Cytotoxic and antibacterial activities of compounds isolated from the fruits and stem-bark of Tetrapleura tetraptera (Schumach. & Thonn.) Taub. (Fabaceae)
A new glyceride, 2,3-dihydroxypropyl-31-hydroxyhentriacontanoate ( 1 ), a new glucoside stigmasterol derivative, stigmasterol 3- O - β -D-glucopyranoside 6’-hexadecanoate ( 2 ) along with eleven known compounds ( 3 - 13 ) were isolated from the fruits and the stem bark of Tetrapleura tetraptera (Sch...
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| Veröffentlicht in: | Medicinal chemistry research 2022-11, Vol.31 (11), p.1948-1958 |
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| creator | Kamdem, Michael Hermann Kengne Melacheu, Gertrude Laura Foudjo Silihe, Kevine Kamga More, Garland Kgosi Mphahlele, Mokgadi Precious Moswetsa, Tebogo Amos Tata, Charlotte Mungho Tonga, Jordan Lembe Ojo, Olusesan Fonkui, Thierry Younbi Mmutlane, Edwin Mpho Ndinteh, Derek Tantoh |
| description | A new glyceride, 2,3-dihydroxypropyl-31-hydroxyhentriacontanoate (
1
), a new glucoside stigmasterol derivative, stigmasterol 3-
O
-
β
-D-glucopyranoside 6’-hexadecanoate (
2
) along with eleven known compounds (
3
-
13
) were isolated from the fruits and the stem bark of
Tetrapleura tetraptera
(Schumach. & Thonn.) Taub. using silica gel vacuum liquid and column chromatography. The structures of the isolated compounds were elucidated based on spectroscopic and spectrometry methods including NMR (1D and 2D), high-resolution mass spectrometry (HRESIMS) and comparison with data reported in the literature. The crude extract and the isolated compounds were evaluated for their antibacterial activity against a panel of bacterial strains using the microdilution technique and for their cytotoxic potential on breast cancer cell lines (MCF-7, MDA-MB-231) using doxorubicin as reference medicine. All the tested compounds exhibited significant antibacterial activity against
Klebsiella aerogenes
and
Bacillus subtilis
with an MIC value of 18.5 µg/mL. Furthermore, compounds (
3
) and (
9
) were active against all bacterial strains with MICs values ranging from 18.5 to 74
µ
g/mL. Compounds (
12
-
13
) and the crude extract were cytotoxic against MDA-MB-231 cells with their CC
50
values ranging between 14.5 and 20.0
µ
g/mL. These results confirm that
T. tetraptera
is a potential source of antibacterial agents and exhibits selective toxicity against breast cancer cell lines. Apart from compound (
3
) and compounds (
10-12
), all the other compounds were isolated from
Tetrapleura
genus for the first time. Compounds (
1
), (
2
), (
6
), (
7
) and (
8
) were also isolated from the Fabaceae family for the first time.
Graphical abstract |
| doi_str_mv | 10.1007/s00044-022-02956-1 |
| format | Article |
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1
), a new glucoside stigmasterol derivative, stigmasterol 3-
O
-
β
-D-glucopyranoside 6’-hexadecanoate (
2
) along with eleven known compounds (
3
-
13
) were isolated from the fruits and the stem bark of
Tetrapleura tetraptera
(Schumach. & Thonn.) Taub. using silica gel vacuum liquid and column chromatography. The structures of the isolated compounds were elucidated based on spectroscopic and spectrometry methods including NMR (1D and 2D), high-resolution mass spectrometry (HRESIMS) and comparison with data reported in the literature. The crude extract and the isolated compounds were evaluated for their antibacterial activity against a panel of bacterial strains using the microdilution technique and for their cytotoxic potential on breast cancer cell lines (MCF-7, MDA-MB-231) using doxorubicin as reference medicine. All the tested compounds exhibited significant antibacterial activity against
Klebsiella aerogenes
and
Bacillus subtilis
with an MIC value of 18.5 µg/mL. Furthermore, compounds (
3
) and (
9
) were active against all bacterial strains with MICs values ranging from 18.5 to 74
µ
g/mL. Compounds (
12
-
13
) and the crude extract were cytotoxic against MDA-MB-231 cells with their CC
50
values ranging between 14.5 and 20.0
µ
g/mL. These results confirm that
T. tetraptera
is a potential source of antibacterial agents and exhibits selective toxicity against breast cancer cell lines. Apart from compound (
3
) and compounds (
10-12
), all the other compounds were isolated from
Tetrapleura
genus for the first time. Compounds (
1
), (
2
), (
6
), (
7
) and (
8
) were also isolated from the Fabaceae family for the first time.
