大豆皂醇 E | 6750-59-0

• 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
• 中文名称: 大豆皂醇 E
• 中文别名: 大豆皂醇E；大豆皂甙元E；大豆甾醇E
• 英文名称: soyasapogenol E
• 英文别名: (4aR,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,4a,6a,6b,9,12a-heptamethyl-3,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picen-4-one
• CAS: 6750-59-0
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: FNRBOAGVUNHDIL-LMZUXBMISA-N

物化性质

• 沸点：
  554.6±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  大豆皂醇 E 在 硼烷四氢呋喃络合物 、 camphor-10-sulfonic acid 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 40.75h， 生成 22β-hydroxymethyl-3β,24-isopropilidenedioxyolean-12-ene
  参考文献：
  名称：

  Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model

  摘要：

  To shed light on the structure-activity relationship, various so soyasapogenol B derivatives were synthesized and evaluated for preventive effects on liver injury in the concanavalin A (Con A)-induced hepatitis model in mice, Con A injection into mice induces some pathophysiology of human liver disease such as autoimmune or viral hepatitis, Two hydroxyl groups on the A ring of soyasapogenol B are required for amelioration of liver damage, Modification of the C-22 hydroxyl moiety with an acyloxy or alkyloxy group, or removal of the hydroxyl group. resulted in I greatly enhanced percentage of alleviation. Among the series of soyasapogenol B derivatives examined, six compounds exhibited preventive effects on liver damage. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.074
• 作为产物：
  描述：

  去氢大豆皂甙I 在 盐酸 作用下， 反应 1.25h， 生成 大豆皂醇 E
  参考文献：
  名称：

  满天金（Desmodium styracifolium）成分的研究。

  摘要：

  从Desmodii Herba [满地香（Desmodium styracifolium（Osbeck）Merr）干燥的整株植物中分离出了两个三萜皂苷（1和2）。（豆科）]及其化学结构被表征为大豆皂苷I和新的皂苷3-O- [α-L-鼠李糖基-（1 ---- 2）-β-D-吡喃半乳糖基-（1 ---- 2）通过化学和光谱方法分别测定β-D-D-葡萄糖醛酸吡喃糖基]大豆皂酚E。

  DOI：

  10.1248/cpb.37.2229

文献信息

• [EN] BILE ACIDS AND USE IN DISEASE TREATMENT<br/>[FR] ACIDES BILIAIRES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES
  申请人：UNIV CALIFORNIA

  公开号：WO2020154397A1

  公开（公告）日：2020-07-30

  Compositions and methods of use for modulating bile acids, including phenylalanocholic acid, tyrosocholic acid and leucocholic acid, to treat diseases, such as inflammatory bowel disease. In embodiments, the invention provides pharmaceutical compositions that modulate levels of a bile acid conjugate in a subject. In embodiments, the invention provides pharmaceutical compositions that modulate levels of a bile acid conjugate in a particular organ or bodily region of the subject.

  调节胆汁酸，包括苯丙氨胆酸、酪氨酸胆酸和亮氨酸胆酸等的使用组合物和方法，用于治疗炎症性肠病等疾病。在实施例中，本发明提供了调节受试者体内胆汁酸共轭物水平的药物组合物。在实施例中，本发明提供了调节受试者特定器官或身体区域内胆汁酸共轭物水平的药物组合物。
• Regioselective Oxidation of the Hydroxyl Group in Polyhydroxylated Triterpenes by the Indirect Anodic Oxidation Method.
  作者：Masayuki YOSHIKAWA、Toshiyuki MURAKAMI、Nobuhiro YAGI、Nobutoshi MURAKAMI、Johji YAMAHARA、Hisashi MATSUDA、Hatsuo MAEDA、Hidenobu OHMORI

  DOI：10.1248/cpb.45.570

  日期：——

  Indirect anodic oxidation of soyasapogenol B (3β, 22β, 24-trihydroxyolean-12-ene) was carried out using KI as a mediator in t-BuOH-H2O solution, so that the 3-ketone derivative was obtained as the only oxidation product in a favorable yield. As a result of application to various polyhydroxylated triterpenes, selective electrochemical oxidation was shown to occur in the C-3 hydroxyl group of the polyhydroxyl triterpenes with the C-24 hydroxyl group. The reaction pathway is discussed.

  以 KI 为介质，在 t-BuOH-H2O 溶液中对大豆苷元 B（3β, 22β, 24-三羟基油菜素-12-烯）进行了间接阳极氧化，从而获得了 3-酮衍生物作为唯一的氧化产物，且产率较高。对各种多羟基三萜的应用结果表明，多羟基三萜的 C-3 羟基与 C-24 羟基发生了选择性电化学氧化反应。对反应途径进行了讨论。
• Soyasaponins from Soybean Flour Medium for the Liquid Culture of Ganoderma applanatum
  作者：So-Young Lee、Ju-Sun Kim、Sang-Hee Shim、Sam-Sik Kang

