Three novel dihydrochalcones from Flemingia lineata (L.) W.T. Aiton and their antiplasmodial activity.

Three novel dihydrochalcones, flemilineatins C-E (1-3), and two known flavanones (4-5) were isolated from Flemingia lineata (L.) W.T. Aiton leaves. Dihydrochalcones 1-3 structures were established using NMR spectrum and high-resolution ESIMS data. Compounds 1-5 were assayed to Plasmodium falciparum lactate dehydrogenase (PfLDH) for their antiplasmodial activity. Compounds 2 and 5 exhibited high activity with an IC50 value of 0.74 and 0.79 µg/mL, respectively.

4-Propyl- and 4-phenylcoumarins from mesua lepidota T. Anderson and their cytotoxic activity.

Two new 4-phenylcoumarins, mesulepidotins A (1) and B (2), one new 4-propylcoumarin, mesulepidotin C (3), and one known 4-phenylcoumarin (4) were isolated from Mesua lepidota stem barks. The structures of 4-propyl- and 4-phenylcoumarins were identified by analysing 1D and 2D NMR spectra combined with high-resolution ESIMS data. Compounds 1-4 were assayed to MCF-7 and HeLa cells for their cytotoxic activity. Mesulepidotin A (1) showed high activity with an IC50 value of 1.59 and 1.41 µM, respectively.

Dihydrostilbenes from Macaranga javanica (Blume) Müll. Arg. and their antiplasmodial activity.

An undescribed dihydrostilbene, macajavanicin D (1), and three known analogs, malayheyneiin A (2) and laevifolins A-B (3-4), were isolated from Macaranga javanica (Blume) Müll. Arg. leaves. Macajavanicin D (1) structure was determined based on a combination of ESI-HRMS data and NMR spectra. Compounds 1-4 were evaluated to Plasmodium falciparum strain 3D7. Macajavanicins D (1) and laevifolin A (3) showed potent activity with an IC50 value of 0.85 and 1.03 µg/mL, respectively.

Three new dihydrochalcones from the leaves of Artocarpus sericicarpus Jarrett and their activity against Plasmodium falciparum.

Three new dihydrochalcones: artoserichalcone A-C (1-3), were isolated from the leaves of Artocarpus sericicarpus. The structures of compounds were determined based on NMR spectrum (1H, 13C, and 2D) and HRESIMS spectroscopic analysis. Compounds (1) and (3) showed active antimalarial activity with IC50 values of 16.90 and 13.56 µM, respectively. Meanwhile, compound (2) with an IC50 value of 63.01 µM was categorised as a moderate antimalarial substance. The cytotoxicity against Huh7, HepG2, BHK-21, and Vero cells showed that compounds (1-3) with CC50 values > 20 µg/mL could be considered non-cytotoxic. Compounds (1-3) exhibited antimalarial activity against Plasmodium falciparum and non-toxic as an antimalarial agent.

Two new flavonols from Macaranga inermis pax & K.Hoffm.

Four isoprenylated flavonols, including two new compounds, macainermisins A-B (1-2), and two known compounds, sinoflavonoid P (3), broussoflavonol F (4), were isolated from the leaves of Macaranga inermis. A combination of HRESIMS, UV, 1D, and 2D NMR spectra elucidated the structures of 1-2. Flavonols (1-4) were evaluated against three cancer cells. Compound 1 showed high cytotoxicity against WiDR with an IC50 value of 0.93 µM, and compound 2 was active towards HeLa and WiDR (IC50 values of 0.90 and 0.94 µM), and compound 3 showed high activity towards 4T1 and HeLa (IC50 values of 0.83 and 0.98 µM).

Three novel quinolinone alkaloids from the leaves of Melicope denhamii.

Three previously unreported quinolinone alkaloids: melicodenines J-L (1-3) and six known compounds (4-9), were isolated from the leaves of Melicope denhamii (Seem) T.G. Hartley. The structures of three quinolinone alkaloids were identified based on HRESIMS and NMR spectra. Compounds 1-9 were assayed in three cancer cells (MCF-7, HeLa, and P-388). Compounds 1 and 5 showed high cytotoxic activity against HeLa cells with IC50 values of 1.8 and 0.8 µM, respectively.

Two new chromanone acids from the stem bark of Calophyllum peekelii Lauterb.

Three chromanone acids were isolated from the stem bark of Calophyllum peekelii Lauterb. Among them are two new chromanone acids, calopeekelioic acids A (1) and B (2), along with calolongic acid (3), Their structures were established by analyzing a combination of HRESIMS, 1 D, and 2 D NMR spectra. Chromanone acids 1-3 were evaluated for their antiplasmodial activity against Plasmodium falciparum strain 3D7. Compounds 1-2 showed high activity with an IC50 value of 1.70 and 1.01 µg/mL, respectively.

Two new pyranoxanthones from the stem bark of Calophyllum pseudomolle P.F. Stevens.

Two new pyranoxanthones, calotetrapterins D (1) and E (2), were isolated from the stem bark of Calophyllum pseudomolle P.F. Stevens along with α-mangostin (3). The structures of compounds 1-2 were determined based on 1D NMR (1H, 13C) and 2D NMR (HMQC, HMBC), as well as HRESIMS spectroscopic analysis. Compounds 1-2 showed moderate activity against HeLa and murine leukaemia P-388 cells.

Alkaloid and benzopyran compounds of Melicope latifolia fruit exhibit anti-hepatitis C virus activities.

