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ABSTRACT. 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. Key words: Aglaia cucullata, , A549 cell lines, cytotoxic activity, Meliaceae, sesquiterpenoids.

ABSTRACT. 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. Keywords: Azadirone-type limonoid, Chisocheton pentandrus, cytotoxic activity, Meliaceae.

Abstract In recent decades, the interest in natural products with immunomodulatory properties has increased due to their therapeutic potential. These products have a wider range of pharmacological activities and demonstrate lower toxicity levels when compared to their synthetic counterparts. Therefore, this study aimed to investigate the immunomodulatory effects of sesquiterpenoids (SQs) and sesquiterpenoid dimers (SQDs) isolated from Dysoxylum parasiticum (Osbeck) Kosterm. stem bark on human and murine cells, particularly focusing on toll-like receptor 4 (TLR4). Utilizing the secreted alkaline phosphatase (SEAP) assay on engineered human and murine TLR4 of HEK-Blue cells, antagonist TLR4 compounds were identified, including SQs 6, 9, and 10, as well as SQDs 17 and 22. The results showed that 10-hydroxyl-15-oxo-α-cadinol (9) had a potent ability to reduce TLR4 activation induced by LPS stimulation, with minimal toxicity observed in both human and murine cells. The SEAP assay also revealed diverse immune regulatory effects for the same ligand. For instance, SQs 12, 14, and 16 transitioned from antagonism on human to murine TLR4. The SQs (4, 7, 11, and 15) and SQDs (18–20) offered partial antagonist effect exclusively on murine TLR4. Furthermore, these selected SQs and SQDs were assessed for their influence on the production of proinflammatory cytokines TNF-α, IL-1α, IL-1β, and IL-6 of the NF-κB signaling pathway in human and murine macrophage cell lines, showing a dose-dependent manner. Additionally, a brief discussion on the structure-activity relationship was presented.

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. Keywords: cytotoxic activity, Dysoxylum excelsum, HeLa, Meliaceae, sesquiterpenoid.

Four triterpenoids, known as dammarane-type, dammaradienone (1), 20(S),25-epoxy-5α-dammar-20-en-3-one (2), 20(S)-5α-dammar-24-en-3α,20-diol-3-acetate (3) and 3α-acetyl-20S,24S-epoxy-25-hydroxydammarane (4), were isolated from Aglaia cucullata peel fruit. The structures of isolated compounds were identified based on their HR-TOFMS data and extensive NMR spectroscopic analysis, as well as compared with literature data. Compounds 1-4 were assessed for cytotoxic effects against HeLa cervical and B16-F10 melanoma skin cancer cells. All compounds showed moderate to weak activity against B16-F10 cancer cells, while compound 2 exhibited the strongest activity against HeLa cancer cells with IC50 of 7.10 µg/mL indicating that the existence of an epoxy moiety at the side chain increases the cytotoxicity to HeLa cells.

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 research was aimed to elucidate the structure of sesquiterpenoids from the peel fruit of Aglaia cucullata and their cytotoxic activities against two human cancer cell lines. The n-hexane extract was separated and further purified by various chromatographic methods to yiled three sesquiterpenoids. The structure of these sesquiterpenoids were identified by spectroscopy analysis including MS, IR, 1H-NMR, 13C-NMR and DEPT as well as compared with spectral data which reported previously. The sesquiterpenoid compounds 1-3 were identified as spathulenol (1), alismol (2), and 10-oxo-isodauc-3-en-15-al (3). The cytotoxic activity of three sesquiterpenoid compounds were tested against HeLa cervical cancer cell and B16-F10 skin cancer cell using the PrestoBlue method. Compound 2 exhibited the highest activity against both HeLa and B16-F10 cancer cell lines with IC50 48.11 μg/mL and 57.05 μg/mL, respectively.

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 substances were tested for their lethal potential against the A549 lung cancer cell type. A seco structure in the A ring of dammarane-type triterpenoid might play an important part in the lethal activity of component 4, which showed the greatest activity with an IC50 value of 32.17 µM against the A549 lung cancer cell line.

Sesquiterpenoids are derivatives of terpenoid compound that have a diverse skeleton and broad spectrum of biological activities, particularly anticancer activity. This research reported the isolation and elucidation structure of sesquiterpenoid from Chisocheton lasiocarpus stem bark, as well as their cytotoxic activity. Four sesquiterpenoid compounds, namely eudesm-4(15)-ene-1β,6β-diol (1), allo-aromadendrane-10α,14-diol (2), allo-aromadendrane-10β,14-diol (3) and guaianediol (4), were isolated for the first time from Chisocheton lasiocarpus stem bark. The chemical structure of all compounds was identified by spectroscopic analysis, including IR, MS, 1H-NMR, 13C-NMR and DEPT, and compared with previous reported spectral data. The cytotoxic activity of the isolated compounds against MCF-7 breast cancer line were examined by using the resazurin method. The results showed compound 1 shown the highest cytotoxic activity with IC50 108.08 ± 0.58 µM.

