Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr
Purpose: 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 μ...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-02-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844024017948 |
| _version_ | 1797267806234869760 |
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| author | Thi-Minh-Dinh Tran Chanat Aonbangkhen Thuc-Huy Duong Thu-Hoang-Mai Nguyen Minh-Truong-Tho Ho Warinthorn Chavasiri Sutthida Wongsuwan Jaruwan Chatwichien Thi-Phi Giao Vo Ngoc-Hong Nguyen Duangnapa Kiriwan Kiattawee Choowongkomon |
| author_facet | Thi-Minh-Dinh Tran Chanat Aonbangkhen Thuc-Huy Duong Thu-Hoang-Mai Nguyen Minh-Truong-Tho Ho Warinthorn Chavasiri Sutthida Wongsuwan Jaruwan Chatwichien Thi-Phi Giao Vo Ngoc-Hong Nguyen Duangnapa Kiriwan Kiattawee Choowongkomon |
| author_sort | Thi-Minh-Dinh Tran |
| collection | DOAJ |
| description | Purpose: 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. Methods: 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 (Mpro) 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. Results: 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 Mpro 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. Conclusion: 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 Mpro 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. |
| first_indexed | 2024-03-07T23:38:17Z |
| format | Article |
| id | doaj.art-6103bbc4e1b240e3b37be85217c73f30 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-25T01:22:26Z |
| publishDate | 2024-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-6103bbc4e1b240e3b37be85217c73f302024-03-09T09:26:10ZengElsevierHeliyon2405-84402024-02-01104e25763Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii ZahlbrThi-Minh-Dinh Tran0Chanat Aonbangkhen1Thuc-Huy Duong2Thu-Hoang-Mai Nguyen3Minh-Truong-Tho Ho4Warinthorn Chavasiri5Sutthida Wongsuwan6Jaruwan Chatwichien7Thi-Phi Giao Vo8Ngoc-Hong Nguyen9Duangnapa Kiriwan10Kiattawee Choowongkomon11Department of Biology, Ho Chi Minh City University of Education, 280 an Duong Vuong Street, District 5, Ho Chi Minh City, 748342, Viet Nam; KU Institute for Advanced Studies, Kasetsart University, Bangkok, 10900, Thailand; Corresponding author. Department of Biology, Ho Chi Minh City University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City, 748342, Viet Nam.Center of Excellence in Natural Products Chemistry, Department of Chemistry, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemistry, Ho Chi Minh City University of Education, 280 an Duong Vuong Street, District 5, Ho Chi Minh City, 748342, Viet NamDepartment of Chemistry, Ho Chi Minh City University of Education, 280 an Duong Vuong Street, District 5, Ho Chi Minh City, 748342, Viet NamDepartment of Chemistry, Ho Chi Minh City University of Education, 280 an Duong Vuong Street, District 5, Ho Chi Minh City, 748342, Viet NamCenter of Excellence in Natural Products Chemistry, Department of Chemistry, Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand; Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Chulalongkorn University, Bangkok, 10330, ThailandProgram in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Bangkok, 10210, ThailandProgram in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Bangkok, 10210, ThailandUniversity of Science, Vietnam National University Ho Chi Minh City, Ho Chi Minh City, Viet NamCirTech Institute, HUTECH University, 475 A Dien Bien Phu Street, Binh Thanh District, Ho Chi Minh City, Viet NamDepartment of Biochemistry, Kasetsart University, Bangkok, ThailandKU Institute for Advanced Studies, Kasetsart University, Bangkok, 10900, Thailand; Department of Biochemistry, Kasetsart University, Bangkok, Thailand; Corresponding author. KU Institute for Advanced Studies, Kasetsart University, Bangkok, 10900, Thailand.Purpose: 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. Methods: 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 (Mpro) 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. Results: 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 Mpro 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. Conclusion: 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 Mpro 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.http://www.sciencedirect.com/science/article/pii/S2405844024017948Cultured lichen mycobiontGraphis handeliiDepsidoneHandeloneAlpha-glucosidase inhibitionMpro inhibition |
| spellingShingle | Thi-Minh-Dinh Tran Chanat Aonbangkhen Thuc-Huy Duong Thu-Hoang-Mai Nguyen Minh-Truong-Tho Ho Warinthorn Chavasiri Sutthida Wongsuwan Jaruwan Chatwichien Thi-Phi Giao Vo Ngoc-Hong Nguyen Duangnapa Kiriwan Kiattawee Choowongkomon Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr Heliyon Cultured lichen mycobiont Graphis handelii Depsidone Handelone Alpha-glucosidase inhibition Mpro inhibition |
| title | Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr |
| title_full | Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr |
| title_fullStr | Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr |
| title_full_unstemmed | Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr |
| title_short | Diphenyl ethers from the cultured lichen mycobiont of Graphis handelii Zahlbr |
| title_sort | diphenyl ethers from the cultured lichen mycobiont of graphis handelii zahlbr |
| topic | Cultured lichen mycobiont Graphis handelii Depsidone Handelone Alpha-glucosidase inhibition Mpro inhibition |
| url | http://www.sciencedirect.com/science/article/pii/S2405844024017948 |
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