(+/-)-glyceollin I | 57103-57-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: (+/-)-glyceollin I
• 英文别名: glyceollin I；(-)-glyceollin I；17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
• CAS: 57103-57-8
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: YIFYYPKWOQSCRI-UHFFFAOYSA-N

物化性质

• 熔点：
  95-101 °C(Solv: methanol (67-56-1))
• 沸点：
  527.4±50.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 palladium 10% on activated carbon 哌啶 、 盐酸 、 锂硼氢 、 3-甲基吡啶 、 thallium(III) nitrate trihydrate 、 甲基磺酰胺 、 水 、 氢气 、 potassium carbonate 、 N-甲基吗啉氧化物 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 、 xylene 为溶剂， -20.0~130.0 ℃ 、103.42 kPa 条件下， 反应 69.5h， 生成 (+/-)-glyceollin I
  参考文献：
  名称：

  METHODS FOR SYNTHESIZING GLYCINOLS, GLYCEOLLINS I AND II, COMPOSITIONS OF SELECTED INTERMEDIATES, AND THERAPEUTIC USES THEREOF

  摘要：

  公开并声明了两种不同的方法，用于合成甘油素I和甘油素II，作为混合物和其纯形式。立体化学异构体和各种合成中间体也被合成并声明为其新颖的物质组成。所有化合物及其混合物均声明用于制剂，用于治疗或预防癌症，或具有作为选择性雌激素受体调节剂的效用，这些制剂包括增强食品、膳食补充剂和伦理药物代理。

  公开号：

  US20110144195A1

文献信息

• Biomimetic Syntheses and Antiproliferative Activities of Racemic, Natural (−), and Unnnatural (+) Glyceollin I
  作者：Rahul S. Khupse、Jeffrey G. Sarver、Jill A. Trendel、Nicole R. Bearss、Michael D. Reese、Thomas E. Wiese、Stephen M. Boue、Matthew E. Burow、Thomas E. Cleveland、Deepak Bhatnagar、Paul W. Erhardt

  DOI：10.1021/jm101619e

  日期：2011.5.26

  A 14-step biomimetic synthetic route to glyceollin I (1.5% overall yield) was developed and deployed to produce the natural enantiomeric form in soy, its unnatural stereoisomer, and a racemic mixture. Enantiomeric excess was assessed by asymmetric NMR shift reagents and chiral HPLC. Antiproliferative effects were measured in human breast, ovarian, and prostate cancer cell lines, with all three chiral forms exhibiting growth inhibition (GI) in the low to mid mu M range for all cells. The natural enantiomer, and in some cases the racemate, gave significantly greater GI than the unnatural stereoisomer for estrogen receptor positive (ER+) versus ER- breast/ovarian cell lines as well as for androgen receptor positive (AR(+)) versus AR(-) prostate cancer cells. Surprisingly, differences between ER+ and ER- cell lines were not altered by media estrogen conditions. These results suggest the antiproliferative mechanism of glyceollin I stereoisomers may be more complicated than strictly ER interactions.
• Antiestrogenic glyceollins suppress human breast and ovarian carcinoma proliferation and tumorigenesis
  申请人：Cleveland Thomas E.

  公开号：US20080200537A1

  公开（公告）日：2008-08-21

  The flavonoid family of phytochemicals, particularly those derived from soy, has received attention regarding their hormonal activity and their effects on human health and disease. The types and amounts of these compounds in soy and other plants are controlled by both constitutive expression and stress-induced biosynthesis. The health benefits of soy may therefore be dependent upon the amounts of the various hormonally active phytochemicals present. We have identified increased biosynthesis of the isoflavonoid phytoalexin compounds, Glyceollins I, II and III, in soy plants grown under stressed conditions (elicited soy), which exhibit marked anti-estrogenic effects on ER function. Here we demonstrate that specific glyceollins, isolated from elicited soy, displayed anti-estrogenic activity, suppressing basal and estrogen stimulated colony formation of ER-positive estrogen dependent breast cancer cells and inhibiting ER-dependent gene expression of progesterone receptor (PgR) and stromal derived factor-1 (SDF1/CXCL12). Examining the effects of glyceollin on in vivo tumor formation/growth we demonstrate the ability of glyceollins to significantly suppress basal and estrogen-stimulated tumor growth of ER-positive MCF-7 breast and BG-1 ovarian carcinoma cells in ovariectomized female nude mice. We further demonstrate that the effects of glyceollins on suppression of tumor growth correlate with inhibition of estrogen stimulated PgR expression. In contrast to the uterotropic activity of tamoxifen the glyceollins displayed no uterine agonist activity. The Glyceollin (I-III) compounds may represent an important component of the health effects of soy as well as represent novel anti-estrogens useful in the prevention or treatment of breast and ovarian carcinoma.
• Compositions and Methods for Treating Obesity and Diabetes
  申请人：BUROW Matthew E.

  公开号：US20110237505A1

  公开（公告）日：2011-09-29

  Disclosed are methods of modulating the expression of genes linked to adipocytokine signaling, carbohydrate metabolism, fatty acid metabolism, arachidonic acid metabolism, PPAR signaling, insulin signaling, lipid metabolism, extracellular matrix (ECM)-receptor interaction, or combinations thereof, methods of treating hyperlipidemia, obesity, excessive cholesterol, cardiovascular disease, liver disease, diabetes, or combinations thereof, and methods of stimulating glucose uptake in an animal in need thereof, comprising administering a composition comprising at least one isolated glyceollin to said animal.
• Glyceollins Suppress Androgen-Responsive Prostate Cancer
  申请人：Cleveland Thomas E.

  公开号：US20130041022A1

  公开（公告）日：2013-02-14

  The present disclosure demonstrates the molecular effects of glyceollins on human prostate cancer cell LNCaP to further elucidate its potential effects on prostate cancer prevention. The glyceollins inhibited LNCaP cell growth similar to that of the soy isoflavone genistein. The growth inhibitory effects of the glyceollins appeared to be due to an inhibition on G1/S progression and correlated with an up-regulation of cyclin-dependent kinase inhibitor A1 and B1 mRNA and protein levels. By contrast, genistein only up-regulates cyclin-dependent kinase inhibitor A1. In addition, glyceollin treatments led to down-regulated mRNA levels for androgen responsive genes. In contrast to genistein, this effect of glyceollins on androgen responsive genes appeared to be mediated through modulation of an estrogen- but not androgen-mediated pathway. Hence, the glyceollins exerted multiple effects on LNCaP cells that may be considered cancer preventive and the mechanisms of action appeared to be different from other soy-derived phytochemicals.
• US8323706B2
  申请人：——

  公开号：US8323706B2

  公开（公告）日：2012-12-04