Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity

• Published in: Phytochemistry (Oxford) 2012-05, Vol.77, p.238-244
• Main Authors: Siddiqui, Bina Shaheen, Khatoon, Nasima, Begum, Sabira, Farooq, Ahsana Dar, Qamar, Kehkashan, Bhatti, Huma Aslam, Ali, Syed Kashif
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - toxicity; Apocynaceae; Cardenolides; Cardenolides - chemistry; Cardenolides - isolation & purification; Cardenolides - toxicity; Cell Line, Tumor; Cell Proliferation - drug effects; Flavonoidal glycosides; Flavonoids - chemistry; Flavonoids - isolation & purification; Flavonoids - toxicity; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - toxicity; Humans; MCF-7 Cells; Nerium - chemistry; Nerium - metabolism; Nerium oleander; Nuclear Magnetic Resonance, Biomolecular; Pentacyclic triterpene; Pentacyclic Triterpenes - chemistry; Pentacyclic Triterpenes - isolation & purification; Pentacyclic Triterpenes - toxicity; Plant Extracts - chemistry; Plant Leaves - chemistry; Structure and cytotoxicity
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2012.01.001

A triterpene (1), two flavonoidal glycosides (2 and 3), a cardenolide (4), and 11 known compounds, were isolated from Nerium oleander leaves (Apocynaceae). Eight compounds were evaluated against the MCF-7 human breast cancer cell line. Three compounds were further assayed using a panel of 57 human cancer cell lines. [Display omitted] ► Isolation of flavonoids, triterpenes and cardenolides from Nerium oleander leaves. ► Structure elucidation by TOFESIMS and 1D and 2D NMR spectroscopy. ► Cytotoxicity assays of adynerin, oleandrin, odoroside A and B against MCF-7 cells. ► Evaluation of oleandrin, odoroside A and B against 57 cell lines of human cancer. ► First report of cytotoxicity of oleandrin, odoroside A and B against 57 cell lines. A pentacyclic triterpene, oleanderocioic acid, two flavonoidal glycosides, quercetin-5-O-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside and kaempferol-5-O-[α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, and a cardenolide, oleandigoside, together with 11 known compounds, were isolated from the leaves of Nerium oleander. Their structures were elucidated on the basis of spectroscopic analysis. The growth inhibitory and cytotoxic activities of eight compounds were evaluated against the MCF-7 human breast cancer cell line using a sulforhodamine B assay. Three compounds, oleandrin, odoroside A and B were further assayed using a panel of 57 human cancer cell lines.