Abstract
Three acylated iridoid glycosides (E)-6-O-(2", 4"-diacetyl-3" -O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol (scopolioside A) (1), (E)-6-O-(2"-acetyl-3", 4"-di-O,O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol (scrophuloside A(4)) (2) and (E)-6-O-(2",3"-diacetyl-4"-O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol (scrovalentinoside) (3) have been isolated from the dried seed pods of Scrophularia nodosa by HPLC. Their structures were determined by 1D and 2D NMR, UV/Vis and mass spectroscopy and by comparison with published data. All three compounds were shown in vitro to stimulate the growth of human dermal fibroblasts. The effect was negatively dose-dependent for 2 and 3 for which fibroblast growth stimulation was highest at 0.78 microg/mL but was not significantly different from the control at 100 microg/mL. The presence of these compounds in the mature seed pods may explain the ethnobotanical use of this plant in Europe for healing wounds.
Copyright 2002 John Wiley & Sons, Ltd.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbohydrate Sequence
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Cell Line
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Cinnamates / chemistry
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Cinnamates / isolation & purification
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Cinnamates / pharmacology*
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Dose-Response Relationship, Drug
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Fibroblasts / cytology
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Fibroblasts / drug effects
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Glucosides / chemistry
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Glucosides / isolation & purification
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Glucosides / pharmacology*
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Glycosides / chemistry
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Glycosides / isolation & purification
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Glycosides / pharmacology*
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Humans
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Iridoid Glucosides
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Iridoid Glycosides
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Iridoids / isolation & purification
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Iridoids / pharmacology*
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Molecular Sequence Data
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Molecular Structure
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Plant Extracts / chemistry
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Plant Extracts / isolation & purification
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Plant Extracts / pharmacology
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Pyrans / chemistry
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Pyrans / isolation & purification
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Pyrans / pharmacology*
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Scrophulariaceae*
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Wound Healing / drug effects*
Substances
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6-O-(2'', 4''-diacetyl-3'' -O-p-methoxycinnamoyl)-rhamnopyranosyl catalpol
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Cinnamates
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Glucosides
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Glycosides
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Iridoid Glucosides
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Iridoid Glycosides
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Iridoids
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Plant Extracts
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Pyrans
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scrophuloside A(4)
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scrovalentinoside
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scropolioside A