Polyacetylene and phenolic constituents from the roots of Codonopsis javanica

Chemical investigation of the roots of Codonopsis javanica resulted in isolation of 12 compounds, including one new polyacetylene, codojavanyol (1), one new phenolic glycoside, codobenzyloside (7), and 10 known compounds, (2E,8E)-9-(tetrahydro-2H-pyran-2-yl)nona-2,8-diene-4,6-diyl-1-ol (2), lobetyol...

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Published in:Natural product research 2022-05, Vol.36 (9), p.2314-2320
Main Authors: Phan, Nguyen Huu Toan, Thuan, Nguyen Thi Dieu, Hien, Nguyen Thi Thu, Huyen, Pham Van, Duyen, Nguyen Huu Huong, Hanh, Tran Thi Hong, Cuong, Nguyen Xuan, Quang, Tran Hong, Nam, Nguyen Hoai, Minh, Chau Van
Format: Article
Language:English
Subjects:
Campanulaceae
Campanumoea javanica
Codonopsis - chemistry
Codonopsis javanica
cytotoxic
Glycosides - chemistry
Humans
Molecular Structure
phenolic
Phenols - analysis
Plant Roots - chemistry
polyacetylene
Polyacetylene Polymer
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Summary:Chemical investigation of the roots of Codonopsis javanica resulted in isolation of 12 compounds, including one new polyacetylene, codojavanyol (1), one new phenolic glycoside, codobenzyloside (7), and 10 known compounds, (2E,8E)-9-(tetrahydro-2H-pyran-2-yl)nona-2,8-diene-4,6-diyl-1-ol (2), lobetyol (3), lobetyolin (4), lobetyolinin (5), cordifolioidyne B (6), benzyl-α-L-arabinopyranosyl (1-6)-β-D-glucopyranoside (8), (Z)-8-β-D-glucopyranosyloxycinnamic acid (9), syringin (10), syringaresinol (11), and tryptophan (12). Their structures were elucidated by 1 D and 2 D NMR and MS spectroscopic analyses in comparison with the data reported in the literature. The stereochemistry of the C-2′ position of 1 was identified based on time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculation. Among the isolates, compounds 3-5 were shown to have weak cytotoxicity toward three human carcinoma cell lines, including lung (A549), liver (HepG2), and breast (MCF7), with the induction of 41.4 to 55.6% cell death at the concentration of 100 µM.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2020.1833200