A sugar ester and an iridoid glycoside from Scrophularia ningpoensis

Phytochemistry. 2005 May;66(10):1186-91. doi: 10.1016/j.phytochem.2005.03.023.

Abstract

From cytotoxic extracts of the roots of Scrophularia ningpoensis Hemsl. (Scrophulariaceae) a new sugar ester, ningposide D (3-O-acetyl-2-O-p-methoxycinnamoyl-alpha(beta)-L-rhamnopyranose) (1) and a new iridoid glycoside, scrophuloside B4 (6-O-(2''-O-acetyl-3''-O-cinnamoyl-4''-O-p-methoxycinnamoyl-alpha-L-rhamnopyranosyl) catalpol) (2) along with known compounds: oleanonic acid (3), ursolonic acid (4), cinnamic acid (5), 3-hydroxy-4-methoxy benzoic acid (6), 5-(hydroxymethyl)-2-furfural (7) and beta-sitosterol (8) were isolated. The structures of the new compounds were elucidated by spectral data (1, 2D NMR, EI, HRESI-MS and MS/MS). Oleanonic acid (3) and ursolonic acid (4) were found to be cytotoxic against a series of human cancer cell lines with IC50=4.6, 15.5 microM on MCF7; 4.2, 14.5 microM on K562; 14.8, 44.4 microM on Bowes; 24.9, 43.6 microM on T24S; 61.3, 151.5 microM on A549, respectively. Beta-sitosterol (8) inhibited Bowes cells growth at IC50=36.5 microM. Scrophuloside B4 (2) showed activity on K562 and Bowes cells at IC50=44.6, 90.2 microM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carbohydrates / chemistry*
  • Carbohydrates / pharmacology
  • Cell Line, Tumor
  • Esters / chemistry*
  • Esters / pharmacology
  • Humans
  • Iridoids / chemistry*
  • Iridoids / pharmacology
  • Molecular Structure
  • Plant Roots / chemistry
  • Scrophularia / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Carbohydrates
  • Esters
  • Iridoids