Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities.
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 O2(-)-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.
Sakagami
Hiroshi
H
Department of Dental Pharmacology, Meikai University School of Dentistry, Sakado, Saitama 350-0283, Japan. sakagami@dent.meikai.ac.jp
Hashimoto
Ken
K
Suzuki
Fumika
F
Ogiwara
Takako
T
Satoh
Kazue
K
Ito
Hideyuki
H
Hatano
Tsutomu
T
Takashi
Yoshida
Y
Fujisawa
Sei-ichiro
S
D000818:Animals; D001205:Ascorbic Acid / Q000494:pharmacology; D002241:Carbohydrates / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D004357:Drug Synergism; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D008031:Lignin / Q000737:chemistry* / Q000494:pharmacology*; D008264:Macrophages / Q000378:metabolism; D051379:Mice; D008970:Molecular Weight; D009569:Nitric Oxide / Q000096:biosynthesis
D002241:Carbohydrates; D016166:Free Radical Scavengers; D009569:Nitric Oxide; D008031:Lignin; D001205:Ascorbic Acid