Graphical abstract</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-022-02956-1</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Antibacterial activity ; Antibacterial agents ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Bioorganic Chemistry ; Breast cancer ; Column chromatography ; Cytotoxicity ; Doxorubicin ; Fabaceae ; Fruits ; Inorganic Chemistry ; Klebsiella ; Mass spectrometry ; Mass spectroscopy ; Medicinal Chemistry ; Minimum inhibitory concentration ; NMR ; Nuclear magnetic resonance ; Original Research ; Pharmacology/Toxicology ; Scientific imaging ; Silica gel ; Spectroscopy ; Strains (organisms) ; Tetrapleura tetraptera ; Toxicity ; Tumor cell lines</subject><ispartof>Medicinal chemistry research, 2022-11, Vol.31 (11), p.1948-1958</ispartof><rights>The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022. Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c249t-7724f0ba46b4fa8a5545cfaf710ec9c1503d747b9473a332c2bb36cd7f789b43</citedby><cites>FETCH-LOGICAL-c249t-7724f0ba46b4fa8a5545cfaf710ec9c1503d747b9473a332c2bb36cd7f789b43</cites><orcidid>0000-0002-2883-3173</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00044-022-02956-1$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00044-022-02956-1$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Kamdem, Michael Hermann Kengne</creatorcontrib><creatorcontrib>Melacheu, Gertrude Laura Foudjo</creatorcontrib><creatorcontrib>Silihe, Kevine Kamga</creatorcontrib><creatorcontrib>More, Garland Kgosi</creatorcontrib><creatorcontrib>Mphahlele, Mokgadi Precious</creatorcontrib><creatorcontrib>Moswetsa, Tebogo Amos</creatorcontrib><creatorcontrib>Tata, Charlotte Mungho</creatorcontrib><creatorcontrib>Tonga, Jordan Lembe</creatorcontrib><creatorcontrib>Ojo, Olusesan</creatorcontrib><creatorcontrib>Fonkui, Thierry Younbi</creatorcontrib><creatorcontrib>Mmutlane, Edwin Mpho</creatorcontrib><creatorcontrib>Ndinteh, Derek Tantoh</creatorcontrib><title>Cytotoxic and antibacterial activities of compounds isolated from the fruits and stem-bark of Tetrapleura tetraptera (Schumach. & Thonn.) Taub. (Fabaceae)</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>A new glyceride, 2,3-dihydroxypropyl-31-hydroxyhentriacontanoate (
1
), a new glucoside stigmasterol derivative, stigmasterol 3-
O
-
β
-D-glucopyranoside 6’-hexadecanoate (
2
) along with eleven known compounds (
3
-
13
) were isolated from the fruits and the stem bark of
Tetrapleura tetraptera
(Schumach. & Thonn.) Taub. using silica gel vacuum liquid and column chromatography. The structures of the isolated compounds were elucidated based on spectroscopic and spectrometry methods including NMR (1D and 2D), high-resolution mass spectrometry (HRESIMS) and comparison with data reported in the literature. The crude extract and the isolated compounds were evaluated for their antibacterial activity against a panel of bacterial strains using the microdilution technique and for their cytotoxic potential on breast cancer cell lines (MCF-7, MDA-MB-231) using doxorubicin as reference medicine. All the tested compounds exhibited significant antibacterial activity against
Klebsiella aerogenes
and
Bacillus subtilis
with an MIC value of 18.5 µg/mL. Furthermore, compounds (
3
) and (
9
) were active against all bacterial strains with MICs values ranging from 18.5 to 74
µ
g/mL. Compounds (
12
-
13
) and the crude extract were cytotoxic against MDA-MB-231 cells with their CC
50
values ranging between 14.5 and 20.0
µ
g/mL. These results confirm that
T. tetraptera
is a potential source of antibacterial agents and exhibits selective toxicity against breast cancer cell lines. Apart from compound (
3
) and compounds (
10-12
), all the other compounds were isolated from
Tetrapleura
genus for the first time. Compounds (
1
), (
2
), (
6
), (
7
) and (
8
) were also isolated from the Fabaceae family for the first time.
