Antitumor agents, 145. Cytotoxic asprellic acids A and C and asprellic acid B. new p-coumaroyl triterpenes, from Ilex asprella.
Three new p-coumaroyl triterpenes, asprellic acids A [1], B [2], and C [3], were isolated from the EtOH extract of dried leaves of Ilex asprella. The structures for 1-3 have been established as 3,27-di-O-trans-p-coumaroyl [1], 3-O-trans-p-coumaroyl-27-O-cis-p-coumaroyl- [2], and 3-O-cis-p-coumaroyl-27-O-trans-p-coumaroyl- [3] 3 beta,27-dihydroxyolean-12-en-28-oic acid, respectively, by spectral and chemical examinations. Asprellic acid A [1] exhibited potent cytotoxicity against the RPMI-7951 cell line with an ED50 value of 0.62 micrograms/ml, while the cytotoxicity of asprellic acid C [3] against RPMI-7951 was marginal (ED50 5.5 micrograms/ml). Compounds 1 and 3 also showed cytotoxicity against KB cells with ED50 values of 3.75 and 2.86 micrograms/ml, respectively. Asprellic acid B [2] did not show cytotoxicity (> 10 micrograms/ml) against KB or RPMI-7951 cell lines.
Kashiwada
Y
Y
Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill 27599.
Zhang
D C
DC
Chen
Y P
YP
Cheng
C M
CM
Chen
H T
HT
Chang
H C
HC
Chang
J J
JJ
Lee
K H
KH
D000230:Adenocarcinoma / Q000188:drug therapy; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D002294:Carcinoma, Squamous Cell / Q000188:drug therapy; D003373:Coumaric Acids / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005770:Gastrointestinal Neoplasms / Q000188:drug therapy; D006801:Humans; D007624:KB Cells; D007941:Leukemia P388 / Q000188:drug therapy; D008545:Melanoma / Q000188:drug therapy; D051379:Mice; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D003373:Coumaric Acids; C086360:asprellic acid A; D009828:Oleanolic Acid