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Microbial transformation and bioactivation of isoflavones from Pueraria flowers by human intestinal bacterial strains

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Abstract

The flowers from Pueraria, which are called Puerariae Flos, have been used since ancient times for recovery from alcohol intoxication. We elucidated the microbial transformation of the main isoflavones (1, 1a and 2) by using 29 commercially available human intestinal bacterial strains together with the bioactivation of the hepatoprotective activity of their metabolites. Tectoridin (1a), which contains only one glucosyl moiety, was metabolized to its aglycone 1b by various bacterial strains. On the other hand, the metabolism of 1 and 2, which both have disaccharide groups, was limited to specific bacterial strains. The metabolites 1c and 2c obtained from the Peptostreptococcus productus strain were completely different from those produced by the other strains. These metabolites were identified as 6-hydroxygenistein and 6-hydroxybiochanin A, respectively. The glycosides 1, 1a and 2 did not show any hepatoprotective activity, whereas aglycones 1b and 2b showed moderate activity. Furthermore, the hepatoprotective activity of the demethylated metabolites 1c and 2c was extremely potent. Although not all people have P. productus in their gastrointestinal tract, the O-demethylated compounds might become one of the bioactivated metabolites when Puerariae Flos is administered orally.

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References

  1. Keung WM, Vallee BL (1998) Kudzu root: an ancient Chinese source of modern antidipsotropic agents. Phytochemistry 47:499–506

    Article  PubMed  CAS  Google Scholar 

  2. Niiho Y, Yamazaki T, Nakajima Y, Itoh H, Takeshita T, Kinjo J, Nohara T (1990) Pharmacological studies on Puerariae Flos. II. The effects of Puerariae Flos on alcohol-induced unusual metabolism and experimental liver injury in mice. Yakugaku Zasshi 110:604–611

    PubMed  CAS  Google Scholar 

  3. Yamazaki T, Nakajima Y, Niho Y, Hosono T, Kurashige T, Kinjo J, Nohara T (1997) Pharmacological studies on Puerariae Flos III: protective effects of kakkalide on ethanol-induced lethality and acute hepatic injury in mice. J Pharm Pharmacol 49:831–833

    PubMed  CAS  Google Scholar 

  4. Yamazaki T, Hosono T, Matsushita Y, Kawashima K, Someya M, Nakajima Y, Narui K, Hibi Y, Ishizaki M, Kinjo J, Nohara T (2002) Pharmacological studies on Puerariae Flos. IV. Effects of Pueraria thomsonii dried flower extracts on blood ethanol and acetaldehyde levels in humans. Int J Clin Pharmacol Res 22:23–28

    PubMed  CAS  Google Scholar 

  5. Jang MH, Shin MC, Kim YJ, Chung JH, Yim SV, Kim EH, Kim Y, Kim CJ (2001) Protective effects of Puerariae Flos against ethanol-induced apoptosis on human neuroblastoma cell line SK-N-MC. Jpn J Pharmacol 87:338–342

    Article  PubMed  CAS  Google Scholar 

  6. Yamazaki T, Yaguchi M, Nakajima Y, Hosono T, Niiho Y, Hibi Y, Kinjo J, Nohara T (2005) Effects of an aqueous extract of Puerariae Flos (Thomsonide) on impairment of passive avoidance behavior in mice. J Ethnopharmacol 100:244–248

    Article  PubMed  Google Scholar 

  7. Lee HU, Bae EA, Kim DH (2005) Hepatoprotective effect of tectoridin and tectorigenin on tert-butyl hyperoxide-induced liver injury. J Pharmacol Sci 97:541–544

    Article  PubMed  CAS  Google Scholar 

  8. Oh SR, Kinjo J, Shii Y, Ikeda T, Nohara T, Ahn KS, Kim JH, Lee HK (2000) Effects of triterpenoids from Pueraria lobata on immunohemolysis. β-d-glucuronic acid plays an active role in anticomplementary activity in vitro. Planta Med 66:506–510

    Article  PubMed  CAS  Google Scholar 

  9. Kinjo J, Aoki K, Okawa M, Shii Y, Hirakawa T, Nohara T, Nakajima Y, Yamazaki T, Hosono T, Niiho Y, Kurashige T (1999) HPLC profile analysis of hepatoprotective oleanene-glucuronides in Puerariae Flos. Chem Pharm Bull 47:708–710

