2. Academic Validation
  3. 6-Methoxyflavonols from the aerial parts of Tetragonia tetragonoides (Pall.) Kuntze and their anti-inflammatory activity

6-Methoxyflavonols from the aerial parts of Tetragonia tetragonoides (Pall.) Kuntze and their anti-inflammatory activity

  • Bioorg Chem. 2019 Jul;88:102922. doi: 10.1016/j.bioorg.2019.102922.
Yeong-Geun Lee 1,  Hwan Lee 2,  Jin Ah Ryuk 3,  Joo Tae Hwang 4,  Hyoung-Geun Kim 1,  Dong-Sung Lee 5,  Yeon-Ju Kim 6,  Deok-Chun Yang 7,  Byoung Seob Ko 8,  Nam-In Baek 9
Affiliations

Affiliations

  • 1 Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University, Yongin 17104, Republic of Korea.
  • 2 College of Pharmacy, Chosun University, Gwangju 61452, Republic of Korea.
  • 3 Korea Institute of Oriental Medicine, Daejeon 34054, Republic of Korea. Electronic address: yukjinah@kiom.re.kr.
  • 4 Korea Institute of Oriental Medicine, Daejeon 34054, Republic of Korea. Electronic address: jthwang@kiom.re.kr.
  • 5 College of Pharmacy, Chosun University, Gwangju 61452, Republic of Korea. Electronic address: dslee2771@chosun.ac.kr.
  • 6 Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University, Yongin 17104, Republic of Korea. Electronic address: yeonjukim@khu.ac.kr.
  • 7 Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University, Yongin 17104, Republic of Korea. Electronic address: dcyang@khu.ac.kr.
  • 8 Korea Institute of Oriental Medicine, Daejeon 34054, Republic of Korea. Electronic address: bsko@kiom.re.kr.
  • 9 Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University, Yongin 17104, Republic of Korea. Electronic address: nibaek@khu.ac.kr.
PMID: 31003077 DOI: 10.1016/j.bioorg.2019.102922
Abstract

Dried aerial parts of Tetragonia tetragonoides were extracted with 70% EtOH, and the evaporated residue was successively separated into EtOAc, n-BuOH, and H2O fractions. As a result of repeated SiO2, ODS, and Sephadex LH-20 column chromatography, four new 6-methoxyflavonol glycosides (2-4, 8) along with four known ones (1, 5-7) were isolated. Several spectroscopic data led to determination of chemical structures for four new 6-methoxyflavonol glycosides (2-4, 8) and four known ones, 6-methoxykaempferol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl-7-O-(6‴'-(E)-caffeoyl)-β-d-glucopyranoside (1), 6-methoxyquercetin (5), 6-methoxykaempferol (6), and 6-methoxykaempferol 7-O-β-d-glucopyranoside (7). Methoxyflavonol glycosides 2-8 also have never been reported from T. tetragonoides in this study. 6-Methoxyflavonols 5 and 6 showed high radical scavenging potential in DPPH and ABTS test. Also, all compounds showed significant anti-inflammatory activities such as reduction of NO and PGE2 formation and suppression of TNF-α, IL-6, IL-1β, iNOS, and COX-2 expression in LPS-stimulated RAW 264.7 macrophages. In general, the aglycones exhibited higher activity than the glycosides. In addition, quantitative analysis of 6-methoxyflavonols in the T. tetragonoides aerial parts extract was conducted through HPLC.

Keywords

6-Methoxyflavonol; Anti-inflammatory; Anti-oxidant; Quantitative analysis; Tetragonia tetragonoides; Tetragonoside.

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