Wound healing activity of acylated iridoid glycosides from Scrophularia nodosa.
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.
Stevenson
Philip C
PC
Jodrell Laboratory, Royal Botanic Gardens, Kew, Richmond, TW9 3DS, UK.
Simmonds
Monique S J
MS
Sampson
Julia
J
Houghton
Peter J
PJ
Grice
Peter
P
D002240:Carbohydrate Sequence; D002460:Cell Line; D002934:Cinnamates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D057888:Iridoid Glucosides; D057889:Iridoid Glycosides; D039823:Iridoids / Q000302:isolation & purification / Q000494:pharmacology*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D028083:Scrophulariaceae; D014945:Wound Healing / Q000187:drug effects*
C453360:6-O-(2'', 4''-diacetyl-3'' -O-p-methoxycinnamoyl)-rhamnopyranosyl catalpol; D002934:Cinnamates; D005960:Glucosides; D006027:Glycosides; D057888:Iridoid Glucosides; D057889:Iridoid Glycosides; D039823:Iridoids; D010936:Plant Extracts; D011714:Pyrans; C453361:scrophuloside A(4); C115546:scrovalentinoside; C406483:scropolioside A