三角叶薯蓣皂苷 | 55659-75-1

• 物质功能分类: 生物化工 - 提取物
• 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: 三角叶薯蓣皂苷
• 英文名称: deltonin
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 55659-75-1
• 化学式: C₄₅H₇₂O₁₇
• 分子量: 885.056
• InChiKey: OLAMGHNQGZIWHZ-YIKYYZBWSA-N

物化性质

• 熔点：
  298-300 °C (decomp)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  256
• 氢给体数：
  9
• 氢受体数：
  17

制备方法与用途

概述

黄姜，学名盾叶薯蓣（Dioscorea zhingiberensis C.H.Wright），是薯蓣科薯蓣属植物的一种。该植物是我国特有的野生植物资源之一。三角叶薯蓣皂苷（Deltonin）是从盾叶薯蓣中提取出的一种甾体皂苷，具有多种药理活性，在对抗心血管疾病方面表现突出，如保护血管内皮细胞、降血脂、预防和治疗血栓、改善冠状动脉供血及预防和治疗心肌梗死。

生物活性

Deltonin 能够抑制 ERK1/2 和 AKT 的活化，并具有抗肿瘤活性。

靶点
ERK1
ERK2
Akt
人类内源性代谢物

体外研究

Deltonin 抑制 ERK1/2 和 AKT 的活化。在多种结肠癌细胞系（包括 SW480、SW620、LOVO 和 C26）中，Deltonin (0.5-8 μM) 显著抑制了细胞增殖，IC50 值分别为 1.3、1.29、2.11 和 1.22 μM。此外，在 C26 细胞中 Deltonin 还导致 G2-M 期阻滞并诱导凋亡。Deltonin (0-5 μM) 减少了 MDA‑MB‑231 细胞中 AKT 和 ERK1/2 的磷酸化水平，并以剂量依赖性方式抑制了这些细胞的增殖，同时导致 ROS 产生和凋亡。

体内研究

Deltonin (20 和 40 mg/kg, p.o.) 在小鼠中减少了肿瘤生长 37.7% 和 56.7%，并分别在第 50 天导致生存率为 60% 和 50%。此外，Deltonin 还抑制了小鼠的肿瘤血管生成。

反应信息

• 作为反应物：
  描述：

  三角叶薯蓣皂苷 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 薯蓣皂素
  参考文献：
  名称：

  Watanabe, Yoshiaki; Sanada, Shuichi; Ida, Yoshiteru, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 10, p. 3486 - 3495

  摘要：

  DOI：
• 作为产物：
  描述：

  盾叶新苷 在 steroidal saponin-β-glucosidase from Aspergillus flavus 作用下， 以 aq. buffer 为溶剂， 生成 三角叶薯蓣皂苷
  参考文献：
  名称：

  Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin

  摘要：

  A new steroidal saponin-beta-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal beta-D-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-beta-glucosidase was 50 degrees C and pH 5.0. The steroidal saponin-beta-glucosidase was stable at 30-60 degrees C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a beta-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-beta-glucosidase and steroidal saponin-alpha-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.09.013

文献信息

• Steroidal saponins from the bulbs of Lilium longiflorum and their antitumour-promoter activity
  作者：Yoshihiro Mimaki、Osamu Nakamura、Yutaka Sashida、Yoshiko Satomi、Atsuko Nishino、Hoyoku Nishino

  DOI：10.1016/0031-9422(94)85030-5

  日期：1994.1

  3-O-(O-alpha-L-rhamnopyranosyl-(1 --> 2)- O-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranoside). The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

  从长花百合的新鲜鳞茎中分离出两种新的螺甾醇皂苷和两种新的呋甾醇皂苷以及几种已知的皂苷。新化合物的结构被确定为 (25S)-spirost-5-ene-3 beta, 27-diol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-O- [alpha -L-阿拉伯吡喃糖基-(1-->3)]-β-D-吡喃葡萄糖苷)，(25R)-27-O-[(S)-3-羟基-3-甲基戊二酰基]-spirost-5-ene-3 β,27二醇3-O-(O-α-L-吡喃鼠李糖基-(1-->2)-O-[α-L-阿拉伯吡喃糖基-(1-->3)]-β-D-吡喃葡萄糖苷)， 22-O-甲基-26-O-β-D-吡喃葡萄糖基-(25R)-furost-5-ene-3 beta,22 xi, 26-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1 -->2)-O-[α-L
• Steroidal Glycosides from the Aerial Parts of <i>Avena sativa</i> L. and Their Cytotoxic Activity
  作者：Akihito Yokosuka、Keita Ishihara、Tsuyoshi Yamada、Tomoki Iguchi、Yoshihiro Mimaki

  DOI：10.1021/acs.jafc.1c05782

  日期：2021.12.8

  Twelve steroidal glycosides (1–12) were isolated from the aerial parts of Avena sativa L. (Poaceae). Among the isolated compounds, 1 was directly isolated from the plant for the first time, and 2–6 were new steroidal glycosides. The structures of 1–6 were determined by analysis of their spectroscopic data, chemical transformations, and chromatographic and spectroscopic analyses of the hydrolyzed products

  十二甾体糖苷（1 - 12）获自的地上部分分离燕麦L.（禾本科）。分离出的化合物中，有1种为首次从植物中直接分离得到，2～6种为新的甾体苷。的结构1 - 6被他们的光谱数据，化学转化，以及水解产物的色谱和光谱分析的分析来确定。化合物5和6是具有B环收缩骨架的新型甾体糖苷（B-nor steroid）。化合物1 , 9 ,图11和12对HL-60人早幼粒细胞白血病细胞、MIA PaCa-2人胰腺癌细胞和A549人肺腺癌细胞具有细胞毒性，IC 50值范围为0.79至13.5μM。用1处理的 HL-60 细胞表现出凋亡特征，即核染色质凝聚、亚 G1 细胞的积累和 caspase-3 的激活。此外，在1处理的 HL-60 细胞中，线粒体膜电位的丧失和细胞色素c释放到细胞质中表明1通过线粒体依赖性细胞凋亡途径诱导细胞凋亡。
• Hirai, Yasuaki; Sanada, Shuichi; Ida, Yoshiteru, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 10, p. 4003 - 4011
  作者：Hirai, Yasuaki、Sanada, Shuichi、Ida, Yoshiteru、Shoji, Junzo

  DOI：——

  日期：——
• Watanabe, Yoshiaki; Sanada, Shuichi; Ida, Yoshiteru, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 10, p. 3486 - 3495
  作者：Watanabe, Yoshiaki、Sanada, Shuichi、Ida, Yoshiteru、Shoji, Junzo

  DOI：——

  日期：——
• Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin
  作者：Hongzhi Huang、Min Zhao、Li Lu、Dawei Tan、Wenbin Zhou、Chengqi Xiong、Yang Zhao、Xinbo Song、Liyan Yu、Baiping Ma

  DOI：10.1016/j.molcatb.2013.09.013

  日期：2013.12

  A new steroidal saponin-beta-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal beta-D-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-beta-glucosidase was 50 degrees C and pH 5.0. The steroidal saponin-beta-glucosidase was stable at 30-60 degrees C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a beta-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-beta-glucosidase and steroidal saponin-alpha-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study. (C) 2013 Elsevier B.V. All rights reserved.