Cucurbitacin E

Cucurbitacin E
Skeletal structure of Cucuribitacin E
Names
IUPAC name
(23E)-2,16α,20-Trihydroxy-3,11,22-trioxo-19-nor-9β,10α-lanosta-1,5,23-dien-25-yl acetate
Systematic IUPAC name
(3E,6R)-6-[(1R,2R,3aS,3bS,9aR,9bR,11aR)-2,8-Dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-2,3,3a,3b,4,6,7,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2-methyl-5-oxohept-3-en-2-yl acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.463 Edit this at Wikidata
UNII
  • InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
    Key: NDYMQXYDSVBNLL-MUYMLXPFSA-N
  • InChI=1/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
    Key: NDYMQXYDSVBNLL-MUYMLXPFBV
  • CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)C)O)O
Properties
C32H44O8
Molar mass 556.696 g·mol−1
Density 1.249 g/cm3
Melting point 228 to 232 °C; 442 to 449 °F; 501 to 505 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cucurbitacin E is a biochemical compound from the family of cucurbitacins. These are found in plants which are member of the family Cucurbitaceae, most of them coming from traditional Chinese medicinal plants, but also in other plants such as pumpkins and gourds.

Cucurbitacin E is a highly oxidated steroid consisting of a tetracyclic triterpene. Specific modifications in this molecule under certain conditions can form other types of cucurbitacins such as cucurbitacin I, J, K and L.

As of 2020, it is being investigated for its potential biological effects. Cucurbitacin E has been found to increase activity of anti-cancer drugs in certain types of cancers.[1] It selectively increases chemosensitivity of nutrient receptors, on or inside cancer cells, to anti-cancer drug molecules, thereby decreasing binding of the nutrients to cancer cells, and decreasing their growth, leading to selective cell death of cancer cells.[1]

Cucumbers belong to the family Cucurbitaceae
Watermelons are a rich source of cucurbitacin E
  1. ^ a b Yang, Peng; Liu, Wen; Fu, Rong; Ding, Guo-bin; Amin, Sajid; Li, Zhuoyu (2020-12-02). "Cucurbitacin E Chemosensitizes Colorectal Cancer Cells via Mitigating TFAP4/Wnt/β-Catenin Signaling". Journal of Agricultural and Food Chemistry. 68 (48): 14148–14160. doi:10.1021/acs.jafc.0c05551. ISSN 0021-8561. PMID 33205649. S2CID 227038679.