Determination of Phytochemical Compounds, and Tyrosinase Inhibitory and Antimicrobial Activities of Bioactive Compounds from Streblus ilicifolius (S Vidal) Corner

Purpose: To determine the phytochemical content, and tyrosinase inhibitory and antimicrobial activities of the wood from Streblus ilicifolius (S. Vidal) CornerMethods: The dried wood of S. ilicifolius (8.70 kg) was extracted by maceration to give petroleum ether, ethyl acetate, ethanol and water extracts, respectively. Dopachrome method was used to determine antityrosinase activity. Agar disc diffusion and modified broth microdilution methods were used to determine antimicrobial activity. Chromatographic techniques were used for phytochemical investigation. The structures elucidation of isolated compounds were identified by physical properties and spectroscopic data including UV, IR, NMR and MS data and confirmed by comparison with previously reports.Results: The ethanol extract exhibited tyrosinase inhibition and antimicrobial activity against the Grampositive bacteria, Staphylococcus epidermidis and S. aureus. Phytochemical investigation showed five compounds, namely, (E)-2,4-dihydroxy-3 (3,7-dimethyl-2,6-octadienyl) benzaldehyde (1), phydroxybenzoic acid methyl ester (2), umbelliferone (3), moracin M (4), trans-resveratrol (5). Compound 4 exhibited tyrosinase inhibition with half maximal inhibitory concentration (IC50) of 67.69 μg/ml, while compound 1 displayed strong activity against S. epidermidis, S. aureus and methicillin-resistant S. aureus (MRSA) with minimum inhibitory concentration (MIC) of 8, 4 and 8 μg/ml, respectively and minimum bactericidal concentration (MBC) of 32, 16 and 64 μg/ml, respectively.Conclusion: This is the first report of the biological activities and phytochemical composition of S. ilicifolius and the results indicate the high potentials of the plant for commercial applications such as in facial whitening and anti-acne cream.Keywords: Streblus ilicifolius, Moraceae, Tyrosinase inhibition, Antimicrobial, Anti-acne, Methicillinresistant Staphylococcus aureu

Phytochemical Investigation and Biological Activities of Desmodium heterocarpon Extract as Anti-Tyrosinase: Isolation of Natural Compounds, In Vitro and In Silico Study

Tyrosinase is an important enzyme in the biosynthesis of melanin. Many skin-whitening agents that inhibit tyrosinase activity from natural sources have been identified because they are harmless and non-toxic. In this work, 114 samples of 54 Fabaceae plants were assessed for their anti-tyrosinase activity using a dopachrome method. The results found that Desmodium heterocarpon stems and roots demonstrated the highest tyrosinase inhibitory activity at 20 µg/mL (92.50 ± 1.09%), whereas the water extract of Artocarpus lacucha and kojic acid demonstrated 87.41 ± 0.61% and 95.71 ± 0.33%, respectively. Six compounds were isolated from this plant, including genistein (1); hexadecanoic acid (2); salicylic acid (3); β-sitosterol-D-glucoside (4); 2,3-dihydroxybenzoic acid (5); and 2,5-dihydroxybenzoic acid (6). Among them, 2,5-dihydroxybenzoic acid demonstrated a potential effect for tyrosinase inhibition with an IC50 of 57.38 µg/mL, while standards of kojic acid and the water extract of A. lacucha showed 2.46 and 0.15 µg/mL, respectively. 2,3-dihydroxybenzoic acid had a similar structure as 2,5-dihydroxybenzoic acid; however, it was shown to have tyrosinase inhibitory activity, with an IC50 of 128.89 µg/mL. Studies using computer simulations confirmed this reservation. The determination of antimicrobial activities found that 2,5-dihydroxybenzoic acid showed the strongest inhibitory activity against Staphylococcus aureus, with MIC and MBC of 5 and 5 µg/mL, respectively. In addition, it inhibited MRSA, S. epidermidis, Propionibacterium acnes, Escherichia coli, and Pseudomonas aeruginosa, with MIC and MBC of 15–30 and 15–40 µg/mL. It showed potential activities against yeast and filamentous fungi, such as Candida albicans, Microsporum gypseum, Trichophyton rubrum, and T. mentagrophytes, with MIC and MFC of 15 µg/mL. So, 2,5-dihydroxybenzoic acid could inhibit tyrosinase activity and microorganisms that cause skin diseases. Therefore, it can be concluded that this plant has advantageous properties that will be investigated and further developed for possible uses, particularly in the cosmetic and pharmaceutical industries.This study was financially supported by the Graduate School, Prince of Songkla University, the Discipline of Excellence (DOE) in Pharmacy Project, Dissertation Funding for Thesis, Faculty of Pharmaceutical Sciences, Prince of Songkla University and a Postdoctoral Fellowship from Prince of Songkla University, Thailand.Graduate School, Prince of Songkla Universitythe Discipline of Excellence (DOE) in Pharmacy ProjectFaculty of Pharmaceutical Sciences, Prince of Songkla University and a Postdoctoral Fellowship from Prince of Songkla University, Thailan

BIO-ACTIVITIES AND PHYTOCHEMICAL INVESTIGATION OF CNESTIS PALALA (LOUR.) MERR.

