Chemistry, physiological properties, and microbial production of hydroxycitric acid

Applied Microbiology and Biotechnology

Volumn 75, Issue 5, 2007, Pages 977-982

  Yamada, Takashi ^a   Hida, Hiroyuki ^b   Yamada, Yasuhiro ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

^b KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

Genome shuffling; Hydroxycitric acid; Microbial production; Streptomyces

Indexed keywords

BACTERIA; ENZYMES; GENES; PHYSIOLOGY; PLANTS (BOTANY);

GENOME SHUFFLING; HYDROXYCITRIC ACIDS; MICROBIAL PRODUCTION; STREPTOMYCES;

ORGANIC ACIDS;

HYDROXYCITRIC ACID;

BACTERIUM; CHEMISTRY; CITRIC ACID; ENZYME ACTIVITY; FATTY ACID; INHIBITOR; MICROBIAL ACTIVITY; MUTATION; SHRUB;

ANALYTIC METHOD; BACTERIAL STRAIN; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; ENANTIOMER; GENOME; MICROORGANISM; MUTANT; NONHUMAN; PHYSIOLOGY; PLANT; PLANT TISSUE; PURIFICATION; SCREENING; SHORT SURVEY; STEREOCHEMISTRY;

BACTERIA (MICROORGANISMS); GARCINIA CAMBOGIA; HIBISCUS; STREPTOMYCES;

EID: 34250678991     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-007-0962-4     Document Type: Short Survey

References (40)

