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Limonoid compounds are found in the Meliaceae family, especially in the genus Chisocheton. This genus belongs to medicinal plants with limonoid content that contains various biological activities such as anticancer, antimalarial, anti-inflammatory, insecticide, antiviral, neuroprotective and antimicrobial properties. One of them which was not much reported is Chisocheton lasiocarpus. This study aims to get the new limonoid compound of C. lasiocarpus seeds. C. lasiocarpus seeds were macerated using methanol and were partitioned using n-hexane, ethyl acetate and butanol. The presence of limonoid was guided using the Ehrlich reagent. Extract of n-hexane was collected and purified by the chromatographic method until two pure isolates was obtained as nimonol (1) and 6α-acetoxy-14β,15β-epoxyazadirone (2). The chemical structure of isolates were identified by spectroscopic data including UV, IR, NMR (1H, 13C, DEPT 135°, HMQC, HMBC, 1H-1H COSY) and by comparison to those related spectra reported previously.

In this study, we describe the isolation and structure elucidation of three triterpenoids (1) lansioside C, (2) 3-oxo-24-cycloarten-21-oic acid and (3) α, γ- onoceradienedione from the seeds, the leaves and the fruit peels of L. domesticum cv piedjietan Hasskl., respectively. The chemical structures of compound 1, 2 and 3 were identified with spectroscopic data. These compounds (1-3) had been reported from L. domesticum cv piedjietan Hasskl. Antifeedant activities of compounds 1, 2 and 3 (1% w/v) were evaluated using choice method against the fourth instar larvae of Epilachna vigintioctopunctata and showed activity of 65%, 43% and 53% respectively.

The Chisocheton genus belongs to the Meliaceae family which produces various structures and activities of compounds, such as antimalarial, antimicrobial, antitumor, anti-inflammatory, and cytotoxic. This plant has 53 species that are spread in tropical and sub-tropical forests, including Indonesia. Chisocheton plants have been known as plants that produce limonoids, namely triterpenoid compounds that have been modified to lose four terminal carbons (tetranortriterpenoids). One of the species whose phytochemical reports are still few and interesting for research on limonoid content is Chisocheton macrophyllus. Chisocheton macrophyllus is a tall plant that grows in the rainforest in the northern part of the island of Sulawesi, Indonesia, has the regional name ma aa, gula, pasak lingga, gending, ta suea, bekak, or pithraj tree. This paper will describe a limonoid compound, namely nimonol which has been isolated from Chisocheton macrophyllus. Nimonol is known to have the molecular formula C28H36O5 from a group of havanensin. The structure was determined by spectroscopic methods UV, IR, 1D-NMR (1H-NMR, 13C-NMR, and DEPT), 2D-NMR (1H-1H COSY, HMQC, and HMBC), and mass spectroscopy.

The Aglaia genus, a member of the Meliaceae family, is generally recognized to include a number of secondary metabolite compounds with diverse structures and biological activities, including triterpenoids. Among the members of this genus, Aglaia cucullata has been reported to have unique properties and thrives exclusively in mangrove ecosystems. This plant is also known to contain various metabolites, such as flavaglines, bisamides, and diterpenoids, but there are limited reports on the isolation of triterpenoid compounds from its stem bark. Therefore, this research attempted to isolate and elucidate seven triterpenoids belonging to dammarane-type (1–7) from the stem bark of Aglaia cucullata. The isolated compounds included 20S,24S-epoxy-3α,25-dihydroxy-dammarane (1), dammaradienone (2), 20S-hydroxy-dammar-24-en-3-on (3), eichlerianic acid (4), (20S,24RS)-23,24-epoxy-24-methoxy-25,26,27-tris-nor dammar-3-one (5), 3α-acetyl-cabraleahydroxy lactone (6), and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (7). Employing spectroscopic techniques, the chemical structures of the triterpenoids were identified using FTIR, NMR, and HRESITOF-MS. The cytotoxic activity of compounds 1–7 was tested with the PrestoBlue cell viability reagent against MCF-7 breast cancer, B16-F10 melanoma, and CV-1 normal kidney fibroblast cell lines. The results displayed that compound 5 had the highest level of bioactivity compared to the others. Furthermore, the IC50 values obtained were more than 100 μM, indicating the low potential of natural dammarane-type triterpenoids as anticancer agents. These findings provided opportunities for further studies aiming to increase their cytotoxic activities through semi-synthetic methods.

