Chemical composition and the anti-inflammatory effect of volatile compounds from Anaxagorea luzonensis A. Gray.

Anaxagorea luzonensis A. Gray, a member of the Annonaceae family, has been used to treat a variety of illnesses for a long time. For the first time, A. luzonensis volatile compounds (ALVCs) were extracted from the leaves, and the components were identified using gas chromatography-mass spectrometry (GC-MS). Further, the main compositions of ALVCs were also assessed for their ability to bind with anti-inflammatory proteins using a docking model. In addition, in vitro tests e.g. inhibition of protein degradation and the inhibition of nitric oxide release using RAW264.7 macrophage cells were utilized for evaluating the anti-inflammatory activity. The results showed that the principal compounds of ALVCs were bulnesol (34.1 %), cubitene (17.8 %), ß-eudesmol (10.4 %), epi-longipinanol (5.9 %), and (Z)-nerolidyl acetate (5.5 %). Three compounds viz. bulnesol, cubitene, and ß-eudesmol bound firmly to cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), as shown by the in silico analysis, similar to the positive control diclofenac. ALVCs effectively inhibited protein degradation with the IC50 of 31 ± 2.3 µg/mL and inhibited nitric oxide production with the IC50 of 43.30 ± 3.37 µg/mL. These findings showed that ALVCs might have a promising anti-inflammatory effect by blocking several inflammatory proteins.

Essential Oil from Vietnamese Peperomia leptostachya Hook. & Arn. (Piperaceae): Chemical Composition, Antioxidant, Anti-Inflammatory, Cytotoxic Activities, and In Silico Analysis.

This study is the first to investigate the chemical composition and antioxidant, anti-inflammatory, and cytotoxic activities of Peperomia leptostachya leaf oil. A yellow oil was obtained through hydro-distillation, with a yield of 0.1% (w/w). The GC-MS analysis revealed 66 compounds, constituting 99.6% of the oil. Sesquiterpene hydrocarbons predominated (70.4%), followed by monoterpene hydrocarbons (13.2%), oxygenated sesquiterpenes (12.4%), non-terpenic compounds (2.0%), and oxygenated monoterpenes (1.6%). Major constituents included germacrene D (25.1%), (E)-caryophyllene (17.4%), bicyclogermacrene (6.6%), α-pinene (6.2%), and ß-pinene (4.7%). The assessment of antioxidant capacity via 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay yielded a weak effect, with an IC50 value > 100 µg/mL. The inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells was quantified using the MTT assay, showing an IC50 value of 15.15 ± 0.68 µg/mL. Furthermore, cytotoxic effects on SK-LU-1 cell line growth were evaluated using the sulforhodamine B assay, resulting in an IC50 value of 37.45 ± 2.43 µg/mL. The anti-inflammatory activity was notable among the analyzed bioactivities of this oil. By employing a computational model, the predominant secondary metabolites in the essential oil were selected as candidates for interaction analysis with cyclooxygenase-2, an enzyme implicated in the inflammatory response. Our findings suggest that P. leptostachya leaf oil could serve as a potential source of natural compounds with prospective therapeutic effects in treating inflammatory conditions.

Chemical Composition, Anti-bacterial Activity and Molecular Docking Studies of Essential Oil Isolated from Sa Sam Nam (Launaea sarmentosa).

Launaea sarmentosa, also known as Sa Sam Nam, is a widely used remedy in Vietnamese traditional medicine and cuisine. However, the chemical composition and bioactivity of its essential oil have not been elucidated yet. In this study, we identified 40 compounds (98.6% of total peak area) in the essential oil via GC-MS analysis at the first time. Among them, five main compounds including Thymohydroquinone dimethyl ether (52.4%), (E)-α-Atlantone (9.0%), Neryl isovalerate (6.6%), Davanol D2 (isomer 2) (3.9%), and trans-Sesquisabinene hydrate (3.9%) have accounted for 75.8% of total peak area. The anti-bacterial activity of the essential oil against 4 microorganisms including Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa has also investigated via agar well diffusion assay. The results showed that the essential oil exhibited a strong antibacterial activity against Bacillus subtilis with the inhibition zones ranging from 8.2 to 18.7 mm. To elucidate the anti-bacterial effect mechanism of the essential oil, docking study of five main compounds of the essential oil (Thymohydroquinone dimethyl ether, (E)-α-Atlantone, Neryl isovalerate, Davanol D2 (isomer 2), and trans-Sesquisabinene hydrate) against some key proteins for bacterial growth such as DNA gyrase B, penicillin binding protein 2A, tyrosyl-tRNA synthetase, and dihydrofolate reductase were performed. The results showed that the main constituents of essential oil were highly bound with penicillin binding protein 2A with the free energies ranging -27.7 to -44.8 kcal/mol, which suggests the relationship between the antibacterial effect of essential oil and the affinity of main compounds with penicillin binding protein. In addition, the free energies of main compounds of the essential oil with human cyclooxygenase 1, cyclooxygenase 2, and phospholipase A2, the crucial proteins related with inflammatory response were less than diclofenac, a non-steroidal antiinflammatory drug. These findings propose the essential oil as a novel and promising anti-bacterial and anti-inflammatory medicine or cosmetic products.

