Curdlan
Part 5. Polysaccharides
Dr. In-Young Lee,
Dr. In-Young Lee
- [email protected]
- +82-428620722 | Fax: +82-428620702
Korea Research Institute of Bioscience and Biotechnology and DawMaJin Biotech Corp., P.O. Box 115, Daeduk Valley, Daejon, Korea, 305-600
Search for more papers by this authorDr. In-Young Lee,
Dr. In-Young Lee
- [email protected]
- +82-428620722 | Fax: +82-428620702
Korea Research Institute of Bioscience and Biotechnology and DawMaJin Biotech Corp., P.O. Box 115, Daeduk Valley, Daejon, Korea, 305-600
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Structure
- Beta-1,3-glucan
- Conformation in Solution
- Gel Structure
- Occurrence
- Biosynthesis
- Molecular Genetics
- Production
- Carbon Source
- Nitrogen Effect
- Oxygen Supply
- Phosphate Effect
- pH Effect
- Batch Production
- Continuous Production
- Isolation Process
- Properties
- Gel Formation
- Immunestimulatory Activity
- Applications
- Food Applications
- Pharmaceutical Applications
- Agricultural Applications
- Other Industrial Applications
- Outlook and Perspectives
- Patents
- Acknowledgments
References
- Aizawa, M., Takahashi, M., Suzuki, S. (1974) Gel formation of curdlan-type polysaccharide in DMSO-H2O mixed solvents, Chem. Lett. 193–196.
- Aketagawa, J., Tanaka, S., Tamura, H., Shibata, Y., Saito, H. (1993) Activation of Limulus coagulation factor G by several (1→3)-β-D-glucans: comparison of the potency of glucans with identical degree of polymerization but different conformations, J. Biochem. 113, 683–686.
- Akihiro, S., Takaaki, I. (1998) Quality improving agent for fishery paste product and production of fishery paste product. Japanese patent 10014541.
- Akira, K., Atsushi, I. (1989) Edible film. Japanese patent 01289457.
- Azuma, I. (1987) Development of immunostimulants in Japan, in: Immunostimulants: Now and Tomorrow ( I. Azuma, G. Jolles, Eds.), Tokyo: Japan Sci. Soc. Press/Berlin: Springer-Verlag, 41–45.
- Bohn, J. A., BeMiller, J. N. (1995) (1→3)-β-D-glucans as biological response modifiers: a review of structure–functional activity relationships, Carbohydr. Res. 28, 3–14.
- Chuah, C. T., Sarko, A., Deslandes, Y., Marchessault, R. H. (1983) Triple-helical crystalline structure of curdlan and paramylon hydrates, Macromolecules 16, 1375–1382.
- Conti, E., Flaibani, A., O'Regan, M., Sutherland, I. W. (1994) Alginate from Pseudomonas fluorescens and P. putida: production and properties, Microbiology 140, 1125–1132.
- Deslandes, Y., Marchessault, R. H., Sarko, A. (1980) Triple-helical structure of (1→3)-β-D-glucan, Macromolecules 13, 1466–1471.
- Di Luzio, N. R. (1983) Immunopharmacology of glucan: a broad spectrum enhancer of host defence mechanisms, Trends Pharmacol. Sci. 4, 344–347.
- Di Luzio, N. R., Williams, D. L., McNamee, R. B., Edwards, B. F., Kitahama, A. (1979) Comparative tumor-inhibitory and anti-bacterial activity of soluble and particulate glucan, Int. J. Cancer 24, 773–779.
- Evans, S. G., Morrison, D., Kaneko, Y., Havlik, I. (1998) The effect of curdlan sulfate on development in vitro of Plasmodium falciparum, Trans. R. Soc. Trop. Med. Hyg. 92, 87–89.
- Farina, J. I., Sineriz, F., Molina, O. E., Perotti, N. I. (2001) Isolation and physico-chemical characterization of soluble scleroglucan from Sclerotium rolfsii. Rheological properties, molecular weight and conformational characteristics, Carbohydr. Res. 44, 41–50.
- Farres, J., Caminal, G., Lopez-Santin, J. (1997) Influence of phosphate on rhamnose-containing exopolysaccharide rheology and production by Klebsiella 1-714, Appl. Microbiol. Biotechnol. 48, 522–527.
