Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb.
Piper sarmentosum Roxb. (Piperaceae) is a traditional medicinal plant in South-East Asian countries. The chemical investigation of leaves from this species resulted in the isolation of three previously not described compounds, namely 4″-(3-hydroxy-3-methylglutaroyl)-2″-β-D-glucopyranosyl vitexin (1)...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI
2023
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| Online Access: | http://eprints.utm.my/105804/1/IsmailWare2023_CharacterizationandBioactivePotentialofSecondary.pdf |
| _version_ | 1811132206493466624 |
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| author | Ware, Ismail Franke, Katrin Dube, Mthandazo Ali El Enshasy, Hesham Wessjohann, Ludger A. |
| author_facet | Ware, Ismail Franke, Katrin Dube, Mthandazo Ali El Enshasy, Hesham Wessjohann, Ludger A. |
| author_sort | Ware, Ismail |
| collection | ePrints |
| description | Piper sarmentosum Roxb. (Piperaceae) is a traditional medicinal plant in South-East Asian countries. The chemical investigation of leaves from this species resulted in the isolation of three previously not described compounds, namely 4″-(3-hydroxy-3-methylglutaroyl)-2″-β-D-glucopyranosyl vitexin (1), kadukoside (2), and 6-O-trans-p-coumaroyl-D-glucono-1,4-lactone (3), together with 31 known compounds. Of these known compounds, 21 compounds were isolated for the first time from P. sarmentosum. The structures were established by 1D and 2D NMR techniques and HR-ESI-MS analyses. The compounds were evaluated for their anthelmintic (Caenorhabditis elegans), antifungal (Botrytis cinerea, Septoria tritici and Phytophthora infestans), antibacterial (Aliivibrio fischeri) and cytotoxic (PC-3 and HT-29 human cancer cells lines) activities. Methyl-3-(4-methoxyphenyl)propionate (8), isoasarone (12), and trans-asarone (15) demonstrated anthelmintic activity with IC50 values between 0.9 and 2.04 mM. Kadukoside (2) was most active against S. tritici with IC50 at 5.0 µM and also induced 94% inhibition of P. infestans growth at 125 µM. Trans-asarone (15), piperolactam A (23), and dehydroformouregine (24) displayed a dose-dependent effect against B. cinerea from 1.5 to 125 µM up to more than 80% inhibition. Paprazine (19), cepharadione A (21) and piperolactam A (23) inhibited bacterial growth by more than 85% at 100 µM. Only mild cytotoxic effects were observed. |
| first_indexed | 2024-09-23T23:59:41Z |
| format | Article |
| id | utm.eprints-105804 |
| institution | Universiti Teknologi Malaysia - ePrints |
| language | English |
| last_indexed | 2024-09-23T23:59:41Z |
| publishDate | 2023 |
| publisher | MDPI |
| record_format | dspace |
| spelling | utm.eprints-1058042024-05-18T01:51:14Z http://eprints.utm.my/105804/ Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. Ware, Ismail Franke, Katrin Dube, Mthandazo Ali El Enshasy, Hesham Wessjohann, Ludger A. QD Chemistry Piper sarmentosum Roxb. (Piperaceae) is a traditional medicinal plant in South-East Asian countries. The chemical investigation of leaves from this species resulted in the isolation of three previously not described compounds, namely 4″-(3-hydroxy-3-methylglutaroyl)-2″-β-D-glucopyranosyl vitexin (1), kadukoside (2), and 6-O-trans-p-coumaroyl-D-glucono-1,4-lactone (3), together with 31 known compounds. Of these known compounds, 21 compounds were isolated for the first time from P. sarmentosum. The structures were established by 1D and 2D NMR techniques and HR-ESI-MS analyses. The compounds were evaluated for their anthelmintic (Caenorhabditis elegans), antifungal (Botrytis cinerea, Septoria tritici and Phytophthora infestans), antibacterial (Aliivibrio fischeri) and cytotoxic (PC-3 and HT-29 human cancer cells lines) activities. Methyl-3-(4-methoxyphenyl)propionate (8), isoasarone (12), and trans-asarone (15) demonstrated anthelmintic activity with IC50 values between 0.9 and 2.04 mM. Kadukoside (2) was most active against S. tritici with IC50 at 5.0 µM and also induced 94% inhibition of P. infestans growth at 125 µM. Trans-asarone (15), piperolactam A (23), and dehydroformouregine (24) displayed a dose-dependent effect against B. cinerea from 1.5 to 125 µM up to more than 80% inhibition. Paprazine (19), cepharadione A (21) and piperolactam A (23) inhibited bacterial growth by more than 85% at 100 µM. Only mild cytotoxic effects were observed. MDPI 2023-01 Article PeerReviewed application/pdf en http://eprints.utm.my/105804/1/IsmailWare2023_CharacterizationandBioactivePotentialofSecondary.pdf Ware, Ismail and Franke, Katrin and Dube, Mthandazo and Ali El Enshasy, Hesham and Wessjohann, Ludger A. (2023) Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. International Journal of Molecular Sciences, 24 (2). pp. 1-21. ISSN 1661-6596 http://dx.doi.org/10.3390/ijms24021328 DOI: 10.3390/ijms24021328 |
| spellingShingle | QD Chemistry Ware, Ismail Franke, Katrin Dube, Mthandazo Ali El Enshasy, Hesham Wessjohann, Ludger A. Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. |
| title | Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. |
| title_full | Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. |
| title_fullStr | Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. |
| title_full_unstemmed | Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. |
| title_short | Characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb. |
| title_sort | characterization and bioactive potential of secondary metabolites isolated from piper sarmentosum roxb |
| topic | QD Chemistry |
| url | http://eprints.utm.my/105804/1/IsmailWare2023_CharacterizationandBioactivePotentialofSecondary.pdf |
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