Chemical composition and in vitro cytotoxic and antileishmanial activities of extract and essential oil from leaves of Piper cernuum
Fractionation of the MeOH extract from leaves of Piper cernuum Vell. (Piperaceae) afforded six phenylpropanoid derivatives: 3',4'-dimethoxydihydrocinnamic acid (1), piplaroxide (2), methyl 4'-hydroxy-3',5'-dimethoxy cinnamate (3), 3',4',5'-trimethoxydihydrocinnamic acid (3), dihydropiplartine (5), and piplartine (6). The structures of isolated metabolites were characterized by NMR and MS spectral data analysis. The chemical composition of essential oil from the leaves was determined using GC/LREIMS followed by the determination of Kovats indexes. This procedure allowed the identification of nineteen terpenoids, with β-elemene (7), bicyclogermacrene (8), germacrene D (9), and (E)-caryophyllene (10) as the main compounds. Compounds 1 and 3-6 displayed no in vitro cytotoxicity against cancer cell lineages B16F10-Nex2, U87, HeLa, HL-60, HCT, and A2058 while 2 showed moderate activity against B16F10-Nex2 and HL-60 lines. Otherwise, compounds 7-10 displayed high cytotoxic activity. Evaluation against non-tumorigenic HFF cells indicated a reduced selectivity of compounds 7-10 to tumoral cells. No antileishmanial activity on macrophages infected with L. (L.) amnazonensis was found for the crude MeOH extract and compounds 1-6. The crude essential oil and compounds 7-10 reduced parasitism and eliminated the majority of infected and non-infected cells at 50 μg/mL.
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2015 |
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| Erschienen: |
2015 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:10 |
|---|---|
| Enthalten in: |
Natural product communications - 10(2015), 2 vom: 15. Feb., Seite 285-8 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Capello, Tabata M [VerfasserIn] |
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| Themen: |
Antineoplastic Agents, Phytogenic |
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| Anmerkungen: |
Date Completed 16.06.2015 Date Revised 29.04.2015 published: Print Citation Status MEDLINE |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM248496530 |
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| 100 | 1 | |a Capello, Tabata M |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Chemical composition and in vitro cytotoxic and antileishmanial activities of extract and essential oil from leaves of Piper cernuum |
| 264 | 1 | |c 2015 | |
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| 500 | |a Date Completed 16.06.2015 | ||
| 500 | |a Date Revised 29.04.2015 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Fractionation of the MeOH extract from leaves of Piper cernuum Vell. (Piperaceae) afforded six phenylpropanoid derivatives: 3',4'-dimethoxydihydrocinnamic acid (1), piplaroxide (2), methyl 4'-hydroxy-3',5'-dimethoxy cinnamate (3), 3',4',5'-trimethoxydihydrocinnamic acid (3), dihydropiplartine (5), and piplartine (6). The structures of isolated metabolites were characterized by NMR and MS spectral data analysis. The chemical composition of essential oil from the leaves was determined using GC/LREIMS followed by the determination of Kovats indexes. This procedure allowed the identification of nineteen terpenoids, with β-elemene (7), bicyclogermacrene (8), germacrene D (9), and (E)-caryophyllene (10) as the main compounds. Compounds 1 and 3-6 displayed no in vitro cytotoxicity against cancer cell lineages B16F10-Nex2, U87, HeLa, HL-60, HCT, and A2058 while 2 showed moderate activity against B16F10-Nex2 and HL-60 lines. Otherwise, compounds 7-10 displayed high cytotoxic activity. Evaluation against non-tumorigenic HFF cells indicated a reduced selectivity of compounds 7-10 to tumoral cells. No antileishmanial activity on macrophages infected with L. (L.) amnazonensis was found for the crude MeOH extract and compounds 1-6. The crude essential oil and compounds 7-10 reduced parasitism and eliminated the majority of infected and non-infected cells at 50 μg/mL | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Antineoplastic Agents, Phytogenic |2 NLM | |
| 650 | 7 | |a Antiprotozoal Agents |2 NLM | |
| 650 | 7 | |a Oils, Volatile |2 NLM | |
| 650 | 7 | |a Plant Extracts |2 NLM | |
| 650 | 7 | |a Plant Oils |2 NLM | |
| 700 | 1 | |a Martins, Euder G A |e verfasserin |4 aut | |
| 700 | 1 | |a de Farias, Camyla F |e verfasserin |4 aut | |
| 700 | 1 | |a Figueiredo, Carlos R |e verfasserin |4 aut | |
| 700 | 1 | |a Matsuo, Alisson L |e verfasserin |4 aut | |
| 700 | 1 | |a Passero, Luiz Felipe D |e verfasserin |4 aut | |
| 700 | 1 | |a Oliveira-Silva, Diogo |e verfasserin |4 aut | |
| 700 | 1 | |a Sartorelli, Patricia |e verfasserin |4 aut | |
| 700 | 1 | |a Lago, João Henrique G |e verfasserin |4 aut | |
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