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Planta Med 2010; 76(15): 1635-1641
DOI: 10.1055/s-0030-1250120
Reviews
© Georg Thieme Verlag KG Stuttgart · New York

1,5-Anhydro-D-Fructose and its Derivatives: Biosynthesis, Preparation and Potential Medical Applications[*]

Roland Fiskesund1 , Kazuhiro Abeyama2 , 3 , Kazuhiro Yoshinaga4 , Jun-ichi Abe5 , Yongbing Yuan6 , Shukun Yu7
  • 1Department of Medicine, Unit of Emergency Medicine, Karolinska Institute, Huddinge, Stockholm, Sweden
  • 2Taikai Clinic, Chugo Satsuma-Sendai, Japan
  • 3Department of Functional Biology and Pharmacology, Kagoshima University, Sakuragaoka, Kagoshima, Japan
  • 4R & D Division, Nihon Denpun, Ltd. Kagoshima, Japan
  • 5Department of Bioscience and Technology, Faculty of Agriculture, Kagoshima University, Kagoshima, Japan
  • 6Laboratory of Biorenew and Applied Enzymology, Qingdao Agricultural University, Qingdao, China
  • 7Enzyme R & D, Genencor Division, Danisco A/S, Aarhus, Denmark
Further Information

Publication History

received May 9, 2010 revised June 5, 2010

accepted June 14, 2010

Publication Date:
19 July 2010 (online)

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Abstract

1,5-Anhydro-D-fructose (AF) was first found in fungi and red algae. It is produced by the degradation of glycogen, starch and maltosaccharides with α-1,4-glucan lyase (EC 4.2.2.13). In vivo, AF is metabolized to 1,5-anhydro-D-glucitol (AG), ascopyrone P (APP), microthecin and other derivatives via the anhydrofructose pathway. The genes coding for the enzymes in this pathway have been cloned, enabling the large-scale production of AF and related products in a cell-free reactor. The possible applications of these products in medicine have been evaluated using both in vitro and in vivo systems. Thus AF is a useful anticariogenic agent as it inhibits the growth of the oral pathogen Streptococcus mutans, impairing the production of plaque-forming polysaccharides and lactic acid. AF also shows anti-inflammatory and anticancer effects. AG is used as a diabetic marker for glycemic control. AG also stimulates insulin secretion in insulinoma cell lines. In vivo, APP has been shown to lengthen the life span of cancer-afflicted mice. It interferes with tumor growth and metastasis by its cidal effects on fast multiplying cells. Microthecin inhibits the growth of the human pathogen Pseudomonas aeruginosa PAO1, particularly under anaerobic conditions. The pharmaceutical usefulness of the other AF metabolites 1,5-anhydro-D-mannitol,1-deoxymannojirimycin, haliclonol, 5-epipentenomycin I, bissetone, palythazine, isopalythazine, and clavulazine remains to be investigated. In this review AF and its metabolites as the bioactive natural products for their pharmaceutical potentials are discussed.

Key words

1,5‐anhydro‐D‐fructose - anhydrofructose pathway - anticancer activity - diabetes - inflammation - dental care - morels - red algae

1 Dedication Dedicated to Professor Inge Lundt, Department of Chemistry, Technical University of Denmark

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1 Dedication Dedicated to Professor Inge Lundt, Department of Chemistry, Technical University of Denmark

Roland Fiskesund, MD

Department of Medicine
Unit of Emergency Medicine
Karolinska Institute, Huddinge

SE-171 77 Stockholm

Sweden

Phone: +46 7 02 65 04 77

Email: roland.fiskesund@ki.se