Isoprenoid glycosides from Liriosma ovata.
A methanol extract of the dried bark of Liriosma ovata afforded two new isoprenoid glycosides, a eudesmane sesquiterpene, 1alpha(beta- d-glucopyranosyloxy)eudesma-3alpha,4beta, 11-triol ( 1), and a C 13-norisoprenoid, 3alpha,6alpha-dihydroxymegastigman-7-en-9-one 3- O-beta- d-apiofuranosyl-(1-->6)-beta- d-glucopyranoside ( 2), as well as a known constituent, isopropyl-beta- d-apiofuranosyl-(1-->6)-beta- d-glucopyranoside ( 3). The structures of 1 and 2 were determined using spectroscopic methods. The methanol extract had a significant topical anti-inflammatory activity (ID 50, dose inducing 50% edema inhibition = 780 microg/cm (2)) about 8 times less than that of indomethacin (ID 50, 93 microg/cm (2)) assayed by the croton oil ear test in mice. In addition, the chloroform extract and compounds 1 and 2 showed weak antimicrobial activity against S taphylococcus aureus (MIC = 5.1, 2.1, and 4.0 mg/mL, respectively) using a broth microdilution assay.
Picerno
Patrizia
P
Dipartimento di Scienze Farmaceutiche, University of Salerno, Via Ponte Don Melillo, 84084, Fisciano, Salerno, Italy.
Mencherini
Teresa
T
Rastrelli
Luca
L
Piccinelli
Annalisa
A
Aquino
Rita
R
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D003436:Croton Oil / Q000494:pharmacology; D004431:Ear, External / Q000187:drug effects; D004487:Edema / Q000188:drug therapy; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D007558:Italy; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D045792:Norisoprenoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D031656:Olacaceae / Q000737:chemistry*; D024301:Plant Bark / Q000737:chemistry; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects
C528201:1alpha(beta-D-glucopyranosyloxy)eudesma-3alpha,4beta,11-triol; D000894:Anti-Inflammatory Agents, Non-Steroidal; C528203:C13-norisoprenoid, 3alpha,6alpha-dihydroxymegastigman-7-en-9-one 3- O-beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside; D005960:Glucosides; D045792:Norisoprenoids; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C528202:isopropyl-beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside; D003436:Croton Oil