New Cytotoxic Lupane Triterpenoids from the Twigs of Coussarea paniculata

Abstract

Bioassay-guided fractionation of a CH(2)Cl(2)-MeOH extract of the twigs of Coussarea paniculata using a yeast-based assay for potential DNA-damaging agents resulted in the isolation of three new lupane triterpenoids, 1-3, in addition to eight known triterpenoids, lupeol (4), lupeyl acetate (5), betulin (6), betulinic acid (7), 3-epi-betulinic acid (8), 3-epi-betulinaldehyde (9), oleanolic acid (10), and ursolic acid (11). The structures of the new compounds were established as lup-20(29)-en-3beta,25-diol (1), lup-20(29)-en-11alpha-ol-25,3beta-lactone (2), and 3-deoxybetulonic acid (3), on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversion.

Betulinic Acid: Recent Advances in Chemical Modifications, Effective Delivery, and Molecular Mechanisms of a Promising Anticancer Therapy

“…The following are the sources of plants used to isolate BetA: Quisqualis fructus , Coussarea paniculata , Caesalpinia paraguariensis , Vitex negundo , Ilex macropoda , Anemone raddeana , Doliocarpus schottianus , Tovomita krukovii , Chaenomeles lagenaria , Berlinia grandiflora , Vietnamese Orthosiphon stamineus , Eucalyptus camaldulensis , Physocarpus intermedium , Tetracentron sinense , Syncarpa glomulifera , Combretum quadrangulare , Tetracera boiviniana , Zizyphus joazeiro , Uapaca nidida , Ipomea pescaprae , Ancistrocladus heyneanus , Diospyros leucomelas leaves of Syzrgium claviforum , Sarracenia flava , Diospyros spp., Inga punctate , Ziziphus spp., Vauquelinia corymbosa , and Syzygium spp .…”

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

“…21 Isolation of ursolic acid from leaves of Ilex aquifolium L. I. has been reported by Schindler et al 22 Chemical investigation of bark, peel, and leaf of Punica granatum (L.) also revealed the presence of ursolic acid. The other plants contained ursolic acid were Coussarea paniculata, 23 Salvia sochifolia, 24 Gentiana tizuensis, 25 Alysicarpus monolifer, 26 Ilex psammophila, 27 Debregeasia salicifolia, 28 Uncaria macrophylla, 29 Rabdosia excise,…”

Antibacterial Triterpenoids from the Bark of Sonneratia alba (Lythraceae)

“…The coupling constants of H-3 ( H 3.20, dd, J = 10.5, 5.5 Hz) observed in the 1 H NMR spectrum indicated a -orientation of the hydroxyl group at C-3 [17][18][19]. The relative configuration of 1 was identical to that of dihydrobetulinic acid, lupeol and and lupan-3-ol based on the J value and the chemical shifts in the 1 H NMR spectrum [20][21][22]. Therefore, the structure of 1 was determined to be 3-hydroxy-lup-9(11),12-dien, 28-oic acid or 9(11), 12-dien dihydrobetulinic acid.…”