4651-48-3Relevant academic research and scientific papers
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.
ECDYSTERONE FROM STEM OF DIPLOCLISIA GLAUCESCENS
Bandara, B. M. Ratnayake,Jayasinghe, Lalith,Karunaratne, Veranja,Wannigama, G. Percy,Bokel, Michael,et al.
, p. 1073 - 1076 (1989)
The stem of Diploclisia glaucescens afforded ecdysterone in a high yield of over 3percent. 13C NMR of the tetraacetate and NOE studies on the triacetate provided further data on the structure and comformation of this phytoecdysteroid.Hemolytic, insecticidal and spermicidal activity are reported for the compound. - Keywords: Diploclisia glaucescens; Menispermeaceae; stigmasterol; ecdysterone; saponins; 13C NMR; NOE; bioactivity.
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.
Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material
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Paragraph 0010; 0035; 0036, (2021/05/05)
The invention provides a novel industrial method for preparing vitamin D3 by taking stigmasterol as a raw material. The method comprises the following steps: sequentially carrying out hydroxyl acetylation, side chain oxidation, side chain isopentane reduction and hydrogenation on stigmasterol to obtain cholesterol acetate, and then sequentially carrying out oxidation, hydrazone formation, hydrazone removal, hydrolysis, illumination and the like to obtain the vitamin D3. The invention provides a novel method for preparing vitamin D3 from stigmasterol, and the method has the advantages of mild reaction conditions and high yield, and is suitable for industrial production.
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 search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples
Bus, Katarzyna,Ofiara, Karol,Sitkowski, Jerzy,Szterk, Arkadiusz,Zmys?owski, Adam
, (2020/06/08)
It has been proven that at increased temperature, sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid extraction, solid-phase extraction and gas chromatography coupled with mass spectrometry. Additionally, for the analyses, suitable standards were synthetized from native sterols. To identify the mechanism of 3β,3′β-disteryl ether formation at high temperatures, an attempt was made to use the proposed synthesis method. Additionally, due to the association of sterols and sterol derivatives with atherosclerosis, preliminary studies with synthetized 3β,3′β-disteryl ethers on endothelial cells were conducted.
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.
Phytochemical investigation and characterization of isolated chemical constituents from Kyllinga triceps Rottb.
Verma, Nishant,Jha,Ahmad, Shamim,Chaudhary, Sudhir,Ali, Mohammad
, p. 1393 - 1400 (2017/05/02)
Four compounds have been isolated by column chromatography from Kyllinga triceps namely quercetin dihydrate (1), rutin (2), β-sitosterol (3) and stigmasterol (4). Their structures have been elucidated by, FTIR, HR-EIMS, 1H NMR and 13C NMR spectroscopic studies.
Synthesis of some steroidal derivatives with side chain of 20-and 22-hydrazone aromatic heterocycles and their antiproliferative activity
Gan, Chunfang,Liu, Liang,Cui, Jianguo,Liu, Zhiping,Shi, Haixin,Lin, Qifu,Sheng, Haibing,Yang, Chunhui,Huang, Yanmin
, p. 375 - 383 (2017/06/20)
Background: The modification of steroidal structure is commonly used to change the biological activity of steroids in medicinal chemistry. Some steroids containing heterocycles exhibit distinct cytotoxicity against various cancer cell lines and have been receiving wide attention over the years by medicinal chemists for drug discovery. Methods: Using pregnenolone and stigmasterol as starting materials, via different chemical reaction, two series of heterosteroids with side chain of 20- and 22-hydrazone aromatic cycles or heterocycles in their structures were synthesized and characterized by IR, NMR and HRMS. The antiproliferative activity of the compounds in vitro was evaluated against human HT-29, HeLa, Bel 7404 and SGC 7901 cancer cells by MTT assays. Results: The steroidal compounds with side chain of 20-hydrazone aromatic cycles or heterocycles exhibited distinct cytotoxicity. However, analogues with the side chain of 22-hydrazone resulted in a dramatic decrease of the cytotoxicity. The result of Annexin V assay showed that the 20-hydrazone compounds were potent apoptotic inducers against these carcinoma cells. Conclusion: Steroidal compounds with the side-chain of 20-hydrazone aromatic heterocycles exhibit distinct antiproliferative activity in vitro. However, the compounds with the side-chain of 22-hydrazone aromatic heterocycle decreased the cytotoxicity of the compounds.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Paragraph 0574; 0575; 0576, (2016/02/16)
Provided are methods of evaluating or treating a patient, e.g., a patient having a disorder described herein, comprising: a) optionally, acquiring a patient sample; b) acquiring an evaluation of and/or evaluating the sample for an alteration in the level S24(S)-hydroxycholesterol compared to a reference standard.
