Combretum quadrangulare Kurz is widely used in folk medicine in Eastern Asia and is associated with various ethnopharmacological properties including hepatoprotective, antipyretic, analgesic, antidysenteric, and anthelmintic activities. Previous phytochemical investigations reported the presence of numerous triterpenes (mostly cycloartanes, ursanes, lupanes, and oleananes) along with dozens of flavonoids. However, the extracts of C. quadrangulare and isolated flavonoids have not been evaluated for their alpha-glucosidase inhibition. In the frame of our efforts dedicated to the chemical investigation of Vietnamese medicinal plants and their biological activities, a phytochemical study of the MeOH extract of the leaves of C. quadrangulare using bioactive guided isolation was undertaken. In this paper, the isolation and structure elucidation of twelve known compounds, 5-hydroxy-3,7,4′-trimethoxyflavone (1), ayanin (2), kumatakenin (3), rhamnocitrin (4), ombuin (5), myricetin-3,7,3′,5′-tetramethyl ether (6), gardenin D (7), luteolin (12), apigenin (13), mearnsetin (14), isoorientin (15), and vitexin (16) were reported. Bromination was applied to compounds 2 and 3 to provide four new synthetic analogues 8–11. All isolated and synthesized compounds were evaluated for alpha-glucosidase inhibition and antibacterial activity. Compounds 4 and 5 showed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus while others were inactive. All compounds failed to reveal any activity toward extended spectrum beta-lactamase-producing Escherichia coli. Compounds 2, 4, 6–9, and 11–14 showed good alpha-glucosidase inhibition with IC₅₀ values in the range of 30.5–282.0 µM. The kinetic of enzyme inhibition showed that 8 and 11 were noncompetitive type inhibition against alpha-glucosidase. In silico molecular docking model indicated that compounds 8 and 11 were potential inhibitors against enzyme α-glucosidase.

Bioactive-guided phytochemical investigation of Euphorbia antiquorum L. growing in Vietnam led to the isolation of five ent-atisanes, one seco-ent-atisane, and one lathyrane (ingol-type). The structures were elucidated as ent-1α,3α,16β,17-tetrahydroxyatisane (1), ethyl ent-3,4-seco-4,16β,17-trihydroxyatisane-3-carboxylate (2), ent-atisane-3-oxo-16β,17-acetonide (3), ent-3α-acetoxy-16β,17-dihydroxyatisane (4), ent-16β,17-dihydroxyatisane-3-one (5), calliterpenone (6), and ingol 12-acetate (7). Their chemical structures were unambiguously determined by analysis of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and high resolution mass spectrometry, as well as by comparison with literature data. Among them, 1 is a new compound while 2 is an ethylated artifact of ent-3,4-seco-4,16β,17-trihydroxyatisane-3-carboxylic acid, a new compound. Isolates were evaluated for alpha-glucosidase inhibition. Compound 3 showed the most significant inhibitory activity against alpha-glucosidase with an IC₅₀ value of 69.62 µM. Further study on mechanism underlying yeast alpha-glucosidase inhibition indicated that 3 could retard the enzyme function by noncompetitive.

Traditionally, lichen has been used for many purposes, but there remains a lack of understanding regarding the chemical composition and antimicrobial characteristics of Diorygma pruinosum, a lichen native to Vietnam.

