Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies
The chemical investigation of <i>Homotrigona apicalis</i> propolis collected in Binh Dinh province, Vietnam, led to the isolation of nine compounds, including four sesquiterpenes: spathulenol (<b>1</b>), 1<i>α</i>H,5<i>β</i>H-aromandendrane-4<i>β...
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MDPI AG
2023-08-01
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| author | Diep Thi Lan Phuong Nguyen Van Phuong Nguyen Le Tuan Nguyen Thanh Cong Nguyen Thu Hang Le Nguyen Thanh Vu Thi Hue Nguyen Quoc Vuong Nguyen Thi Thu Ha Milena Popova Boryana Trusheva Vassya Bankova |
| author_facet | Diep Thi Lan Phuong Nguyen Van Phuong Nguyen Le Tuan Nguyen Thanh Cong Nguyen Thu Hang Le Nguyen Thanh Vu Thi Hue Nguyen Quoc Vuong Nguyen Thi Thu Ha Milena Popova Boryana Trusheva Vassya Bankova |
| author_sort | Diep Thi Lan Phuong |
| collection | DOAJ |
| description | The chemical investigation of <i>Homotrigona apicalis</i> propolis collected in Binh Dinh province, Vietnam, led to the isolation of nine compounds, including four sesquiterpenes: spathulenol (<b>1</b>), 1<i>α</i>H,5<i>β</i>H-aromandendrane-4<i>β</i>,10<i>α</i>-diol (<b>2</b>), 1<i>β</i>,6<i>α</i>-dihydroxy-4(15)-eudesmene (<b>3</b>), and 1<i>β</i>H,5<i>β</i>H-aromandendrane-4<i>α</i>,10<i>β</i>-diol (<b>4</b>); three triterpenes: acetyl oleanolic acid (<b>5</b>), 3<i>α</i>-hydroxytirucalla-8,24-dien-21-oic acid (<b>6</b>), and ursolic acid (<b>7</b>); and two xanthones: cochinchinone A (<b>8</b>) and <i>α</i>-mangostin (<b>9</b>). Sesquiterpens <b>1</b>–<b>4</b> and triterpene <b>6</b> were isolated for the first time from stingless bee propolis. Plants in the <i>Cratoxylum</i> and <i>Aglaia</i> genus were suggested as resin sources of the propolis sample. In the antibacterial activity evaluation, the EtOH extract only showed moderate activity on <i>S. aureus</i>, while the isolated compounds <b>7</b>–<b>9</b> showed good antibacterial activity, with IC<sub>50</sub> values of 0.56 to 17.33 µg/mL. The EtOH extract displayed selective cytotoxicity against the A-549 cancer cell line, with IC<sub>50</sub> values of 22.82 ± 0.86 µg/mL, and the xanthones <b>8</b> and <b>9</b> exhibited good activity against the KB, HepG-2, and A-549 cancer cell lines, with IC<sub>50</sub> values ranging from 7.55 ± 0.25 µg/mL to 29.27 ± 2.07 µg/mL. The cytotoxic effects of xanthones <b>8</b> and <b>9</b> were determined by the inhibition of the EGFR and HER2 pathways using a molecular docking study. Compounds <b>8</b> and <b>9</b> displayed strong binding affinity with EFGR and HER2, with values of −9.3 to −9.9 kcal/mol. Compounds <b>5</b>, <b>8,</b> and <b>9</b> showed potential <i>α</i>-glucosidase inhibitory activities, which were further confirmed by computational studies. The binding energies of compounds <b>5</b>, <b>8,</b> and <b>9</b> were lower than that of arcabose. |
| first_indexed | 2024-03-10T23:47:30Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 2075-1729 |
| language | English |
| last_indexed | 2024-03-10T23:47:30Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Life |
| spelling | doaj.art-5f90a729a1ad4fbda40249737cf511c02023-11-19T01:54:04ZengMDPI AGLife2075-17292023-08-01138168210.3390/life13081682Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking StudiesDiep Thi Lan Phuong0Nguyen Van Phuong1Nguyen Le Tuan2Nguyen Thanh Cong3Nguyen Thu Hang4Le Nguyen Thanh5Vu Thi Hue6Nguyen Quoc Vuong7Nguyen Thi Thu Ha8Milena Popova9Boryana Trusheva10Vassya Bankova11Faculty of Natural Sciences, Quy Nhon University, Binh Dinh 55000, VietnamDepartment of Pharmacognosy, Faculty of Pharmacognosy and Traditional Medicines, Hanoi University of Pharmacy, Hanoi 11000, VietnamFaculty of Natural Sciences, Quy Nhon University, Binh Dinh 55000, VietnamDepartment of Pharmacognosy, Faculty of Pharmacognosy and Traditional Medicines, Hanoi University of Pharmacy, Hanoi 11000, VietnamDepartment of Pharmacognosy, Faculty of Pharmacognosy and