cauloside D | 12672-45-6

• 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: cauloside D
• 英文别名: hederagenin 3-O-α-L-arabinopyranoside 28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester；Kizuta saponin K₁₀；[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 12672-45-6
• 化学式: C₅₃H₈₆O₂₂
• 分子量: 1075.25
• InChiKey: UEHILKCNLIKLEV-LXABABOZSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  75
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  354
• 氢给体数：
  13
• 氢受体数：
  22

制备方法与用途

生物活性方面，Cauloside D 是从 Caulophyllum robustum Max 中分离出的一种三萜苷类化合物。研究显示，Cauloside D 能够通过抑制 iNOS 和促炎细胞因子的表达来发挥抗炎作用。

反应信息

• 作为反应物：
  描述：

  cauloside D 在 氢氧化钾 、 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 常春藤皂苷元
  参考文献：
  名称：

  摘要：

  The previously known triterpenoid 3-O-alpha -L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-alpha -L-rhamnopyranosyl-(1 -->4)-O-beta -D-glucopyranosyl-(1-6)-O-beta -D-glucopyranosyl ethers of the 3-O-alpha -L-arabinopyranoside of hederagenin, and 3-O-beta -D-glucopyranosyl-(1 -->2)-O-alpha -L-arbinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical Methods and (CNMR)-C-13 spectroscopy.

  DOI：

  10.1023/a:1002891507725
• 作为产物：
  描述：

  hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 在 氢氧化钾 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 cauloside D
  参考文献：
  名称：

  Studies on the constituents of Hedera rhombea Bean. IV. On the hederagenin glycosides. (2)

  摘要：

  基于化学和物理化学证据，确定了从常春藤（Hedera rhombea BEAN，五加科）的茎和树皮中分离出的两种新的常春素双甙的结构，分别命名为Kizuta皂苷K8（X）和K11（I），其结构如下：X为3-O-α-L-阿拉伯呋喃糖基-常春素28-O-α-L-鼠李呋喃糖基-(1→4)-6-O-乙酰基-β-D-葡萄吡喃糖基-(1→6)-β-D-葡萄吡喃糖基酯；I为3-O-α-L-鼠李呋喃糖基-(1→2)-α-L-阿拉伯呋喃糖基-常春素28-O-α-L-鼠李呋喃糖基(1→4)-6-O-乙酰基-β-D-葡萄吡喃糖基-(1→6)-β-D-葡萄吡喃糖基酯。基于化学和物理化学证据，认为葡萄糖苷混合物（XIII）是油菜甾醇（微量）、豆甾醇和β-谷甾醇的β-D-葡萄吡喃糖苷混合物。

  DOI：

  10.1248/cpb.33.3473

文献信息

• Triterpene Glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from Leaves of Kalopanax septemlobum var. Maximowichii Introduced to Crimea
  作者：V. I. Grishkovets、D. A. Panov、V. V. Kachala、A. S. Shashkov

  DOI：10.1007/s10600-005-0110-2

  日期：2005.3

  Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum.

  从引入克里米亚的刺楸变种Kalopanax septemlobum var. maximowichii叶中，通过色谱方法分离出了已知的8种常春藤苷元和新的三萜皂苷3-O-β-D-吡喃木糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-O-α-L-吡喃阿拉伯糖基-28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯常春藤苷元。在鵺中首次观察到已知的3-O-α-L-吡喃阿拉伯糖基-28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯常春藤苷元。
• Triterpenoid glycosides from Stauntonia hexaphylla
  作者：Huai-Bin Wang、Ralf Mayer、Gerhard Rücker

  DOI：10.1016/0031-9422(91)80035-y

  日期：1993.11

  On the basis of spectroscopic and chemical methods, the structures of two new bisdesmosidic triterpenoid glycosides, named staunoside D and E, which were isolated from Stauntonia hexaphylla, were established as 3-O-(beta-D-glucopyranosyl(1-->2)-[beta-D- glucopyranosyl(1-->3)]-beta-D-glucopyranosyl)-hederagenin-28- O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester and 28-O-[alpha-L-rhamnopyranosyl