- Fumio, I., Kimikazu, I., Satoshi, S. (1989) Polysaccharide having activity for multiplying Bifidobacterium. Japanese patent 01137990A.
- Hadden, J. W. (1993) Immunostimulants, Immunology Today 14, 275–280.
- Harada, T. (1965) Succinoglucan 10C3: a new acidic polysaccharide of Alcaligenes faecalis var. myxogenes, Arch. Biochem. Biophys. 112, 65–69.
-
Harada, T.
(1977)
Production, properties, and application of curdlan, in: Extracellular Microbial Polysaccharides ( P. A. Sanford, A. Laskin, Eds.), Washington, DC: American Chemical Society,
265–283.
10.1021/bk-1977-0045.ch020 Google Scholar
- Harada, T., Yoshimura, T. (1965) Rheological properties of succinoglucan 10C3 from Alcaligenes faecalis var. myxogenes, Agr. Biol. Chem. 29, 1027–1032.
- Harada, T., Yoshimura, T., Hidaka, H., Koreeda, A. (1965) Production of a new acidic polysaccharide, succinoglucan by Alcaligenes faecalis var.myxogenes, Agr. Biol. Chem. 29, 757–762.
- Harada, T., Masada, M., Fujimori, K., Maeda, I. (1966) Production of a firm, resilient gel-forming polysaccharide by a mutant of Alcaligenes faecalis var. myxogenes 10C3, Agr. Biol. Chem. 30, 196–198.
- Harada, T., Misaki, A., Saito, H. (1968) Curdlan: a bacterial gel-forming β-1,3-glucan, Arch. Biochem. Biophys. 124, 292–298.
-
Harada, T.,
Terasaki, M.,
Harada, A.
(1993)
Curdlan, in: Industrial Gums ( R. L. Whistler, J. N. BeMiller, Eds.), San Diego, CA: Academic Press, Inc.,
427–445.
10.1016/B978-0-08-092654-4.50019-X Google Scholar
- Hideaki, Y., Chieko, M., Takeshi, A. (1993) Ganmodoki and its production. Japanese patent 05207859.
- Hiroki, O., Etsuko, M. (1993) Noodle-like soybean protein-containing food. Japanese patent 05076290.
- Hiroshi, S., Nobuyoshi, N., Yutaro, K., Toru, M. (1997) Medicine for treating dementia. Japanese patent 09255579.
- Hiroshi, Y., Yuichi, S., Norio, I., Nana, I. (1999) Frozen dessert food and its production. Japanese patent 11187819.
- Ielpi, L., Couso, R. O., Dankert, M. A. (1993) Sequential assembly and polymerization of the polyphenol-linked pentasaccharide repeating unit of the xanthan polysaccharide in Xanthomonas campestris, J. Bacteriol. 175, 2490–2500.
- Jagodzinski, P. P., Wiaderkiewicz, R., Kurzawski, G., Kloczewiak, M., Nakashima, H., Hyjek, E., Yamamoto, N., Uryu, T., Kaneko, Y., Posner, M. R., Kozbor, D. (1994) Mechanism of the inhibitory effect of curdlan sulfate on HIV-1 infection in vitro, Virology 202, 735–745.
- Janusz, M. J., Austen, K. F., Czop, J. K. (1986) Isolation of soluble yeast β-glucans that inhibit human monocyte phagocytosis mediated by β-glucan receptors, J. Immunol. 137, 3270–3276.
- Jong, S. C., Birmingham, J. M. (1993) Medicinal and therapeutic value of the Shiitake mushroom, Adv. Appl. Microbiol. 39, 153–184.
- Kai, A., Ishino, T., Arashida, T., Hatanaka, K., Akaike, Y., Matsuzaki, K., Kaneko, Y., Mimura, T. (1993) Biosynthesis of curdlan from culture media containing 13C-labeled glucose as the carbon source, Carbohydr. Res. 240, 153–159.
- Kamisato, J. K., Nowakowski, M. (1988) Morphological and biochemical alterations of macrophages produced by a glucan, PSK, Immunopharmacology 16, 88–96.
