Isolation and Structure Elucidation of Cytotoxic Secondary Metabolites in Cytotoxic Extracts and Fractions of Hernandia voyronii
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Date
2025-05
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The Ohio State University
Abstract
Cancer is one of the leading causes of death worldwide. In 2022 alone, 20 million new cases of cancer were diagnosed, and 9.7 million cancer-related deaths occurred worldwide. The threat of cancer is only growing, as there are projected to be 29.9 million new cancer cases and 15.3 million cancer-related deaths by 2040. Furthermore, current cancer treatments do not effectively address the needs for all patients, and the treatments that are available are often harmful, causing many serious and detrimental side effects. Therefore, new and non-toxic treatment options are needed to address this growing health crisis to ensure better health outcomes for all patients.
Natural products have a long history of being a successful source for cancer treatments with 74% of all new chemical entities for cancer from 1981 to 2002 having their roots in natural products, making them a promising starting point for improved treatment options. For example, paclitaxel (Taxol) and etoposide, both widely utilized anti-cancer drugs, are originally derived from natural products.
In this study, the plant Hernandia voyronii was identified as a potential natural product of interest due to its use in traditional medicine in Madagascar as a treatment for fever, malaria, hepatitis, digestive problems, cancer-like symptoms, and wounds. Extraction and fractionation of Hernandia voyronii led to the identification of several fractions active against hepatocellular carcinoma (HCC) cell lines using an antiproliferation assay. Fractions of interest were further purified using various chromatographic methods yielding 8 compounds identified as perillaldehyde (1), perillic acid (2), (S)-3-hydroxyperillaldehyde (3), methylpluviatolide (4), dimethylmatairesinol (5), arctigenin (6), (-)-kusunokinin (7), and 3’-demethylarctigenin (8). Isolated compounds were structurally elucidated using Nuclear Magnetic Resonance (NMR) spectra analysis and comparison with data published in the literature. Optical rotation testing is needed to determine the exact stereochemistry of the isolated compounds; however, current stereochemistry assignments were made based on comparison with published NMR data. The antiproliferative activities of compounds 1-4 were evaluated against HCC cell lines.
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Keywords
Pharmacognosy, Drug discovery from Madagascan natural products, Cytotoxic Compound Isolation, Cytotoxic Compound Structure Elucidation, Nuclear Magentic Resonance (NMR)