3-O-β-D-gluxopyranosyl-20(S),24(R)-epoxydammarane-3β,12β,15-triol | 211926-61-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-O-β-D-gluxopyranosyl-20(S),24(R)-epoxydammarane-3β,12β,15-triol
• 英文别名: 3β-O-β-D-glucopyranosyl-(20S,24R)-epoxydammarane-12β,25-diol；(20S,24R)-3-O-β-D-glucopyranosyldammar-20,24-epoxy-3β,12β,25-triol；3-O-β-D-glucopyranosyl 20S,24R-epoxydammarane-3β,12β-triol；Jzs13ujl7J；(2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 211926-61-3
• 化学式: C₃₆H₆₂O₉
• 分子量: 638.883
• InChiKey: ZIRHYQFOBJNNCZ-KVGQQVSNSA-N

物化性质

• 沸点：
  730.7±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (20S,24R)-epoxydammarane-3β,12β,25-triol 在 4 A molecular sieve 、 sodium methylate 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-O-β-D-gluxopyranosyl-20(S),24(R)-epoxydammarane-3β,12β,15-triol
  参考文献：
  名称：

  Glycosylation of triterpenoids of the dammarane series. VI. 3-mono- and 3,12-di-O-β-D-glucopyranosides of pyxinol

  摘要：

  DOI：

  10.1007/bf00579815

文献信息

• Semisynthesis and bioactive evaluation of oxidized products from 20(S)-ginsenoside Rg3, Rh2, protopanaxadiol (PPD) and their 20(R)-epimers as cytotoxic agents
  作者：Jie Yang、Xuwen Li、Ting Sun、Yan Gao、Yanxin Chen、Yongri Jin、Yang Li

  DOI：10.1016/j.steroids.2015.12.005

  日期：2016.2

  eight compounds (3, 8, 9, 10, 15, 16, 19 and 22) with the cyclized side chain were firstly identified. Most of the tested compounds possessed cytotoxicity to a certain degree against the two types of cells which implied these oxidized products could play a certain role on anti-cancer functions of the raw materials in vivo. Meanwhile, the results proved that the configurations at C-20 or C-24 and the number

  已从20（S）-人参皂苷Rg3，Rh2、20（S）-原人参二醇（PPD）和它们的20（R）表观分子系统地合成了一系列氧化产物，并评估了其中大多数产物的抗细胞毒性活性首次通过MTT法检测HeLa细胞和HepG2细胞。根据全面的（1）H NMR，（13）C NMR，二维（2D）NMR和质谱数据，获得了22种产物并进行了阐明，其结果在以前的文献中已有报道。获得全部四种奥古洛尔型皂苷（20S，24R（delta86，delta85）; 20S，24S（delta87，delta88）; 20R，24R（delta86，delta86）; 20R，24S（delta86，delta87），此外，还得到了8种化合物首先鉴定了具有环化侧链的（3、8、9、10、15、16、19和22）。大多数测试化合物对两种类型的细胞都具有一定程度的细胞毒性，这暗示这些氧化产物可能对原料的体内抗癌功能起一定作用。同时，结
• Study on Antidepressant Activity of Pseudo-Ginsenoside HQ on Depression-Like Behavior in Mice
  作者：Li-xue Chen、Zeng Qi、Zi-jun Shao、Shan-shan Li、Yu-li Qi、Kun Gao、Song-xin Liu、Zhuo Li、Yin-shi Sun、Ping-ya Li

  DOI：10.3390/molecules24050870

  日期：——

  Suppressive effects of ginsenoside Rh2 (Rh2), (24R)-pseudo-ginsenoside HQ (R-PHQ), and (24S)-pseudo-ginsenoside HQ (S-PHQ) against lipopolysaccharide (LPS)-induced depression-like behavior were evaluated using the forced swimming test (FST) and tail suspension test (TST) in mice. Pretreatment with Rh2, R-PHQ, and S-PHQ significantly decreased immobility time in FST and TST with clear dose-dependence, and significantly downregulated levels of serum tumor necrosis factor-α and interleukin-6, and upregulated superoxide dismutase activity in the hippocampus of LPS-challenged mice. Furthermore, R-PHQ and S-PHQ significantly increased the expression of the brain-derived neurotrophic factor (BDNF), tropomyosin-related kinase B (TrkB), sirtuin type 1 (Sirt1), and nuclear-related factor 2, and inhibited the phosphorylation of inhibitor of κB-α and nuclear factor-κB (NF-κB) in the hippocampus of LPS-challenged mice. Additionally, the antidepressant-like effect of R-PHQ was found related to the dopaminergic (DA), γ-aminobutyric acid (GABA)ergic, and noradrenaline systems, while the antidepressive effect of S-PHQ was involved in the DA and GABAergic systems. Taken together, these results suggested that Rh2, R-PHQ, and S-PHQ produced significant antidepressant-like effects, which may be related to the BDNF/TrkB and Sirt1/NF-κB signaling pathways.

