Cytotoxicity and Structure Activity Relationship of Dammarane-Type Triterpenoids from the Bark of Aglaia elliptica against P-388 Murine Leukemia Cells (original) (raw)
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Molecules
Two new dammarane-type triterpenoid fatty acid ester derivatives, 3β-oleate-20S-hydroxydammar-24-en (1) and 3β-oleate-20S,24S-epoxy-25-hydroxydammarane (2) with a known dammarane-type triterpenoid compound, such as 20S-hydroxydammar-24-en-3-on (3), were isolated from the stem bark of Aglaiaelliptica (C.DC.) Blume. The chemical structures were determined by spectroscopic methods, including FTIR, NMR (one and two-dimensional), and HRESITOF-MS analysis, as well as chemical derivatization and comparison with previous literature. Furthermore, the synthetic analog resulting from transesterification of 1 and 2 also obtained 3β,20S-dihydroxy-dammar-24-en (4) and 20S,24S-epoxy-3β,25-dihydroxydammarane (5), respectively. The cytotoxic effect of all isolated and synthetic analog compounds was evaluated using PrestoBlue reagent against MCF-7 breast cancer cell and B16-F10 melanoma cell lines. The 20S-hydroxydammar-24-en-3-on (3) showed the strongest activity against MCF-7 breast cancer and B16-...
Oriental Journal of Chemistry
Four dammarane-type triterpenoids, dammardienon (1), aglaiabbreviatin E (2), dammar-20,25-dien-3b,24-diol (3) and dammar-24-en-3b,20-diol (4) were isolated from methanolic extract of the bark of Aglaia glabrata. The structures of all triterpenoids were elucidated by 1D-, 2D-NMR, and comparison with previously reported data. All triterpenoids were applied into in vitro bioassay against P-388 murine leukemia cell. Dammar-24-en-3b,20-diol (4) has cytotoxic activity with IC50 value of 9.45 mM towards P-388 murine leukemia cell lines.
Molekul, 2022
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...
Cytotoxic Steroids from the Bark of Aglaia argentea (Meliaceae)
Chiang Mai University Journal of Natural Sciences, 2017
The study aimed to find a potential anticancer agent by isolating and identifying the chemical structure of compounds from Aglaia argentea and testing their cytotoxic effects against P-388 murine leukimia cells. Five steroids-stigmast-5-en-3β-ol (β-sitosterol) (1), stigmast-5-en-3β-ol-3β-oleate (β-sitosterol oleate) (2), stigmast-5-en-3β-ol-3-O-(6′-O-oleoyl)-β-D-glucopyranoside (sitoindoside II) (3), stigmast-5-en-3β-ol-3-O-β-D-glucopyranoside (β-sitosterol glucoside) (4), stigmast-5,22-dien-3β-ol-3-O-β-D-glucopyranoside (stigmasterol glucoside) (5)-were isolated from the bark of Aglaia argentea. The chemical structures of 1-5 were identified with spectroscopic data, including IR, NMR (1 H, 13 C, DEPT 135°, HMQC, HMBC, 1 H-1 H COSY) and HRTOFMS, as well as by comparing with previously reported spectral data. All compounds were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1-5 showed cytotoxicity against P-388 murine leukemia cell with IC 50 values of 12.
Cytotoxic constituents from the bark of Aglaia eximia (Meliaceae)
Phytochemistry Letters, 2014
The new stigmastane steroid, 3,4-epoxy-(22R,25)-tetrahydrofuran-stigmast-5-en (1), along with two known triterpenoids (2-3) and two known steroids (4-5) were isolated from the stem bark of Aglaia eximia. The chemical structures of the new compound were elucidated on the basis of spectroscopic data. All of the compounds were tested for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1-5 showed cytotoxicity against P-388 murine leukemia cells with IC 50 values of 11.42, 4.26, 29.10, 45.96, and 52.09 mg/mL, respectively.
Cytotoxic Triterpenoids from the Stembark of Aglaia argentea (Meliaceae)
Indonesian Journal of Chemistry, 2018
Four dammarane-type triterpenoid compounds, dammar-24-en-3a-ol (1), 3-epi-cabraleahydroxy lactone (2), (E)-25-hydroperoxydammar-23-en-3b,20-diol (3), and dammar-24-en-3β,20-diol (4), were isolated from the methanolic extract of the stembark of Aglaia argentea. Compounds 1-4 were isolated for first time from this plant. The structure of isolated compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as mass spectrometric analysis. Compounds, 1-4, along with a known synthetic analog, 20-hydroxy-dammar-24-en-3-on (5), were evaluated their cytotoxic activity against P-388 murine leukemia cells in vitro. The IC50 values of compounds, 1-5 were 9.09 ± 0.10, 68.53 ± 0.08, 5.89 ± 0.08, 22.40 ± 0.11, and 11.53 ± 0.08 µg/mL, respectively. Among the dammarane-type triterpenoids, compounds 1, 3, 4 and 5 having opened side chain showed the stronger activity, wheres compound 2 with cyclic side chain showed weak or no activity. In addition, compound 3 showe...