- Kanegae, Y., Yutani, A., Nakatsui, I. (1996) Mutant strains of Agrobacterium for producing beta-1,3-glucan. US patent 5508191.
- Kanke, M., Koda, K., Koda, Y., Katayama, H. (1992) Application of curdlan to controlled drug delivery. I. The preparation and evaluation of theophylline-containing curdlan tablets, Pharmaceut. Res. 9, 414–418.
-
Kasai, N.,
Harada, T.
(1980)
Ultrastructure of curdlan. in: Fiber Diffraction Methods, ( A. D. French, K. H. Gardner, Eds.), Washington, DC: American Chemical Society Symposium Series,
363–383.
10.1021/bk-1980-0141.ch024 Google Scholar
- Kazushi, M. (1999) Production of bean curd including ingredient. Japanese patent 11178533.
- Ken, O., Akirou, M. (1992) Soybean protein-containing solid food. Japanese patent 04197148.
- Kim, B.-S., Jung, I.-D., Kim, J.-S., Lee, J.-H., Lee, I.-Y., Lee, K.-B. (2000) Curdlan gels as protein drug delivery vehicles, Biotechnol. Lett. 22, 1127–1130.
-
Kim, M.-K.,
Lee, I.-Y.,
Ko, J.-H.,
Rhee, Y.-H.,
Park, Y.-H.,
(1999)
Higher intracellular levels of uridine monophosphate under nitrogen-limited conditions enhance metabolic flux of curdlan synthesis in Agrobacterium species,
Biotechnol. Bioeng. 62,
317–323.
10.1002/(SICI)1097-0290(19990205)62:3<317::AID-BIT8>3.0.CO;2-7 CAS PubMed Web of Science® Google Scholar
- Kim, M.-K., Lee, I.-Y., Lee, J.-H, Kim, K.-T., Rhee, Y.-H., Park, Y.-H. (2000) Residual phosphate concentration under nitrogen-limiting conditions regulates curdlan production in Agrobacterium species, J. Ind. Microbiol. Biotechnol. 25, 180–183.
- Kimura, H., Moritaka, S., Misaki, M. (1973) Polysaccharide 13140: a new thermo-gelable polysaccharide, J. Food Sci. 38, 668–670.
- Kojima, T., Tabata, K., Itoh, W., Yanaki, T. (1986) Molecular weight dependence of the antitumor activity of schizophyllan, Agr. Biol. Chem. 50, 231–232.
- Koreeda, A., Harada, T., Ogawa, K., Sato, S., Kasai, N. (1974) Study of the ultrastructure of gel-forming (1→3)-β-D-glucan (curdlan-type polysaccharide) by electron microscopy, Carbohydr. Res. 33, 396–399.
- Lawford, H. G., Rousseau, J. D. (1991) Bioreactor design considerations in the production of high-quality microbial exopolysaccharide, Appl. Biochem. Biotechnol. 28/29, 667–684.
- Lawford, H. G., Rousseau, J. D. (1992) Production of β-1,3-glucan exopolysaccharide in low shear systems, Appl. Biochem. Biotechnol. 34/35, 597–612.
- Lawford, H., Keenan, J., Phillips, K., Orts, W. (1986) Influence of bioreactor design on the rate and amount of curdlan-type exopolysaccharide production by Alcaligenes faecalis, Biotechnol. Lett. 8, 145–150.
- Lee, J.-H, Lee, I.-Y., Kim, M.-K., Park, Y.-H. (1999) Optimal pH control of batch processes for production of curdlan by Agrobacterium species, J. Ind. Microbiol. Biotechnol. 23, 143–148.
- Lee, I.-Y., Seo, W.-T., Kim, K.-G., Kim, M.-K., Park, C.-S., Park, Y.-H. (1997) Production of curdlan using sucrose or sugar cane molasses by two-step fed-batch cultivation of Agrobacterium species, J. Ind. Microbiol. Biotechnol. 18, 255–259.
- Lee, I.-Y, Kim, M.-K., Lee, J.-H., Seo, W.-T., Jung, J.-K., Lee, H.-W., Park, Y.-H., (1999a) Influence of agitation speed on production of curdlan by Agrobacterium species, Bioprocess Eng. 20, 283–287.