Essential oil of the leaves of psychotria asiatica L.: chemical composition, antioxidant, anti-inflammatory, and cytotoxic properties.

This study is focused on investigating the chemical composition and bioactive properties of the essential oil extracted from Psychotria asiatica L., a plant species known for its medicinal properties. Utilising gas chromatography-mass spectrometry (GC-MS) analysis, the essential oil from P. asiatica was found to contain 53 distinct constituents. Major compounds identified include (E)-citral (20.6%), 10-epi-γ-eudesmol (15.9%), (Z)-citral (10.5%), geraniol (7.4%), α-cadinol (6.7%), 7-epi-α-eudesmol (4.4%), linalool (3.7%), and α-muurolol (3.4%). The essential oil did not exhibit antioxidant activity, as indicated by an IC50 value of > 100 µg/mL, whereas the positive control L-Ascorbic acid had an IC50 of 7.37 ± 0.27 µg/mL in the DPPH model. Assessment of its anti-inflammatory potential revealed an inhibitory effect on NO production, with an IC50 value of 29.08 ± 1.54 µg/mL in Lipopolysaccharide-induced RAW264.7 macrophage cells. Furthermore, the essential oil demonstrated significant cytotoxicity against the SK-LU-1 cancer cell line, with an IC50 value of 39.75 ± 1.79 µg/mL according to the sulforhodamine B (SRB) assay.

Conamonin A and dihydrochalcones from the whole plants of Conamomum rubidum (Lamxay & N.S.Lý) Skornick. & A.D. Poulsen showing anti-inflammatory and cytotoxic activities.

A new compound, conamonin A (1), was isolated from the whole plants of Conamomum rubidum with eight known dihydrochalcones (2-9). Their structures were elucidated by a combination of spectroscopic methods as well as by comparison with previously reported data. The absolute configuration of 1 was assigned by TDDFT-ECD method. Compounds 1 and 8 showed inhibitory activity against LPS-induced NO production in the RAW 264.7 cells, with IC50 values of 58.29 ± 2.88 and 81.77 ± 5.99 µM, respectively. Compounds 3/4 and 5/6 exhibited inhibitory effects, with IC50 values of 28.76 ± 1.16 and 29.89 ± 1.79 µg/mL, respectively. Compounds 2, 7-9 exhibited significant cytotoxic activity against human lung carcinoma (the SK-LU-1 cell line) with IC50 values ranging from 9.87 to 17.99 µM. This study offers valuable insights into the chemical constituents and biological activities of Conamomum rubidum, highlighting its potential as a source for discovering new anti-inflammatory and cytotoxic agents.

Chemical composition and biological activities of essential oil from Grewia bulot leaves.

This study focused on the chemical composition and biological activities of the essential oil derived from Grewia bulot, a plant species known for its medicinal properties. The analysis of Grewia bulot essential oil revealed the presence of 78 constituents. The major compounds were α-cadinol (13.5%), 1,8-cineole (12.7%), 1,10-di-epi-cubenol (9.8%), epi-α-cadinol (6.7%), (E,E)-α-farnesene (5.9%), (E)-citral (4.0%), selin-11-en-4-α-ol (4.0%), citronellol isobutanoate (3.9%), and geranic acid (3.7%). The essential oil exhibited promising antioxidant potential with an IC50 value of 452.65 ± 28.40 µg/mL in DPPH model. This oil did not show NO production inhibitory effect in RAW 264.7 cells. In addition, the essential oil exhibited significant cytotoxicity against KB, Hep-G2, MCF-7, and SK-LU-1 cancer cell lines, with IC50 values ranging from 44.04 ± 1.47 to 74.20 ± 3.71 µg/mL.