Cytotoxic Sesquiterpenoids from the Stem Bark of Aglaia harmsiana (Meliaceae)
Indonesian Journal of Chemistry, 2020
Three aromadendrane-type sesquiterpenoids, spathulenol (1), 4β,10α-dihydroxyaromadendrane (2), and 4α,10α-dihydroxyaromadendrane (3) were isolated from the stem bark of Aglaia harmsiana (Meliaceae). Compound 3 was isolated for the first time from Aglaia genus. The chemical structures of isolated compounds were elucidated by various spectroscopic methods, including one and two-dimensional NMR, as well as mass spectroscopy analysis. These sesquiterpenoids 1-3 were evaluated for their cytotoxic activity against MCF-7 breast cancer cell lines. The IC50 value of compound 1-3 were 31.65 ± 0.1, 8.41 ± 0.04 and 2.80 ± 0.02 µM, respectively. Among the aromadendrane-type sesquiterpenoids, compounds 2 and 3, which do not have a double bond, showed higher activity than compound 1. Whereas, compound 3 showed the strongest activity indicate that α configuration of hydroxyl group increases the cytotoxic activity.
Indonesian Journal of Chemistry
The Aglaia species, which contains triterpenoids, is the most numerous in the Meliaceae family. The A. cucullata species, of which there are only a few known examples, has received scant research attention. This investigation aims to identify triterpenoids in an n-hexane preparation of A. cucullata stem bark and evaluate their effects against the A549 lung cancer cell line. Five dammarane-type triterpenoids were isolated from the A. cucullata trunk bark, which is (1) (20S)-20-hydroxydammar-24-en-3-one, (2) cabraleone, (3) cabralealactone, (4) eichlerianic acid, and (5) (+)-fouquierol. Their chemical structures were determined using infrared, high-resolution mass spectrometry, and nuclear magnetic resonance, as well as through data comparison of the reported compounds. Compound 1 was priorly separated from the Aglaia genus, compounds 2–4 were first isolated from the A. cucullata species, and compound 5 has been reportedly isolated from the Meliaceae family and the Aglaia genus. All s...
Bioorganic & Medicinal Chemistry, 2006
Activity-guided fractionation of a CHCl 3 -soluble partition of the MeOH extract of the bark of Aglaia crassinervia collected in Indonesia led to the isolation of three new glabretal-type triterpenoids, aglaiaglabretols A-C (1-3), as well as nine known compounds, 3-epi-cabraleahydroxylactone (4), cabraleahydroxylactone (5), rocaglaol (6), 2b,3b-dihydroxy-5a-pregn-17(20)-(E)-16one, scopoletin, and mixtures of cabraleadiol and epicotillol and of b-sitosterol and stigmasterol. The structures of compounds 1-3 were determined on the basis of spectroscopic and chemical methods. The structure of aglaiaglabretol A (1) was confirmed by singlecrystal X-ray analysis, and the absolute stereochemistry of this isolate was established by the Mosher ester method. The cytotoxic activity of all isolates and several chemical transformation products obtained in the present study was evaluated. The known cyclopenta[b]benzofuran, rocaglaol (6), was found to be significantly active and comparable in potency to the positive controls, paclitaxel and camptothecin. Aglaiaglabretol B (2) was further tested in an in vivo hollow fiber model.
Indonesian Journal of Chemistry, 2021
Four sesquiterpenoid derivatives, i.e., 4β,10α-dihydroxyaromadendrane (1), caryophyllenol-II (2), senecrassidiol (3), and clovane-2β,9α-diol (4) have been isolated from the stem bark of Aglaia simplicifolia. The chemical structures of compounds 1-4 were determined based on spectroscopic data, including one and two-dimensional NMR and mass spectroscopy. In addition, these sesquiterpenoids 1-4, were also tested for their cytotoxic activity against B16-F10 melanoma skin cancer cell lines through in vitro assay. Among the isolated compounds 1-4, compound 1 showed the highest activity with an IC50 value of 44.8 μg/mL, suggesting the presence of a cyclopropane ring that plays an essential role in cytotoxic activity against B16-F10 melanoma skin cancer cell lines.