- Lee, I.-Y., Kim, S.-W., Lee, J.-H., Kim, M.-K., Cho, I.-S., Park, Y.-H. (1999b) A high viscosity of curdlan at alkaline pH increases segregational resistance of concrete, Korean J. Biotechnol. Bioeng. 14, 1–5.
- Maeda, I., Saito, H., Masda, M., Misaki, A., Harada, T. (1967) Properties of gels formed by heat treatment of curdlan, a bacterial β-1,3 glucan, Agr. Biol. Chem. 31, 1184–1188.
- Masaaki, A., Takaaki, I. (1995) Quality improver for wheat flour product and wheat flour product having improved texture. Japanese patent 07274876.
- Masahiro, K., Masaru, N. (1993) Preparation of processed edible meat. Japanese patent 05288909.
- Masahiro, K., Masaaki, K., Shinji, M., Hiroaki, K. (1998a) Immunoactivator. Japanese patent 10194977.
- Masahiro, K., Mikitomo, A., Akitomo, A., Tomonori, Y. (1998b) Feed composition for fish kind cultivation. Japanese patent 10313794.
- Masanori, T., Tetsuya, T., Yukihiro, N. (1992) Noodles. Japanese patent 04210507.
- Masao, K., Toshimi, T. (1999) Jelly-like food. Japanese patent 11075726.
- Masataka, M., Hideo, Y., Yukihiro, N. (1997) Devil's-tongue jelly and its production. Japanese patent 09075017.
- Masatoshi, H., Masami, F., Kenichi, H., Hiromi, K. (1993) Devil's tongue for frozen food and its production. Japanese patent 05184310.
- Masayuki, T., Yukihiro, N. (1990) Noodle made of rice powder and producing method thereof. Japanese patent 02249466.
- Mikio, K., Yoshiro, O., Hirotomo, O., Yoshikazu, K., Hiroshi, I., Hisashi, M., Takeshi, K. (1995) Water soluble β-1,3-glucan derivative and antiviral agent containing the derivative. Japanese patent 07228601.
- Misaki, A., Kishida, E., Kakuta, M., Tabata, K. (1993) Antitumor fungal (1→3)-β-D-glucans: structural diversity and effects of chemical modification. In: Carbohydrates and Carbohydrate Polymers ( M. Yalpani, Ed.), Mount Prospect, IL: ATL Press, 116–129.
- Murooka, Y., Yamada, T., Harada, T. (1977) Affinity chromatography of Klebsiella arylsulfatase on tyrosyl-hexamethylenediamine-β-1,3-glucan and immunoadsorbent, Biochim. Biophys. Acta 485, 134–140.
- Naganishi, I., Kimura, K., Kusui, S., Yamazaki, E. (1974) Complex formation of gel-forming bacterial (1→3)-β-D-glucan (curdlan type polysaccharide) with dyes in aqueous solution, Carbohydr. Res. 32, 47–52.
- Naganishi, I., Kimura, K., Suzuki, T., Ishikawa, M., Banno, I., Sakene, T., Harada, T. (1976) Demonstration of curdlan-type polysaccharide and some other β-1,3-glucan in microorganisms with aniline blue, J. Gen. Appl. Microbiol. 22, 1–11.
- Nakata, M., Kawaguchi, T., Kodama, Y., Konno, A. (1998) Characterization of curdlan in aqueous sodium hydroxide, Polymer 39, 1475–1481.
- Numasaki, Y., Kikuchi, M., Sugiyama, Y., Ohba, Y. (1990) A glucan Sizofiran: T cell adjuvant property and antitumor and cytotoxic macrophage inducing activities, Oyo Yakuri Pharmacometrics 39, 39–48.
- Ogawa, K., Watanabe, T., Tsurugi, J., Ono, S. (1972) Conformational behavior of a gel-forming (1→3)-β-D-glucan in alkaline solution, Carbohydr. Res. 23, 399–405.
- Ogawa, K., Tsurugi, J., Watanabe, T. (1973a) Effect of salt on the conformation of gel-forming β-1,3-D-glucan in alkaline solution, Chem. Lett. 95–98.
- Ogawa, K., Miyagi, M., Fukumoto, T., Watanabe, T. (1973b) Effect of 2-chloroethanol, dioxane, or water on the conformation of a gel-forming β-1,3-glucan in DMSO, Chem. Lett. 943–946.
