Pharbitic Acid D

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Pharbitic Acid D
• 英文别名: (3S,11S)-11-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-methyl-4-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-3-hydroxytetradecanoic acid
• 化学式: C₅₀H₈₈O₃₀
• 分子量: 1169.23
• InChiKey: BDRSIIATOXLDQS-FFPJSITRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  80
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  472
• 氢给体数：
  17
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  Pharbitic Acid D 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Resin glycosides. VII. Reinvestigation of the component organic and glycosidic acids of pharbitin, the crude ether-insoluble resin glycoside ("convolvulin") of pharbitidis semen (seeds of Pharbitis nil).

  摘要：

  Alkaline hydrolysis of the ether-insoluble resin glycoside ("convolvulin") fraction, pharbitin, of the seeds of Pharbitis nil (Convolvulaceae) provided three organic acids, S-2-methylbutyric acid, (2R, 3R)-nilic acid and tiglic acid, and a new glycosidic acid named pharbitic acid B along with the known compounds pharbitic acids C and D. Pharbitic acid B was characterized as (3S, 11S)-3, 11-dihydroxyhexadecanoic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-quinovopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside. The structures of the sugar moieties of pharbitic acids C and D were revised.

  DOI：

  10.1248/cpb.38.1892
• 作为产物：
  描述：

  methyl (3S,11S)-11-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6R)-3-hydroxy-5-[(2R,3R)-3-[(2R,3R)-3-hydroxy-2-methylbutanoyl]oxy-2-methylbutanoyl]oxy-6-methyl-4-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-3-hydroxytetradecanoate 在 水 、 potassium hydroxide 作用下， 反应 1.0h， 以7 mg的产率得到Pharbitic Acid D
  参考文献：
  名称：

  甲醇中氯化铟（III）处理的无毒费比氏菌种子的粗糖苷（Pharbitin）生成的羟基脂肪酸甲酯的酰化糖苷

  摘要：

  用甲醇中的氯化铟（III）处理零种法氏酵母（Pharbitis Semen）种子，称为法比汀，制得粗制的醚不溶性树脂糖苷（卷积蛋白），提供了被2-甲基-3部分酰化的七个羟基脂肪酸甲酯低聚糖苷-羟基丁酸（硝酸）和2 S-甲基丁酸。根据NMR和MS数据以及化学转化率阐明了它们的结构。

  DOI：

  10.1021/np1004888

文献信息

• Pharesinosides A-G, acylated glycosidic acid methyl esters derivatized by NH 2 silica gel on-column catalyzation from the crude resin glycosides of Pharbitis Semen
  作者：Li-Juan Bai、Jian-Guang Luo、Chen Chen、Ling-Yi Kong

  DOI：10.1016/j.tet.2017.03.059

  日期：2017.5

  of Pharbitis nil), led to the isolation of seven new acylated glycosidic acid methyl esters, Pharesinosides A-G (1–7), along with four known ones (8–11). These compounds (1–11) were considered to be generated via methyl esterification of the carboxyl group in acylated glycosidic acids. Their structures including stereochemistry were elucidated on the basis of a combination of the spectroscopic and chemical

  NH中的应用2使用CH硅胶柱色谱2氯2被发现显示牵牛精液的粗树脂苷的分离令人满意的分辨率（种子-MeOH裂叶牵牛），导致了七个新酰化糖苷酸的隔离酯，Pharesinosides AG（1 – 7），以及四个已知的酯（8 – 11）。这些化合物（1 – 11）被认为是通过酰化的糖苷酸中的羧基的甲基酯化产生的。基于光谱和化学方法的结合，阐明了它们的结构，包括立体化学。用人结肠癌细胞系HCT-116评估所有分离株的抗肿瘤迁移活性，化合物7表现出有效的迁移抑制活性。
• Acylated Glycosides of Hydroxy Fatty Acid Methyl Esters Generated from the Crude Resin Glycoside (Pharbitin) of Seeds of <i>Pharbitis nil</i> by Treatment with Indium(III) Chloride in Methanol
  作者：Masateru Ono、Ayako Takigawa、Tomoko Mineno、Hitoshi Yoshimitsu、Toshihiro Nohara、Tsuyoshi Ikeda、Emiko Fukuda-Teramachi、Naoki Noda、Kazumoto Miyahara

  DOI：10.1021/np1004888

  日期：2010.11.29

  Treatment of the crude ether-insoluble resin glycoside (convolvulin) from seeds of Pharbitis nil (Pharbitis Semen), called pharbitin, with indium(III) chloride in methanol provided seven oligoglycosides of hydroxy fatty acid methyl esters partially acylated by 2-methyl-3-hydroxybutyric (nilic) and 2S-methylbutyric acids. Their structures were elucidated on the basis of NMR and MS data and chemical

  用甲醇中的氯化铟（III）处理零种法氏酵母（Pharbitis Semen）种子，称为法比汀，制得粗制的醚不溶性树脂糖苷（卷积蛋白），提供了被2-甲基-3部分酰化的七个羟基脂肪酸甲酯低聚糖苷-羟基丁酸（硝酸）和2 S-甲基丁酸。根据NMR和MS数据以及化学转化率阐明了它们的结构。
• Resin glycosides. VII. Reinvestigation of the component organic and glycosidic acids of pharbitin, the crude ether-insoluble resin glycoside ("convolvulin") of pharbitidis semen (seeds of Pharbitis nil).
  作者：Masateru ONO、Naoki NODA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.38.1892

  日期：——

  Alkaline hydrolysis of the ether-insoluble resin glycoside ("convolvulin") fraction, pharbitin, of the seeds of Pharbitis nil (Convolvulaceae) provided three organic acids, S-2-methylbutyric acid, (2R, 3R)-nilic acid and tiglic acid, and a new glycosidic acid named pharbitic acid B along with the known compounds pharbitic acids C and D. Pharbitic acid B was characterized as (3S, 11S)-3, 11-dihydroxyhexadecanoic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-quinovopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside. The structures of the sugar moieties of pharbitic acids C and D were revised.