麦角甾醇葡萄糖苷 | 130155-33-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 麦角甾醇葡萄糖苷
• 英文名称: ergosterol 3-O-β-D-glucopyranoside
• 英文别名: ergosteryl 3-beta-D-glucoside；(2R,3R,4S,5S,6R)-2-[[(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 130155-33-8
• 化学式: C₃₄H₅₄O₆
• 分子量: 558.799
• InChiKey: MKZPNGBJJJZJMI-GBLVNJONSA-N

物化性质

• 熔点：
  308 °C (decomp)
• 沸点：
  677.5±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  麦角甾醇葡萄糖苷 在 Eosin Y 、 氧气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以62%的产率得到5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-D-glucopyranoside
  参考文献：
  名称：

  Antitumor sterols from the mycelia of Cordyceps sinensis

  摘要：

  Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-glucopyranoside and 22-dihydroergosteryl-3-O-beta-D-glucopyranoside were also isolated. The structures of hitherto unknown sterols were established by 1D and 2D NMR spectroscopic techniques with the former synthesized in order to confirm the identity of the sugar moiety by chemical correlation. The glycosylated form of ergosterol peroxide was found to be a greater inhibitor to the proliferation of K562, Jurkat, WM-1341, HL-60 and RPMI-8226 tumor cell lines by 10 to 40% at 10 mu g/ml than its previously identified aglycone, 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-ol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00128-4
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 麦角甾醇葡萄糖苷
  参考文献：
  名称：

  Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicineCordyceps sinensis

  摘要：

  Ergosterol 3-O-beta-D-glucopyranoside (1a) and ergosterol 3-O-beta-D-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by H-1, C-13 NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.

  DOI：

  10.1080/10286020.2012.670220

文献信息

• Synthesis of Ergosterol and 5,6-Dihydroergosterol Glycosides and Their Inhibitory Activities on Lipopolysaccharide-Induced Nitric Oxide Production
  作者：HoonGyu Park、Tae Hoon Lee、Fei Chang、Hyun Ji Kwon、Jiyoung Kim、Hakwon Kim

  DOI：10.5012/bkcs.2013.34.5.1339

  日期：2013.5.20

  We have synthesized several glycosyl ergosterols and 5,6-dihydroergosterols (DHE) and examined their effects on production of nitric oxide (NO) and iNOS protein expression in LPS-treated RAW264.7 macrophage cells. Our results showed that DHE derivatives inhibited production of NO and iNOS protein expression more strongly than ergosterol derivative. Especially, DHE-Glc exhibited most potent inhibitory activity without cytotoxicity up to the concentration of $100\mu}M$.

  我们合成了几种糖基麦角固醇和5,6-二氢麦角固醇（DHE），并研究了它们对LPS处理后的RAW264.7巨噬细胞中一氧化氮（NO）产生和iNOS蛋白表达的影响。我们的结果显示，DHE衍生物对NO产生和iNOS蛋白表达的抑制效果比麦角固醇衍生物更强。特别是，DHE-Glc在浓度低于100μM时表现出最强的抑制活性且没有细胞毒性。
• Ergosteryl-β-glucosidase (Egh1) involved in sterylglucoside catabolism and vacuole formation in<i>Saccharomyces cerevisiae</i>
  作者：Takashi Watanabe、Motohiro Tani、Yohei Ishibashi、Ikumi Endo、Nozomu Okino、Makoto Ito

  DOI：10.1093/glycob/cwv045

  日期：2015.10

  Sterylglucosides (SGs) are composed of a glucose and sterol derivatives, and are distributed in fungi, plants and mammals. We recently identified EGCrP1 and EGCrP2 (endoglycoceramidase-related proteins 1 and 2) as a β-glucocerebrosidase and steryl-β-glucosidase, respectively, in Cryptococcus neoformans. We herein describe an EGCrP2 homologue (Egh1; ORF name, Yir007w) involved in SG catabolism in Saccharomyces cerevisiae. The purified recombinant Egh1 hydrolyzed various β-glucosides including ergosteryl β-glucoside (EG), cholesteryl β-glucoside, sitosteryl β-glucoside, para-nitrophenyl β-glucoside, 4-methylumberifellyl β-glucoside and glucosylceramide. The disruption of EGH1 in S. cerevisiae BY4741 (egh1Δ) resulted in the accumulation of EG and fragmentation of vacuoles. The expression of EGH1 in egh1Δ (revertant) reduced the accumulation of EG, and restored the morphology of vacuoles. The accumulation of EG was not detected in EGH1 and UGT51(ATG26) double-disrupted mutants (ugt51Δegh1Δ), indicating that EG was synthesized by Ugt51(Atg26) and degraded by Egh1 in vivo. These results clearly demonstrated that Egh1 is an ergosteryl-β-glucosidase that is functionally involved in the EG catabolic pathway and vacuole formation in S. cerevisiae.