Cyclopurpuracin is a cyclooctapeptide isolated from the methanol extract of Annona purpurea seeds with a sequence of cyclo-Gly-Phe-Ile-Gly-Ser-Pro-Val-Pro. In our previous study, the cyclisation of linear cyclopurpuracin was problematic; however, the reversed version was successfully cyclised even though the NMR spectra revealed the presence of a mixture of conformers. Herein, we report the successful synthesis of cyclopurpuracin using a combination of solid- and solution-phase synthetic methods. Initially, two precursors of cyclopurpuracin were prepared, precursor linear A (NH2-Gly-Phe-Ile-Gly-Ser(t-Bu)-Pro-Val-Pro-OH) and precursor linear B (NH-Pro-Gly-Phe-Ile-Gly-Ser(t-Bu)-Pro-Val-OH, and various coupling reagents and solvents were trialled to achieve successful synthesis. The final product was obtained when precursors A and B were cyclised using the PyBOP/NaCl method, resulting in a cyclic product with overall yields of 3.2% and 3.6%, respectively. The synthetic products were characterised by HR-ToF-MS, 1H-NMR, and 13C-NMR, showing similar NMR profiles to the isolated product from nature and no conformer mixture. The antimicrobial activity of cyclopurpuracin was also evaluated for the first time against S. aureus, E. coli, and C. albicans, showing weak activity with MIC values of 1000 µg/mL for both synthetic products, whereas the reversed cyclopurpuracin was more effective with an MIC of 500 µg/mL.

A nortriterpenoid, 3-epi-cabraleahydroxylactone (1) and a steroid, stigma-4-en-3-on (2) were isolated from the n-hexane extract of stem bark of Aglaia angustifolia Miq. Compound (2) was isolated for the first time from this Genus. The structure of both compounds were identified by spectroscopic datas including one and two-dimensional NMR as well as infrared spectrum, high-resolution mass spectrometric analysis and by comparing with those spectral data previously.

A new ergostane-type steroid named (22E)-3α,6α,9α-ergosta-7,22-diene-3,6,9-triol (1), along with six known steroids 5α,8α-epidioxy-24-ethyl-cholest-6-en-3β-ol (2), ergosterol-5,8-peroxide (3), cerevisterol (4), isocyathisterol (5), 6β-hydroxystigmast-4-en-3-one (6), 6β-hydroxy-4-campesten-3-one (7), were isolated from the fermented unpolished rice media by Periconia pseudobyssoides K5 (Periconiaceae), an endophytic fungus from medicinal plant Toona sureni (Meliaceae). The fermentation takes at 28 ± 2 °C for 30 days. The structure of new steroid (1) was elucidated by extensive spectroscopic measurements (IR, HR-ESI-TOFMS, and 1D and 2D NMR) analyses. The isolated compounds (1–7) were evaluated for heme polymerization inhibition assay (HPIA). The IC50 HPIA value of 1 is 8.24 ± 0.03 mg/ml.

Introduction: One strategy for molecular cancer therapy is to know the key mechanism of cytotoxic compounds that can kill cancer cells. Ramie (Boehmeria nivea L. Gaud.) leaves contain active compounds that have important effects on cancer chemoprevention. Objective: To obtain the active fraction of a Ramie leaf extract in inhibiting the proliferation of MCF-7 breast cancer cell lines and to determine the mechanism of apoptosis induction using MCF-7 and Saccharomyces cerevisiae strains 1140, 1353, and 1138. Method: Fractions were prepared using n-hexane, dichloromethane (CH2Cl2), ethyl acetate, and n-butanol as solvents. All fractions were tested qualitatively through phytochemical. The MTT-based cytotoxicity assay used MCF-7 (in vitro) to obtain the IC50 value, whereas the model system that targets the enzymatic (topoisomerase) used a yeast-based bioassay to obtain the IC12 value. Apoptotic induction of the active fraction in MCF-7 was performed using flow cytometry and qPCR (2-ΔΔCt method). Results: The phytochemical analysis indicated that the extract fraction consisted of alkaloids and steroids. The smallest IC50 value was obtained from the CH2Cl2 fraction as 3.79 g/mL, potentially act as an anticancer. A higher percentage of apoptosis than that of necrotizing cells and live cells was observed through flow cytometry. The CH2Cl2 fraction with an IC12 value < 8000 in strains 1140, 1353, and 1138 consistently showed the mechanism of apoptosis induction as topoisomerase I and II inhibitors. Also, another mechanism could be through the intrinsic pathway, indicated by the highest expression level in p53. Conclusions: The CH2Cl2 fraction of Ramie leaves can inhibits the proliferation of MCF-7 cells in the active and strong categories. The CH2Cl2 fraction induces apoptosis by increasing p53 gene expression and inhibiting topoisomerase I and II. Thus, it showed potential as an anticancer drug candidate.

