槐花二醇 | 6822-47-5

• 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: 槐花二醇
• 英文名称: sophoradiol
• 英文别名: 12-oleanene-3β,22β-diol；olan-12-ene-3β,22β-diol；olean-12-ene-3β,22β-diol；Olean-12-en-3β,22β-diol；3β,22β-Dihydroxy-oleanen-(12)；(3S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol
• CAS: 6822-47-5
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: ZEGUWBQDYDXBNS-FVFJQADASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  槐花二醇 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以7 mg的产率得到anhydrosophoradiol
  参考文献：
  名称：

  Saponin and sapogenol. XXXI. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (1). Triterpenoidal sapogenols and 3-furanmethanol .BETA.-D-glucopyranoside.

  摘要：

  从赤豆（Vigna angularis (Willd.) Ohwi et Ohashi 豆科）种子中分离得到3-呋喃甲醇β-D-吡喃葡糖苷（1）和（+）-儿茶素7-O-β-D-吡喃葡糖苷（3），并确定了它们的结构。从赤豆中还分离得到了总赤豆皂苷混合物。通过酶解、酸解和光化学降解，从总赤豆皂苷中分离出了4种真正的皂苷元，其中包括3种已知的皂苷元：染料木苷元（7）、大豆苷元B（8）、皂土酸（9）和一个新的皂苷元，命名为赤豆皂苷元（10），并阐明了其结构。作为总赤豆皂苷酸解释放的假皂苷元之一，分离得到了一个新的皂苷元，命名为无水染料木苷元（5），并阐明了其结构。

  DOI：

  10.1248/cpb.31.664
• 作为产物：
  描述：

  大豆甾醇 B 在 吡啶 、 盐酸 、 氢氧化钾 、 一水合肼 、 pyridinium chlorochromate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.33h， 生成 槐花二醇
  参考文献：
  名称：

  Kitagawa, Isao; Wang, Hui Kang; Taniyama, Toshio, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 153 - 161

  摘要：

  DOI：

文献信息

• Chemical Modification of Oleanene Type Triterpenes and Their Inhibitory Activity against HIV-1 Protease Dimerization.
  作者：Chao-mei MA、Norio NAKAMURA、Masao HATTORI

  DOI：10.1248/cpb.48.1681

  日期：——

  Oleanolic acid derivatives with different lengths of 3-O-acidic acyl chains were synthesized and evaluated for their inhibitory activity against HIV-1 protease. The lengths of the acidic chains were optimized to 6 and 8 carbons. Changing a 3-ester bond to an amide bond or dimerization of the triterpenes retained their inhibitory activity against HIV-1 protease. Introduction of an additional acidic chain to C-28 of oleanolic acid increased the inhibitory activity appreciably, though a derivative with only one acidic chain linked at C-28 also showed potent activity against HIV-1 protase.The inhibitory mechanism was proved directly by size exclusion chromatography to be inhibition of dimerization of the enzyme polypeptides. The ester bonds of the triterpene derivatives were found to be stable to lipase under mild alkaline conditons.

  合成了不同长度的3-O-酸性酰基链的齐墩果酸衍生物，并评估其对HIV-1蛋白酶的抑制活性。酸性链的长度经过优化为6和8个碳。将3-酯键更改为酰胺键或三萜的二聚化保留了它们对HIV-1蛋白酶的抑制活性。在齐墩果酸C-28位引入额外的酸性链显著提高了抑制活性，尽管只在C-28位连接一个酸性链的衍生物同样对HIV-1蛋白酶表现出强效活性。通过尺寸排阻色谱直接证明了抑制机制为对酶多肽二聚化的抑制。在温和碱性条件下，发现三萜衍生物的酯键对脂肪酶具有稳定性。
• Saponin and sapogenol. XXXII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (2). Azukisaponins I,II,III, and IV.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.674

  日期：——

  Six oleanene-oligoglycosides named azukisaponins I (1), II (2), III (3), IV (4), V, and VI were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae). Among them, the structures of azukisaponins I, II, III, and IV were elucidated as 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] sophoradiol (1), 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasapogenol B (2), 3-O[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] azukisapogenol (3), and 3-O-(β-D-glucopyranosyl)-28-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] gypsogenic acid (4), respectively on the basis of chemical and physicochemical evidence.

  从赤小豆（Vigna angularis (WILLD.) OHWI et OHASHI (豆科) 的种子）中分离出六种名为赤小豆皂苷 I (1)、II (2)、III (3)、IV (4)、V和 VI 的烯烃醇寡糖苷。其中，赤小豆皂苷 I、II、III 和 IV 的结构分别阐明为 3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 番荔枝醇 (1)、3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 大豆皂苷醇 B (2)、3-O[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 赤小豆皂苷醇 (3)、以及 3-O-(β-D-吡喃葡萄糖)-28-O-[β-D-吡喃葡萄糖（1→6）-β-D-葡萄糖醛酸吡喃] 石膏酸 (4)，这些均是基于化学和物理化学证据的结果。
• TRITERPENE OXIDASE DERIVED FROM PLANT BELONGING TO GENUS GLYCYRRHIZA, GENE ENCODING THE SAME, AND METHOD OF USING THE SAME
  申请人：Muranaka Toshiya

  公开号：US20120246760A1

  公开（公告）日：2012-09-27

  Identification of a protein having an activity of oxidizing oleanane-type triterpene, and a gene encoding the protein, the protein and the gene, and use thereof are provided. For example, a protein having an activity of oxidizing oleanane-type triterpene obtained from a plant in the family Fabaceae, a gene encoding the protein and use thereof are provided. The protein is shown in, for example, SEQ ID NO: 4, 14 or 18, and the gene encoding the protein is shown in, for example, SEQ ID NO: 3, 13 or 17. A transformant into which the gene is introduced can be produced, and thereby a triterpene oxidase can be obtained.

