Chemo-enzymatic transformation of naturally abundant naringin to luteolin, a flavonoid with various biological effects

Ryohei Kobayashi, Takasi Itou, Kengo Hanaya, Mitsuru Shoji, Noriyasu Hada, Takeshi Sugai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Luteolin [3′,4′,5,7-tetrahydroxyflavone], having multiple biological effects such as anti-inflammation, anti-allergy and anti-cancer, was prepared by chemo-enzymatic synthesis from naringin, a naturally abundant flavonoid glycoside. On the occasion of Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on peracetylated form of naringin, an acetate on C-4′ was exclusively deprotected to give the key intermediate. The oxidation with 2-iodoxybenzoic acid (IBX) followed by the reductive workup provided regioselectively C-3′and C-4′ catechol functionality. After protection of the above-mentioned diol with methoxymethyl (MOM) groups and subsequent hydrolysis of all acetyl groups, a dehydrogenative introduction of double bond between C-2 and C-3 was done by the treatment with I2. Acid-catalyzed simultaneous removal of MOM groups and glycoside provided luteolin in total 8 steps and 36% overall yield from the starting material. Throughout the synthesis, diglycoside side chain effectively worked as the protective group on C-7 hydroxy group.

Original languageEnglish
Pages (from-to)14-18
Number of pages5
JournalJournal of Molecular Catalysis B: Enzymatic
Volume92
DOIs
Publication statusPublished - 2013 Aug

Fingerprint

Luteolin
Glycosides
Flavonoids
Allergies
Acids
Candida
Transesterification
Lipases
Hydrolysis
Hypersensitivity
Acetates
Inflammation
Oxidation
Neoplasms
naringin
Novozyme 435
catechol
2-iodoxybenzoic acid
Candida antarctica lipase B

Keywords

  • Flavonoids
  • Lipase
  • Regioselective reaction
  • Transesterification

ASJC Scopus subject areas

  • Biochemistry
  • Bioengineering
  • Catalysis
  • Process Chemistry and Technology

Cite this

Chemo-enzymatic transformation of naturally abundant naringin to luteolin, a flavonoid with various biological effects. / Kobayashi, Ryohei; Itou, Takasi; Hanaya, Kengo; Shoji, Mitsuru; Hada, Noriyasu; Sugai, Takeshi.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 92, 08.2013, p. 14-18.

Research output: Contribution to journalArticle

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