Journals / Turkish Journal of Chemistry / 2004 / Cilt: 28 - Sayı: 1

Saponin, Iridoid, Phenylethanoid and Monoterpene Glycosides from Verbascum pterocalycinum var. mutense

Saponin, Iridoid, Phenylethanoid and Monoterpene Glycosides from Verbascum pterocalycinum} var. mutense

Pages
111–122
DOI
—

Abstract

Ilwensisaponin C (= 3-O-{[α-L-rhamnosyl-(1→4)-(β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl]- (1→2)-β-D-fucopyranosyl}-11-methoxy-olean-12-ene-3β, 23, 28-triol) (1), ilwensisaponin A (= mimengoside A = 3-O-{[α-L-rhamnosyl-(1→4)-(β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl]-(1→2)-β-Dfucop- yranosyl}-13β, 28-epoxyolean-11-ene-3β, 23-diol) (2), ajugol (3), picroside IV (= 60 -O-trans-phydroxycin- namoylcatalpol) (4), verbascoside {= acteoside, [β-(3,4-dihydroxyphenyl)-ethyl]-(30 -O-α-Lrhamnopyra- nosyl)-(40 -O-caffeoyl)-β-D-glucopyranoside} (5) and 1-(β-D-glucopyranosyl)-8-hydroxy-3, 7-dimethyl-oct-2(E), 6(E)- dienoate (6) were isolated from the flowers of Verbascum pterocalycinum var. mutense Hub.-Mor. The structures of the compounds were determined primarily from 1D and 2D NMR experiments. This is the first phytochemical study performed on V . pterocalycinum var. mutense and the first report of the presence of 1-(β-D-glucopyranosyl)-8-hydroxy-3, 7-dimethyl-oct-2(E), 6(E)- dienoate (5) as a monoterpene glycoside along with picroside IV (= 60 -O-trans-p-hydroxycinnamoylcatalpol) (4) from the genus Verbascum.

Özet

Ilwensisaponin C (= 3-O-{[a-L-rhamnosyl-(1 \to 4)-(b-D-glucopyranosyl-(1 \to 3)]-b-D-glucopyranosyl]-(1 \to 2)-b-fucopyranosyl}-11-methoxy-olean-12-ene-3b, 23, 28-triol) (1), ilwensisaponin A (= mimengoside A = 3-O-{[a-L-rhamnosyl-(1 \to 4)-(b-D-glucopyranosyl-(1 \to 3)]-b -D-glucopyranosyl]-(1 \to 2)-b-fucop- yranosyl}-13b, 28-epoxyolean-11-ene-3b, 23-diol) (2), ajugol (3), picroside IV (= 6\prime-O-trans- p-hydroxycin- namoylcatalpol) (4), verbascoside {= acteoside, [b -(3,4-dihydroxyphenyl)-ethyl]-(3^{\prime-O-a-L-rhamnopyra- nosyl)-(4^{\prime-O-caffeoyl)-b-D-glucopyranoside} (5) and 1-(b -D-glucopyranosyl)-8-hydroxy-3, 7-dimethyl-oct-2(E), 6(E)- dienoate (6) were isolated from the flowers of Verbascum pterocalycinum var. mutense Hub.-Mor. The structures of the compounds were determined primarily from 1D and 2D NMR experiments. This is the first phytochemical study performed on V. pterocalycinum var. mutense and the first report of the presence of 1-(b -D-glucopyranosyl)-8-hydroxy-3, 7-dimethyl-oct-2(E), 6(E)- dienoate (5) as a monoterpene glycoside along with picroside IV (= 6^{\prime}-O-trans-p-hydroxycinnamoylcatalpol) (4) from the genus Verbascum.

Keywords: Verbascum pterocalycinum var. mutense, Scrophulariaceae, saponin glycosides, ilwensisaponin C and ilwensisaponin A, iridoid glucosides, ajugol and picroside IV, phenylethanoid glycoside, verbascoside, monoterpene glucoside, 1-(b-D-glucopyranosyl)- 8