  在光谱和化学方法的基础上，从六叶石蕊中分离出的两种新的双桥苷三萜糖苷，命名为 staunoside D 和 E 的结构被确定为 3-O-(beta-D-glucopyranosyl(1-->2 )-[β-D-吡喃葡萄糖基(1-->3)]-β-D-吡喃葡萄糖基)-hederagenin-28-O-[β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]酯和 28-O-[α-L-吡喃鼠李糖基 (1-->4)-β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]酯，分别。还分离了三种已知的三萜糖苷。从酯糖苷键的断裂中分离出一种新的糖苷原，并对其结构进行了表征。
• Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis
  作者：Xiao-Yang Wang、Hui Gao、Wei Zhang、Yuan Li、Guang Cheng、Xiao-Li Sun、Hai-Feng Tang

  DOI：10.1016/j.bmcl.2013.08.006

  日期：2013.10

  extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1–12, prosapogenins 4a, 5a, 10a–12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines

  所述的调查Ñ的根茎的提取物-BuOH海葵太白导致了五个新的齐墩果烷型三萜皂甙（隔离1 - 5），用七个已知皂苷（一起6 - 12）。通过广泛使用1 D和2 D NMR实验以及ESIMS分析和酸水解来确定其结构。的糖苷配基1，2和4被确定为siaresinolic酸，其据报道该属首次。皂苷1 – 12，促皂甙元的细胞毒性分别评估了4a，5a，10a – 12a和皂苷元唾液酸树脂（SA），齐墩果酸（OA），二十碳皂素（HE）针对五种人类癌细胞系，包括HepG2，HL-60，A549，HeLa和U87MG。所述monodesmosidic皂苷6 - 8，5A，10A - 12A和皂苷元SA，OA，HE表现出细胞毒性活性对所有癌细胞系，用IC 50个值范围为2.25至57.28微米。值得注意的是，双糖苷皂苷1 –图4和9显示了对U87MG细胞的选择性细胞毒性。
• New triterpenoid saponins from the whole plants of Clematis heracleifolia
  作者：Qian Zhang、Yun-Yang Lu、Liu Yang、Hai-Feng Tang

  DOI：10.1016/j.fitote.2022.105179

  日期：2022.6

  Three new triterpenoid saponins, heracleifolianosides A-C (1–3), together with seven known compounds (4–10), were isolated from the whole plants of Clematis heracleifolia. Moreover, three new secondary saponins (1a, 2a and 3a), two known secondary metabolites (5a and 7a) were obtained by alkaline hydrolysis. Their structures were elucidated by extensive spectroscopic analysis and chemical evidences

  三种新的三萜皂甙，heracleifolianosides AC ( 1-3 )，连同七种已知化合物 ( 4-10) ，从铁线莲的全株中分离得到。此外，通过碱解获得了三种新的次生皂苷（1a、2a和3a），两种已知的次生代谢产物（5a和7a） 。通过广泛的光谱分析和化学证据阐明了它们的结构。采用MTT法评价8种天然皂苷和5种皂苷元对人乳腺肿瘤MDA-MB-231和胃癌SGC-7901细胞系的细胞毒性。值得注意的是，prosapogenin monodesmosidic saponin图7a显示了对MDA-MB-231或SGC-7901细胞系的显着细胞毒性，IC 50值在6.05-6.32 μmol/L范围内。提示通过简单的碱解过程将无活性的双桥三萜皂苷转化为有活性的单桥皂苷可能是一种可行的方法。
• Triterpene saponins of Caltha polypetala. Glycosides G and I
  作者：M. M. Vugalter、G. E. Dekanosidze、O. D. Dzhikiya、A. S. Shashkov、�. P. Kemertelidze

  DOI：10.1007/bf00596749

  日期：——