Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities

Hiroshi Sakagami, Ken Hashimoto, Fumika Suzuki, Takako Ogiwara, Kazue Satoh, Hideyuki Ito, Tsutomu Hatano, Yoshida Takashi, Sei Ichiro Fujisawa

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Lignins are major cell wall components formed by the dehydrogenative polymerization of three monolignols, p-coumaryl, coniferyl and sinapyl alcohols. We prepared lignin-carbohydrate complexes (Fr. VI and Fr. VII) from pine cones by acid and ethanol precipitation, and investigated which part of these molecules is essential for expression of biological activities. They showed potent antiviral activity upon direct interaction with the virus. The antiviral activity of Frs. VI and VII required the higher-order structure of polyphenols without polysaccharides. Pretreatment of mice with Fr. VI or VII induced higher antiparasite activity than those of natural and chemically modified antitumor polysaccharides. Fr. VI or VII at higher concentrations enhanced the radical intensity and cytotoxic activity of vitamin C, whereas tannins counteracted the effect of vitamin C. Fr. VI at lower concentrations enhanced the O 2 --scavenging activity of vitamin C. Frs. VI and VII stimulated mouse macrophage-like cells Raw 264.7 to produce nitric oxide (NO), citrulline (CIT) and asparagine (ASN), via the enhanced expression of iNOS and ASN synthetase, whereas phenylpropenoid monomers and polymers inhibited NO/CIT/ASN production. These data suggest that the polymerized structure of phenylpropenoids in lignin-carbohydrate complexes is required for the induction of antiviral activity, and that the higher-order structure of phenylpropenoid polymers and polysaccharides is required for immunopotentiation, including macrophage activation.

Original languageEnglish
Pages (from-to)2108-2120
Number of pages13
JournalPhytochemistry
Volume66
Issue number17 SPEC. ISS.
DOIs
Publication statusPublished - Sep 2005

Fingerprint

Lignin
Bioactivity
Ascorbic Acid
Antiviral Agents
Polysaccharides
bioactive properties
lignin
citrulline
Citrulline
polysaccharides
Macrophages
ascorbic acid
Asparagine
Carbohydrates
asparagine
carbohydrates
nitric oxide
polymers
Polymers
Nitric Oxide

Keywords

  • Antitumor activity
  • Antiviral activity
  • Asparagine
  • iNOS
  • Lignin
  • Macrophage
  • Nitric oxide
  • Pinaceae
  • Pine cone
  • Pinus parviflora Sieb. et Zucc.
  • Polyphenol

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Sakagami, H., Hashimoto, K., Suzuki, F., Ogiwara, T., Satoh, K., Ito, H., ... Fujisawa, S. I. (2005). Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities. Phytochemistry, 66(17 SPEC. ISS.), 2108-2120. https://doi.org/10.1016/j.phytochem.2005.05.013

Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities. / Sakagami, Hiroshi; Hashimoto, Ken; Suzuki, Fumika; Ogiwara, Takako; Satoh, Kazue; Ito, Hideyuki; Hatano, Tsutomu; Takashi, Yoshida; Fujisawa, Sei Ichiro.

In: Phytochemistry, Vol. 66, No. 17 SPEC. ISS., 09.2005, p. 2108-2120.

Research output: Contribution to journalArticle

Sakagami, H, Hashimoto, K, Suzuki, F, Ogiwara, T, Satoh, K, Ito, H, Hatano, T, Takashi, Y & Fujisawa, SI 2005, 'Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities', Phytochemistry, vol. 66, no. 17 SPEC. ISS., pp. 2108-2120. https://doi.org/10.1016/j.phytochem.2005.05.013
Sakagami H, Hashimoto K, Suzuki F, Ogiwara T, Satoh K, Ito H et al. Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities. Phytochemistry. 2005 Sep;66(17 SPEC. ISS.):2108-2120. https://doi.org/10.1016/j.phytochem.2005.05.013
Sakagami, Hiroshi ; Hashimoto, Ken ; Suzuki, Fumika ; Ogiwara, Takako ; Satoh, Kazue ; Ito, Hideyuki ; Hatano, Tsutomu ; Takashi, Yoshida ; Fujisawa, Sei Ichiro. / Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities. In: Phytochemistry. 2005 ; Vol. 66, No. 17 SPEC. ISS. pp. 2108-2120.
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