A novel 2,3-epoxy naphthoquinol, named (6R,7R,8R)-theissenone A (1), possessing an oxatricyclo[5.4.0.03,5]undeca-trien-2-one skeleton, together with two known compounds, (6S,7R,8R)-theissenone (2) and arthrinone (3), were produced by an endophytic fungus, Arthrinium marii M-211, which was isolated from mangrove plants. The structure of 1, including the absolute stereochemistry, was elucidated by analysis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) data and time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Additionally, the absolute structure of 2 was deduced as a diastereomer of 1 using ECD spectral data analysis. Compounds 1, 2 and 3 exhibited cytotoxic activity against the H4IIE rat hepatoma cells, with IC50 values of 67.5, 46.6 and 13.4 µM, respectively.

Chisocarpene A (

Three new β-resorcylic acid derivatives, 1–3, were obtained from the endophytic strain Lasiodiplodia theobromae GI-1005, which was isolated from the mangrove plant Rhizopora mucronata. The structures of new compounds together with five known compounds were elucidated by NMR and MS analyses, and chemical means. The isolated compounds were evaluated for phytotoxicity against Digitaria ciliaris (southern crabgrass) and Lactuca sativa (lettuce). Compound 1 showed growth inhibitory effects against D. ciliaris in a dose-dependent manner.

Three new dammarane-type triterpenoids, namely elliptaglin A-C (

The diversity of structures of triterpenoids provides a variety of interesting pharmacological effects, one of them being anticancer. Sources of triterpenoids are found in Dysoxylum excelsum, it is still rarely studied, and it potentially contains triterpenoids with cytotoxic activity. Therefore, the research aimed to isolate the triterpenoids from the stem bark of D. excelsum and determine their cytotoxic efficacy against the breast cancer cells of MCF-7. The dried stem bark of D. excelsum was macerated using methanol and then fractionated with n-hexane and ethyl acetate to obtain the corresponding fractions. Two triterpenoids, 3α,7α-dihydroxyapotirucalla-14,24-Z-dien-26-oic acid (1) and masticadienonic acid or 3-oxo-tirucalla-7,24-Z-dien-26-oic acid (2) were isolated in the first place from the Dysoxylum genus. Compounds 1 and 2 were assayed for their cytotoxic potency anti- MCF-7 using the MTT assay and gave moderate IC50 values of 60.87 and 72.86 µM, respectively. Based on their analogs, partial structure modification of the compounds might increase the activity; thus, it can be further utilized as better lead compounds for anticancer drugs candidate.

Two steroid compounds, ergosterol peroxide (1) and stigmasterol (2) have been isolated from the stembark of Aglaia simplicifolia belong to Meliaceae family. The chemical structures of 1 and 2 were identified based on spectroscopic evidence including UV, IR, 1D NMR, 2D NMR as well as mass spectra and by comparison with those previously reported spectra data. Both compounds were evaluated for their cytotoxic effects against cervical cancer HeLa cells in vitro. Compounds 1 and 2 showed cytotoxicity activity against HeLa cervical cancer cells with IC50 values of 0.80 and 26.42 µM, respectively.

Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n -hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1) , epicatechin (2) , epigallocatechin-3- O -gallate (3) , and epicatechin-3- O -gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods ( 1 H-NMR, 13 C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.

Background: Currently, infectious diseases caused by pathogenic and resistant bacteria are more challenging for anti-bacterial drug discovery. The discovery of new anti-bacterial agents developed in many mechanisms includes disruption of the bacterial cell wall formations. The MurA is a key enzyme contributing to the first step of bacterial peptidoglycan biosynthesis and is, therefore, proposed as an effective bactericidal target. Objective: The purpose of this research is to identify anti-bacterial compounds from U. gambir Roxb and to predict the potential inhibitory activities against murA enzyme by in silico study. Materials and Methods: Investigation and discovery of new inhibitors of MurA enzyme were conducted on the medicinal plant of Gambir (Uncaria gambir Roxb) and those that reportedly contained anti-bacterial agents. The anti-bacterial compounds were isolated by combinations of chromatography methods guided by anti-bacterial activity against bacteria of E. faecalis, S. mutans, and S. sanguinis. The structures of active compounds were characterized by spectroscopic methods, and the anti-bacterial activity was evaluated by the microdilution method (in vitro) combined with molecular docking of the MurA enzyme (in silico). Results: The anti-bacterial flavonoids of catechin were isolated from U. gambir Roxb with MIC values of 6250 and 12500 ppm, respectively, against S. sanguinis and E. faecalis. The in silico study showed that catechin has a binding affinity of -8.5 Kcal/mol to MurA which is higher than fosfomycin as a positive control. Conclusions: The catechin is predicted to have potential as a new natural inhibitor of the MurA enzyme to inhibit bacterial cell wall biosynthesis.