- Ogawa, K., Tsurugi, J., Watanabe, T. (1973c) The dependence of the conformation of a (1→3)-β-D-glucan on chain length in alkaline solution, Carbohydr. Res. 29, 397–403.
- Ohno, N., Miura, N. N., Chiba, N., Adachi, Y., Yadomae, T. (1995) Comparison of the immunopharmacological activities of triple and single-helical schizophyllan in mice, Biol. Pharm. Bull. 18, 1242–1247.
- Ohno, N., Hashimoto, T., Adachi, Y., Yadomae, T. (1996) Conformation dependency of nitric oxide synthesis of murine peritoneal macrophages by β-glucans in vitro, Immunol. Lett. 52, 1–7.
- Okazaki, M., Adachi, Y., Ohno, N., Yadomae, T. (1995) Structure–activity relationship of (1→3)-β-D-glucans in the induction of cytokine production from macrophages, in vitro, Biol. Pharm. Bull. 18, 1320–1327.
- Okuyama, K., Obata, Y., Noguchi, K., Kusaba, T., Ito, Y., Ohno, S. (1996) Single structure of curdlan triacetate, Biopolymers 38, 557–566.
- Phillips, K. R., Lawford, H. G. (1983) Curdlan: Its properties and production in batch and continuous fermentations, in: Progress Industrial Microbiology ( D. E. Bushell, Ed.), Amsterdam: Elsevier Scientific Publishing Co., 201–229.
- Read, S. M., Currie, G., Bacic, A. (1996) Analysis of the structural heterogeneity of laminarin by electrospray-ionisation-mass spectrometry, Carbohydr. Res. 281, 187–201.
- Saito, H., Misaki, A., Harada, T. (1968) Comparison of structure of curdlan and pachyman, Agr. Biol. Chem. 32, 1261–1269.
- Saito, H., Ohki, T., Sasaki, T. (1977) A 13C Nuclear Magnetic Resonance study of gel-forming (1→3)-β-D-glucans. Evidence of the presence of single-helical conformation in a resilient gel of a curdlan-type polysaccharide 13140 from Alcaligenes faecalis var. myxogenes IFO 13140, Biochemistry 16, 908–914.
- Saito, H., Yoshioka, Y., Uehara, N., Aketagawa, J., Tanaka, S., Shibata, Y. (1991) Relationship between conformation and biological response for (1→3)-β-D-glucans in the activation of coagulation factor G from limulus amebocyte lysate and host-mediated antitumor activity. Demonstration of single-helix conformation as a stimulant, Carbohydr. Res. 217, 181–190.
- Sakurai, T., Suzuki, I., Kinoshita, A., Oikawa, S., Masuda, A., Ohsawa, M., Tadomae, T. (1991) Effect of intraperitoneally administered β-1,3-glucan, SSG, obtained from Sclerotinia sclerotiorum IFO 9395 on the functions of murine alveolar macrophages, Chem. Pharm. Bull. 39, 214–217.
- Sasaki, T., Takasuka, N. (1976) Further study of the structure of lentinan, an anti-tumor polysaccharide from Lentinus edodes, Carbohydr. Res. 47, 99–104.
- Sasaki, T., Abiko, N., Sugino, Y., Nitta, K. (1978) Dependence on chain length of antitumor activity of (1→3)-β-D-glucan from Alcaligenes faecalis var. myxogenes, IFO 13140, and its acid-degraded products, Cancer Res. 38, 379–383.
- Shunsuke, O., Masatoshi, S. (1992) Production of uncooked Chinese noodle and boiled Chinese noodle. Japanese patent 04330256.
- Spicer, E. J. F., Goldenthal, E. I., Ikeda, T. (1999) A toxicological assessment of curdlan, Fd. Chem. Toxicol. 37, 455–479.
- Stasinopoulos, S. J., Fisher, P. R., Stone, B. A., Stanisich, V. A. (1999) Detection of two loci involved in (1→3)-β-glucan (curdlan) biosynthesis by Agrobacterium sp. ATCC 31749, and comparative sequence analysis of the putative curdlan synthase gene, Glycobiology 9, 21–31.