  本研究评估了人参皂苷Rh2（Rh2）、（24R）-伪人参皂苷HQ（R-PHQ）和（24S）-伪人参皂苷HQ（S-PHQ）对脂多糖（LPS）诱导的抑郁样行为的抑制作用，使用小鼠强制游泳试验（FST）和尾悬试验（TST）进行评估。Rh2、R-PHQ和S-PHQ的预处理显著减少了FST和TST中的不动时间，并呈明显的剂量依赖性，显著降低了LPS挑战小鼠血清肿瘤坏死因子-α和白细胞介素-6水平，并上调了海马中超氧化物歧化酶活性。此外，R-PHQ和S-PHQ显著增加了脑源性神经营养因子（BDNF）、肌动蛋白相关激酶B（TrkB）、sirtuin类型1（Sirt1）和核相关因子2的表达，并抑制了LPS挑战小鼠海马中抑制κB-α和核因子κB（NF-κB）的磷酸化。另外，R-PHQ的抗抑郁效应与多巴胺能（DA）、γ-氨基丁酸（GABA）能和去甲肾上腺素系统有关，而S-PHQ的抗抑郁效应与DA和GABA能系统有关。综上所述，这些结果表明Rh2、R-PHQ和S-PHQ具有显著的抗抑郁样效应，可能与BDNF / TrkB和Sirt1 / NF-κB信号通路有关。
• Synthesis of Ocotillol-Type Ginsenosides
  作者：Renzeng Shen、Xin Cao、Stephane Laval、Jiansong Sun、Biao Yu

  DOI：10.1021/acs.joc.6b01265

  日期：2016.11.4

  A total of 14 ocotillol-type ginsenosides were conveniently synthesized employing glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I) catalyst as the key step. Relying on a rational protecting group strategy and the unexpected regioselectivity of the glycosylation of the 3,25-diol sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the configuration at the C-24 is either R or S.
• Novel ginsenoside derivative 20(S)-Rh2E2 suppresses tumor growth and metastasis in vivo and in vitro via intervention of cancer cell energy metabolism
  作者：Qi Huang、Hui Zhang、Li Ping Bai、Betty Yuen Kwan Law、Haoming Xiong、Xiaobo Zhou、Riping Xiao、Yuan Qing Qu、Simon Wing Fai Mok、Liang Liu、Vincent Kam Wai Wong

  DOI：10.1038/s41419-020-02881-4

  日期：——

  Increased energy metabolism is responsible for supporting the abnormally upregulated proliferation and biosynthesis of cancer cells. The key cellular energy sensor AMP-activated protein kinase (AMPK) and the glycolytic enzyme alpha-enolase (α-enolase) have been identified as the targets for active components of ginseng. Accordingly, ginseng or ginsenosides have been demonstrated with their potential values for the treatment and/or prevention of cancerviathe regulation of energy balance. Notably, our previous study demonstrated that theR-form derivative of 20(R)-Rh2, 20(R)-Rh2E2 exhibits specific and potent anti-tumor effect via suppression of cancer energy metabolism. However, the uncertain pharmacological effect ofS-form derivative, 20(S)-Rh2E2, the by-product during the synthesis of 20(R)-Rh2E2 from parental compound 20(R/S)-Rh2 (with bothR- andS-form), retarded the industrialized production, research and development of this novel effective candidate drug. In this study, 20(S)-Rh2E2 was structurally modified from pure 20(S)-Rh2, and this novel compound was directly compared with 20(R)-Rh2E2 for their in vitro and in vivo antitumor efficacy. Results showed that 20(S)-Rh2E2 effectively inhibited tumor growth and metastasis in a lung xenograft mouse model. Most importantly, animal administrated with 20(S)-Rh2E2 up to 320 mg/kg/day survived with no significant body weight lost or observable toxicity upon 7-day treatment. In addition, we revealed that 20(S)-Rh2E2 specifically suppressed cancer cell energy metabolism via the downregulation of metabolic enzyme α-enolase, leading to the reduction of lactate, acetyl-coenzyme (acetyl CoA) and adenosine triphosphate (ATP) production in Lewis lung cancer cells (LLC-1), but not normal cells. These findings are consistent to the results obtained from previous studies using a similar isomer 20(R)-Rh2E2. Collectively, current results suggested that 20(R/S)-Rh2E2 isomers could be the new and safe anti-metabolic agents by acting as the tumor metabolic suppressors, which could be generated from 20(R/S)-Rh2 in industrialized scale with low cost.
• Glycosylation of triterpenoids of the dammarane series. VI. 3-mono- and 3,12-di-O-β-D-glucopyranosides of pyxinol
  作者：L. N. Atopkina、N. I. Uvarova

  DOI：10.1007/bf00579815

  日期：1986.7