Three new metabolites, including two alkaloids, vancouverone A (1) and vancouverone B (2), one α-pyrone, 10,11-dihydroxy-citreoviridin (3), and two known compounds, neocitreoviridinol (4) and PF1140 (5), were isolated from Penicillium vancouverense YY-1 derived from gastric flora of the sea snail Monodonta neritoides. Their structures and configurations were elucidated using spectroscopic analyses. Compound 2 exhibited phytotoxicity against plant species (Lactuca sativa, Trifolium repens, Raphanus sativus var. longipinnatus, and Brassica rapa var. perviridis).

A seco-apotirucallane-type triterpenoid, namely angustifolianin (1), along with three dammarane-type triterpenoids, (20S, 24S)-epoxy-dammarane-3β,25-diol (2), 3-epi-cabraleahydroxylactone (3), and ...

Nine analogues of antioxidant peptide SCAP1 were successfully synthesised using a solid-phase method on a 2-chlorotrytil resin. The compounds were obtained in a range of yields of 7.0–57.8%. The occurrence of aggregation during the synthesis is suspected to be responsible for the poor yields. All peptides were characterized by high-resolution time-of-flight mass spectrometry (HR-TOFMS) and nuclear magnetic resonance (NMR). The antioxidant activities of the SCAP1 analogues as well as SCAP1 were analysed utilising the 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) assay. The results revealed that all of the analysed peptides exhibited moderate antioxidant properties. Moreover, the evaluation of the structure–activity relationship showed that the Asn residue is an important requirement for the antioxidant activity of SCAP1. The replacement of Asn with other amino acid residues (Thr, Pro, Tyr, Trp and Phe) resulted in a decrease in the IC50 values of the peptides. Notably, however, the replacement of the Lys residue with Val marginally increased the activity.

Three new limonoids namely pentandricines B–D (1–3), were isolated from n-hexane extract of the stem bark of Chisocheton pentandrus, along with four known limonoids (4-7). The chemical structures of pentandricines B–D, were fully elucidated based on UV, IR, HR-TOFMS, 1D- and 2D-NMR spectra. Furthermore, compounds 1-7 were evaluated for their cytotoxic activity against MCF-7 breast cancer cells in vitro, with compound 7 (nimonol) showing strongest cytotoxicity activity with an IC50 value of 22.03 ± 0.026 μM.

[Leu]6-aureobasidin K 1 is an analog of AbK, in which aIle residue at the sixth position of AbK is replaced by Leu. [Leu]6-AbK 1 was successfully synthesized using a combination of solid- and solution-phase that has a difference with the previous method applied for the synthesis of other aureobasidin analogues, [2S,3S-Hmp]-AbL 2. The linear precursor was prepared by using solid-phase method with Fmoc strategy, in which an ester bond was constructed on the resin. The cyclic product was obtained from a solution-phase reaction of the linear precursor using HATU reagent. The crude of the cyclic peptide was purified using a column chromatography technique to obtain [Leu]6-AbK 1 with a percent yield of 5.31% that is higher compared to previous similar method for synthesis of [2S,3S-Hmp]-AbL 2. The purity level of cyclic product was analyzed using analytical RP-HPLC (tR = 6.49 min) and analysis of structure using 1H-NMR.

Two new azadirone-type limonoids, namely lasiocarpine A (

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.

Two new azadirone-type limonoids, namely lasiocarpine A (1) and lasiocarpine B (2) were isolated from the fruit of Chisocheton lasiocarpus along with three known limonoids (3–5). UV, IR, one- and two- dimensional NMR, and mass spectrometry were used to determine the chemical structure of the isolated compounds. Furthermore, their cytotoxic activity against breast cancer cell line MCF-7 was evaluated using PrestoBlue reagent. From these compounds, lasiocarpine A (1) showed the strongest activity with an IC50 value of 43.38 μM.

