A1 Journal article (refereed)
Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species (2018)

Yaouba, S., Valkonen, A., Coghi, P., Gao, J., Guantai, E. M., Derese, S., Wong, V. K. W., Erdélyi, M., & Yenesew, A. (2018). Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species. Molecules, 23(12), Article 3199. https://doi.org/10.3390/molecules23123199

JYU authors or editors

Publication details

All authors or editors: Yaouba, Souaibou; Valkonen, Arto; Coghi, Paolo; Gao, Jiaying; Guantai, Eric M.; Derese, Solomon; Wong, Vincent K. W.; Erdélyi, Máté; Yenesew, Abiy

Journal or series: Molecules

ISSN: 1420-3049

eISSN: 1420-3049

Publication year: 2018

Volume: 23

Issue number: 12

Article number: 3199

Publisher: MDPI

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/molecules23123199

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/60617

Abstract

A phytochemical investigation of the roots of Aspilia plurisetaled to the isolation of ent-kaurane-type diterpenoids and additional phytochemicals (1⁻23). The structures of the isolated compounds were elucidated based on Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analyses. The absolute configurations of seven of the ent-kaurane-type diterpenoids (3⁻6, 6b, 7 and 8) were determined by single crystal X-ray diffraction studies. Eleven of the compounds were also isolated from the roots and the aerial parts of Aspilia mossambicensis. The literature NMR assignments for compounds 1 and 5 were revised. In a cytotoxicity assay, 12α-methoxy-ent-kaur-9(11),16-dien-19-oic acid (1) (IC50 = 27.3 ± 1.9 µM) and 9β-hydroxy-15α-angeloyloxy-ent-kaur-16-en-19-oic acid (3) (IC50 = 24.7 ± 2.8 µM) were the most cytotoxic against the hepatocellular carcinoma (Hep-G2) cell line, while 15α-angeloyloxy-16β,17-epoxy-ent-kauran-19-oic acid (5) (IC50 = 30.7 ± 1.7 µM) was the most cytotoxic against adenocarcinomic human alveolar basal epithelial (A549) cells.

Keywords: naturally occurring substances; terpenes; x-ray crystallography; cytostatic drugs; Asteraceae

Free keywords: Aspilia mossambicensis; Aspilia pluriseta; Asteraceae; X-ray crystal structure; cytotoxicity; ent-kaurane diterpenoid.

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Ministry reporting: Yes

Reporting Year: 2018

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