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This work was conducted to isolate the steroid compounds from an endophytic fungus Cladosporium anthropophilum and determine their effects against 4 strains of bacteria. The fungi were afforded from a mangrove plant Avicennia marina (Forssk.) Vierh of Acanthaceae family, growing in West Java, Indonesia. The fermentation and isolation of C. anthropophilum yielded 3 ergostane-type steroids including a highly oxidized one, identified as penicisteroid A (1), ergosterol (2), and ergosterol-5,8-peroxide (3), together with 2 stigmastanes, characterized as stigmasterol (4), and stigmasterol-5,8-peroxide (5). The elucidation structure of all isolated steroids was performed by extensive spectroscopic measurements (MS, IR, 1D, and 2D NMR) and supported by a comparison of previously reported spectral data. Subsequently, the potential of the 5 steroids as well as methanol, n-hexane, and ethyl acetate extracts were evaluated against 2 Grampositive bacteria, Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and 2 Gram-negative bacteria, Vibrio harveyi ATCC 5339 and Escherichia coli ATCC 25922. The results showed that none of the isolated steroids were active, while the 3 extracts exhibited significant inhibition against all the tested bacteria's growth and enabled us to propose the synergistic effects between active compounds in these extracts and their antibacterial activity. [ABSTRACT FROM AUTHOR]

Dysoxylum alliaceum belongs to the Dysoxylum genus (Meliaceae) and there are few reports concerning the phytochemical components of this plant. To examine the chemical constituents of Dysoxylum alliaceum stem bark, a phytochemical study has been conducted and identified five known steroids, 3β,16β-dihydroxy-24(S)-methyl cholestenol (1), ergosta-5,22-dien-3β-ol (2), ergosta-7,24(28)-dien-3β-ol (3), 22(E)-ergosta-6,22-dien-3β,5α,8α-triol (4), and 20α-dihydroprogesterone (5) from its ethanolic extract. Spectroscopic data such as FT-IR, HR-ESI-MS, 1D, and 2D NMR as well as comparison with previously published spectral data were used to identify the chemical structures of compounds 1-5. Furthermore, these steroids 1-5 were assessed in vitro regarding their cytotoxic effect against A549 lung cancer cell lines and revealed weak to inactive with IC50 values ranging from 68.52 to >150 μM. [ABSTRACT FROM AUTHOR]

Alliaceumolide A (1), a new macrolide together with known ivorenolide B (2) were isolated from Dysoxylum alliaceum (Blume) Blume ex A.Juss. These compounds were classified as 17-membered macrolide, which is a rare structure for plant-derived natural products. The structures were elucidated by extensive spectroscopic analyses, and the absolute configuration of 1 was determined by electronic circular dichroism (ECD) using TDDFT method. Furthermore, compounds 1 and 2 were tested for cytotoxic activity against two cancer MCF-7 and HeLa cell lines. [Display omitted] • Two 17-membered macrolides were isolated from Dysoxylum alliaceum stem bark. • A rare undescribed macrolide was identified. • The absolute configuration was determined by ECD technique. • Compounds 1 and 2 were tested against two human cancer cell lines. [ABSTRACT FROM AUTHOR]

A new seco-A tirucallane triterpenoid named excelxylin A (1), along with two known seco-A triterpenoids (2–3), were isolated from the n-hexane extract of Dysoxylum excelsum (Spreng.) Blume ex G.Don stem bark. The structure and stereochemistry configuration of compounds 1–3 was established by NMR, IR, and HR-ESI-MS spectroscopic data analyses and comparison of their NMR data with literatures. The compounds exhibited the carbon framework for seco-A ring tirucallane triterpenoid, first reported in the Dysoxylum genus. All compounds were tested for their cytotoxicity against human cervical HeLa cells. [ABSTRACT FROM AUTHOR]

Limonoid group belongs to triterpenoid that has undergone further oxidation accompanied by the loss of four carbon atoms to form a furan ring in the chain. This limonoid compound is often found in the Chisocheton genus. Limonoid compounds have been known as compounds with high structural variations and this makes limonoids have diverse and interesting activities, including cytotoxic and anticancer. In the course of our continuing study for limonoid constituents that have cytotoxic activity against cancer cell lines, methanol extract of stem bark from the Chisocheton pentandrus plant provides significant activity. The methanol extract was separated using various chromatographic techniques in the normal and reverse stationary phase to produce four azadirone-type limonoid compounds (1-4). The elucidation structure of 1-4 was determined using spectroscopic methods including, UV-Visible, IR, and 1D-NMR as well as optical rotation. All four known compounds were established as trichilenone acetate (1), toonaciliaton C (2), 11α-acetoxiazadiron (3), and 16β- hydroxydisobinine (4). The cytotoxicity of compounds 1-4 was assessed by examination using the resazurin method, which showed that compound 4 was the promising constituent against the MCF-7 cells with an IC50 value of 43.1 µM and was stronger than its positive control. [ABSTRACT FROM AUTHOR]

