Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L.

Abstract

Two pentacyclic triterpenoids, betulinic acid (3beta-hydroxylup-20-(29)-en-28-oic acid) (3), and ursolic acid (2beta-hydroxyurs-12-en-28-oic acid) (4), were isolated for the first time from leaves of Vitex negundo L. along with three other compounds; an aliphatic alcohol n-hentriacontanol (1), beta-sitosterol (2) and p-hydroxybenzoic acid (5). Their antifeedant activity against the larvae of an agricultural pest, the castor semilooper (Achoea janata), in a no-choice laboratory assay and their antibacterial activity against Bacillus subtilis and Escherichia coli, by the paper disc method, were tested. Ursolic acid (4) showed more effective antifeedant activity than the betulinic acid (3). However, both these compounds have shown a very mild antibacterial activity. The other three compounds; n-hentriacontanol (1), beta-sitosterol (2) and p-hydroxybenzoic acid (5) have shown a little antifeedant activity against the larvae and did not show any antibacterial activity.

Immunomodulatory Studies on Triterpenoids from Scoparia dulcis Linn

“…All the spectral data of the compound 1 was unambiguously matched with reported data in literature [18]. Structure of compounds, coixol (2), friedelin (3), glutinol (4), and betulinic acid (5) were identified by comparing their spectral data with reported data in literature [19][20][21][22]. Among all tested compounds, compound 1 (glutinone) (IC 50 = 4.30 µg ⁄ mL) exerted potent inhibition of oxidative burst from whole blood cells, whereas, remaining compounds showed no effect (IC 50 > 100 µg ⁄ mL) (Figure 1).…”

URSOLIC ACID AND CIS-TILIROSIDE PRODUCED BY Merremia tomentosa AFFECT OVIPOSITION OF Leucoptera coffeella ON COFFEE PLANTS

“…This result seems to be in accordance with the antifeedant activity against Spodoptera litura (Fabricius, 1775) (Lepidoptera: Noctuidae), that was previously described for this substance 53 and some analogs. 54 Ursolic acid also showed antifeedant activity against Spilosoma obliqua (Walker, 1855) (Lepidoptera: Arctiidae), 53 and Achaea janata Linnaeus, 1758 (Lepidoptera: Noctuidae), 55 and presented growth inhibition and acute toxicity against larvae of Spodoptera frugiperda (J.E. Smith, 1797) (Lepidoptera: Noctuidae), and Drosophila melanogaster (Meigen, 1830) (Diptera: Drosophilidae).…”

“…One example is taraxerol, which is active against 55 These results suggest that at least part of the mechanism of action of these substances against insects consists of inhibiting their glycogen phosphorylases, which could become important targets for the development of new products to control insects.…”

Update: Biological and Chemical Aspects of Senna spectabilis

“…31,61,62 Betulinic acid, isolated from leaves, fruits and flowers of Senna, is a highly bioactive triterpene, displaying anti-HIV, antibacterial, antimalarial and anti-inflammatory effects. 5,31,[63][64][65] Commonly known as 3β-hydroxy-lup-20-(29)-en-28-oic acid, this triterpene promises to be a potential drug for cancer treatment due to its cytotoxicity against various cancer cell lines (lung, ovarian, neuroand glioblastoma and head/neck carcinomas), selective inhibition of human melanoma, apoptosis induction in human neurobastoma and low toxicity to healthy cells. 66 Ursolic acid, found either free or bounded to saponins, is a common constituent of fruits from human diet such as apple, guava and blueberry.…”