title: Triterpenoids from Eugenia grandis: structure elucidation by NMR spectroscopy.
abstract: 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.
authors.affiliation: Department of Chemistry, National University of Singapore, Science Drive 3, 117543 Singapore.
authors.forename: Karuppiah Pillai
authors.initials: KP
authors.lastname: Manoharan
authors.forename: Fan Jing
authors.initials: FJ
authors.lastname: Song
authors.forename: Tan Kwong Huat
authors.initials: TK
authors.lastname: Benny
authors.forename: Daiwen
authors.initials: D
authors.lastname: Yang
mesh_terms: 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
chemical_list: 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