Three new dammarane-type triterpenoids, namely elliptaglin A-C (1–3) were isolated from the stem bark of Aglaia elliptica (C.DC.) Blume along with three known derivatives, namely (20S)-hydroxydammar-24-en-3-on (4), cabralealactone (5), and E-25-hydroperoxydammar-23-en-20-ol-3-one (6). Subsequently, their chemical structures were determined using HR-ESI-MS, FTIR, 1D and 2D-NMR spectroscopic analysis as well as comparison with previous studies. The cytotoxicity activities of the isolated compounds against MCF-7 breast cancer and B16-F10 melanoma cell lines were then tested using PrestoBlue reagent. The analysis results showed that elliptaglin B (2) had the strongest activity against both cell lines with IC50 values of 60.98 and 51.83 µM, respectively.

Two undescribed sesquiterpenoids, namely dysoticans A and B, and three undescribed sesquiterpenoid dimers, namely dysoticans C-E, together with six analogs, were isolated from the stem bark of Dysoxylum parasiticum (Osbeck) Kosterm. (Meliaceae), growing in West Java, Indonesia. Their structures were elucidated based on extensive spectroscopic analysis and theoretical simulations of ECD spectra and

A novel 2,3-epoxy naphthoquinol, named (6

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.

In the course of our continuing search for anticancer compounds from Chisocheton species, three steroids, stigmast-5-en-3β-ol ( 1 ), stigmast-5-en-3β-ol-3- O -β- D -glucopyranoside ( 2 ) and stigmast-5,22-dien-3β-ol-3- O -β- D -glucopyranoside ( 3 ), were obtained from the stembark of Chisocheton celebicus . The structures of compound 1 - 3 were identified with spectroscopic data including IR, 1D-NMR, 2D-NMR and TOF-MS, as well as by comparing with those spectral data previously. Compounds 1 - 3 , were evaluated for their cytotoxic effects against P-388 murine leukemia cells and displayed the cytotoxicity activity with IC 50 values of 12.45 ± 0.050, 52.27 ± 0.031 and 62.52 ± 0.076 µg/mL, respectively.

The endophytic fungus, Clonostachys rosea B5-2 was isolated from mangrove plants and subjected to the one strain many compounds (OSMAC) methodology. By this approach, it was found that modification...

Two new naphthoquinone derivatives, 6-hydroxy-astropaquinone B (1) and astropaquinone D (2) as well as the known compound 3-O-methyl-9-O-methylfusarubin (3) were isolated from Fusarium napiforme, an endophytic fungus isolated from the mangrove plant, Rhizophora mucronata. The structures of 1 and 2 were determined by 1D and 2D NMR spectroscopic analyses. Compounds 1, 2 and 3 exhibited moderate antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa. Furthermore, 1, 2 and 3 were phytotoxic action in lettuce seeding at a concentration of 30 μg · mL−1.

Fractionation of ethyl acetate extract obtained by culturing the endophytic fungus Pseudocosmospora sp. Bm-1-1 resulted in the isolation of four new meroterpenoids, cosmosporin A (1), 6-carboxy-cosmosporin A (2), rel-(6aS,10aR)-Δ9-tetrahydrocannabiorcolic acid B (3) and 8′-hydroxy-cannabiorcichromenic acid (4), in addition to four known compounds 5–8. Structures were elucidated by spectral analysis, as well as by directly comparing the spectral data of new compounds with those of known compounds. Cannabiorcichromenic acid (5), decarboxy-cannabiorcichromenic acid (6), and rel-(6aS,10aR)-decarboxy-Δ9-tetrahydrocannabiorcolic acid B (8) restored growth of a Saccharomyces cerevisiae mutant strain involving Ca2+ signal transduction. Furthermore, compounds 3 and 8 had cytotoxic activity against HL60 cells (3: IC50 = 24.1 μM and 8: IC50 1.6 μM).

Four new triterpenoids, namely, chisopaten A-D (1-4), were isolated from the n-hexane extract of the bark of Chisocheton patens Blume. The chemical structures of new compounds were elucidated on the basis of spectroscopic data interpretation. All isolated compounds were evaluated for their cytotoxic activity against MCF-7 breast cancer lines. Chisopaten A and C, showed strongest cytotoxicity activity with IC50 values of 4.01 ± 0.008 and 4.33 ± 0.009 μM, respectively.

