Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots
Plants from Salacia genus are used in traditional medicine for a wide range of diseases. Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α‐dihydroxyfriedelan‐3‐one (1) was obtained from the ro...
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| Veröffentlicht in: | Chemistry & biodiversity 2023-10, Vol.20 (10), p.e202301207-n/a |
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| creator | Marinho Miguel, Elizabeth Luciana Sousa, Grasiely Faria Duarte, Lucienir Pains Guerra de Aguilar, Mariana Silva, Sabrina França Ferreira Soares, Daniel Crístian Johann, Susana Andrade Santana, Luiz Felipe Thomaz Oliveira, Kamila Montes Vidal, Diogo |
| description | Plants from Salacia genus are used in traditional medicine for a wide range of diseases. Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α‐dihydroxyfriedelan‐3‐one (1) was obtained from the roots of Salacia elliptica, along with seven known compounds: friedelan‐3‐one (2), friedelan‐3β‐ol (3), friedelan‐1,3‐dione (4), friedelan‐3,15‐dione (5), 15α‐hydroxyfriedelan‐3‐one (6), 15α,26‐dihydroxyfriedelan‐3‐one (7), and 26‐hydroxyfriedelan‐3,15‐dione (8). Additionally, one steroid, spinasterol (9), was also identified. The chemical structures of all compounds were established through 1H and 13C‐NMR. Compound 1 was analysed by additional 2D experiments (HMBC, HSQC, COSY, and NOESY) for complete elucidation. Furthermore, the cytotoxicity of compounds 2, 3, 6, 7 and 8 against the A549 lung cancer cells model was evaluated. The flow cytometry analysis revealed a significant cytotoxic activity similar to that exhibited by the triterpenoid lupeol. Additionally, compounds 2, 3, 6, and 7 were tested for in vitro antifungal activity against Candida, Cryptococcus and Sporothrix strains. However, all compounds showed no activity at the tested concentrations. |
| doi_str_mv | 10.1002/cbdv.202301207 |
| format | Article |
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Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α‐dihydroxyfriedelan‐3‐one (1) was obtained from the roots of Salacia elliptica, along with seven known compounds: friedelan‐3‐one (2), friedelan‐3β‐ol (3), friedelan‐1,3‐dione (4), friedelan‐3,15‐dione (5), 15α‐hydroxyfriedelan‐3‐one (6), 15α,26‐dihydroxyfriedelan‐3‐one (7), and 26‐hydroxyfriedelan‐3,15‐dione (8). Additionally, one steroid, spinasterol (9), was also identified. The chemical structures of all compounds were established through 1H and 13C‐NMR. Compound 1 was analysed by additional 2D experiments (HMBC, HSQC, COSY, and NOESY) for complete elucidation. Furthermore, the cytotoxicity of compounds 2, 3, 6, 7 and 8 against the A549 lung cancer cells model was evaluated. The flow cytometry analysis revealed a significant cytotoxic activity similar to that exhibited by the triterpenoid lupeol. Additionally, compounds 2, 3, 6, and 7 were tested for in vitro antifungal activity against Candida, Cryptococcus and Sporothrix strains. However, all compounds showed no activity at the tested concentrations.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202301207</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>antifungal ; Antifungal activity ; Biocompatibility ; Celastraceae ; Cytotoxicity ; Diketones ; Flow cytometry ; Fungi ; Fungicides ; Lung cancer ; Medicinal plants ; NMR ; Nuclear magnetic resonance ; Pentacyclic triterpenoids ; Roots ; Salacia ; Salacia elliptica ; Toxicity ; triterpenoid ; Triterpenoids ; Two dimensional analysis</subject><ispartof>Chemistry & biodiversity, 2023-10, Vol.20 (10), p.e202301207-n/a</ispartof><rights>2023 Wiley‐VHCA AG, Zurich, Switzerland</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3457-3f18e42fb877b15973053689841c987446b1ab289c616be38ba94f5d1224962a3</cites><orcidid>0000-0003-4852-1430 ; 0000-0002-1157-4179 ; 0009-0006-2975-1205 ; 0000-0002-8885-6625 ; 0000-0001-8068-1720 ; 0009-0007-3046-1675</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.202301207$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202301207$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids></links><search><creatorcontrib>Marinho