Chemical Composition and in vitro Cytotoxic and Antileishmanial Activities of Extract and Essential Oil from Leaves of Piper cernuum

• Published in: Natural product communications Vol. 10; no. 2; pp. 285 - 288
• Main Authors: Capello, Tabata M., Martins, Euder G. A., de Farias, Camyla F., Figueiredo, Carlos R., Matsuo, Alisson L., Passero, Luiz Felipe D., Oliveira-Silva, Diogo, Sartorelli, Patricia, Lago, João Henrique G.
• Format: Journal Article
• Language: English
• Published: Los Angeles, CA SAGE Publications 01.02.2015
• Subjects: Animals; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - pharmacology; Cell Line, Tumor; Humans; Leishmania - drug effects; Macrophages - parasitology; Mice; Molecular Structure; Oils, Volatile - chemistry; Oils, Volatile - pharmacology; Piper - chemistry; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Leaves - chemistry; Plant Oils - chemistry; Plant Oils - pharmacology; Phenylpropanoid derivatives; Antiparasitic; Cytotoxic; Piper cernuum Vell; Essential oil composition
• ISSN: 1934-578X; 1555-9475
• DOI: 10.1177/1934578X1501000217

Fractionation of the MeOH extract from leaves of Piper cernuum Vell. (Piperaceae) afforded six phenylpropanoid derivatives: 3′,4′-dimethoxy-dihydrocinnamic 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.) amazonensis 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 50μg/mL.