Background: In traditional medicines, the root of Cnestis palala was used for the treatment of stomach ache, malaria, urinary track disorders and snakebite. The seed was used for poisoning rat and stray dogs. However, the bioactivities and chemical constituents have not been reported. So, this will be the first report. Material and Methods: Biological investigations of C. palala extracts against bacteria (Staphylococcus aureus, Staphylococcus epidermidis, Propionibacterium acnes, Escherichia coli, and Pseudomonas aeruginosa), fungi (Trichophyton mentagrophytes, Trichophyton rubrum and Microsporum gypseum), yeast (Candida albicans), tuberculosis (Mycobacterium tuberculosis), malaria (Plasmodium falciparum) and cancer cell lines (MCF-7 and HT-29) were evaluated. The chromatographic and spectroscopic techniques were used for the isolation and identification of pure compounds. Results: The results showed that the ethanol leaf and bark extracts were active against S. aureus and S. epidermidis. The hexane leaf and seed extracts and petroleum ether bark and root extracts showed strongly inhibition values against MCF-7. Moreover, the petroleum ether bark extract exhibited high inhibition value against HT-29. Seven compounds were isolated as β-sitosterol-glucoside (CP1), hydroquinone (CP2), β-sitosterol (CP3), mixture of fatty acids (CP4) and ethyl caffeate (CP5), scopoletin (CP6) and 2-nonenal (CP7). The CP2 was strongly active against S. aureus and S. epidermidis, the MIC was showed 30.10 µg/ml and 15.05 µg/ml and the MBC was showed 15 µg/ml and 7.5 µg/ml, respectively. Conclusion: These results suggested that C. palala is a great potential source of anti-microbial agents. Hence, this is the first study, which will be the database for chemical constituents and bioactivities of C. palala

Antioxidant and cytotoxic activities of Thai medicinal plants named Khaminkhruea: Arcangelisia flava, Coscinium blumeanum and Fibraurea tinctoria

The stems of Arcangelisia flava, Coscinium blumeanum and Fibraurea tinctoria, collectively known in southern Thailand as Khaminkhruea, were sequentially extracted with petroleum ether, chloroform, methanol, and boiling water to afford 12 crude extracts. All extracts have been assessed for antioxidant activity against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical and cytotoxic activity against brine shrimp and human cancer cell line MCF-7 (breast adenocarcinoma). Methanol extract of A. flava (AFM), and methanol and chloroform extracts of C. blumeanum (CBM and CBC) exhibited moderate antioxidant activity with EC50 values of 25-55 μg/ml. Chloroform extracts of A. flava (AFC) and F. tinctoria (FTC), AFM, CBC and CBM showed pronounced cytotoxic activity against brine shrimp and MCF-7 cells with LC50 and IC50 values of 210-278 and 8-12 μg/ml, respectively. Bioassay-guided chemical investigation led to the isolation of berberine as a main compound of AFC, AFM, CBC and CBM. Palmatine and jatrorrhizine were found to be main alkaloids of FTC, and minor alkaloids of AFC, AFM, CBC and CBM. In addition, an ester triacontanyl caffeate was isolated for the first time from C. blumeanum (CBC). Chemical structures of the isolated compounds were determined by spectroscopic methods particularly NMR and mass spectrometry. Triacontanyl caffeate was mainly responsible for antioxidant activity of C. blumeanum with an EC50 value of 6.8 μg/ml. Jatrorrhizine possessed moderate antioxidant activity with an EC50 value of 98.0 μg/ml, whereas palmatine and berberine were found to be considerably less active (EC50 >100 μg/ml). The LC50 values of the four isolated compounds on brine shrimp were ranging from 37-206 μg/ml. The IC50 values of berberine, palmatine and jatrorrhizine against MCF-7 cells were in the range of 1-4 μg/ml. Triacontanyl caffeate was considerably less cytotoxic than the alkaloids with an IC50 value of 15.5 μg/ml

Flavonoid Constituents and Alpha-Glucosidase Inhibition of Solanum stramonifolium Jacq. Inflorescence with In Vitro and In Silico Studies

Solanum stramonifolium Jacq. (Solanaceae) is widely found in South East Asia. In Thailand, it is used as vegetable and as a component in traditional recipes. The results of an alpha-glucosidase inhibitory screening test found that the crude extract of S. stramonifolium inflorescence exhibited the potential effect with IC50 81.27 μg/mL. The separation was performed by the increasing solvent polarity method. The ethyl acetate, ethanol, and water extracts of S. stramonifolium inflorescence showed the synergistic effect together with acarbose standard. The phytochemical investigation of these extracts was conducted by chromatographic and spectroscopic techniques. Six flavonoid compounds, myricetin 3, 4′, 5′, 7-tetramethyl ether (1), combretol (2), kaempferol (3), kaempferol 7-O-glucopyranoside (4), 5-hydroxy 3-7-4′-5′-tetramethoxyflavone-3′-O-glucopyranoside (5), and a mixture (6) of isorhamnetin 3-O-glucopyranoside (6a) and astragalin (6b) were isolated. This discovery is the first report of flavonoid-glycoside 5. Moreover, the selected flavonoids, kaempferol and astragalin, were representatives to explore the mechanism of action. Both of them performed mixed-type inhibition. The molecular docking gave a better understanding of flavonoid compounds’ ability to inhibit the alpha-glucosidase enzyme