Graphical abstract</description><subject>Antibacterial activity</subject><subject>Antibacterial agents</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Breast cancer</subject><subject>Column chromatography</subject><subject>Cytotoxicity</subject><subject>Doxorubicin</subject><subject>Fabaceae</subject><subject>Fruits</subject><subject>Inorganic Chemistry</subject><subject>Klebsiella</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Medicinal Chemistry</subject><subject>Minimum inhibitory concentration</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Scientific imaging</subject><subject>Silica gel</subject><subject>Spectroscopy</subject><subject>Strains (organisms)</subject><subject>Tetrapleura tetraptera</subject><subject>Toxicity</subject><subject>Tumor cell lines</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kc1KAzEUhQdRUKsv4CogiC6m5rfpLKX4B4ILZx9uMomNdiY1yYi-ik9rbAV3Li73W5xzbsKpqhOCpwRjeZkwxpzXmNIyjZjVZKc6IELwek4o3i2MC1NB2X51mNILxkxiLg6qr8VnDjl8eINg6Mpkr8FkGz2sUAH_7rO3CQWHTOjXYRy6hHwKK8i2Qy6GHuWlLTD6nDYRKdu-1hBffzytzRHWKztGQHnDJRrQ-ZNZjj2Y5RSdoXYZhmF6gVoY9RSd30B5gAV7cVTtOVgle_y7J1V7c90u7uqHx9v7xdVDbShvci0l5Q5r4DPNHcyhfFoYB04SbE1jiMCsk1zqhksGjFFDtWYz00kn543mbFKdbmPXMbyNNmX1EsY4lIuKSjKnVMy4KCq6VZkYUorWqXX0PcRPRbD6qUBtK1ClArWpQJFiYltTKuLh2ca_6H9c31S2iqo</recordid><startdate>20221101</startdate><enddate>20221101</enddate><creator>Kamdem, Michael Hermann Kengne</creator><creator>Melacheu, Gertrude Laura Foudjo</creator><creator>Silihe, Kevine Kamga</creator><creator>More, Garland Kgosi</creator><creator>Mphahlele, Mokgadi Precious</creator><creator>Moswetsa, Tebogo Amos</creator><creator>Tata, Charlotte Mungho</creator><creator>Tonga, Jordan Lembe</creator><creator>Ojo, Olusesan</creator><creator>Fonkui, Thierry Younbi</creator><creator>Mmutlane, Edwin Mpho</creator><creator>Ndinteh, Derek Tantoh</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-2883-3173</orcidid></search><sort><creationdate>20221101</creationdate><title>Cytotoxic and antibacterial activities of compounds isolated from the fruits and stem-bark of Tetrapleura tetraptera (Schumach. & Thonn.) Taub. (Fabaceae)</title><author>Kamdem, Michael Hermann Kengne ; Melacheu, Gertrude Laura Foudjo ; Silihe, Kevine Kamga ; More, Garland Kgosi ; Mphahlele, Mokgadi Precious ; Moswetsa, Tebogo Amos ; Tata, Charlotte Mungho ; Tonga, Jordan Lembe ; Ojo, Olusesan ; Fonkui, Thierry Younbi ; Mmutlane, Edwin Mpho ; Ndinteh, Derek Tantoh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c249t-7724f0ba46b4fa8a5545cfaf710ec9c1503d747b9473a332c2bb36cd7f789b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Antibacterial activity</topic><topic>Antibacterial agents</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Bioorganic Chemistry</topic><topic>Breast cancer</topic><topic>Column chromatography</topic><topic>Cytotoxicity</topic><topic>Doxorubicin</topic><topic>Fabaceae</topic><topic>Fruits</topic><topic>Inorganic Chemistry</topic><topic>Klebsiella</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>Medicinal Chemistry</topic><topic>Minimum inhibitory concentration</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Scientific imaging</topic><topic>Silica gel</topic><topic>Spectroscopy</topic><topic>Strains (organisms)</topic><topic>Tetrapleura tetraptera</topic><topic>Toxicity</topic><topic>Tumor cell lines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamdem, Michael Hermann Kengne</creatorcontrib><creatorcontrib>Melacheu, Gertrude Laura Foudjo</creatorcontrib><creatorcontrib>Silihe, Kevine Kamga</creatorcontrib><creatorcontrib>More, Garland Kgosi</creatorcontrib><creatorcontrib>Mphahlele, Mokgadi Precious</creatorcontrib><creatorcontrib>Moswetsa, Tebogo Amos</creatorcontrib><creatorcontrib>Tata, Charlotte Mungho</creatorcontrib><creatorcontrib>Tonga, Jordan Lembe</creatorcontrib><creatorcontrib>Ojo, Olusesan</creatorcontrib><creatorcontrib>Fonkui, Thierry