Tetrahydroxanthone–chromanone heterodimers from lichen Usnea aciculifera and their cytotoxic activity against human cancer cell lines

Four new tetrahydroxanthone–chromanone heterodimers, usneaxanthones E–H (1–4) together with eleven known compounds (5–15) were isolated from lichen Usnea aciculifera Vain (Parmeliaceae). Their structures and absolute configurations, particularly the central and axial chiralities, were unambiguously...

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Bibliographic Details
Published in:Fitoterapia 2020-11, Vol.147, p.104732, Article 104732
Main Authors: Tuong, Truong L., Do, Lien T.M., Aree, Thammarat, Wonganan, Piyanuch, Chavasiri, Warinthorn
Format: Article
Language:English
Subjects:
Biotechnology
Breast cancer
Circular dichroism
Colon
Colon cancer
Colorectal carcinoma
Crystallography
Cytotoxicity
Dichroism
Dimeric xanthones
Lichens
Lung cancer
NMR
Nuclear magnetic resonance
Ovarian cancer
Single crystals
Tetrahydroxanthone chromanone heterodimers
Toxicity testing
Tumor cell lines
Usnea
Usnea aciculifera
Usneaxanthones E–H
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Summary:Four new tetrahydroxanthone–chromanone heterodimers, usneaxanthones E–H (1–4) together with eleven known compounds (5–15) were isolated from lichen Usnea aciculifera Vain (Parmeliaceae). Their structures and absolute configurations, particularly the central and axial chiralities, were unambiguously demonstrated by a combination of spectroscopic data (1D, 2D NMR, HRESIMS), electronic circular dichroism (ECD) experiments, and single-crystal X-ray crystallographic analyses. The cytotoxicity of new compounds was evaluated on four human cancer cell lines including HCT116 colorectal cancer, MCF-7 breast cancer, A549 lung cancer, and OVCAR-3 ovarian cancer. Compounds 1–4 exhibited good cytotoxicity against all tested cancer cell lines, except ovarian cancer, with the best IC50 value of 3.37 μM. All compounds showed potent cytotoxicity against HCT116 colon cancer with IC50 value from 3.37 to 4.53 μM. [Display omitted]
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2020.104732