Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Young Hye Seo, Ju Hyun Jeon, Miran Jeong, Seung Mok Ryu, Won Kyung Jeon, Dae Sik Jang, Sang Hee Shim, Dongho Lee, Jung Hye Choi, Jun Lee

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Apios americana is an important food crop producing edible tubers with high nutritional and medicinal values and is widely cultivated in many countries. Despite its usefulness, research on its secondary metabolites and biological activities has been limited. In the present study, a new coumaronochromone, (2R,3S)-3,7,4′-trihydroxy-5-methoxycoumaronochromone (1), and two new isoflavone glucosides, 7,2′,4′-trihydroxy-5-methoxyisoflavone-4′-O-β-d-glucopyranoside (3) and 5,7,4′-trihydroxyisoflavone-7-O-β-d-gentiotrioside (5), were isolated from the tubers of A. americana via chromatographic separation. Seventeen known compounds (2, 4, and 6-20) were also obtained from this plant part. The chemical structures of 1, 3, and 5 were determined by the interpretation of spectroscopic data. The absolute structure of the new compound 1 was established from experimental and calculated electronic circular dichroism spectra. This is the first study to determine the absolute configuration of a 3-hydroxycoumaronochromone derivative. The potential anti-inflammatory activity of the 20 isolates obtained was evaluated by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Among the isolates, seven compounds (1, 3, 6-8, 15, and 20) showed substantial inhibition of nitric oxide production in RAW 264.7 cells, with the most active being compound 1 (IC50 value of 0.38 ± 0.04 μM).

Original languageEnglish
Pages (from-to)1598-1603
Number of pages6
JournalJournal of Natural Products
Volume81
Issue number7
DOIs
Publication statusPublished - 2018 Jul 27

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Macrophages
Lipopolysaccharides
Nitric Oxide
Isoflavones
Nutritive Value
Glucosides
Metabolites
Circular Dichroism
Bioactivity
Inhibitory Concentration 50
Crops
Anti-Inflammatory Agents
Derivatives
Food
Research
RAW 264.7 Cells

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages. / Seo, Young Hye; Jeon, Ju Hyun; Jeong, Miran; Ryu, Seung Mok; Jeon, Won Kyung; Jang, Dae Sik; Shim, Sang Hee; Lee, Dongho; Choi, Jung Hye; Lee, Jun.

In: Journal of Natural Products, Vol. 81, No. 7, 27.07.2018, p. 1598-1603.

Research output: Contribution to journalArticle

Seo, Young Hye ; Jeon, Ju Hyun ; Jeong, Miran ; Ryu, Seung Mok ; Jeon, Won Kyung ; Jang, Dae Sik ; Shim, Sang Hee ; Lee, Dongho ; Choi, Jung Hye ; Lee, Jun. / Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages. In: Journal of Natural Products. 2018 ; Vol. 81, No. 7. pp. 1598-1603.
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AU - Jeon, Won Kyung

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