Terpenoids from the Stem bark of Aglaia elaeagnoidea and their cytotoxic activity against HeLa and DU145 Cancer Cell lines

Abstract

Aglaia is the largest genus of the Meliaceae family which contains terpenoid compounds. This type of compounds showed a diverse structures and biological activities that can be found in natural resources. Aglaia elaeagnoidea is a species from Aglaia genus that only has a few previous research. This study was aimed to isolate and determine the chemical structure of terpenoid compounds from the ethyl acetate extract of A. elaeagnoidea stem bark. Ethyl acetate extracts were separated and purified by various chromatographic techniques to obtain compounds 1-5. Compounds 1-5 were identified their chemical structures by spectroscopic methods (IR, MS, and NMR) and comparison with previous reported spectral data. Compounds 1 and 2 were identified as eudesmane-type sesquiterpenoids, 5-epi-eudesm-4(15)-ene-1β,6β-diol (1) and 6α-Hydroxy-eudesm-4(15)-en-1-one (2). Compounds 3-5 were identified as dammarane-type triterpenoids, 20S,24S-epoxy-25-hydroxydammarane-3-one (3), 20S,24S-epoxydammarane-3α,25-diol (4), and 3α-epi-cabraleahydroxy lactone (5). These compounds are first time reported from this plant. Compounds 1-5 were tested for cytotoxicity against HeLa cervical cancer cell and DU145 prostate cancer cell and as a result, compound 4 (20S,24S-epoxydammarane-3α,25-diol) showed the stronger activity compared to other compounds.

The Cytotoxic Activity of Dammarane-Type Triterpenoids Isolated from the Stem Bark of Aglaia cucullata (Meliaceae)

“…Furthermore, the FTIR spectrum showed the appearance of hydroxyl (3457 cm −1 ), gem -dimethyl (1380 cm −1 ), and ether groups (1055 cm −1 ). The 13 C NMR ( Table 1 ), along with the DEPT 135° and 1 H-NMR spectra ( Table 2 ), demonstrated that the NMR data of 1 had high similarity with the 20 S ,24 S -epoxy-3α,25-dihydroxy-dammarane isolated from A. elaeagnoidea [ 35 ]. A 2D NMR spectrum of this compound ( Figure 2 ) was also obtained to determine the exact structure of compound 1 .…”

“…The FTIR spectrum presented the appearance of a gem -dimethyl (1387 cm −1 ) and a carbonyl group (1715 cm −1 ). The 13 C NMR ( Table 1 ), DEPT 135°, and 1 H-NMR spectra ( Table 3 ) demonstrated that the NMR data of compound 6 had high similarity with cabraleahydroxy lactone isolated from A. elaeagnoidea [ 35 ]. The sole distinction was the addition of an acetyl group at compound 6 , which was identified based on the addition of two carbon atoms.…”

“…In a previous study, triterpenoids belonging to the dammarane type from A. smithii and A. eximia were found to exhibit cytotoxicity against P388 murine leukemia cells [ 7 , 34 ]. Furthermore, those obtained from A. elaeagnoidea had effects on cervical cancer (HeLa) and human prostate cancer (DU145) cells [ 35 ], and others from A. elliptica [ 31 , 32 ] showed cytotoxic effects against breast cancer (MCF-7) and melanoma (B16–F10) cells.…”

Review of Comprehensive Study on Different Activities of Priyangu

“…[5] 2.Cytotoxic Activity: Bark from the stem of A. elaeagnoidea was acquired from the Bogor Botanical Garden located in Bogor, West Java, Indonesia. [4] The plant's identification was supplied by the Bogor, Indonesia, Botanic Gardens of the Centre for Plant Conservation.…”

Dammarane-Type Triterpenoid from the Stem Bark of Aglaia elliptica (Meliaceae) and Its Cytotoxic Activities

“…Novel dammarane-type triterpenoids isolated from A. eximia and A. smithii were cytotoxic against P388 murin leukemia cells [ 6 , 23 ]. Oktaviani et al [ 24 ] isolated three dammarane-type triterpenoids and showed cytotoxicity against cervical (HeLa) and human prostate cancer cells (DU145). Therefore, they can be used as an anticancer agent in the future.…”