Vernonioside A3 | 140395-74-0

• 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
• 英文名称: Vernonioside A3
• 英文别名: (3R,5S)-3-[(3S,5S,10S,13S,14R,17R)-10,13-dimethyl-16-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,12,14,15,17-decahydrocyclopenta[a]phenanthren-17-yl]-5-[(2R,3S)-3-methyl-2-propan-2-yloxiran-2-yl]oxolan-2-one
• CAS: 140395-74-0
• 化学式: C₃₅H₅₀O₁₀
• 分子量: 630.776
• InChiKey: OGJQOSZFJOEENK-ZRPZOYRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Vernonioside A3 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 72.08h， 生成 Vernonioside A₂ aglycone
  参考文献：
  名称：

  Bitter steroid glucosides, vernoniosides A1, A2, and A3, and related B1 from a possible medicinal plant, Vernonia amygdalina, used by wild chimpanzees.

  摘要：

  From Vernonia amygdalina, a possible medicinal plant used by wild chimpanzees, three bitter steroid glucosides, vernoniosides A1,A2 and A3 and a nonbitter vernonioside B1, were isoluted. The oxygenation patterns of the aglycone parts were new, especially the pattern of the carboxyl group at C21. The oxygen functionalities at C16 were important for the bitter taste.

  DOI：

  10.1016/s0040-4020(01)88123-0

文献信息

• Toward the chemical ecology of medicinal plant use in chimpanzees: The case ofVernonia amygdalina, a plant used by wild chimpanzees possibly for parasite-related diseases
  作者：Hajime Ohigashi、Michael A. Huffman、Daisuke Izutsu、Koichi Koshimizu、Masanori Kawanaka、Hiromu Sugiyama、Geoffrey C. Kirby、David C. Warhurst、David Allen、Colin W. Wright、J. David Phillipson、Pierre Timon-David、Florence Delmas、Riad Elias、Guy Balansard

  DOI：10.1007/bf02059596

  日期：1994.3

  The bitter and related constituents have been isolated from Vernonia amygdalina (Compositae), a plant ingested by wild chimpanzees possibly suffering from parasite-related diseases in the Mahale Mountains National Park, Tanzania. Isolated from the plant were four known sesquiterpene lactones, seven new steroid glucosides, and two aglycones of the glucosides. The sesquiterpene lactones showed significant in vitro antischistosomal, plasmodicidal, and leishmanicidal activities. Antischistosomal activity was also found for the major steroid glucoside, vernonioside B-1. A trend in the glucosides to show significant antischistosomal, plasmodicidal, and amebicidal activities when the sugar moiety was removed, was observed. Vernodalin, judged as the most significant constituent for antiparasitic activities in vitro, was tested for in vivo antischistosomal effect. It was, however, highly toxic to the cercaria-infected mouse. Chimpanzees have been only rarely observed to ingest anything but the pith of the young stem. The occurrence of vernonioside B-1 and its aglycone vernoniol B-1, the major constituents among the steroid-related constituents, were detected at significant levels in the pith. However, vernodalin was abundant only in the leaves and bark. Thus, chimpanzees at Mahale were hypothesized to control parasite-related diseases by ingesting the young pith of this tree containing steroid-related constituents.