A sugar ester and an iridoid glycoside from Scrophularia ningpoensis.
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.
Nguyen
Anh-Tho
AT
Laboratory of Pharmacognosy, Bromatology and Human Nutrition, Institute of Pharmacy CP 205-9, Université Libre de Bruxelles, B-1050 Brussels, Belgium. annhthng@ulb.ac.be
Fontaine
Jeanine
J
Malonne
Hugues
H
Claeys
Magda
M
Luhmer
Michel
M
Duez
Pierre
P
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D002241:Carbohydrates / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004952:Esters / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D039823:Iridoids / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D032266:Scrophularia / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D002241:Carbohydrates; D004952:Esters; D039823:Iridoids