Five polyketides, paralactonic acids A-E (1-5) were isolated from Paraconiothyrium sp. SW-B-1, an endophytic fungus isolated from the seaweed, Chondrus ocellatus Holmes. Their structures were determined by various spectroscopic methods, predominantly by 2D NMR spectroscopic analyses. The absolute configurations of compounds 1-5 were determined by comparison of the experimental and calculated ECD spectra. Compound 5 showed moderate antibacterial activity and restored the growth of a mutant yeast strain inhibited by hyperactivated Ca2+-signaling.

SCAP1e is an alanine-rich-pentapeptide, analog of SCAP1 an antioxidant peptide. The previous solid-phase synthesis on this peptide resulted in low yield of the product (7%) due to the aggregation that might occur during synthesis. The aim of the research was to resynthesize this peptide using the similar method but with a slight modification in the resin loading step. SCAP1e was successfully synthesized through solid-phase method with an improved yield 87.9% and high purity (90.2%) based on the HPLC analysis. The reduction of resin loading value from 1.2 mmol/gram to 0.63 mmol/gram has made a good impact for the improvement of the synthetic yield.

A new havanensin-type limonoid, 16β-hydroxydysobinin (1), along with four known limonoids (2–5), have been isolated from the seeds of Chisocheton macrophyllus. The chemical structure of the new compound was determined by referencing spectroscopic data, and by comparison to those related spectra previously reported. Each compound was evaluated for their cytotoxic effects against Michigan Cancer Foundation-7 (MCF-7) breast cancer cells and display no significant activity.

Antimicrobial peptides (AMPs) are interesting compounds owing to their ability to kill several pathogens. In order to identify new AMPs, c-PLAI analogues were synthesized and evaluated together with their linear precursors for their antimicrobial properties against two Gram-positive bacteria ( Staphylococcus aureus and Bacillus cereus ), two Gram-negative bacteria ( Escherichia coli and Klebsiella pneumoniae ), and two fungal strains ( Candida albicans and Trichophyton mentagrophytes ). The new c-PLAI analogues were prepared through a combination of solid- and solution-phase syntheses, as previously employed for the synthesis of c-PLAI. The antimicrobial activity tests showed that the synthetic parent peptide c-PLAI was inactive or weakly active towards the bioindicators employed in the assay. The tests also indicated that cyclic c-PLAI analogues possessed enhanced antimicrobial properties against most of the bacteria and fungi tested. Furthermore, this study revealed that analogues containing cationic lysine residues displayed the highest activity towards most bioindicators. A combination of lysine and aromatic residues yielded analogues with broad-spectrum antimicrobial properties.

Nine new β-resorcylic acid derivatives, (15S)-de-O-methyllasiodiplodin (1), (13S,15S)-13-hydroxy-de-O-methyllasiodiplodin (2), (14S,15S)-14-hydroxy-de-O-methyllasiodiplodin (3), (13R,14S,15S)-13,14-dihydroxy-de-O-methyllasiodiplodin (4), ethyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (5), ethyl 2,4-dihydroxy-6-(8-hydroxyheptyl)benzoate (6), ethyl 2,4-dihydroxy-6-(4-methoxycarbonylbutyl)benzoate (7), 3-(2-ethoxycarbonyl-3,5-dihydroxyphenyl)propionic acid (8), and isobutyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (9), together with a known ethyl 2,4-dihydroxy-6-(8-oxononyl)benzoate (10) were obtained from Lasiodiplodia theobromae GC-22. The structures of these compounds were elucidated by extensive spectroscopic analyses. Compounds 1, 3, and 6 showed growth inhibitory effects against Digitaria ciliaris. Conversely, treatment with compounds 5, 6, 7, 9, and 10 stimulated elongation activity toward the root of Lactuca sativa. These data expand the repertoire of new β-resorcylic acid derivatives that may function as lead compounds in the synthesis of new agrochemical agents.

Eleven undescribed triterpenoids (pentandrucines A to K) were isolated from the n-hexane extract of the stem bark of Chisocheton pentandrus (Blanco) Merr. These comprised ten undescribed dammarane-type triterpenoids and one undescribed apotirucallane-type triterpenoid. Additionally, two dammarane-type triterpenoids, four apotirucallane-type triterpenoids and two tirucallane-type triterpenoids were also isolated. The chemical structures of pentandrucine A-K, were fully elucidated using 1D and 2D-NMR, and high resolution MS. All of the compounds were evaluated for cytotoxic activity against MCF-7 breast cancer cells in vitro. Melianodiol proved to be the most active with an IC50 of 16.84 μM comparing favourably with Cisplatin (13.2 μM).

A seco-apotirucallane-type triterpenoid, namely angustifolianin (

Two new compounds, a new lactone, quercilactone A (