Traditional Medicines, Hanoi University of Pharmacy, Hanoi 11000, VietnamGraduate University of Science and Technology, Vietnam Academy of Science and Technology (VAST), Hanoi 10000, VietnamInstitute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), Hanoi 10000, VietnamGraduate University of Science and Technology, Vietnam Academy of Science and Technology (VAST), Hanoi 10000, VietnamGraduate University of Science and Technology, Vietnam Academy of Science and Technology (VAST), Hanoi 10000, VietnamInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., bl. 9, 1113 Sofia, BulgariaThe chemical investigation of <i>Homotrigona apicalis</i> propolis collected in Binh Dinh province, Vietnam, led to the isolation of nine compounds, including four sesquiterpenes: spathulenol (<b>1</b>), 1<i>α</i>H,5<i>β</i>H-aromandendrane-4<i>β</i>,10<i>α</i>-diol (<b>2</b>), 1<i>β</i>,6<i>α</i>-dihydroxy-4(15)-eudesmene (<b>3</b>), and 1<i>β</i>H,5<i>β</i>H-aromandendrane-4<i>α</i>,10<i>β</i>-diol (<b>4</b>); three triterpenes: acetyl oleanolic acid (<b>5</b>), 3<i>α</i>-hydroxytirucalla-8,24-dien-21-oic acid (<b>6</b>), and ursolic acid (<b>7</b>); and two xanthones: cochinchinone A (<b>8</b>) and <i>α</i>-mangostin (<b>9</b>). Sesquiterpens <b>1</b>–<b>4</b> and triterpene <b>6</b> were isolated for the first time from stingless bee propolis. Plants in the <i>Cratoxylum</i> and <i>Aglaia</i> genus were suggested as resin sources of the propolis sample. In the antibacterial activity evaluation, the EtOH extract only showed moderate activity on <i>S. aureus</i>, while the isolated compounds <b>7</b>–<b>9</b> showed good antibacterial activity, with IC<sub>50</sub> values of 0.56 to 17.33 µg/mL. The EtOH extract displayed selective cytotoxicity against the A-549 cancer cell line, with IC<sub>50</sub> values of 22.82 ± 0.86 µg/mL, and the xanthones <b>8</b> and <b>9</b> exhibited good activity against the KB, HepG-2, and A-549 cancer cell lines, with IC<sub>50</sub> values ranging from 7.55 ± 0.25 µg/mL to 29.27 ± 2.07 µg/mL. The cytotoxic effects of xanthones <b>8</b> and <b>9</b> were determined by the inhibition of the EGFR and HER2 pathways using a molecular docking study. Compounds <b>8</b> and <b>9</b> displayed strong binding affinity with EFGR and HER2, with values of −9.3 to −9.9 kcal/mol. Compounds <b>5</b>, <b>8,</b> and <b>9</b> showed potential <i>α</i>-glucosidase inhibitory activities, which were further confirmed by computational studies. The binding energies of compounds <b>5</b>, <b>8,</b> and <b>9</b> were lower than that of arcabose.https://www.mdpi.com/2075-1729/13/8/1682<i>Homotrigona apicalis</i>sesquiterpenestriterpenesxanthones<i>α</i>-glucosidasecytotoxicity |
| spellingShingle | Diep Thi Lan Phuong Nguyen Van Phuong Nguyen Le Tuan Nguyen Thanh Cong Nguyen Thu Hang Le Nguyen Thanh Vu Thi Hue Nguyen Quoc Vuong Nguyen Thi Thu Ha Milena Popova Boryana Trusheva Vassya Bankova Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies Life <i>Homotrigona apicalis</i> sesquiterpenes triterpenes xanthones <i>α</i>-glucosidase cytotoxicity |
| title | Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies |
| title_full | Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies |
| title_fullStr | Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies |
| title_full_unstemmed | Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies |
| title_short | Antimicrobial, Cytotoxic, and <i>α</i>-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from <i>Homotrigona apicalis</i> Propolis—In Vitro and Molecular Docking Studies |
| title_sort | antimicrobial cytotoxic and i α i glucosidase inhibitory activities of ethanol extract and chemical constituents isolated from i homotrigona apicalis i propolis in vitro and molecular docking studies |
| topic | <i>Homotrigona apicalis</i> sesquiterpenes triterpenes xanthones <i>α</i>-glucosidase cytotoxicity |
| url | https://www.mdpi.com/2075-1729/13/8/1682 |
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