Beccaridiol, an unusual 28-nortriterpenoid from the leaves of Diplectria beccariana.
A C29-triterpene, beccaridiol (1), a dihydrochalcone natural product, 2',4'-dihydroxy-3-(4-methoxyphenyl)-propiophenone (2), as well as three known compounds, 4'-hydroxy-1',2'-dihydro-beta-ionone, 4'-O-methyldavidigenin (3), and ursolic acid, have been isolated from an EtOAc-soluble extract of the leaves of Diplectria beccariana. Beccaridiol (1) was characterized as an ursane-type 28-nortriterpene possessing an unusual aromatic E-ring by spectroscopic data interpretation. The relative configuration of this unusual isolate was established by analyzing the observed NOESY NMR correlations, and the absolute stereochemistry of 1 was then determined based on the circular dichroism (CD) spectrum of its 2,3-di-p-bromobenzoate (1b) derivative. All isolates were evaluated for their potential cancer chemopreventive properties utilizing a cell culture assay to determine quinone reductase induction.
Jang
Dae Sik
DS
Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Su
Bao-Ning
BN
Pawlus
Alison D
AD
Kang
Young-Hwa
YH
Kardono
Leonardus B S
LB
Riswan
Soedarsono
S
Afriastini
Johar J
JJ
Fong
Harry H S
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D004790:Enzyme Induction; D035322:Melastomataceae / Q000737:chemistry*; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
D014315:Triterpenes; C514301:beccaridiol; D016660:NAD(P)H Dehydrogenase (Quinone)