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Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species.
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2018 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 23, no 12, article id 3199Article in journal (Refereed) Published
Abstract [en]

A phytochemical investigation of the roots of Aspilia pluriseta led to the isolation of ent-kaurane-type diterpenoids and additional phytochemicals (123). 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 (36, 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.

Place, publisher, year, edition, pages
2018. Vol. 23, no 12, article id 3199
Keywords [en]
Aspilia mossambicensis, Aspilia pluriseta, Asteraceae, X-ray crystal structure, cytotoxicity, ent-kaurane diterpenoid
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-372097DOI: 10.3390/molecules23123199ISI: 000454523000149PubMedID: 30518152OAI: oai:DiVA.org:uu-372097DiVA, id: diva2:1275348
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Swedish Research Council, 2016-05857Available from: 2019-01-05 Created: 2019-01-05 Last updated: 2019-01-25Bibliographically approved

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Erdélyi, Máté

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