- Sutherland, I. W. (1977) Microbial exopolysaccharide synthesis, in: Extracellular Microbial Polysaccharides ( P. A. Sanford, A. Laskin, Eds.), Washington, DC: American Chemical Society, 40–57.
-
Sutherland, I. W.
(1993)
Biosynthesis of extracellular polysaccharides, in: Industrial Gums ( R. L. Whistler, J. N. BeMiller, Eds.), San Diego, CA: Academic Press, Inc.,
69–85.
10.1016/B978-0-08-092654-4.50008-5 Google Scholar
- Suzuki, T., Ohno, N., Saito, K., Yamdomae, T. (1992) Activation of the complement system by (1,3)-β-D-glucan having different degrees of branching and different ultrastructures, J. Pharmacobiodyn. 15, 277–285.
- Tada, T., Matsumoto, T., Masuda, T. (1997) Influence of alkaline concentration on molecular association structure and viscoelastic properties of curdlan aqueous systems, Biopolymers 42, 479–487.
- Taguchi, T., Hiroshi, K., Yukihiro, N. (1991) Production of linear gel. Japanese patent 03157401.
- Takaaki, I. (1999) Quality improver for bean jam product and production of bean jam product. Japanese patent 11056246.
- Takashi, T., Junji, K. (1991) Anti-retrovirus agent. Japanese patent 03218317.
- Takeda technical report. (1997) Pureglucan: basic properties and food applications. Takeda Chemical Industries, Ltd. Japan.
- Takeda-Hirokawa, N., Neoh, L. P., Akimoto, H., Kaneko, H., Hishikawa, T., Sekigawa, I., Hashimoto, H., Hirose, S.-I., Murakami, T., Yamamoto, N., Mimura, T., Kaneko, Y. (1997) Role of curdlan sulfate in the binding of HIV-1 gp120 to CD4 molecules and the production of gp120-mediated THF-α, Microbiol. Immunol. 41, 741–745.
- Toshio, O. (1986) Immobilized enzyme, or the like and preparation thereof. Japanese patent 61015688.
- Toshiko, S. (1992) Sustained release suppository. Japanese patent 04074115.
- Toshiyuki, U., Yoshio, T., Minoru, Y. (1995) Additive for concrete. Japanese patent 07010624.
- Tsuneo, A., Koichi, K., Junji, K. (1990) Blood coagulation inhibitor. Japanese patent 02124902.
- Williams, D. L., Pretus, H. A., Ensley, H. E., Browder, I. W. (1994) Molecular weight analysis of a water-insoluble, yeast-derived (1→3)-β-D-glucan by organic-phase size-exclusion chromatography, Carbohydr. Res. 253, 293–298.
- Yanaki, T., Ito, W., Tabata, K., Kojima, T., Norysuye, T., Takano, N., Fujita, H. (1983) Correlation between the antitumor activity of a polysaccharide schizophyllan and its triple-helical conformation in dilute aqueous solution, Biophys. Chem. 17, 337–342.
- Yasuhiro, S. (1994) Formed jelly-containing liquid food and its production. Japanese patent 06335370.
- Yoichi, T., Hiroshi, S., Makiko, K. (1996) Biodegradable component for protecting ink jet recording head. Japanese patent 0818787.
- Yoshioka, Y., Tabeta, R., Saito, R., Uehara, N., Fukuoka, F. (1985) Antitumor polysaccharides from P. ostreatus (Fr.) Quel: isolation and structure of a beta-glucan, Carbohydr. Res. 140, 93–100.
- Young, S.-H., Dong, W.-J., Jacobs, R. R. (2000) Observation of a partially opened triple-helix conformation in (1→3)-β-glucan by fluorescence resonance energy transfer spectroscopy, J. Biol. Chem. 275, 11874–11879.
- Yukihiro, N., Takahiro, F. (1993) Ground fish meat or fish or cattle paste product and composition therefor. Japanese patent 05023143.
- Zhang, L., Ding, Q., Zhang, P., Zhu, R., Zhou, Y. (1997) Molecular weight and aggregation behaviour in solution of β-D-glucan from Poria cocos sclerotium, Carbohydr. Res. 303, 193–197.
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