1998
DOI: 10.1021/np970447u
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Gmelinosides A−L, Twelve Acylated Iridoid Glycosides from Gmelina arborea

Abstract: Besides the known iridoids 6-O-α-l-rhamnopyranosylcatalpol (1), 6-O-(3‘‘-O-trans-feruloyl)-α-l-rhamnopyranosylcatalpol (14), 6-O-(2‘‘-O-acetyl-3‘‘,4‘‘-O-di-trans-cinnamoyl)-α-l-rhamnopyranosylcatalpol (15) and the known phenylpropanoid glycosides verbascoside (acteoside) and martynoside, 12 new acylated iridoid glycosides named gmelinosides A−L (2−13) have been isolated from the leaves of Gmelina arborea. These compounds were structurally characterized using a variety of spectral methods.

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Cited by 45 publications
(26 citation statements)
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“…Hentriacontanol[6] and lignans such as arboreol, isoarboreol, methyl arboreol, arborone, gmelanone, gummadiol, and 7-oxodihydrogmelinol[789] have been isolated from heartwood of the plant. Few coumarin glycosides[10] and iridoid glycosides[11] have been reported in roots and leaves, respectively. Three iridoid glycosides 6-O-(3“- O -benzoyl)-α-L-rhamnopyranosylcatalpol, 6- O -(3“- O -trans-cinnamoyl)-α-L-rhamnopyranosylcatalpol and 6- O -(3“- O -cis-cinnamoyl)-α-L-rhamnopyranosylcatalpol were isolated from aerial parts of G. arborea and structures were elucidated by spectral analysis.…”
Section: Introductionmentioning
confidence: 99%
“…Hentriacontanol[6] and lignans such as arboreol, isoarboreol, methyl arboreol, arborone, gmelanone, gummadiol, and 7-oxodihydrogmelinol[789] have been isolated from heartwood of the plant. Few coumarin glycosides[10] and iridoid glycosides[11] have been reported in roots and leaves, respectively. Three iridoid glycosides 6-O-(3“- O -benzoyl)-α-L-rhamnopyranosylcatalpol, 6- O -(3“- O -trans-cinnamoyl)-α-L-rhamnopyranosylcatalpol and 6- O -(3“- O -cis-cinnamoyl)-α-L-rhamnopyranosylcatalpol were isolated from aerial parts of G. arborea and structures were elucidated by spectral analysis.…”
Section: Introductionmentioning
confidence: 99%
“…Lignans such as arboreol, isoarboreol, methyl arboreol, arborone, gmelanone, gummadiol, and 7-oxodihydrogmelinol [4][5][6] have been isolated from heartwood of the plant. Few coumarin glycosides [7] and iridoid glycosides [8] have been reported in roots and leaves, respectively. Three iridoid glycosides 6-O-(3-O-benzoyl)--l-rhamnopyranosylcatalpol, 6-O-(3-O-transcinnamoyl)--l-rhamnopyranosylcatalpol a n d 6 -O -( 3  -O -c i s -c i n n a m o y l ) - -lrhamnopyranosylcatalpol were isolated from aerial parts of G. arborea and structures were elucidated by spectral analysis.…”
Section: Introductionmentioning
confidence: 99%
“…On the other hand, the presence of an O-glycosidic bond at C-3 of kaempferol was confi rmed by the correlation signal between C-3 and H-1'' at δ C 133.6 ppm/δ H 5.56 ppm. In the 1 H NMR spectrum of 4, trans-confi guration of the cinnamic acid moieties was evidenced by four proton signals at δ H 6.40 (H-8'''), 6.67 (H-8 IV ), 7.40 (H-7'''), and 7.70 ppm (H-7 IV ) with a coupling constant of J = 16.0 Hz (Markham, 1982;Markham and Geiger, 1994;Abdel-Shafeek et al, 2000;Hosny and Rosazza, 1998). The values of the chemical shifts of the proton pairs H-8''',H-7''' and H-8 IV ,H-7 IV were assigned on the basis of the correlation displayed in COSY and HSQC spectra.…”
Section: Resultsmentioning
confidence: 99%