Antitumor agents, 145. Cytotoxic asprellic acids A and C and asprellic acid B. new p-coumaroyl triterpenes, from Ilex asprella

J Nat Prod. 1993 Dec;56(12):2077-82. doi: 10.1021/np50102a008.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adenocarcinoma / drug therapy
  • Animals
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carcinoma, Squamous Cell / drug therapy
  • Coumaric Acids / isolation & purification*
  • Coumaric Acids / pharmacology
  • Drug Screening Assays, Antitumor
  • Gastrointestinal Neoplasms / drug therapy
  • Humans
  • KB Cells
  • Leukemia P388 / drug therapy
  • Melanoma / drug therapy
  • Mice
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Plants, Medicinal / chemistry*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Coumaric Acids
  • asprellic acid A
  • Oleanolic Acid