Miguel, Elizabeth Luciana</creatorcontrib><creatorcontrib>Sousa, Grasiely Faria</creatorcontrib><creatorcontrib>Duarte, Lucienir Pains</creatorcontrib><creatorcontrib>Guerra de Aguilar, Mariana</creatorcontrib><creatorcontrib>Silva, Sabrina França</creatorcontrib><creatorcontrib>Ferreira Soares, Daniel Crístian</creatorcontrib><creatorcontrib>Johann, Susana</creatorcontrib><creatorcontrib>Andrade Santana, Luiz Felipe</creatorcontrib><creatorcontrib>Thomaz Oliveira, Kamila</creatorcontrib><creatorcontrib>Montes Vidal, Diogo</creatorcontrib><title>Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots</title><title>Chemistry & biodiversity</title><description>Plants from Salacia genus are used in traditional medicine for a wide range of diseases. Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α‐dihydroxyfriedelan‐3‐one (1) was obtained from the roots of Salacia elliptica, along with seven known compounds: friedelan‐3‐one (2), friedelan‐3β‐ol (3), friedelan‐1,3‐dione (4), friedelan‐3,15‐dione (5), 15α‐hydroxyfriedelan‐3‐one (6), 15α,26‐dihydroxyfriedelan‐3‐one (7), and 26‐hydroxyfriedelan‐3,15‐dione (8). Additionally, one steroid, spinasterol (9), was also identified. The chemical structures of all compounds were established through 1H and 13C‐NMR. Compound 1 was analysed by additional 2D experiments (HMBC, HSQC, COSY, and NOESY) for complete elucidation. Furthermore, the cytotoxicity of compounds 2, 3, 6, 7 and 8 against the A549 lung cancer cells model was evaluated. The flow cytometry analysis revealed a significant cytotoxic activity similar to that exhibited by the triterpenoid lupeol. Additionally, compounds 2, 3, 6, and 7 were tested for in vitro antifungal activity against Candida, Cryptococcus and Sporothrix strains. However, all compounds showed no activity at the tested concentrations.</description><subject>antifungal</subject><subject>Antifungal activity</subject><subject>Biocompatibility</subject><subject>Celastraceae</subject><subject>Cytotoxicity</subject><subject>Diketones</subject><subject>Flow cytometry</subject><subject>Fungi</subject><subject>Fungicides</subject><subject>Lung cancer</subject><subject>Medicinal plants</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pentacyclic triterpenoids</subject><subject>Roots</subject><subject>Salacia</subject><subject>Salacia elliptica</subject><subject>Toxicity</subject><subject>triterpenoid</subject><subject>Triterpenoids</subject><subject>Two dimensional analysis</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAcxYMoOKdXzwEvXjrzo02T46ybCgPBX0dDmqaS0TWzSaf9782YTPDi6ft4fN6XxwPgHKMJRohc6bLaTAgiFGGC8gMwwgyTBHOODvc6J8fgxPtl5KPPR-BttlFNr4J1LXQ1LIbggvuy2oYBqraC0zbYum_fVQOnOtjN1o_cvLOmMo1qjYd151bwSTVKWwVN09h1sFrBR-eCPwVHtWq8Ofu5Y_Aynz0Xd8ni4fa-mC4STdMsT2iNuUlJXfI8L3EmcooyyrjgKdaC52nKSqxKwoVmmJWG8lKJtM4qTEgqGFF0DC53f9ed--iND3JlvY5lYkPXe0k4o0QwQUVEL_6gS9d3bWwXqVyklFLMIzXZUbpz3nemluvOrlQ3SIzkdm65nVvu544BsQt82sYM_9CyuL55_c1-A9uJgsI</recordid><startdate>202310</startdate><enddate>202310</enddate><creator>Marinho Miguel, Elizabeth Luciana</creator><creator>Sousa, Grasiely Faria</creator><creator>Duarte, Lucienir Pains</creator><creator>Guerra de Aguilar, Mariana</creator><creator>Silva, Sabrina França</creator><creator>Ferreira Soares, Daniel Crístian</creator><creator>Johann, Susana</creator><creator>Andrade Santana, Luiz Felipe</creator><creator>Thomaz Oliveira, Kamila</creator><creator>Montes Vidal, Diogo</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4852-1430</orcidid><orcidid>https://orcid.org/0000-0002-1157-4179</orcidid><orcidid>https://orcid.org/0009-0006-2975-1205</orcidid><orcidid>https://orcid.org/0000-0002-8885-6625</orcidid><orcidid>https://orcid.org/0000-0001-8068-1720</orcidid><orcidid>https://orcid.org/0009-0007-3046-1675</orcidid></search><sort><creationdate>202310</creationdate><title>Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots</title><author>Marinho Miguel, Elizabeth Luciana ; Sousa, Grasiely Faria ; Duarte, Lucienir Pains ; Guerra de Aguilar, Mariana ; Silva, Sabrina França ; Ferreira Soares, Daniel Crístian ; Johann, Susana ; Andrade Santana, Luiz Felipe ; Thomaz Oliveira, Kamila ; Montes Vidal, Diogo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3457-3f18e42fb877b15973053689841c987446b1ab289c616be38ba94f5d1224962a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>antifungal</topic><topic>Antifungal activity</topic><topic>Biocompatibility</topic><topic>Celastraceae</topic><topic>Cytotoxicity</topic><topic>Diketones</topic><topic>Flow cytometry</topic><topic>Fungi</topic><topic>Fungicides</topic><topic>Lung cancer</topic><topic>Medicinal plants</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pentacyclic triterpenoids</topic><topic>Roots</topic><topic>Salacia</topic><topic>Salacia elliptica</topic><topic>Toxicity</topic><topic>triterpenoid</topic><topic>Triterpenoids</topic><topic>Two dimensional analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Marinho Miguel, Elizabeth Luciana</creatorcontrib><creatorcontrib>Sousa, Grasiely Faria</creatorcontrib><creatorcontrib>Duarte, Lucienir Pains</creatorcontrib><creatorcontrib>Guerra de Aguilar, Mariana</creatorcontrib><creatorcontrib>Silva, Sabrina França</creatorcontrib><creatorcontrib>Ferreira Soares, Daniel Crístian</creatorcontrib><creatorcontrib>Johann, Susana</creatorcontrib><creatorcontrib>Andrade Santana, Luiz Felipe</creatorcontrib><creatorcontrib>Thomaz Oliveira, Kamila</creatorcontrib><creatorcontrib>Montes Vidal, Diogo</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Marinho Miguel, Elizabeth Luciana</au><au>Sousa, Grasiely Faria</au><au>Duarte, Lucienir Pains</au><au>Guerra de Aguilar, Mariana</au><au>Silva, Sabrina França</au><au>Ferreira Soares, Daniel Crístian</au><au>Johann, Susana</au><au>Andrade Santana, Luiz Felipe</au><au>Thomaz Oliveira, Kamila</au><au>Montes Vidal, Diogo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots</atitle><jtitle>Chemistry & biodiversity</jtitle><date>2023-10</date><risdate>2023</risdate><volume>20</volume><issue>10</issue><spage>e202301207</spage><epage>n/a</epage><pages>e202301207-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>Plants from Salacia genus are used in traditional medicine for a wide range of diseases. Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α‐dihydroxyfriedelan‐3‐one (1) was obtained from the roots of Salacia elliptica, along with seven known compounds: friedelan‐3‐one (2), friedelan‐3β‐ol (3), friedelan‐1,3‐dione (4), friedelan‐3,15‐dione (5), 15α‐hydroxyfriedelan‐3‐one (6), 15α,26‐dihydroxyfriedelan‐3‐one (7), and 26‐hydroxyfriedelan‐3,15‐dione (8). Additionally, one steroid, spinasterol (9), was also identified. The chemical structures of all compounds were established through 1H and 13C‐NMR. Compound 1 was analysed by additional 2D experiments (HMBC, HSQC, COSY, and NOESY) for complete elucidation. Furthermore, the cytotoxicity of compounds 2, 3, 6, 7 and 8 against the A549 lung cancer cells model was evaluated. The flow cytometry analysis revealed a significant cytotoxic activity similar to that exhibited by the triterpenoid lupeol. Additionally, compounds 2, 3, 6, and 7 were tested for in vitro antifungal activity against Candida, Cryptococcus and Sporothrix strains. However, all compounds showed no activity at the tested concentrations.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/cbdv.202301207</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-4852-1430</orcidid><orcidid>https://orcid.org/0000-0002-1157-4179</orcidid><orcidid>https://orcid.org/0009-0006-2975-1205</orcidid><orcidid>https://orcid.org/0000-0002-8885-6625</orcidid><orcidid>https://orcid.org/0000-0001-8068-1720</orcidid><orcidid>https://orcid.org/0009-0007-3046-1675</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | antifungal Antifungal activity Biocompatibility Celastraceae Cytotoxicity Diketones Flow cytometry Fungi Fungicides Lung cancer Medicinal plants NMR Nuclear magnetic resonance Pentacyclic triterpenoids Roots Salacia Salacia elliptica Toxicity triterpenoid Triterpenoids Two dimensional analysis |
| title | Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots |
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