Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Constituents from the Fruiting Bodies of Ganoderma applanatum and Their Aldose Reductase Inhibitory Activity

  • Lee, Sang-Hyun (Department of Applied Plant Science, College of Industrial Science, Chung-Ang University) ;
  • Shim, Sang-Hee (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
  • Published : 2006.06.01
Download PDF
⟨ Previous Next ⟩

Abstract

Eight compounds were isolated from the fruiting bodies of Ganoderma applanatum, and were identified as 2-methoxyfatty acids (1), 5-dihydroergosterol (2), ergosterol peroxide (3) $3{\beta},7{\beta},20,23{\zeta}-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic$ acid (4), $7{\beta},20,23{\zeta}-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic$ acid (5), cerevisterol (6), $7{\beta},23{\zeta}-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic$ acid (7), and $7{\beta}-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic$ acid methyl ester (8) by spectral analysis. All compounds were isolated for the first time from this fruiting bodies, and their effect on rat lens aldose reductase (RLAR) activity was tested. Among these eight compounds, ergosterol peroxide (3) was found to exhibit potent RLAR inhibition, its $IC_{50}$ value being $15.4\;{\mu}g/mL$.

Keywords

References

  1. Aida, K., Tawata, M., Shindo, H., Onaya, T., Sasaki, H., Yamaguchi, T., Chin, M., and Mitsuhashi, H., Isoliquiritigenin: a new aldose reductase inhibitor from Glycyrrhizae radix. Planta Med., 56, 254-258 (1990) https://doi.org/10.1055/s-2006-960950
  2. Domínguez, X. A., Butruillr, D., Zamudio, A., Reyes, C., and Castillo, J., Ergosterol et L-mannitol dans des champignons parasites. Phytochemistry, 11, 2616 (1972)
  3. Haraguchi, H., Ohmi, I., Sakai, S., Fukuda, A., Toihara, Y., Fujimoto, T., Okamura, N., and Yagi, A., Effect of Polygonum hydropiper sulfated flavonoids on lens aldose reductase and related enzymes. J. Nat. Prod., 59, 443-445 (1996) https://doi.org/10.1021/np9601622
  4. Haraguchi, H., Kanada, M., Fukuda, A., Naruse, K., Okamura, N., and Yagi, A., An inhibitor of aldose reductase and sorbitol accumulation from Anthocepharus chinensis. Planta Med., 64, 68-69 (1998) https://doi.org/10.1055/s-2006-957369
  5. Haraguchi, H., Hayashi, R., Ishizu, T., and Yagi, A., A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro. Planta Med. 69, 853-855 (2003) https://doi.org/10.1055/s-2003-43218
  6. Hayman, S. and Kinoshita, J. H., Isolation and properties of lens aldose reductase. J. Biol. Chem., 240, 877-882 (1965)
  7. Ishizuka, T., Yaoita, Y., and Kikuchi, M., Sterols from fruit bodies of Grifola frondosa. Nat. Med., 52, 276-278 (1998)
  8. Jinming, G., Lin, H., and Jikai, L., A novel sterol from Chinese truffles Tuber indicum. Steroids, 66, 771-775 (2001) https://doi.org/10.1016/S0039-128X(01)00105-2
  9. Kawagishi, H., Katsumi, R., Sazawa, T., Mizuno, T., Hagiwara, T., and Nakamura T., Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry, 27, 2777-2779 (1988) https://doi.org/10.1016/0031-9422(88)80662-9
  10. Kim, H. W. and Kim, B. K., Biomedicinal triterpenoids of Ganoderma lucidum (Curt.: Fr.) P. Karst (Aphyllophoromycetideae). Int. J. Med. Mushr., 1, 121-138 (1999) https://doi.org/10.1615/IntJMedMushrooms.v1.i2.20
  11. Kobayashi, M., Krishna, M. M., and Anjaneyulu, V., Marine sterols. XXIV. Isolation of 24-methylenecholestane-1${\alpha}$,3${\beta}$,5${\alpha}$, 6${\beta}$,16${\beta}$-pentol from Sinularia sp. of soft coral. Chem. Pharm. Bull., 40, 2845-2846 (1992) https://doi.org/10.1248/cpb.40.2845