Essential Oils of Five Syzygium Species Growing Wild in Vietnam: Chemical Compositions and Antimicrobial and Mosquito Larvicidal Potentials.

The essential oils of five Vietnamese Syzygium species (Syzygium levinei, S. acuminatissimum, S. vestitum, S. cumini, and S. buxifolium) were first hydro-distilled and analyzed using GC-FID/MS (gas chromatography-flame ionization detection/mass spectrometry). Monoterpene hydrocarbons, sesquiterpene hydrocarbons, and oxygenated sesquiterpenoids were the main chemical classes in these oils. All these essential oils showed good-excellent antimicrobial activities against Gram-positive bacteria Enterococcus faecalis, Staphylococcus aureus, and Bacillus cereus, and the yeast Candida albicans. S. levinei leaf essential oil, rich in bicyclogermacrene (25.3%), (E)-ß-elemene (12.2%), (E)-caryophyllene (8.2%), and ß-selinene (7.4%), as well as S. acuminatissimum fruit essential oil containing (E)-caryophyllene (14.2%), α-pinene (12.1%), caryophyllene oxide (10.9%), ß-selinene (10.8%), α-selinene (8.0%), and α-humulene (5.7%), established the same MIC value of 8 µg/mL against E. faecalis and B. cereus, which were much better than the positive control streptomycin (MIC 128-256 µg/mL). The studied essential oils showed the potential to defend against mosquitoes since they caused the 24 and 48 h LC50 values of less than 50 µg/mL against the growth of Culex quinquefasciatus and Aedes aegypti larvae. Especially, S. buxifolium leaf essential oil strongly inhibited Ae. aegypti larvae with 24 and 48 h LC50 values of 6.73 and 6.73 µg/mL, respectively, and 24 and 48 h LC90 values of 13.37 and 10.83 µg/mL, respectively. These findings imply that Vietnamese Syzygium essential oils might have potential for use as supplemental antibacterial agents or as "green" alternatives for the control of mosquitoes.

Essential Oils of the Leaves of Epaltes australis Less. and Lindera myrrha (Lour.) Merr.: Chemical Composition, Antimicrobial, Anti-inflammatory, Tyrosinase Inhibitory, and Molecular Docking Studies.

Epaltes australis Less. has been traditionally used to treat fever and snake bites, whereas Lindera myrrha (Lour.) Merr. is well-known for addressing colds, chest pain, indigestion, and worm infestations. This study marks the first report on the chemical compositions and biological potentials of essential oils extracted from the leaves of Epaltes australis and Lindera myrrha. Essential oils obtained by hydro-distillation were analysed using the GC/MS (gas chromatography-mass spectrometry). E. australis exhibited a predominant presence of non-terpenic compounds (46.3 %), with thymohydroquinone dimethyl ether as the major compound, constituting 44.2 % of the oil. L. myrrha leaf oil contained a good proportion of sesquiterpene hydrocarbons (56.8 %), with principal compounds including (E)-caryophyllene (22.2 %), ledene (9.7 %), selina-1,3,7(11)-trien-8-one (9.6 %), and α-pinene (7.0 %). Both essential oils exhibited antimicrobial activity against the bacteria Bacillus subtilis and Clostridium sporogenes, and Escherichia coli, and the fungus Aspergillus brasiliensis. L. myrrha leaf essential oil exhibited potent control over the yeast Saccharomyces cerevisiae with a MIC of 32 µg/mL. Additionally, L. myrrha leaf oil showed strong anti-inflammatory activity with an IC50 value of 15.20 µg/mL by inhibiting NO (nitric oxide) production in LPS (lipopolysaccharide)-stimulated RAW2647 murine macrophage cells. Regarding anti-tyrosinase activity, E. australis leaf oil showed the best monophenolase inhibition with the IC50 of 245.59 µg/mL, while L. myrrha leaf oil successfully inhibited diphenolase with the IC50 of 152.88 µg/mL. From molecular docking study, selina-1,3,7(11)-trien-8-one showed the highest affinity for both COX-2 (cyclooxygenase-2) and TNF-α (tumor necrosis factor-α) receptors. Hydrophobic interactions play a great role in the bindings of ligand-receptor complexes.

