Geun,Suh, Young-Ger
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experimental part
p. 455 - 460
(2012/08/28)
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- PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS
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A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.
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Page/Page column 3
(2008/12/06)
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- Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters. Part I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols
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The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter.
- Geoffroy, Philippe,Julien-David, Diane,Marchioni, Eric,Raul, Francis,Aoude-Werner, Dalal,Miesch, Michel
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p. 702 - 707
(2008/09/21)
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- Novel sterol/stanol phosphorylnitroderivatives and use thereof in treating or preventing cardiovascular disease, its underlying conditions and other disorders
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Sterol and stanol phosphorylnitro derivatives and their use in treating or preventing cardiovascular disease, its underlying conditions and other disorders are disclosed. The disclosed compounds include a phosphate linker, at least one moiety that releases nitric oxide (NO), and a sterol or stanol moiety. Some compounds additionally include an ascorbyl moiety to make the compound more readily soluble in aqueous and non-aqueous media.
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Page/Page column 12; Fig. 1
(2008/06/13)
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- Rapid hydrogenation of unsaturated sterols and bile alcohols using microwaves
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This paper describes an operationally simple, rapid hydrogenation of unsaturated sterols and bile alcohols in a domestic microwave oven. This has been achieved by the addition of catalytic amounts of Pd/C in methylene chloride/propylene glycol solvents in the presence of ammonium formate followed by microwave irradiation. It is suggested that this methodology will be helpful in the identification of saturated and unsaturated sterols with different side-chain structures in rare diseases: sitosterolemia, cerebrotendinous xanthomatosis (CTX), as well as atherosclerosis and diabetes mellitus. Sterols, such as cholesterol, campesterol, sitosterol, and bile alcohols with unsaturated side chains, were converted to their reduced congeners with high yield and purity.
- Dayal,Ertel,Rapole,Asgaonkar,Salen
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p. 451 - 454
(2007/10/03)
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- 3β-Carboxysteranes, a Novel Family of Fossil Steroids
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Two 3β-carboxy-24-ethylcholestanes (24R and 24S) have been isolated as a mixture from a carbonated sediment and characterised by comparison of their mass spectrometric and 1H NMR spectroscopic data with those of synthetic standards; their origin is still unknown, since their carbon skeleton has not yet been reported in living organisms.
- Dany, Fabienne,Riolo, Joseph,Trendel, Jean-Michel,Albrecht, Pierre
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p. 1228 - 1230
(2007/10/02)
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- 5α-STIGMAST-11-EN-3β-YL PALMITATE AND 24-ETHYL-5α-CHOLESTA-8(14),25-DIEN-3β-YL-STEARATE, TWO STERYL ESTERS FROM CRYPTOCORYNE SPIRALIS RHIZOMES
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Two new steryl esters, 5α-stigmast-11-en-3β-yl palmitate and 24-ethyl-5α-cholesta-8(14),25-dien-3β-yl stearate have been isolated from the rhizomes of Cryptocoryne spiralis.Their structures have been established on the basis of chemical and spectroscopic studies. Key Word Index - Cryptocoryne spiralis; Araceae; rhizomes; steryl esters; 5α-stigmast-11-en-3β-yl palmitate; 24-ethyl-5α-cholesta-8(14),25-dien-3β-yl stearate.
- Gupta, Madan, M.,Shukla, Yogendra N.
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p. 1423 - 1426
(2007/10/02)
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- Minor and Trace Sterols in Marine Invertebrates. 31. Isolation and Structure Elucidation of 23H-Isocalysterol, a Naturally Occurring Cyclopropene. Some Comparative Observation on the Course of Hydrogenolytic Ring Opening of Steroidal Cyclopropenes and Cyclopropanes
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A new naturally occuring cyclopropene, 23H-isocalysterol (2), and a novel steroidal cyclopropane, 23,24-dihydrocalysterol (3), were isolated from the sponge Calyx niceaensis.Structure elucidation was accomplished by both NMR and mass spectroscopic analyses.Catalytic hydrogenation and detailed NMR analysis of the products led to the determination of the absolute configuration of calysterol (1) (28R), 23H-isocalysterol (2) (23R), and 23,24-dihydrocalysterol (3b) (23S,24S,28R).Partial synthesis of several hydrogenolysis products as well as synthetic approach to 23,24-dihydrocalysterol are also reported.
- Li, Lian Niang,Li, Hui-ting,Lang, Robert W.,Itoh, Toshihiro,Sica, Donato,Djerassi, Carl
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p. 6726 - 6732
(2007/10/02)
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- BIARYLHEPTANOIDS AND OTHER CONSTITUENTS FROM WOOD OF ALNUS JAPONICA
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The wood of Alnus japonica has been shown to contain a number of biarylheptanoids as well as other phenolics, including secoisolariciresinol diferulate.The co-occurence of cyclized biarylheptanoids with their corresponding acyclic biarylheptanoids has been demonstrated and this fact may have biosynthetic significance.The possible chemotaxonomic importance of biarylheptanoids in members of the Betulaceae is discussed.The isolation and identification of several steroids and triterpenoids are also described.Key Word Index- Alnus japonica; Betulaceae; new biarylheptanoids; biosynthesis; chemotaxonomy; secoisolariciresinol diferulate; steroids; oleanan triterpenoids.
- Nomura, Masayasu,Tokoroyama, Takashi,Kubota, Takashi
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p. 1097 - 1104
(2007/10/02)
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- Constituents of Albizzia zygia
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Lupen-20(30)-3β-ol (1), 14α-stigmast-5-en-3β-ol (3) and 5α-stigmast-7,22-dien-3β-ol (5) were isolated from the bark of Albizzia zygia (Mimosaceae).Leaves also contain these substances and, in addition, a glycoside of 1 as well as four further compounds which give a positive reaction with SbCl3.
- Schoppa, Thomas,Pachaly, Peter
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