New 3-O-Acyl Betulinic Acids from Strychnos vanprukii Craib

Abstract

Three new betulinic acid derivatives, 3beta-O-trans-feruloylbetulinic acid (1), 3beta-O-cis-feruloylbetulinic acid (2), and 3beta-O-cis-coumaroylbetulinic acid (4), along with two known triterpenes, 3beta-O-trans-coumaroylbetulinic acid (3) and ursolic acid (6) were isolated from the leaves and twigs of Strychnos vanprukiiCraib. All isolates showed moderate anti-HIV activity with IC50 values ranging from 3 to 7 microg/mL (5 to 15 microM) in an indicator cell line for HIV infectivity. The structures of the new isolates were elucidated by spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition, the structure of 1 was confirmed by X-ray crystallography.

New bioactive lupane triterpene coumaroyl esters isolated from Buxus cochinchinensis

“…In addition, for pure compounds 1-5, which dissolved in deuterium DMSO or CDCl 3 and stored in room temperature without light prevention for over 72 hours, no alteration were observed between E/Z-coumaryl isomers. Thus, in present study, the co-occurrence of the E/Z-isomers of the coumaryl moieties of the triterpens in Buxus cochinchinensis is more likely derived from a light-independent isomerization, as same as that reported for plants Perrottetia arisanensis and Strychnos vanprukii Craib [18,20]. All pure compounds obtained in the present investigation were evaluated for their cytotoxic activity against the HT-29 human colon cancer cell line.…”

Betulinic Acid and Its Derivatives, Potent DNA Topoisomerase II Inhibitors, from the Bark ofBischofia javanica

“…In our continuous work on the isolation of bioactive constituents from Pinaceae and Euphorbiaceae plants, we have attempted to isolate Topo II inhibitors from the CHCl 3 extract of the bark of B. javanica. Through the bioassay guided-fractionation, betulinic acid ( 3b-hydroxylup-20(29)-en-28-oic acid; 1) [8] and its derivatives, betulonic acid (2) [8], 3b-O-(Z)-coumaroylbetulinic acid (3), and 3b-O-(E)-coumaroylbetulinic acid (4) [9] were isolated as potent …”

“…TLC and recrystallization to give betulinic acid (1; 150 mg), betulonic acid (2; 5 mg), 3b-O-(Z)-coumaroylbetulinic acid (3; 15 mg), and 3b-O-(E)-coumaroylbetulinic acid (4; 28 mg). These compounds were identified by their NMR, MS, and physicochemical data by comparison with the published data [8] [9].…”

Ethnobotany/ethnopharmacology and mass bioprospecting: Issues on intellectual property and benefit-sharing

“…This high number may have been the result of rigorous prioritization criteria in the project, based on pre-existing biological and chemical information (both at species and generic levels), as well as on a chemical dereplication strategy using the resources and expertise available at UIC. The chemical diversity of these new natural products includes alkaloids/amides, macrocyclics, lignans, neolignans, butenolides, phenylpropanoids, terpenes, norditerpenes, triterpenes and steroids (Zhang et al, 2001(Zhang et al, , 2002aChien et al, 2004).…”