Sesquiterpenoids are a class of terpenoid compounds with a remarkable diversity of structures and biological activities. Sesquiterpenoids are primarily found in higher plants, such as the Meliaceae family's Aglaia genus. Aglaia cucullata is a species of Aglaia that is still rarely explored and can potentially contain sesquiterpenoid compounds with cytotoxic activity. Hence, the research intended to isolate sesquiterpenoids from the n-hexane extract of A. cucullata stem bark and evaluate their cytotoxic effect against A549 lung cancer cells. Compounds 1 and 2 were isolated and purified from n-hexane extracts utilizing various chromatographic techniques. The structure of compounds 1 and 2 was determined by analyzing various spectroscopic methods (IR, MS, and NMR) and comparing them to previously reported spectral data. Compound 1 was identified as an isodaucane-type sesquiterpenoid, 10-hydroxy-6,10-epoxy-7(14)-isodaucane, and was first reported in Meliaceae family. Compound 2 was confirmed as an eudesmane-type sesquiterpenoid, eudesm-4(15)-ene-1β,6α-dihydroxy, and was first reported in Aglaia cucullata. Cytotoxic activity of 1 and 2 were investigated in vitro against A549 lung cancer cells using the PrestoBlue assay and resulted in inactive and low cytotoxicity with IC50 values of 292.77 and 90.55 μM, respectively. [ABSTRACT FROM AUTHOR]

Sesquiterpenoids belong to a group of terpenoid compounds with interesting structures that are abundant in natural products especially in higher plants. Sesquiterpenoids have a wide variety of bioactivities with great potential cytotoxic activity. The species Dysoxylum excelsum belongs to the Meliaceae family known as higher plant, but only a few sesquiterpenoids have been reported particularly for their cytotoxic activity. Therefore, this research aims to isolate and elucidate the sesquiterpenoids structure from D. excelsum stem bark and examines their cytotoxicity against HeLa cervical cancer cells. Through various column chromatography separations, four known sesquiterpenes namely β-caryophyllene oxide (1), caryophyllenol II (2), humulene dioxide A (3), and guai-6-en-10β-ol (4) were acquired from the n-hexane extract. Compounds 1-4 were isolated for the first time from D. excelsum species. The sesquiterpenoid structures were elucidated according to Nuclear Magnetic Resonance, Infrared, and HR-TOF-MS analysis. The cytotoxicity compounds 1-4 was determined against HeLa cervical cancer cells by examination with the PrestoBlue method and compound 3 exhibited the most potent cytotoxicity with an IC50 value of 160.74 μM. [ABSTRACT FROM AUTHOR]

Sesquiterpenoids are terpenoid derivative compounds that have a diverse chemical structure and pharmacological effects. Sesquiterpenoids can be found in many plants of Aglaia which is the large source of natural compounds in the Meliaceae family. This investigation was intended to elucidate the structure of sesquiterpenoids from Aglaia cucullata peel fruit and their cytotoxicity against two human cancer cell lines. n-hexane extracts were separated by various chromatographic methods to yield three sesquiterpenoids. These sesquiterpenoids were identified by spectroscopy analysis (HR-TOFMS, IR, ¹H, 13C-NMR, DEPT-135) as well as compared with spectral data which reported previously. The sesquiterpenoid compounds 1-3 were identified as spathulenol (1), alismol (2), and 10-oxoisodauc-3-en-15-al (3). The cytotoxic activity of three sesquiterpenoid compounds were tested against B16-F10 skin cancer cell and HeLa cervical cancer cell using the PrestoBlue method. Compound 2 exhibited the highest activity against both HeLa and B16-F10 cancer cell lines with IC50 218.33 µM and 258.90 µM, respectively. [ABSTRACT FROM AUTHOR]