Younbi</creatorcontrib><creatorcontrib>Mmutlane, Edwin Mpho</creatorcontrib><creatorcontrib>Ndinteh, Derek Tantoh</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamdem, Michael Hermann Kengne</au><au>Melacheu, Gertrude Laura Foudjo</au><au>Silihe, Kevine Kamga</au><au>More, Garland Kgosi</au><au>Mphahlele, Mokgadi Precious</au><au>Moswetsa, Tebogo Amos</au><au>Tata, Charlotte Mungho</au><au>Tonga, Jordan Lembe</au><au>Ojo, Olusesan</au><au>Fonkui, Thierry Younbi</au><au>Mmutlane, Edwin Mpho</au><au>Ndinteh, Derek Tantoh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic and antibacterial activities of compounds isolated from the fruits and stem-bark of Tetrapleura tetraptera (Schumach. & Thonn.) Taub. (Fabaceae)</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2022-11-01</date><risdate>2022</risdate><volume>31</volume><issue>11</issue><spage>1948</spage><epage>1958</epage><pages>1948-1958</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>A new glyceride, 2,3-dihydroxypropyl-31-hydroxyhentriacontanoate (
1
), a new glucoside stigmasterol derivative, stigmasterol 3-
O
-
β
-D-glucopyranoside 6’-hexadecanoate (
2
) along with eleven known compounds (
3
-
13
) were isolated from the fruits and the stem bark of
Tetrapleura tetraptera
(Schumach. & Thonn.) Taub. using silica gel vacuum liquid and column chromatography. The structures of the isolated compounds were elucidated based on spectroscopic and spectrometry methods including NMR (1D and 2D), high-resolution mass spectrometry (HRESIMS) and comparison with data reported in the literature. The crude extract and the isolated compounds were evaluated for their antibacterial activity against a panel of bacterial strains using the microdilution technique and for their cytotoxic potential on breast cancer cell lines (MCF-7, MDA-MB-231) using doxorubicin as reference medicine. All the tested compounds exhibited significant antibacterial activity against
Klebsiella aerogenes
and
Bacillus subtilis
with an MIC value of 18.5 µg/mL. Furthermore, compounds (
3
) and (
9
) were active against all bacterial strains with MICs values ranging from 18.5 to 74
µ
g/mL. Compounds (
12
-
13
) and the crude extract were cytotoxic against MDA-MB-231 cells with their CC
50
values ranging between 14.5 and 20.0
µ
g/mL. These results confirm that
T. tetraptera
is a potential source of antibacterial agents and exhibits selective toxicity against breast cancer cell lines. Apart from compound (
3
) and compounds (
10-12
), all the other compounds were isolated from
Tetrapleura
genus for the first time. Compounds (
1
), (
2
), (
6
), (
7
) and (
8
) were also isolated from the Fabaceae family for the first time.
Graphical abstract</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s00044-022-02956-1</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-2883-3173</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1054-2523 |
| ispartof | Medicinal chemistry research, 2022-11, Vol.31 (11), p.1948-1958 |
| issn | 1054-2523 1554-8120 |
| language | eng |
| recordid | cdi_proquest_journals_2718225645 |
| source | Springer Journals |
| subjects | Antibacterial activity Antibacterial agents Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Breast cancer Column chromatography Cytotoxicity Doxorubicin Fabaceae Fruits Inorganic Chemistry Klebsiella Mass spectrometry Mass spectroscopy Medicinal Chemistry Minimum inhibitory concentration NMR Nuclear magnetic resonance Original Research Pharmacology/Toxicology Scientific imaging Silica gel Spectroscopy Strains (organisms) Tetrapleura tetraptera Toxicity Tumor cell lines |
| title | Cytotoxic and antibacterial activities of compounds isolated from the fruits and stem-bark of Tetrapleura tetraptera (Schumach. & Thonn.) Taub. (Fabaceae) |
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