Cucurbitacin D

Cucurbitacin D
Names
IUPAC name
(23E)-2β,16α,20,25-Tetrahydroxy-9-methyl-19-nor-9β,10α-lanosta-5,23-diene-3,11,22-trione
Systematic IUPAC name
(1R,2R,3aS,3bS,8S,9aR,9bR,11aR)-1-[(2R,4E)-2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-2,3,3a,3b,4,6,8,9,9a,9b,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-7,10-dione
Other names
Elatericin A
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.211.825 Edit this at Wikidata
UNII
  • InChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1
    Key: SRPHMISUTWFFKJ-QJNWWGCFSA-N
  • InChI=1/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1
    Key: SRPHMISUTWFFKJ-QJNWWGCFBO
  • C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O
Properties
C30H44O7
Molar mass 516.675 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cucurbitacin D is a plant triterpene first identified in plants in the family Cucurbitaceae.[1][2] In preliminary in vitro studies, it has shown inhibitory properties against endometrial and ovarian cancer cell lines.[3]

References

  1. ^ Enslin, P. R. (1954). "Bitter principles of the cucurbitaceae. I.—Observations on the chemistry of cucurbitacin A". Journal of the Science of Food and Agriculture. 5 (9): 410–416. doi:10.1002/jsfa.2740050904.
  2. ^ Lavie, David; Willner, David (1958). "The Constituents of Ecballium elaterium L. III. Elatericin a and B1,2". Journal of the American Chemical Society. 80 (3): 710–714. doi:10.1021/ja01536a047.
  3. ^ Ishii, Terukazu; Kira, Naoko; Yoshida, Toshie; Narahara, Hisashi (2013). "Cucurbitacin D induces growth inhibition, cell cycle arrest, and apoptosis in human endometrial and ovarian cancer cells". Tumor Biology. 34 (1): 285–291. doi:10.1007/s13277-012-0549-2. PMID 23150173. S2CID 16889635.
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