  提供了一种具有氧化齐墩果烷型三萜活性的蛋白质的鉴定，以及编码该蛋白质的基因、该蛋白质和基因的使用方法。例如，提供了一种从豆科植物中获得的具有氧化齐墩果烷型三萜活性的蛋白质，编码该蛋白质的基因及其使用方法。该蛋白质可以在例如序列ID编号：4、14或18中显示，编码该蛋白质的基因可以在例如序列ID编号：3、13或17中显示。可以产生转基因体，该基因被引入其中，从而可以获得一种三萜氧化酶。
• The tetramethylallyl cation as a surrogate for the epoxide function as an initiator of biomimetic polyene pentacyclizations. Total synthesis of sophoradiol
  作者：Paul V Fish、William S Johnson

  DOI：10.1016/s0040-4039(00)76734-7

  日期：1994.3

  The tetramethylallyl cation has proven to be an effective substitute for the epoxide as an initiator for biomimetic polyene cyclizations. This methodology was applied to the total synthesis of the pentacyclic triterpenoid sophoradiol (1) whereby the key step of the strategy involved the protic acid-catalyzed pentacyclization of tetramethylallyl alcohol 9 which furnished fluoropentacycle 11 as the major

  四甲基烯丙基阳离子已被证明是环氧化物的有效替代品，可作为仿生多烯环化反应的引发剂。该方法学应用于五环三萜类槐糖二醇（1）的全合成，其中该策略的关键步骤涉及质子酸催化的四甲基烯丙醇9的五环化反应，该产物以31％的收率提供了氟五环11作为主要产物。路易斯酸催化的9的环化反应以50％的收率得到了脱氟化氢的五环化合物12。
• Periandradulcins A, B and C: Phosphodiesterase inhibitors from Periandra dulcis Mart.
  作者：Yoshitaka IKEDA、Masanori SUGIURA、Chikara FUKAYA、Kazumasa YOKOYAMA、Yohei HASHIMOTO、Kazuko KAWANISHI、Midori MORIYASU

  DOI：10.1248/cpb.39.566

  日期：——

  During the course of our screening of bioactive natural products, three new saponins named periandradulcins A (1), B (2) and C (3) were isolated as phosphodiesterase (PDE, EC 3.1.4.17) inhibitors from 80% MeOH extract of the roots of Periandra dulcis MART. (Leguminosae) by a combination of column chromatography and reversed- and normal-phase high-performance liquid chromatography (HPLC). On the basis of -1H, 13C- and two-dimensional nuclear magnetic resonance (NMR) spectral data and chemical evidence, their chemical structures were characterized as 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-hydroxyl-25-formylolean-18-ene-22β-O-syringate, 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]-22β-hydroxyl-25-formylolean-12-ene and 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranosyl]-22β-hydroxyl-25-formylolean-18-ene, respectively.The concentrations of periandradulcins A, B and C required to give 50% inhibition (IC50 values) of PDE from bovine heart, were 0.033, 7.6 and 7.7 μM, respectively. Compound 1 was the most potent among the known PDE inhibitors; it inhibited PDE-I (IC50 : 0.0022 μM) twenty and forty times more effectively than PDE-II and -III, respectively.

  在筛选生物活性天然产物的过程中，我们通过柱层析、反相和正相高效液相色谱法（HPLC）相结合的方法，从豆科植物 Periandra dulcis MART. 的根部 80% MeOH 提取物中分离出了三种新的皂苷，分别命名为 Periandradulcins A (1)、B (2) 和 C (3)，作为磷酸二酯酶（PDE，EC 3.1.4.17）抑制剂。(通过柱色谱法和反相与正相高效液相色谱法（HPLC）相结合的方法，从 Periandra dulcis MART 的根部 80% MeOH 提取物中分离出磷酸二酯酶（PDE）抑制剂。根据-1H、13C 和二维核磁共振（NMR）光谱数据和化学证据，确定其化学结构为 3-O-β-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-羟基-25-formylolean-18-ene-22β-O-丁环酸酯、3-O-β-[α-L-吡喃鼠李糖基（1→2）-β-D-吡喃木糖基（1→2）-β-D-吡喃葡萄糖呋喃糖基]-22β-羟基-25-formylolean-12-烯和 3-O-β-[α-L-吡喃鼠李糖基（1→2）-β-D-吡喃葡萄糖呋喃糖基（1→2）-β-D-吡喃葡萄糖呋喃糖基]-22β-羟基-25-formylolean-18-烯、分别为对牛心脏中的 PDE 产生 50% 抑制作用所需的 Periandradulcins A、B 和 C 浓度（IC50 值）分别为 0.033、7.6 和 7.7 μM。在已知的 PDE 抑制剂中，化合物 1 的效力最强；它对 PDE-I 的抑制作用（IC50：0.0022 μM）分别是 PDE-II 和 PDE-III 的 20 倍和 40 倍。