    PubMed  CAS  Google Scholar 

  10. Kinjo J, Nohara T (2001) Abstracts of papers. In: The 13th symposium on the development and application of naturally occurring drug materials, Osaka, pp 38–43

  11. Hattori M, Endo Y, Takabe S, Kobashi K, Fukasaku N, Namba T (1986) Metabolism magnolol from Magnoliae cortex. II. Absorption, metabolism and excretion of [ring-14C] magnolol in rats. Chem Pharm Bull 34:158–167

    PubMed  CAS  Google Scholar 

  12. Morito K, Hirose T, Kinjo J, Hirakawa T, Okawa M, Nohara T, Ogawa S, Inoue S, Muramatsu M, Masamune Y (2001) Interaction of phytoestrogens with estrogen receptors α and β. Biol Pharm Bull 24:351–356

    Article  PubMed  CAS  Google Scholar 

  13. Kinjo J, Tsuchihashi R, Morito K, Hirose T, Aomori T, Nagao T, Okabe H, Nohara T, Masamune Y (2004) Interactions of phytoestrogens with estrogen receptors α and β (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol Pharm Bull 27:185–188

    Article  PubMed  CAS  Google Scholar 

  14. Tsuchihashi R, Sakamoto S, Kodera M, Nohara T, Kinjo J (2008) Microbial metabolism of soy isoflavones by human intestinal bacterial strains. J Nat Med 62:456–460

    Article  CAS  Google Scholar 

  15. Kinjo J, Hitoshi M, Tsuchihashi R, Korematsu Y, Miyakoshi M, Murakami T, Niiho D, Mizutani K, Tanaka T, Nonaka G, Nohara T, Okabe H (2006) Hepatoprotective constituents in plants 15. Protective effects of natural-occurring flavonoids and miscellaneous phenolic compounds on an HepG2 cell cytotoxicity assay. J Nat Med 60:36–41

    Article  CAS  Google Scholar 

  16. Hon G, Kawabata J (2005) α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors. Bioorg Med Chem 13:1661–1671

    Article  Google Scholar 

  17. Klus K, Wolfgang B (1998) Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin A by bacteria isolated from tempe. Phytochemistry 47:1045–1048

    Article  Google Scholar 

  18. Han YO, Han MJ, Park SH, Kim DH (2003) Protective effects of kakkalide from Flos Puerariae on ethanol-induced lethality and hepatic injury are dependent on its biotransformation by human intestinal microflora. J Pharmacol Sci 93:331–336

    Article  PubMed  CAS  Google Scholar 

  19. Holdeman LV, Good IJ, Moore WE (1976) Human fecal flora: variation in bacterial composition within individuals and a possible effect of emotional stress. Appl Environ Microbiol 31:359–375

    PubMed  CAS  Google Scholar 

  20. Eckburg PB, Bik EM, Bernstein CN, Purdom E, Dethlefsen L, Sargent M, Gill SR, Nelson KE, Relman DA (2005) Diversity of the human intestinal microbial flora. Science 308:1635–1638

    Article  PubMed  Google Scholar 

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Fukuoka, 814-0180, Japan

    Ryota Tsuchihashi, Mitsuru Kodera, Seiichi Sakamoto & Junei Kinjo

  2. Tsukuba Research Institute, Ohta’s Isan Co. Ltd., 957 Shishiko, Ushiku, Ibaraki, 300-1231, Japan

    Yoshijiro Nakajima, Takashi Yamazaki & Yujiro Niiho

  3. Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oehonmachi, Kumamoto, 862-0973, Japan

    Toshihiro Nohara

Authors
  1. Ryota Tsuchihashi
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  2. Mitsuru Kodera
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  3. Seiichi Sakamoto
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  4. Yoshijiro Nakajima
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  5. Takashi Yamazaki
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  6. Yujiro Niiho
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  7. Toshihiro Nohara
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  8. Junei Kinjo
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Correspondence to Junei Kinjo.

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Tsuchihashi, R., Kodera, M., Sakamoto, S. et al. Microbial transformation and bioactivation of isoflavones from Pueraria flowers by human intestinal bacterial strains. J Nat Med 63, 254–260 (2009). https://doi.org/10.1007/s11418-009-0322-z

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  • DOI: https://doi.org/10.1007/s11418-009-0322-z

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