Chemical Composition, Mosquito Larvicidal and Antimicrobial Activities, and Molecular Docking Study of Essential Oils of Cinnamomum melastomaceum, Neolitsea buisanensis and Uvaria microcarpa from Vietnam.

The leaf oil compositions of two Lauraceae and one Annonaceae plants cultivated in Vietnam were analysed by GC/MS (gas chromatography-mass spectrometry) analysis. The leaf oil of the first Lauraceae plant Cinnamomum melastomaceum contained 34 identified compounds, in which benzyl benzoate (38.5 %), linalool (19.9 %), (E)-caryophyllene (10.5 %), and α-terpineol (6.9 %) were the major compounds. The leaves of the second Lauraceae plant Neolitsea buisanensis gave an oil with the main compounds (E)-ß-ocimene (24.0 %), benzyl benzoate (15.8 %), bicyclogermacrene (14.9 %), and (E)-caryophyllene (6.3 %). The leaf oil of the Annonaceae plant Uvaria microcarpa consisted of the principal compounds (E)-caryophyllene (18.0 %), bicyclogermacrene (8.1 %), and δ-elemene (6.1 %). Two Lauraceae oil samples exhibited strong mosquito larvicidal activity against Aedes aegypti, Ae. albopictus, and Culex quinquefasciatus with LC50 and LD90 values of less than 50 µg/mL. The Annonaceae oil sample showed strong antimicrobial activity against the fungus Aspergillus niger ATCC 1015 with the MIC (minimum inhibitory concentration) value of 32 µg/mL. In the docking approach, the major compounds (E)-caryophyllene, bicyclogermacrene, and benzyl benzoate interacted with the mosquito odorant-binding protein 3OGN, whereas (E)-caryophyllene, bicyclogermacrene, and δ-elemene also potentially interacted with the 4ZA5 protein of fungus A. niger.

The anti-inflammatory activity of the compounds isolated from Dichroa febrifuga leaves.

Dichroa febrifuga Lour. is a traditional medicinal herb that has been applied in the treatment of malaria and some other infectious diseases. Studies recently have focused on the anti-inflammation of the extracts of Dichroa febrifuga Lour. although there have not many reports about which compounds play the essential role. Therefore, in this study, we isolated hydrangenoside C (1), isoarborinol (2), and methyl 1,3,4,6-tetra-O-acetyl-fructofuranoside (3) from the leaves of Dichroa febrifuga. Subsequently, the anti-inflammatory property of 1-3 was assessed using an in vivo assay of edema mouse model which was induced by carrageenan. Out of the three, 2 inhibited the edema effectively and dose-dependently, similarly to diclofenac while there was no obvious activity observed in 1 and 3. The in silico results demonstrated that 2 enables binding to 5-LOX and PLA2 via generating h-bonds. This is the first study to mention the anti-inflammation of 2 in Dichroa febrifuga Lour., and would be a contribution to further studies to elucidate the promising bioactivities of this compound.

Structure revision and absolute configuration of 5,7-diepi-2α-hydroxyoplopanone and anti-osteoporotic activities of sesquiterpenoids from the rhizomes of Homalomena pendula.

Five sesquiterpenoids including 2α-hydroxyoplopanone (1), oplopanone (2), 1ß,4ß,6α-trihydroxy-eudesmane (3), 1ß,4ß,7α-trihydroxy-eudesmane (4) and bullatantriol (5) were isolated from Homalomena pendula. The structure of the previously reported compound, 5,7-diepi-2α-hydroxyoplopanone (1a), has been revised to 1 by the spectroscopic evidences (1D-/2D-NMR, IR, UV and HRESIMS) and by comparison between experimental and theoretical NMR data using DP4+ protocol. Furthermore, the absolute configuration of 1 was unambiguously assigned by ECD experiments. Compounds 2 and 4 displayed a potent ability to stimulate osteogenic differentiation of MC3T3-E1 cells at 4 µg/mL (by 123.74% and 131.07%, respectively) and 20 µg/mL (by 112.45% and 126.41%, respectively) whilst 3 and 5 did not show any activities. At 20 µg/mL, 4 and 5 significantly promoted the mineralization of MC3T3-E1 cells with values of 112.95% and 116.37%, respectively, whereas 2 and 3 were inactive. The results indicated that 4 could be an excellent component for anti-osteoporosis studies from the rhizomes of H. pendula.