  12. Lee, H.-S., Rat lens aldose reductase inhibitory activities of Coptis japonica root-derived isoquinoline alkaloids. J. Agric. Food Chem., 50, 7013-7016 (2002) https://doi.org/10.1021/jf020674o
  13. Lee, S., Shim, S. H., Kim, J. S., Shin, K. H., and Kang, S. S., Aldose reductase inhibitors from the fruiting bodies of Ganoderma applanatum. Biol. Pharm. Bull., 28, 1103-1105 (2005) https://doi.org/10.1248/bpb.28.1103
  14. Matsuda, H., Murakami, T., Yashiro, K., Yamahara, J., and Yoshikawa, M., Antidiabetic principles of natural medicines. IV. Aldose reductase and alpha-glucosidase inhibitors from the roots of Salacia oblonga Wall. (Celastraceae): structure of a new friedelane-type triterpene, kotalagenin 16-acetate. Chem. Pharm. Bull., 47, 1725-1729 (1999) https://doi.org/10.1248/cpb.47.1725
  15. Matsuda, H., Morikawa, T., Toguchida, I., and Yoshikawa, M., Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem.Pharm. Bull., 50, 788-795 (2002) https://doi.org/10.1248/cpb.50.788
  16. Ming, D., Chilton, J., Fogarty, F., and Towers, G. H. N., Chemical constituents of Ganoderma applanatum of British Columbia forests. Fitoterapia, 73, 147-152 (2002) https://doi.org/10.1016/S0367-326X(02)00013-8
  17. Sato, S. and Kador, P. F., Inhibition of aldehyde reductase by aldose reductase inhibitors. Biochem. Pharmacol., 40, 1033- 1042 (1990) https://doi.org/10.1016/0006-2952(90)90490-C
  18. Shim, S. H., Ryu, J., Kim, J. S., Kang, S. S., Xu, Y., Jung, S. H., Lee, Y. S., Lee, S., and Shin, K. H., New lanostane-type triterpenoids from Ganoderma applanatum. J. Nat. Prod., 67, 1110-1113 (2004) https://doi.org/10.1021/np030383p
  19. Shimizu, M., Horie, S., Arisawa, M., Hayashi, T., Suzuki, S., Yoshizaki, M., Kawasaki, M., Terashima, S., Tsuji, H., Wada, S., Ueno, H., Morita, N., Berganza L. H., Ferro, E., and Basulado, I., Chemical and pharmaceutical studies on medicinal plants in Paraguay. I. Isolation and identification of lens aldose reductase inhibitor from 'tapecué,' Acanthospermum australe O.K. Chem. Pharm. Bull., 35, 1234-1237 (1987) https://doi.org/10.1248/cpb.35.1234
  20. Shin, K. H., Kang, S. S., Kim, H. J., and Shin, S. W., Isolation of an aldose reductase inhibitor from the fruits of Vitex rotundifolia. Phytomedicine, 1, 145-147 (1994) https://doi.org/10.1016/S0944-7113(11)80033-4
  21. Ueda, H., Kuroiwa, E., Tachibana, Y., Kawanishi, K., Ayala, F., and Moriyasu, M., Aldose reductase inhibitors from the leaves of Myrciaria dubia (H. B. & K.) McVaugh. Phytomedicine, 11, 652-656 (2004) https://doi.org/10.1016/j.phymed.2003.12.002
  22. Wright, J. L. C., Minor and trace sterols of Dunaliella tertiolecta. Phytochemistry, 20, 2403-2405 (1981) https://doi.org/10.1016/S0031-9422(00)82675-8
  23. Yoshikawa, K., Nishimura, N., Bando, S., Arihara, S., Matsumura, E., and Katayama, S., New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata. J. Nat. Prod., 65, 548-552 (2002) https://doi.org/10.1021/np0103160
  24. Yoshikawa, M., Shimada, H., Nishida, N., Li, Y., Toguchida, I., Yamahara, J., and Matsuda, H., Antidiabetic principles of natural medicines. II. Aldose reductase and ${\alpha}$-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): structures of myrciacitrins I and II and myrciaphenones A and B. Chem. Pharm. Bull., 46, 113-119 (1998) https://doi.org/10.1248/cpb.46.113