Scropolioside-D2 and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity.
Five iridoid glycosides, including the two new compounds scropolioside-D(2) (1) and harpagoside-B (2), were isolated from the aerial parts of Scrophularia deserti DEL (Scrophulariaceae). Their structures were elucidated on the basis of spectral data to be 6-O-[2",4"-di-O-acetyl-3"-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-8 alpha-hydroxymethyl-1 alpha,5 beta,6 alpha,7 alpha,9 beta-pentahydro-7(8)-epoxy-2-oxaind-3-ene-1-O-beta-D-glucopyranoside-6'-O-acetate (1) and 5-O-beta-hydroxy-8-O-beta-trans-cinnamoyl-8 alpha-methyl-1,6,7,9-tetrahydro-2-oxaind-3-ene-1-O-beta-D-glucopyranoside (2), respectively. In addition, three more iridoid glycosides, scropolioside-D (3), koelzioside (4), and 8-O-acetyl-harpagide (5), were also isolated and characterized from this source. The biological activity and the structure activity relationship of the compounds were also studied, and scropolioside-D (3) and harpagoside-B (2) were found to possess significant antidiabetic and antiinflammatory activity, respectively.
Ahmed
Bahar
B
Medicinal, Aromatic and Poisonous Plants Research Center, Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. bahmed@ksu.edu.sa
Al-Rehaily
Adnan Jathlan
AJ
Al-Howiriny
Tawfeq Abdullah
TA
El-Sayed
Khaled Abdelatee
KA
Ahmad
Mohammad Shamim
MS
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000627:therapeutic use*; D003921:Diabetes Mellitus, Experimental / Q000139:chemically induced / Q000188:drug therapy; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000627:therapeutic use*; D057888:Iridoid Glucosides; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D008297:Male; D051379:Mice; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use*; D051381:Rats; D017208:Rats, Wistar; D032266:Scrophularia
D000894:Anti-Inflammatory Agents, Non-Steroidal; D006027:Glycosides; D007004:Hypoglycemic Agents; D057888:Iridoid Glucosides; D039823:Iridoids; D010936:Plant Extracts; D011714:Pyrans; C081264:scropolioside D; C033249:harpagoside