Chemical constituents from the Knema globularia fruits and their in vitro cytotoxicity.

Two new compounds, designated as knecorticosanones A-B (1-2), along with three known compounds (3-5) were isolated from the fruits of Knema globularia. Their structures were elucidated by extensive spectroscopy analysis, including 1D- and 2D-NMR, UV, IR, and HRESIMS and by comparison with the reported data in the literature. Compounds 1-5 were evaluated for their cytotoxicity. Knecorticosanone B (2) and malabaricone D (5) exhibited moderate cytotoxic effect against Hep-G2, MCF-7 and SK-LU-1 cell lines with IC50 values ranging from 8.76 ± 1.02 to 18.74 ± 1.75 µM while knecorticosanone A (1), virolane (3) and 7-hydroxy-3',4'-methylenedioxyflavan (4) exhibited weak inhibitory effect against these cell lines with IC50 values ranging from 25.85 ± 2.75 to 66.75 ± 2.08 µM.

Anti-Inflammatory and Antimicrobial Activities of Compounds Isolated from Distichochlamys benenica.

Distichochlamys benenica is a native black ginger that grows in Vietnam. In point of fact, there is limitation of available information in the literature making mention of the chemical constituents and bioactive properties of this plant. This study is aimed at isolating trans-o-coumaric acid (1), trans-cinnamic acid (2), and borneol (3) from the rhizomes of D. benenica Q.B.Nguyen & Skornick and evaluate the anti-inflammatory and antimicrobial activities of 1-3 using the carrageenan paw edema model and the dilution broth method, respectively. This revealed that 1 was as effective as diclofenac in reducing the intensity of the edema development. The in silico research showed that the activity of 1 might be derived from inhibiting COX-2 by generating h-bonds at the positions of Arg 120, Tyr 355, and Arg 513 residues. The antimicrobial activities against Gram-positive strains (Staphylococcus aureus and Bacillus subtilis) were comparable, with the minimum inhibitory concentrations ranging from 1.52 to 3.37 mM. This is the first study of the bioactivity of compounds isolated from D. benenica Q.B.Nguyen & Skornick. Our results suggest that 1 may be a nature-derived compound which demonstrates the anti-inflammatory properties and inhibit the proliferation of several Gram-positive bacteria.

Antioxidant Activity of a New Xanthone Derivative from Aspidistra Letreae: In Vitro and In Silico Studies.

A new xanthone derivative, aspidxanthone A (1), and three known compounds ((2S)-1-(ß-D-galactopyranosyloxy)-3-(hexadecanoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate (2), (25S)-spirostane-1ß,3α,5ß-triol (3), and asparenyldiol (4)) were isolated from the whole of the endemic species Aspidistra letreae in Vietnam. Their structures were elucidated by means of extensive spectroscopic analyses and comparison with published data. In this study, we report the isolation and structure elucidation of a new compound aspidxanthone A, antioxidant activities of the extract and isolates 1-4, and in silico molecular docking of aspidxanthone A. The ethyl acetate extract had good antioxidant activity with an IC50 value of 26.3 µg mL-1 . Among the isolates, aspidxanthone A exhibited DPPH reduction activity with an IC50 value of 11.2 µM, which is in the same range as that of the positive control, ascorbic acid. The mechanism of action of aspidxanthone A on the tyrosinase and xanthine oxidase proteins have been clarified by in silico studies.

Three new steroidal saponins from Aspidistra letreae plants and their cytotoxic activities.

Three new steroidal saponins, aspiletreins A-C (1-3), together with 2H-chromen-2-one (4), and α-tocopherol (5), were isolated from whole Aspidistra letreae plants collected in Vietnam. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR, IR, and HRESIMS, and by comparison with the reported data in the literature. Compounds 1-3 exhibited moderate cytotoxicities against the LU-1, HeLa, MDA-MB-231, HepG2, and MKN-7 human cancer cell lines, with IC50 values ranging from 7.69 ± 0.40 to 20.46 ± 3.11 µM.