HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities
The Melodinus species have been proved to be good resources of bisindole alkaloids. Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis (Lour.) Merr. guided by HRESIMS data analysis. Among them, melokhanines K-M, epi-scandomelonine, and epi-scandomeline posse...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2021-04, Vol.184, p.112673-112673, Article 112673 |
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| creator | Li, Fang-Ru Liu, Lu Liu, Ya-Ping Wang, Jin-Tang Yang, Mei-Lian Khan, Afsar Qin, Xu-Jie Wang, Yu-Dan Cheng, Gui-Guang |
| description | The Melodinus species have been proved to be good resources of bisindole alkaloids. Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis (Lour.) Merr. guided by HRESIMS data analysis. Among them, melokhanines K-M, epi-scandomelonine, and epi-scandomeline possessed aspidosperma-scandine skeleton linked by a C–C bond while meloyine II had a scandine-scandine skeleton. The structures were established by extensive spectroscopic analysis of their HRESIMS and NMR data. Melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. Melokhanine K and meloyine II showed potent inhibitory activity on the production of nitric oxide, interleukin-6, and tumor necrosis factor-α in LPS-induced RAW 264.7 macrophages, whereas epi-scandomelonine and epi-scandomeline exhibited certain cytotoxic activity against MOLT-4 cells with IC50 values 5.2 and 1.5 μM, respectively.
Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis guided by HRESIMS data analysis. Among them, melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. [Display omitted]
•Six bisindole alkaloids were isolated from M. cochinchinensis guided by HRESIMS data analysis.•Anti-inflammatory and cytotoxic activities of the isolated alkaloids were evaluated.•Melokhanine K and meloyine Ⅱ showed potent inhibitory anti-inflammatory activities.•Episcandomelonine and episcandomeline showed certain cytotoxic activity against MOLT-4 cells. |
| doi_str_mv | 10.1016/j.phytochem.2021.112673 |
| format | Article |
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Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis guided by HRESIMS data analysis. Among them, melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. [Display omitted]
•Six bisindole alkaloids were isolated from M. cochinchinensis guided by HRESIMS data analysis.•Anti-inflammatory and cytotoxic activities of the isolated alkaloids were evaluated.•Melokhanine K and meloyine Ⅱ showed potent inhibitory anti-inflammatory activities.•Episcandomelonine and episcandomeline showed certain cytotoxic activity against MOLT-4 cells.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2021.112673</identifier><identifier>PMID: 33556841</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Alkaloids - pharmacology ; Anti-inflammatory ; Anti-Inflammatory Agents - pharmacology ; Apocynaceae ; Aspidosperma ; Bisindole alkaloids ; Cytotoxicity ; Indole Alkaloids - pharmacology ; Melodinus cochinchinensis (Lour.) Merr. (Apocynaceae) ; melokhanines ; Molecular Structure</subject><ispartof>Phytochemistry (Oxford), 2021-04, Vol.184, p.112673-112673, Article 112673</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c371t-af31ab69b6365538e0b3a3519d3d678206e04cf9392a7dc4db1dca8a7f00e93e3</citedby><cites>FETCH-LOGICAL-c371t-af31ab69b6365538e0b3a3519d3d678206e04cf9392a7dc4db1dca8a7f00e93e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0031942221000200$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33556841$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Fang-Ru</creatorcontrib><creatorcontrib>Liu, Lu</creatorcontrib><creatorcontrib>Liu, Ya-Ping</creatorcontrib><creatorcontrib>Wang, Jin-Tang</creatorcontrib><creatorcontrib>Yang, Mei-Lian</creatorcontrib><creatorcontrib>Khan, Afsar</creatorcontrib><creatorcontrib>Qin, Xu-Jie</creatorcontrib><creatorcontrib>Wang, Yu-Dan</creatorcontrib><creatorcontrib>Cheng, Gui-Guang</creatorcontrib><title>HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>The Melodinus species have been proved to be good resources of bisindole alkaloids. Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis (Lour.) Merr. guided by HRESIMS data analysis. Among them, melokhanines K-M, epi-scandomelonine, and epi-scandomeline possessed aspidosperma-scandine skeleton linked by a C–C bond while meloyine II had a scandine-scandine skeleton. The structures were established by extensive spectroscopic analysis of their HRESIMS and NMR data. Melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. Melokhanine K and meloyine II showed potent inhibitory activity on the production of nitric oxide, interleukin-6, and tumor necrosis factor-α in LPS-induced RAW 264.7 macrophages, whereas epi-scandomelonine and epi-scandomeline exhibited certain cytotoxic activity against MOLT-4 cells with IC50 values 5.2 and 1.5 μM, respectively.
Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis guided by HRESIMS data analysis. Among them, melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. [Display omitted]
•Six bisindole alkaloids were isolated from M. cochinchinensis guided by HRESIMS data analysis.•Anti-inflammatory and cytotoxic activities of the isolated alkaloids were evaluated.•Melokhanine K and meloyine Ⅱ showed potent inhibitory anti-inflammatory activities.•Episcandomelonine and episcandomeline showed certain cytotoxic activity against MOLT-4 cells.</description><subject>Alkaloids - pharmacology</subject><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Apocynaceae</subject><subject>Aspidosperma</subject><subject>Bisindole alkaloids</subject><subject>Cytotoxicity</subject><subject>Indole Alkaloids - pharmacology</subject><subject>Melodinus cochinchinensis (Lour.) Merr. (Apocynaceae)</subject><subject>melokhanines</subject><subject>Molecular Structure</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhi0EokvhFcBHLlnsOImTY1UVWqkVEoWz5dgTdpYkDh6nYl-GZ8XLll45WB7J3--Z0cfYOym2Usjmw3677A4puB1M21KUcitl2Wj1jG1kq1WhtBDP2UYIJYuuKssz9opoL4So66Z5yc6UykVbyQ37ff3l6v7m7r74vqIHz5HCaBOGmYeBW1rQB1ogTrYgZ2ePM_B0WID3SDj7MAK34w87BvTEhxgmfgdjyNhK3OXxcD4emAmJ5zhPO8CYq4QFzsNop8mmEA9_31xeKIVf6Lh1CR8wIdBr9mKwI8Gbx_ucfft49fXyurj9_Onm8uK2cErLVNhBSds3Xd-opq5VC6JXVtWy88o3ui1FA6JyQ6e60mrvKt9L72xr9SAEdArUOXt_-neJ4ecKlMyE5GAc7QxhJVNWrdZVXVc6o_qEuhiIIgxmiTjZeDBSmKMcszdPcsxRjjnJycm3j03WfgL_lPtnIwMXJwDyqg8I0ZBDmB14jOCS8QH_2-QPXiqpdQ</recordid><startdate>202104</startdate><enddate>202104</enddate><creator>Li, Fang-Ru</creator><creator>Liu, Lu</creator><creator>Liu, Ya-Ping</creator><creator>Wang, Jin-Tang</creator><creator>Yang, Mei-Lian</creator><creator>Khan, Afsar</creator><creator>Qin, Xu-Jie</creator><creator>Wang, Yu-Dan</creator><creator>Cheng, Gui-Guang</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>202104</creationdate><title>HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities</title><author>Li, Fang-Ru ; Liu, Lu ; Liu, Ya-Ping ; Wang, Jin-Tang ; Yang, Mei-Lian ; Khan, Afsar ; Qin, Xu-Jie ; Wang, Yu-Dan ; Cheng, Gui-Guang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c371t-af31ab69b6365538e0b3a3519d3d678206e04cf9392a7dc4db1dca8a7f00e93e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkaloids - pharmacology</topic><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Apocynaceae</topic><topic>Aspidosperma</topic><topic>Bisindole alkaloids</topic><topic>Cytotoxicity</topic><topic>Indole Alkaloids - pharmacology</topic><topic>Melodinus cochinchinensis (Lour.) Merr. (Apocynaceae)</topic><topic>melokhanines</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Fang-Ru</creatorcontrib><creatorcontrib>Liu, Lu</creatorcontrib><creatorcontrib>Liu, Ya-Ping</creatorcontrib><creatorcontrib>Wang, Jin-Tang</creatorcontrib><creatorcontrib>Yang, Mei-Lian</creatorcontrib><creatorcontrib>Khan, Afsar</creatorcontrib><creatorcontrib>Qin, Xu-Jie</creatorcontrib><creatorcontrib>Wang, Yu-Dan</creatorcontrib><creatorcontrib>Cheng, Gui-Guang</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Fang-Ru</au><au>Liu, Lu</au><au>Liu, Ya-Ping</au><au>Wang, Jin-Tang</au><au>Yang, Mei-Lian</au><au>Khan, Afsar</au><au>Qin, Xu-Jie</au><au>Wang, Yu-Dan</au><au>Cheng, Gui-Guang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2021-04</date><risdate>2021</risdate><volume>184</volume><spage>112673</spage><epage>112673</epage><pages>112673-112673</pages><artnum>112673</artnum><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The Melodinus species have been proved to be good resources of bisindole alkaloids. Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis (Lour.) Merr. guided by HRESIMS data analysis. Among them, melokhanines K-M, epi-scandomelonine, and epi-scandomeline possessed aspidosperma-scandine skeleton linked by a C–C bond while meloyine II had a scandine-scandine skeleton. The structures were established by extensive spectroscopic analysis of their HRESIMS and NMR data. Melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. Melokhanine K and meloyine II showed potent inhibitory activity on the production of nitric oxide, interleukin-6, and tumor necrosis factor-α in LPS-induced RAW 264.7 macrophages, whereas epi-scandomelonine and epi-scandomeline exhibited certain cytotoxic activity against MOLT-4 cells with IC50 values 5.2 and 1.5 μM, respectively.
Six bisindole alkaloids were isolated from the leaves and stems of Melodinus cochinchinensis guided by HRESIMS data analysis. Among them, melokhanines K-M were undescribed compounds, while epi-scandomelonine, epi-scandomeline and meloyine II were known compounds, which were reported from Melodinus species for the first time. The anti-inflammatory and cytotoxic activities of the isolates were also evaluated in vitro. [Display omitted]
•Six bisindole alkaloids were isolated from M. cochinchinensis guided by HRESIMS data analysis.•Anti-inflammatory and cytotoxic activities of the isolated alkaloids were evaluated.•Melokhanine K and meloyine Ⅱ showed potent inhibitory anti-inflammatory activities.•Episcandomelonine and episcandomeline showed certain cytotoxic activity against MOLT-4 cells.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>33556841</pmid><doi>10.1016/j.phytochem.2021.112673</doi><tpages>1</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 2021-04, Vol.184, p.112673-112673, Article 112673 |
| issn | 0031-9422 1873-3700 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Alkaloids - pharmacology Anti-inflammatory Anti-Inflammatory Agents - pharmacology Apocynaceae Aspidosperma Bisindole alkaloids Cytotoxicity Indole Alkaloids - pharmacology Melodinus cochinchinensis (Lour.) Merr. (Apocynaceae) melokhanines Molecular Structure |
| title | HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities |
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