Operculinic acid E | 126465-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Operculinic acid E
• 英文别名: (11S)-11-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,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]oxyhexadecanoic acid
• CAS: 126465-33-6
• 化学式: C₄₀H₇₂O₂₀
• 分子量: 873.0
• InChiKey: ZDVAMQQTCPLGIC-SAAHIEGASA-N

物化性质

• 沸点：
  1009.8±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  60
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  313
• 氢给体数：
  11
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  Operculinic acid E 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 D-葡萄糖 、 L-rhamnopyranose 、 jalapinolic acid
  参考文献：
  名称：

  Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas

  摘要：

  Nine new lipo-oligosaccharides, batatosides H-P, were isolated from the tubers of Ipomoea batatas (Convolvulaceae). Spectral and chemical methods allowed to characterize them as tetra- or penta-saccharides that form a macrolactone with the aglycone, (11S)-hydroxyhexadecanoic acid (jalapinolic acid), the absolute configuration of which was established by Mosher's method. Batatosides L and O showed a weak inhibitory effect on the growth of Hep-2 cells, while the others proved to be inactive. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.022
• 作为产物：
  描述：

  Operculinic acid E methyl ester 在 氢氧化钾 作用下， 反应 1.0h， 以18 mg的产率得到Operculinic acid E
  参考文献：
  名称：

  Resin glycosides. VIII. Four new glycosidic acids, operculinic acids D,E,F, and G, of the ether-soluble crude resin glycosides ("Jalapin") from Rhizoma Jalapae Braziliensis(roots of Ipomoea operculata).

  摘要：

  根据化学和光谱数据，从巴西叶下珠（Ipomoea operculata）根茎的醚溶性粗树脂苷（“jalapin”）的碱性水解产物中分离出四种糖苷酸，即D、E、F和G型operculin酸。它们分别被鉴定为11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside、11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside、11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-

  DOI：

  10.1248/cpb.38.2650

文献信息

• Resin Glycosides. XVI. Marubajalapins I-VII, New Ether-Soluble Resin Glycosides from Pharbitis purpurea.
  作者：Masateru ONO、Takashi UEGUCHI、Hiroko MURATA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.40.3169

  日期：——

  Fifteen new resin glycosides, marubajalapins I-XV, were isolated from the jalapin fraction of the aerial part (leaves and stems) of Pharbitis purpurea. Among them, the structures of marubajalapins I-VII have been determined on the basis of chemical and spectral data. They are the first examples of jalapins with operculinic acid E obtained previously as a minor glycosidic acid of the crude jalapin from Jalapae Braziliensis.

  从紫葳（Pharbitis purpurea）叶和茎的地上部分的jalapin组分中分离出了十五种新的树脂糖苷，命名为marubajalapins I-XV。其中，marubajalapins I-VII的结构已根据化学和光谱数据确定。它们是首例含有先前作为巴西山葫芦（Jalapae Braziliensis）粗jalapin的次要糖苷酸的operculinic acid E的jalapins。
• Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas
  作者：Yong-Qin Yin、Jun-Song Wang、Jian-Guang Luo、Ling-Yi Kong

  DOI：10.1016/j.carres.2008.12.022

  日期：2009.3

  Nine new lipo-oligosaccharides, batatosides H-P, were isolated from the tubers of Ipomoea batatas (Convolvulaceae). Spectral and chemical methods allowed to characterize them as tetra- or penta-saccharides that form a macrolactone with the aglycone, (11S)-hydroxyhexadecanoic acid (jalapinolic acid), the absolute configuration of which was established by Mosher's method. Batatosides L and O showed a weak inhibitory effect on the growth of Hep-2 cells, while the others proved to be inactive. (C) 2009 Elsevier Ltd. All rights reserved.
• Resin glycosides. VIII. Four new glycosidic acids, operculinic acids D,E,F, and G, of the ether-soluble crude resin glycosides ("Jalapin") from Rhizoma Jalapae Braziliensis(roots of Ipomoea operculata).
  作者：Masateru ONO、Tomoji FUKUNAGA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.38.2650

  日期：——

  Four glycosidic acids, operculinic acids D, E, F and G, were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the ether-soluble crude resin glycoside ("jalapin") from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata).They were respectively characterized as 11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside, 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside, 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside and 11S-jalapinolic acid 11-O-(2-O-methyl-β-D-glucopyranosyl-(1→3))-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside, on the bases of chemical and spectroscopic data.

  根据化学和光谱数据，从巴西叶下珠（Ipomoea operculata）根茎的醚溶性粗树脂苷（“jalapin”）的碱性水解产物中分离出四种糖苷酸，即D、E、F和G型operculin酸。它们分别被鉴定为11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside、11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside、11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-