  DOI：10.5012/bkcs.2011.32.10.3650

  日期：2011.10.20

  Two new unusual soyasaponins named 6"-O-methyldehydrosoyasaponin I(7) and desglucosylsoyasaponin $A_1$ (10) along with eight known saponins, dehydrosoyasaponin IV (1), dehydrosoyasaponin III (= impatienoside A) (2), soyasaponin III (3), dehydrosoyasaponin II (= soyasaponin Bg) (4), soyasaponin II (5), dehydrosoyasaponin I (= soyasaponin Be) (6), soyasaponin I (8), and kudzusaponin $SA_3$ (9), were isolated as their methyl esters and identified from the liquid culture of G. applanatum. Their structures were determined by chemical and spectroscopic analyses including 1D- and 2D-NMR as well as by comparison of their spectroscopic data with those of the reported in literatures. Although dehydrosoyasaponin IV was identified by LC-MS/MS method from soy protein isolate, this is the first report of the isolation of this compound. Dehydrosoyasaponin III (2) and kudzusaponin $SA_3$ (9) were also isolated for the first time from soybean. The presence of soyasaponins in Ganoderma species seems to be unusual feature. Thus, we presumed that compounds 1-10 might all be derived from the defatted soybean flour which was added to the culture medium as a nitrogen source.

  两种新的不寻常的大豆皂苷被命名为 6"-O-甲基二氢大豆皂苷 I(7) 和去葡萄糖基大豆皂苷 $A_1$(10) 以及八种已知的皂苷，脱水大豆皂苷 IV (1)，脱水大豆皂苷 III (= impatienoside A) (2)，大豆皂苷 III (3)、(4)、大豆皂苷 II (5)、脱水酰皂苷 I (=大豆皂苷 Be) (6)、大豆皂苷 I (8)和 kudzuSAponin $SA_3$(9)的甲基酯，并从 G. applanatum 的液体培养物中进行了鉴定。applanatum。通过化学和光谱分析（包括一维和二维核磁共振）以及与文献报道的光谱数据进行比较，确定了它们的结构。虽然通过 LC-MS/MS 方法从大豆分离蛋白中鉴定出了脱水酰皂苷 IV，但这是首次报道分离出该化合物。此外，还首次从大豆中分离出脱氢酰基皂苷 III (2) 和 kudzuSAponin $SA_3$ (9)。灵芝物种中存在大豆皂甙似乎是一个不寻常的特征。因此，我们推测 1-10 号化合物可能都来自作为氮源添加到培养基中的脱脂大豆粉。
• Methods of identifying genes for the manipulation of triterpene saponins
  申请人：The Samuel Roberts Noble Foundation

  公开号：US20040002105A1

  公开（公告）日：2004-01-01

  The invention provides methods for the isolation of plant genes and their regulatory sequences involved in the biosynthesis of triterpene saponins. Also provided by the invention are genes involved in the biosynthesis of triterpenes, including squalene synthase, squalene epoxidase and &bgr;-amyrin synthase from Medicago truncatula . The identification of triterpene biosynthesis genes allows genetic modification of the content and composition of triterpene saponins in plants for crop improvement and the development of drugs, nutriceuticals and functional foods.

  本发明提供了用于分离参与三萜皂苷生物合成的植物基因及其调控序列的方法。本发明还提供了参与三萜类物质生物合成的基因，包括来自苜蓿的角鲨烯合酶、角鲨烯环氧化酶和β-阿麦烯合酶。三萜类物质生物合成基因的鉴定允许对植物中三萜皂苷的含量和组成进行遗传修饰，以实现作物改良和开发药物、营养保健品和功能性食品。
• UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds
  作者：Yasunori Kurosawa、Hidenari Takahara、Masakazu Shiraiwa

  DOI：10.1007/s00425-002-0781-x

  日期：2002.8.1

  Abstract. We detected UDP-glucuronic acid:soyasapogenol glucuronosyltransferase (UGASGT) activity in the microsomal fraction from germinating soybean (Glycine max [L.] Merr.) seed. A microsomal fraction was isolated from germinating soybean seed and treated with various detergents to solubilize the enzyme. UGASGT activity was monitored throughout purification using UDP-[U-14C]glucuronic acid and soyasapogenol B

  摘要。我们检测到来自发芽大豆 (Glycine max [L.] Merr.) 种子的微粒体部分中的 UDP-葡萄糖醛酸：大豆皂苷醇葡萄糖醛酸基转移酶 (UGASGT) 活性。从发芽的大豆种子中分离微粒体部分并用各种去污剂处理以溶解酶。使用UDP-[U-14C]葡萄糖醛酸和大豆皂醇B作为底物，在整个纯化过程中监测UGASGT活性。UGASGT 的纯化通过 HiTrap Q、Superdex 200 和 HiTrap Blue 色谱程序实现。这导致相对于起始匀浆的 >205 倍的富集。发现 UGASGT 需要二价阳离子才能发挥活性。对 UGASGT 底物特异性的研究表明，对转移的糖残基的特异性非常高，当 UDP-葡萄糖醛酸被其他 UDP 糖：UDP-葡萄糖和 UDP-半乳糖取代时，几乎没有发现活性。大豆皂苷元是大豆皂苷的苷元，是可用的受体，但甘草次酸、槐二醇、β-香树脂醇和黄酮类化合物不是。