Triterpenoids from Eugenia grandis: structure elucidation by NMR spectroscopy.
A new pentacyclic triterpenoid, 2alpha,3beta-dihydroxylup-12-en-28-oic acid (1) and a rarely encountered pentacyclic triterpenoid, 3beta-hydroxylup-12-en-28-oic acid (2), together with five known compounds, friedelin (3), 3beta-friedelinol (4), betulinic acid (5), oleanolic acid (6) and beta-sitosterol (7) were isolated from the chloroform extract of stem bark of Eugenia grandis (Syn: Syzygium grande). The structure and stereochemistry of the new compound (1) and the rarely encountered compound (2) were established by 1D and 2D NMR spectroscopic techniques. All the above isolated compounds from this plant are reported for the first time.
Manoharan
Karuppiah Pillai
KP
Department of Chemistry, National University of Singapore, Science Drive 3, 117543 Singapore.
Song
Fan Jing
FJ
Benny
Tan Kwong Huat
TK
Yang
Daiwen
D
D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards; D008968:Molecular Conformation; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D053978:Pentacyclic Triterpenes; D011522:Protons; D012015:Reference Standards; D012680:Sensitivity and Specificity; D012855:Sitosterols / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D027842:Syzygium / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification; D000094062:Betulinic Acid; D000094042:Lupanes
D003903:Deuterium; D009828:Oleanolic Acid; D053978:Pentacyclic Triterpenes; D011522:Protons; D012855:Sitosterols; D014315:Triterpenes; D000094062:Betulinic Acid; C519652:2,3-dihydroxylup-12-en-28-oic acid; C519653:3-hydroxylup-12-en-28-oic acid; C055670:friedelinol; C025473:gamma-sitosterol; C060796:friedelin; D000094042:Lupanes