BACKGROUND: New agents for developing alternative or complementary medicine to treat the hepatitis C virus (HCV) are still needed due to high rates of HCV infection globally and the current limitations of available treatments. Treatment of HCV with a combination of direct acting antivirals have been shown to be approximately 90% effective but will be limited in the future due to the emergence of drug resistance and high cost. The leaves of Melicope latifolia have previously been reported to have anti-HCV activity and are a potential source of bioactive compounds for future novel drug development. This study aimed to evaluate the efficacy of the extract of M. latifolia fruit to treat HCV and to isolate its active compounds. METHOD: M. latifolia fruit was extracted using methanol and purified using vacuum liquid chromatography (VLC) and Radial Chromatography. The anti-HCV activity was analyzed using cell culture lines Huh7it-1 and JFH1 (genotype 2a). Time-of-addition and immunoblotting studies were performed to identify the mode of action of the isolated active compounds. The structures of the active compounds were determined using nuclear magnetic resonance (NMR) spectra, UV, IR, and Mass Spectra. RESULTS: Six known compounds were isolated from M. latifolia fruit: O-methyloktadrenolon, alloevodionol, isopimpinellin, alloxanthoxyletin, methylevodionol, and N-methylflindersine. N-methylflidersine was the most active compound with IC50 value of 3.8 µg/ml while methylevodionol, isopimpinellin, and alloevodionol were less active. O-methyloktadrenolon and alloxanthoxyletin were moderately active with IC50 values of 10.9 and 21.72 µg/ml, respectively. N-methylflidersine decreased level of HCV NS3 protein expression in the cells. CONCLUSION: The alkaloid compound, N-methylflindersine which was isolated from M. latifolia possesses anti-HCV activity through post-entry inhibition and suppressed NS3 protein expression.

Calotetrapterins A-C, three new pyranoxanthones and their cytotoxicity from the stem bark of Calophyllum tetrapterum Miq.

Three new pyranoxanthones, calotetrapterins A-C (1-3) were isolated from the stem bark of Calophyllum tetrapterum Miq along with three known xanthones, α-mangostin (4), garciniafuran (5), and pyranojacareubin (6). All structures were elucidated based on their IR, UV, HRESIMS, 1 D (1H, 13C) and 2 D (HMBC, HMQC) NMR spectral data. Compounds 1-6 were tested to P-388 cells for cytotoxic activity, compound 2 exhibited high activity with IC50 value 1.0 µM.

Calodioscurins A and B, two new isoprenylated xanthones from the stem bark of Calophyllum dioscurii P.F. Stevens.

Two new isoprenylated xanthones, calodioscurin A (1) and B (2) were isolated from the stem bark of Calophyllum dioscurii P.F. Stevens along with two known isoprenylated 4-phenylcoumarins, apetalolide (3) and methyl inophyllum P (4). The structures of two new compounds were determined based on their HRESIMS, IR, UV, 1D and 2D NMR spectral data. Compounds 1-4 were assayed on P-388 cells, compound 2 showed IC50 value 11.5 µM and categorised moderate activity.

Two novel coumarins bearing an acetophenone derivative from the leaves of Melicope Quercifolia.

Meliquercifolins A (1), and B (2), two new coumarins are bearing an acetophenone derivative were isolated from the leaves of Melicope quercifolia along with three known compounds, melicodenines E (3), F (4) and I (5). Structures of two new compounds were identified based on spectroscopic analyses (UV, HR-ESI-MS, 1 D and 2 D NMR). Cytotoxic activities of compounds (1-5) towards three human cancer cells (HeLa, MCF-7, P-388), compounds 1, 4 and 5 showed very potent activity against Hela cells with IC50 values 2.6; 0.8; 1.1 µM, respectively.

Two new 2-arylbenzofurans from Sesbania grandiflora L. and their cytotoxicity towards cancer cell.

Two new 2-arylbenzofurans, sesbagrandiflorain D (1) and E (2) along with two known 2-arylbenzofurans, spinosan A (3) and spinosan B (4) were isolated from the stem bark of Sesbania grandiflora L. The structure of two new compounds established by HRESIMS, 1 D NMR (1H, 13C) and 2 D NMR (HMQC, HMBC) spectra. Compounds (1-4) assayed for their cytotoxicity towards three human cancer cells (MCF-7, HeLa, and WiDr). Compound 1 showed very high activity against MCF-7 and WiDr with an IC50 value of 0.06 and 0.60 µg/mL, respectively.

Mesucalophylloidin, a new isoprenylated 4-phenylcoumarin from Mesua calophylloides (Ridl.) Kosterm.

A new isoprenylated 4-phenylcoumarin derivative, mesucalophylloidin (1) along with three known compounds, mammea A/BA cyclo F (2), calolongic acid (3) and isocalolongic acid (4) were isolated from the stem bark of Mesua calophylloides (Ridl.) Kosterm. Structures of all the compounds were elucidated using extensive spectroscopic methods, including UV, IR, HRESIMS, 1D and 2D NMR. Compounds 1-4 were evaluated for their cytotoxicity against P-388 cells, showing that compound 1 gave moderate activity with IC50 6.26 µg/mL.

Airlanggins A-B, two new isoprenylated benzofuran-3-ones from the stem bark of Calophyllum soulattri.

Two new isoprenylated benzofuran 3-ones, airlanggin A (1) and B (2) along with two known xanthones, ananixanthone (3) and trapezifolixanthone (4) were isolated from the stem bark of Calophyllum soulattri. Structures of all the compounds were elucidated using extensive spectroscopic methods, including UV, IR, HRESIMS, 1D and 2D NMR. Compounds 1-4 were evaluated for their cytotoxicity against P-388 cells, showing that compound 3 was the most active with IC50 0.68 µg/mL and compound 1 showed moderate activity with IC50 5.80 µg/mL.