Bioassay-guided isolation of vilasinin-type limonoids and phenyl alkene from the leaves of Trichilia gilgiana and their antiplasmodial activities

Nat Prod Res. 2022 Oct;36(19):5039-5047. doi: 10.1080/14786419.2021.1920017. Epub 2021 May 6.

Abstract

Bioassay-guided fractionation of the CH2Cl2-MeOH (1:1) leaves extract of Trichilia gilgiana, yielded two new vilasinin-type limonoids named gilgianin A (1) and gilgianin B (2), one new phenyl alkene derivative designated as gilgialkene A (3), along with six known compounds: rubescin H (4), TS3 (5), trichirubine A (6), sitosteryl-6'-O-undecanoate-β-D-glucoside (7), scopoletin (8), and octadecane-2-one (9). Their structures were elucidated based on spectroscopic analysis and comparison with literature data. Compounds 5 and 6 exhibited the highest antiplasmodial activity with IC50 values of 1.14 and 1.32 μM respectively. Moreover, compound 5 was very cytotoxic with CC50 value of 0.88 µM, compared to compound 6, which was not cytotoxic (CC50 > 10 µg/mL). Compounds 1 (IC50 = 9.84 µM), 2 (IC50 = 11.04 µM) and 4 (IC50 = 10.71 µM) presented good antiplasmodial activity while also exhibiting significant cytotoxicity, with CC50 values ranging from of 14.45 to 29.7 µM.[Formula: see text].

Keywords: Trichilia gilgiana; antiplasmodial activity; cytotoxicity; limonoids; phenyl alkene.

MeSH terms

  • Alkenes
  • Antimalarials* / chemistry
  • Antimalarials* / pharmacology
  • Biological Assay
  • Glucosides
  • Limonins* / chemistry
  • Limonins* / pharmacology
  • Meliaceae* / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plasmodium falciparum
  • Scopoletin

Substances

  • Alkenes
  • Antimalarials
  • Glucosides
  • Limonins
  • Plant Extracts
  • Scopoletin