Aglaia cucullata is a mangrove plant with a tropical Asian distribution. It is used as traditional medicine for the treatment of diarrhea, inflammation, skin diseases, and heart diseases. Several compounds isolated from A. cucullata have demonstrated cytotoxic activity against various human cancer cells. Cancer therapies such as surgery, chemo-, and radiotherapy have many side effects. However, the use of natural bioactive compounds such as triterpenoid in cancer treatment can be used as an alternative to reduce these side effects. Therefore, the discovery of bioactive compounds from plants is very important to improve aspects of discovery and development of sustainable new anticancer drug candidates. Here, we report the chemical structures of seven known dammarane-type triterpenoids (1–7) isolated from A. cucullata exocarp and evaluate their cytotoxicity against B16-F10 melanoma skin cancer cells. The isolated compounds included cabraleahydroxylactone 3α-acetate (1), (20S)-20-hydroxydammar,24-en-3α-ol (2), (20S)-20-hydroxydammar,24-en-3-on (3), methyl 20(S)-hydroxy-3,4-secodammar-4(28),24-diene-3-oic acid (4), 3-epi ocotillol II (5), cabraleone (6), and ocotillone (7). The n-hexane extract was found to be active against B16-F10 cells, exhibiting an IC50 value of 7.85 ± 0.22 µg/mL. Fractionation of this extract subsequently identified the compound (20S)-20-hydroxydammar 24-en-3-on (3) as an active substance with an IC50 value of 21.55 ± 0.25 µM, comparing favorably with the positive control cisplatin (12.90 µg/mL; 43.00 µM). These results provide further evidence of the genus Aglaia as a source of cytotoxic cancer drug leads. In addition, compound 3 has potential as a convincing therapeutic agent for further research in the context of sustainable drug development, especially the development of new safe cancer chemotherapeutic agents. [ABSTRACT FROM AUTHOR]

Chisocarpene A (1) is a new tirucallane-type triterpenoid together with odoratone (2) and 24-methylenecycloartanol (3), isolated from the stem bark of Chisocheton lasiocarpus. The chemical structures of compounds 1–3 were elucidated through a detailed analysis of their spectroscopic data (IR, MS, 1 D, and 2 D NMR). The isolated compounds were evaluated for cytotoxic activity against the MCF-7 breast cancer cell line using a resazurin-based assay. Compound 1 showed the most potent activity (IC50 26.56 ± 1.01 µM) and was two-fold more active than the positive control. [ABSTRACT FROM AUTHOR]

Lansium domesticum Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have been rarely utilized. The previous chemical investigation of this plant showed the presence of secondary metabolites with many biological activities, including cytotoxic triterpenoid. Triterpenoids is a class of secondary metabolites which contain thirty carbon atoms in the main skeleton. The high modification of this type of compound, including the ring opening, highly oxygenated carbons, and the degradation of its carbon chain to give the nor-triterpenoid structure, is responsible for its cytotoxic activity. In this paper, we isolated and elucidated the chemical structure of two new onoceranoid triterpenes, kokosanolides E (1) and F (2), from the fruit peels of L. domesticum Corr., along with a new tetranortriterpenoid, kokosanolide G (3), from the seeds of L. domesticum Corr. The structural determination of compounds 1–3 was undertaken through FTIR spectroscopic analysis, 1D and 2D NMR, mass spectrometry, as well as through a comparison of the chemical shifts of the partial structures of compounds 1–3 with the literature data. The cytotoxic properties of compounds 1–3 were tested against MCF-7 breast cancer cells using the MTT assay. Moderate activity was shown by compounds 1 and 3, with IC50 values of 45.90 and 18.41 μg/mL, respectively, while compound 2 showed no activity (IC50 168.20 μg/mL). For the onoceranoid-type triterpene, the high symmetrical structure of compound 1 is presumably the reason for its better cytotoxic activity compared with that of compound 2. Compound 3 showed moderate activity, mainly because of the presence of the furan ring, which, based on the literature, gives better cytotoxic activity in a tetranortriterpenoid-type structure. The findings of three new triterpenoid compounds from L. domesticum indicate the significant value of this plant as a source of new compounds. [ABSTRACT FROM AUTHOR]

AbstractAglaia pachyphylla is a species from the Aglaia genus (Meliaceae) and the chemical constituent has not been widely explored. A new cycloartane-type triterpenoid, pachyphyllanone (1), along with four known compounds (2-5) were isolated from Aglaia pachyphylla Miq. Furthermore, the structure of the new compound was elucidated by the interpretation of spectroscopic data, including 1D and 2D-NMR, as well as ECD and NMR calculations (DP4+ analysis). Compounds 1-5 showed cytotoxic activities against MCF-7 with IC50 values ranging from 160.74 to 299.75 μM. [ABSTRACT FROM AUTHOR]