This study focused on bio-guided isolation based on antioxidant activities from Dicranopteris linearis spores and Averrhoa bilimbi branches. The total phenolic content (TPC), total flavonoid content (TFC), and antioxidant activities of the extracts were determined. For D. linearis spores, the ethyl acetate (EA) extract exhibited the highest TPC (120.13 ± 0.04 mg GAE/g) and TFC (21.94 ± 0.30 mg QE/g), along with strong DPPH antioxidant activity (96.3 ± 0.3% inhibition, IC₅₀ of 39.4 ± 0.3 µg/mL). For A. bilimbi branches, the n-hexane–ethyl acetate (HEA) extract showed the highest TPC (165.21 ± 0.24 mg GAE/g) and TFC (26.20 ± 0.01 mg QE/g), with significant DPPH antioxidant activity (89.6 ± 0.7% inhibition, IC₅₀ of 39.7 ± 1.9 µg/mL). Phytochemical investigation led to the identification of ten compounds (D1–D10) from D. linearis spores and twelve compounds (A1–A12) from A. bilimbi branches. Notably, compound A1 was identified as a new natural compound. The chemical structures were elucidated through NMR spectroscopy and comparison with existing literature. The antioxidant activities of selected compounds (D3–D5, D8–D10, and A1–A11) were evaluated using DPPH and ABTS free radical scavenging assays. Among them, compound A3 exhibited the strongest antioxidant activities (IC₅₀ of 7.1 ± 0.1 µg/mL for DPPH and 14.8 ± 0.1 for ABTS, respectively). The results of this study highlight the potential of D. linearis and A. bilimbi for use in natural product-based antioxidant applications.

Cultured lichen mycobionts are valuable sources of new natural compounds. Mycobiont of Graphis handelii growing in Vietnam was isolated, cultivated and chemically investigated. The crude extract of this cultured mycobiont showed potent alpha-glucosidase inhibition with an IC₅₀ value of 50 μg/mL. Multiple chromatographic methods were applied to the extract to isolate compounds. The combination of Nuclear Magnetic Resonance analysis and high-resolution mass spectroscopy determined their chemical structures. Electrophilic bromination/chlorination was applied to obtain new derivatives using NaBr/H₂O₂ and NaCl/H₂O₂ reagents. Compounds were evaluated for enzyme inhibitory activities, including alpha-glucosidase inhibition, HIV-1 reverse transcriptase inhibition, SARS-CoV-2 main protease (M^pro) inhibition, anti-inflammatory activity, and cytotoxicity against several cancer cell lines. A molecular docking study for anti-SARS-CoV-2 was conducted to understand the inhibitory mechanism. A new diphenyl ether, handelone (1) and a known compound xylarinic acid A (2) were isolated and elucidated. Four synthetic products 6'-bromohandelone (1a), 2'-bromohandelone (1b), 2',6'-dibromohandelone (1c), and 2',6'-dichlorohandelone (1d) were prepared. Compound 1 showed good activity against M^pro with an IC₅₀ value of 5.2 μM but it showed weak or inactive activity in other tests. Other compounds were inactive in all assays. A new compound, handelone (1) was isolated from the cultured mycobiont of Graphis handelii. From these compounds, four new derivatives were prepared. Compound 1 showed good activity against M^pro with an IC₅₀ value of 5.2 μM but it showed weak or inactive activity in other tests. Other compounds were inactive in all assays.

Cultured lichen mycobionts have been considered as valuable sources of natural compounds with unique structure scaffolds. Nigrovothelium inspersotropicum, a crustose lichen from the family Trypetheliaceae, is an indigenous species in Vietnam. However, there is a scarcity of chemical and biological information available regarding N. inspersotropicum and its cultured mycobionts. In this study, the mycobiont of N. inspersotropicum was cultivated and subjected to chemical and biological investigations. As a result, six compounds, including 3,4-dihydro-7,8-dihydroxy-6-methoxy-3-methylisocoumarin (1), (+)-(3S)-6,7-dimethoxymellein (2), 8-hydroxy-6,7-dimethoxyisocoumarin (3), aspermytin A (4), subnudatone B (5), and b-sitosterol (6), were isolated and structurally elucidated using extensive spectroscopic analyses (1D- and 2D-NMR and HRESIMS). Notably, compound 1 is new compound, while compound 2 is identified as a new natural compound. The isolated compounds were evaluated for their inhibitory activities against alpha-glucosidase, nitric oxide production, SARS-CoV-2 Mpro, and HIV-1 reverse transcriptase. In summary, this study presents new information on natural compounds derived from the mycobiont of N. inspersotropicum and their promising anti-inflammatory, antihyperglycemic, and antiviral activities.