The n-hexane fraction from the stem bark of Lansium domesticum Corr. Cv. Kokosan afforded 3 sesquiterpenoids, namely eudesm-4(15),7-dien-1β-ol (1), eudesm-4(15)-ene-1β,6α-diol (2), and octahydro-4-hydroxy-3a-methyl-7-methylene-a-(1-methylethyl)-1H-indene-1-methanol (3). These three compounds were discovered in the Lansium genus for the first time. Their chemical structures were determined based on data generated from various spectroscopic methods, including one- and two-dimensional NMR, as well as mass spectroscopy. Sesquiterpenoid compounds (1-3) have also been evaluated on MCF-7 breast cancer cell lines and the compound 1 showed the strongest activity with an IC50 value of 17.97 µg/mL while compounds 2 and 3 showed moderate and weak activity with IC50 values of 121.65 and 201.57 µg/mL, respectively. The implication of the findings of these compounds is as an illustration that one of these sesquiterpenoids has potential as an anticancer with the presence of double bond which played important role in the cytotoxic activity that can be studied for new drug discovery.

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.

Sesquiterpenoids, an important class of natural products possessing three isoprene-derived units, are widely distributed across plants and have a variety of biological activities. All sesquiterpenoids are derived from farnesyl pyrophosphate (FPP), a biosynthesis precursor that can form various carbon skeletons. In order to provide a reference for further research and development of these compounds, this review focused on the increasing number of isolated and volatile sesquiterpenoids found to be produced by plants of the Meliaceae family between 1968 and 2023. The related articles were collected from SciFinder, Google Scholar, and PubMed. According to a literature review, several studies were started for more than 55 years on the plant’s stem barks, twigs, leaves, flowers, seeds, and pericarps, where approximately 413 sesquiterpenoid compounds from several groups such as eudesmane, aromadendrane, cadinane, guaiane, bisabolane, furanoeremophilane, humulene, germacrane, and oppositane-type were isolated and identified with some minor products. Additionally, the hypothetical route of sesquiterpenoids biosynthesis from this family was identified, and eudesmane-type was reported to be 27% of the total compounds. The antimicrobial, antidiabetic, antioxidant, antiplasmodial, antiviral, and cytotoxic activities of the isolated compounds and major volatile sesquiterpenoids constituent on essential oil were also evaluated. The result showed the fundamental of using the sesquiterpenoid compounds from the Meliaceae family in traditional medicine and the discovery of new drugs.

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.

Current issues of energy sector in Indonesia can be summarized as depletion of fossil energy reserves which is dominated by fuel oil and coal. Oil production continues to decline and the increase in oil fuels demand lead to increase imports of crude oil and oil fuels. To use lignocellulosic biomass waste has become a major alternative to replace fossil fuels and chemical feedstocks production. In 2015, total rice production in South Kalimantan reached 2,140,276 ton and rice straws were abundant waste which could be utilized as raw material for bioethanol production. Pretreatment process of lignocellulose is a crucial step to remove lignin because of the complex chemical cross-linking between chemical components. Delignification of lignin can increase the accessibility and digestibility of enzymatic, and help to promote enzymatic hydrolysis. Nowadays, pretreatment process with green chemistry method is continuesly developed by researcher to reduce the production costs and thus avoid adverse effects on human and the environment. This article disscussed about green methods for pretreatment of lignocellulosic material using deep eutectic solvent (DES) to increase second-generation bioethanol production in South Kalimantan.

The second generation of bioethanol derived from various cellulosic biomass materials is one of the latest renewable energy as the alternative of fossil fuel. The cellulosic waste based wood and non-wood materials are the most abundant natural resource on the earth, renewable, and inexpensive. Currently, second generation bioethanol development is still not optimally done due to various obstacles, especially the pretreatment process to eliminate lignin, influencing the conversion process of cellulose into reducing sugar. Hydrothermal method is one of lignocellulose pretreatments, which is widely developed because this method is relatively cheap and environmentally friendly with the utilization of water-based solvent. Hydrothermal methods performed at high temperature and pressure in a relatively short time are able to deconstruct the lignocellulose structure that enables cellulase enzymes to access cellulose for hydrolysis. This study discussed about the development of hydrothermal method for lignocellulose pretreatment process to increase production of second-generation bioethanol. Some aspects studied in this research were structural change, chemical composition, lignocellulosic crystallinity before and after hydrothermal processes, and hydrothermal effect on the production of reducing sugars. Hydrothermal method could be used and developed as an efficient and cheap method as the first treatment of lignocellulose waste in attempt to increase the production of bioethanol.