1. Bischoff H (1994) Pharmacology of α-glucosidase inhibition. Eur J Clin Invest 24:3-10
2. Boll PM, Sorensen E, Balieu E (1969) Naturally occurring lactones and lactames. III. The absolute configuration of the hydroxycitric acid lactones: Hibiscus acid and garcinia acid. Acta Chem Scand 23:286-293
3. Brämer CO, Steinbüchel A (2001) The methylcitric acid pathway in Ralstonia eutropha: new genes identified involved in propionate metabolism. Microbiology 147:2203-2214
4. Brock M, Darley D, Textor S, Buckel W (2001) 2-Methylisocitrate lyases from the bacterium Escherichia coli and the filamentous fungus Aspergillus nidulans. Eur J Biochem 268:3577-3586
5. Cheema-Dhadli S, Halperin ML, Leznoff CC (1973) Inhibition of enzymes which interact with citrate by (-)-hydroxycitrate and 1,2,3-tricarboxybenzene. Eur J Biochem 38:98-102
6. Coppola GM, Schuster HF (1997) Chiral α-hydroxyacids in enantioselective synthesis. Wiley-VCH, Weinheim, Germany
7. Ewering C, Heuser F, Benölken J, Brämer C, Steinbüchel A (2006) Metabolic engineering of strains of Ralstonia eutropha and Pseudomonas putida for biotechnological production of 2-methylcitric acid. Metab Eng 8:587-602
8. Gerike U, Hough DW, Russell NJ, Dyall-Smith ML, Danson MJ (1998) Citrate synthase and 2-methylcitrate synthase: structural, functional and evolutionary relationships. Microbiology 144:929-935
9. Ghosh AK, Koltun ES, Bilcer G (2001) Tartaric acid and tartarates in the synthesis of bioactive molecules. Synthesis 9:1281-1301
10. Guthrie RW, Hamilton JG, Kierstead RW, Miller ON, Sullivan AC (1976) U. S. Patent 3966772
11. Griebel C (1939) Hibiscus "flowers", a drug used in the preparation of food and drink, its principal component a new acid of fruit acid character (hibiscus acid). Zeit Untersuch Lebensmitt 77:561-571
12. Griebel C (1942) The constitution and detection of hibiscus acid ((+)-allohydroxycitric acid lactone). Zeit Untersuch Lebensmitt 83:481-486
13. Hansawasdi C, Kawabata J, Kasai T (2000) α-amylase inhibitors from roselle (Hibiscus sabdariffa Linn.) tea. Biosci Biotechnol Biochem 64:1041-1043
14. Hansawasdi C, Kawabata J, Kasai T (2001) Hibiscus acid as an inhibitor of starch digestion in the Caco-2 cell model system. Biosci Biotechnol Biochem 65:2087-2089
15. Hida H, Yamada T, Yamada Y (2005) Production of hydroxycitric acid by microorganisms. Biosci Biotechnol Biochem 69:1555-1561
16. Hida H, Yamada T, Yamada Y (2006) Absolute configuration of hydroxycitric acid in microorganisms. Biosci Biotechnol Biochem 70:1972-1974
17. Hida H, Yamada T, Yamada Y (2007) Genome shuffling of Streptomyces sp. U121 for improved production of hydroxycitric acid. Appl Microbiol Biotechnol 73:1387-1393
18. Hoffman GE, Andres H, Weiss L, Kreisel C, Sander R (1980) Properties and organ distribution of ATP citrate (pro-3S)-lyase. Biochim Biophys Acta 620:151-158
19. Ibnusaud I, Thomas PT, Rani RN, Sasi PV, Beena T, Hisham A (2002) Chiral γ-butyrolactones related to optically active 2-hydroxycitric acids. Tetrahedron 58:4887-4892
20. Jena BS, Jayaprakasha GK, Singh RP, Sakariah KK (2002) Chemistry and biochemistry of (-)-hydroxycitric acid from Garcinia. J Agric Food Chem 50:10-22
21. Jenkins DJ, Taylor RH, Goff DV, Fielden H, Misiewicz JJ, Sarson DL, Bloom SR, Alberti KG (1981) Scope and specificity of acarbose in slowing carbohydrate absorption in man. Diabetes 30:951-954
22. Kasai T, Kawabata J, Hanswasdi C (2000) Japan Kokai Tokkyo Koho 239164
23. Karaffa L, Kubicek CP (2003) Aspergillus niger citric acid accumulation: do we understand this well working black box? Appl Microbiol Biotechnol 61:189-196
24. Kotera U, Umehara K, Kodama T, Yamada K (1972) Isolation method of highly tartaric acid producing mutants of Gluconobacter suboxydans. Agric Biol Chem 36:1307-1313
25. Lewis YS, Neelakantan S (1965) (-)-Hydroxycitric acid-the principal acid in the fruits of Garcinia cambogia Desr. Phytochemistry 4:619-625
26. Lewis YS (1969) Isolation and properties of hydroxycitric acid. Methods Enzymol 13:613-619
27. Loe YC, Bergeron N, Rodriguez N, Schwarz JM (2001) Gas chromatography/mass spectrometry method to quantify blood hydroxycitrate concentration. Anal Biochem 292:148-154
28. Lowenstein JM (1971) Effect of (-)-hydroxycitrate on fatty acid synthesis by rat liver in vivo. J Biol Chem 246:629-632
29. Lowenstein JM, Brunengraber H (1981) Hydroxycitrate. Methods Enzymol 72:486-497
30. Mattey M (1992) The production of organic acids. Crit Rev Biotechnol 12:87-132
31. Milsom PE (1987) Organic acids by fermentation, especially citric acid. Food Biotechnol (Lond) 1:273-307
32. Patnaik R, Louie S, Gavrilovic V, Perry K, Stemmer WPC, Ryan CM, del Cardayré SB (2002) Genome shuffling of Lactobacillus for improved acid tolerance. Nat Biotechnol 20:707-712
33. Rao RN, Sakariah KK (1988) Lipid-lowering and antiobesity effect of (-)-hydroxycitric acid. Nutr Res 8:209-212
34. Sullivan AC, Triscari J, Hamilton JC, Miller ON (1974) Effects of (-)-hydroxycitrate upon the accumulation of lipid in rat. II. Appetite. Lipids 9:129-134
35. Sullivan AC, Singh M, Srere PA, Glusker JP (1977) Reactivity and inhibitor potential of hydroxycitrate isomers with citrate synthase, citrate lyase, and ATP citrate lyase. J Biol Chem 252:7583-7590
36. Tabuchi T, Serizawa N (1975) The production of 2-methylcitric acid from odd-carbon n-alkanes by a mutant of Candida lipolytica. Agric Biol Chem 39:1049-1054
37. Tattersall R (1993) α-glucosidase inhibition as an adjunct to the treatment of type 1 diabetes. Diabet Med 10:688-693
38. Tsao GT, Cao NJ, Du J, Gong CS (1999) Production of multifunctional organic acids from renewable resources. Adv Biochem Eng Biotechnol 65:243-280
39. Watson JA, Fang M, Lowenstein JM (1969) Tricarballylate and hydroxycitrate: substrate and inhibitor of ATP: citrate oxaloacetate lyase. Arch Biochem Biophys 135:209-217
40. Zhang YX, Perry K, Vinci VA, Powell K, Stemmer WPC, del Cardayré SB (2002) Genome shuffling leads to rapid phenotypic improvement in bacteria. Nature 415:644-646