Inhibition of Aldose Reductase In Vitro by Constituents of Ganoderma lucidum

 

 Buy Article Permissions and Reprints

Abstract

CHCl₃ extract of the fruiting body of Ganoderma lucidum was found to show inhibitory activity on human aldose reductase in vitro. From the acidic fraction, potent human aldose reductase inhibitors, ganoderic acid C2 (1) and ganoderenic acid A (2), were isolated together with three related compounds. It was found that the free carboxyl group of ganoderic acid C2 and ganoderenic acid A is essential in eliciting the inhibitory activity considering the much lower activity of their methyl esters.

References

• 1 Young R J, Ewing D J, Clarke B F. A controlled trial of sorbinil, an aldose reductase inhibitor, in chronic painful diabetic neuropathy.  Diabetes. 1983;  32 938-942
  CrossrefPubMedGoogle Scholar
• 2 Dunlop M. Aldose reductase and the role of the polyol pathway in diabetic nephropathy.  Kidney Int Suppl. 2000;  77 S3-S12
  CrossrefPubMedGoogle Scholar
• 3 Frank R N, Keirn R J, Kennedy A, Frank K W. Galactose induced retinal capillary basement membrane thickening, prevention by sorbinil.  Invest Opthalmol Vis Sci. 1983;  24 1519-1524
  PubMedGoogle Scholar
• 4 Robinson Jr W G, Nagata M, Laver N, Hohman T C, Kinoshita J H. Diabetic-like retinopathy in rats prevented with an aldose reductase inhibitor.  Invest Opthalmol Vis Sci. 1989;  30 2285-2292
  PubMedGoogle Scholar
• 5 Bhatnagar A, Srivastava S K. Aldose reductase: congenial and injurious profiles of an enigmatic enzyme.  Biochem Med Metab Biol. 1992;  48 91-121
  CrossrefPubMedGoogle Scholar
• 6 Patterson R R M. Ganoderma – a theraupetic fungal biofactory.  Phytochemistry. 2006;  67 1985-2001
  CrossrefPubMedGoogle Scholar
• 7 Fatmawati S, Kurashiki K, Takeno S, Kim Y, Shimizu K, Sato M, Imaizumi K, Takahashi K, Kamiya S, Kaneko S, Kondo R. The inhibitory effect on aldose reductase by an extract of Ganoderma lucidum.  Phytother Res. 2009;  23 28-32
  CrossrefPubMedGoogle Scholar
• 8 Hikino H, Konno C, Mirin Y, Hayashi T. Isolation and hypoglycemic activity of ganoderans A and B, glycans of Ganoderma lucidum fruit bodies.  Planta Med. 1985;  51 339-340
  Article in Thieme ConnectPubMedGoogle Scholar
• 9 Min B S, Gao J J, Hattori M, Lee H K, Kim Y H. Anticomplement activity of terpenoids from the spores of Ganoderma lucidum.  Planta Med. 2001;  67 811-814
  Article in Thieme ConnectPubMedGoogle Scholar
• 10 Ha T B T, Gerhäuser C, Zhang W D, Ho-Chong-Line N, Fourasté I. New lanostanoids from Ganoderma lucidum that induce NAD(P)H : Quinone oxidoreductase in cultured hepalclc7 murine hepatoma cells.  Planta Med. 2000;  66 681-684
  Article in Thieme ConnectPubMedGoogle Scholar
• 11 Koyama K, Imaizumi K, Akiba M, Kinoshita K, Takahashi K, Suzuki A, Yano S, Horie S, Watanabe K, Naoi Y. Antinociceptive components of Ganoderma lucidum.  Planta Med. 1997;  63 224-227
  Article in Thieme ConnectPubMedGoogle Scholar
• 12 Liu J, Shiono J, Shimizu K, Kondo R. Ganoderic acids from Ganoderma lucidum: inhibitory activity of osteoclastic differentiation and structural criteria.  Planta Med. DOI: 10.1055/s-0029-1186035 , online publication 8 October 2009
  
  PubMedGoogle Scholar
• 13 Gao J J, Nakamura N, Min B S, Hirakawa A, Zuo F, Hattori M. Quantitative determination of bitter principles in specimens of Ganoderma lucidum using high-performance liquid chromatography and its application to the evaluation of Ganoderma products.  Chem Pharm Bull. 2004;  52 688-695
  CrossrefPubMedGoogle Scholar
• 14 Ma J, Ye Q, Hua Y, Zhang D, Cooper R, Chang M N, Chang J Y, Sun H H. New lanostanoids from the mushroom Ganoderma lucidum.  J Nat Prod. 2002;  65 72-75
  CrossrefPubMedGoogle Scholar
• 15 Lee S H, Shim S H, Kim J S, Shin K H, Kang S S. Aldose reductase inhibitors from the fruiting bodies of Ganoderma applanatum.  Biol Pharm Bull. 2005;  28 1103-1105
  CrossrefPubMedGoogle Scholar
• 16 Lee S H, Shim S H, Kim J S, Kang S S. Constituents from the fruiting bodies of Ganoderma applanatum and their aldose reductase inhibitory activity.  Arch Pharm Res. 2006;  29 479-483
  CrossrefPubMedGoogle Scholar
• 17 Urzhumtsev A, Favier F T, Mitschler A, Barbanton J, Barth P, Urzhumtseva L, Biellmann J F, Podjarny A D, Moras D. A ‘specificity' pocket inferred from the crystal structures of the complexes of aldose reductase with the pharmaceutically important inhibitors tolrestat and sorbinil.  Structure. 1997;  5 601-612
  CrossrefPubMedGoogle Scholar
• 18 Wang X, Liu R, Sun J, Guan S, Yang M, Bi K, Guo D. HPLC method for the determination and pharmacokinetic studies of four triterpenoids in rat plasma after oral administration of Ganoderma lucidum extract.  Biomed Chromatogr. 2007;  21 389-396
  CrossrefPubMedGoogle Scholar
• 19 Kikuchi T, Kanomi S, Kadota S, Murai Y, Tsubono K, Ogita Z. Constituents of the fungus Ganoderma lucidum (Fr.) Karst. I. Structures of ganoderic acid C2, E, I, and K, lucidenic acid F and related compounds.  Chem Pharm Bull. 1986;  34 3695-3712
  PubMedGoogle Scholar
• 20 Komoda Y, Nakamura H, Ishihara S, Uchida M, Kohda H, Yamazaki K. Structures of new terpenoid constituents of Ganoderma lucidum (Fr.) Karst (Polyporaceae).  Chem Pharm Bull. 1985;  33 4829-4835
  PubMedGoogle Scholar
• 21 Kubota T, Asaka Y, Miura I, Mori H. Structures of ganoderic acid A and B, two new lanostane type bitter triterpenes from Ganoderma lucidum (Fr.) Karst.  Helv Chim Act. 1982;  62 611-619
  PubMedGoogle Scholar
• 22 Nishimura C, Yamaoka T, Mizutani M, Yamashita K, Akera T, Tanimoto T. Purification and characterization of the recombinant human aldose reductase expressed in baculovirus system.  Biochim Biophys Act. 1991;  1078 171-178
  CrossrefPubMedGoogle Scholar

Prof. Ryuichiro Kondo

Department of Forest and Forest Products Sciences
Faculty of Agriculture
Kyushu University

6-10-1 Hakozaki, Higashi-ku

Fukuoka 812–8581

Japan

Phone: + 81 9 26 42 28 11

Fax: + 81 9 26 42 28 11

Email: ryukondo@agr.kyushu-u.ac.jp

• Supplementary Material