Biological activities and chemical profiles of selected soil fungi isolated from Sirindhorn Peat Swamp Forest of Narathiwat, Thailand

A total of 54 soil fungi were collected from Sirindhorn peat swamp forest in Narathiwat Province which is the last peat swamp forests in Thailand. They were extracted using four different solvents and 104 crude extracts were obtained. The bioactivity screening of these samples was done employing alpha-glucosidase inhibition, anti-inflammation using nitric oxide inhibition and cytotoxicity using cancer cell line (MCF-7). The results showed that SPSF224 crude extract had the best biological activities in the screening tests and was then selected for further study. The SPSF224 was identified as Penicillium maximae. The crude extracts of P. maximae were determined for chemical profile, IC50 value of alpha-glucosidase inhibition, antioxidant and antimicrobial activities against Staphylococcus aureus, Trichophyton mentagrophytes, and T. rubrum. This was the first report of chemical investigation and biological activity evaluation of P. maximae

Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, Neuropeltis racemosa Wall.

Neuropeltis racemosa Wall. (Convolvulaceae) is wildly distributed in Asia. Its stem is used as the component in traditional Thai recipes for treatments of muscle rigidity, skin disorder, dysentery, and hypoglycemia. However, the chemical constituents and biological activities of N. racemosa have not been reported. From a screening assay, N. racemosa stem crude extract showed the potent effect on alpha-glucosidase inhibition at 2 mg/mL as 96.09%. The bioassay-guiding isolation led to 5 compounds that were identified by spectroscopic techniques as scopoletin (1), syringic acid (2), methyl 3-methyl-2-butenoate (3), N-trans-feruloyltyramine (4), and N-trans- coumaroyltyramine (5). Compounds 1, 4, and 5 exhibited an IC50 of 110.97, 29.87, and 0.92 µg/mL, respectively, while the IC50 of positive standard, acarbose was 272.72 µg/mL. Kinetic study showed that compound 1 performed as the mixed-type inhibition mechanism, whereas compounds 4 and 5 displayed the uncompetitive inhibition mechanism. The docking study provided the molecular understanding of isolated aromatic compounds (1, 2, 4 and 5) to alpha-glucosidase. Hence, this study would be the first report of isolated compounds and their anti-alpha-glucosidase activity with the mechanism of action from N. racemosa. Thus, these active compounds will be further studied to be the lead compounds among natural antidiabetic drugs

Alpha-Glucosidase Inhibitory Assay-Screened Isolation and Molecular Docking Model from Bauhinia pulla Active Compounds

The aim of this research was to establish the constituents of Bauhinia pulla as anti-diabetic agents. A phytochemistry analysis was conducted by chromatographic and spectroscopic techniques. The alpha-glucosidase inhibitory assay screening resulted in the isolation of eight known compounds of quercetin, quercitrin, luteolin, 5-deoxyluteolin, 4-methyl ether isoliquiritigenin, 3,20,40-trihydroxy- 4-methoxychalcone, stigmasterol and �-sitosterol. Ethanol leaf extracts showed potential effects, which led to a strong inhibitory activity of isolated quercetin at 138.95 �g/mL and 5.41 �g/mL of IC50, respectively. The docking confirmed that flavonoids and chalcones had the same potential binding sites and responsibilities for their activity. This study was the first report of Bauhinia pulla chemical constituents and its alpha-glucosidase inhibition

Phytochemical Investigation of Bauhinia winitii Based on Alpha‑Glucosidase Inhibitory Effect and Molecular Docking Affirmation

Background: Bauhinia winitii (BW) (Fabaceae) plant revealed poor phytochemical investigation and anti‑diabetic report. As one of the Bauhinia family which known with abundant flavonoids content, contrary, BW was only used for the treatment of diarrhea in Thai conservative remedy. Objectives: The aim of this study was to investigate the phytochemical constituents and anti‑alpha glucosidase activity of BW. Materials and Methods: Phytochemical study was based on the alpha‑glucosidase inhibitory effect. Isolated compounds were determined by chromatographic and spectroscopic techniques. The alpha‑glucosidase enzymatic inhibitory test was then connected with molecular docking affirmation. Results: The ethyl acetate and ethanol extracts from leaves and woods exhibited the strongest activity with above 60% inhibition. Six compounds were isolated from these extracts, naringenin (1), luteolin (2), isoquercitrin (3), griffonilide (4), lithospermoside (5), and epi‑β amyrin (6). The alpha‑glucosidase inhibitory test showed that flavonoids performed potential results with naringenin as the highest IC50 on 0.41 mM. The docking ensured the flavonoids activated at the same binding of alpha‑glucosidase enzyme active site. Conclusion: This study would be the first report of chemical constituents from BW with its isolated compounds was presented anti‑diabetic activity as alpha‑glucosidase inhibitors