  甾基葡糖苷（SGs）由葡萄糖和甾醇衍生物组成，分布于真菌、植物和哺乳动物中。我们最近发现 EGCrP1 和 EGCrP2（内糖糖苷酶相关蛋白 1 和 2）分别是新隐球菌中的β-葡糖脑苷脂和甾基-β-葡糖苷酶。我们在此描述了参与酿酒酵母中 SG 分解代谢的 EGCrP2 同源物（Egh1；ORF 名称 Yir007w）。纯化的重组 Egh1 可水解各种 β-葡萄糖苷，包括麦角甾基 β-葡萄糖苷（EG）、胆固醇基 β-葡萄糖苷、西固醇基 β-葡萄糖苷、对硝基苯基 β-葡萄糖苷、4-甲基贝壳杉基 β-葡萄糖苷和葡萄糖酰胺。在 S. cerevisiae BY4741（egh1Δ）中破坏 EGH1 会导致 EG 积累和液泡破碎。在 egh1Δ（还原型）中表达 EGH1 可减少 EG 的积累，并恢复液泡的形态。在EGH1和UGT51(ATG26)双中断突变体（ugt51Δegh1Δ）中未检测到EG的积累，表明EG在体内由Ugt51(Atg26)合成并由Egh1降解。这些结果清楚地表明，Egh1 是一种麦角固醇基-β-葡萄糖苷酶，在功能上参与了 S. cerevisiae 的 EG 分解途径和液泡形成。
• THE PREPARATION AND ANTIRACHITIC ACTIVATION OF SOME DERIVATIVES OF ERGOSTEROL AND CHOLESTEROL
  作者：D. W. MacCorquodale、Harry Steenbock、Homer Adkins

  DOI：10.1021/ja01369a051

  日期：1930.6
• Gisvold, Journal of the American Pharmaceutical Association (1912), 1934, vol. 23, p. 402
  作者：Gisvold

  DOI：——

  日期：——
• Molecular cloning and characterization of one member of 3β-hydroxy sterol glucosyltransferase gene family in Withania somnifera
  作者：Lokendra Kumar Sharma、Bhaskara Reddy Madina、Pankaj Chaturvedi、Rajender Singh Sangwan、Rakesh Tuli

  DOI：10.1016/j.abb.2007.01.024

  日期：2007.4

  Sterol glycosides are constituents of plant cell membranes. Glucosylations of the sterols are catalyzed by sterol glucosyltransferases (SGTs), which are members of family 1 glycosyltransferases. We have identified the family of SGT genes expressed in the leaves of a medicinal plant Withania somnifera. One member (SGTL1) of this gene family was cloned. The full-length cDNA sequence of SGTL1 represents 2532 bp, comprising untranslated regions (UTRs) of 337 and 89 bp at the 5' and 3' ends, respectively. The amino acid sequence deduced from the 2103 bp open reading frame (ORF) showed homology (67-45%) to the reported plant SGTs. The presence of two putative transmembrane domains suggested the association of SGTL1 with membrane. The SGTL1 was expressed in Escherichia coli and recombinant enzyme from the supernatant was partially purified and biochemically characterized. The relative activity and kinetic properties of SGTL1 for different sterols were compared with a recombinant SGT (GenBank Accession No. Z83833) of Arabidopsis thaliana (AtSGT). Both the recombinant enzymes showed activity with 3-beta-OH sterols. The distribution of SGTL1 transcript in W. somnifera, as determined by quantitative PCR, showed higher expression in roots and mature leaves. Expression of the SGTL1 transcript in the leaves of W. somnifera was enhanced following the application of salicylic acid. In contrast, it decreased rapidly on exposure of the plants to heat shock, suggesting functional role of the enzyme in biotic and abiotic stresses. (c) 2007 Elsevier Inc. All rights reserved.