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Cucurbitacin D

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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--2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-2,3,3a,3b,4,6,8,9,9a,9b,11,11a-dodecahydro-1H-cyclopentaphenanthrene-7,10-dione
Other names Elatericin A
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.211.825 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: 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/s1Key: SRPHMISUTWFFKJ-QJNWWGCFBO
SMILES
  • C12C((1(CC(=O)3(2CC=C43C(C(=O)C4(C)C)O)C)C)(C)(C(=O)/C=C/C(C)(C)O)O)O
Properties
Chemical formula C30H44O7
Molar mass 516.675 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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 B". 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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