Abstract
Five new secondary metabolites derived from pentanol, namely catathelasmols A–E (1–5), were isolated from the fruiting bodies of the basidiomycete Catathelasma imperiale. Their structures were elucidated on the basis of spectroscopic analysis, and the absolute configurations were determined by computational chemistry. Compounds 3, 4 and 5 showed inhibitory activities against two isozymes of 11-hydroxysteroid dehydrogenases (11-HSD1 and 11-HSD2), with IC50 values of 28.7–62.3 g ml−1 (human 11-HSD1), 30.4–149.2 g ml−1 (mouse 11-HSD1), 5.1–177 g ml−1 (human 11-HSD2) and 32.3–129.1 g ml−1 (mouse 11-HSD2), which catalyze the interconversion of cortisol and cortisone.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Yang, S. P., Xu, J. & Yue, J. M. Sterols from the fungus Catathelasma imperiale. Chin. J. Chem. 21, 1390–1394 (2003).
Liu, J. K. N-containing compounds of macromycetes. Chem. Rev. 105, 2723–2744 (2005).
Liu, J. K. Natural terphenyls: developments since 1877. Chem. Rev. 106, 2209–2223 (2006).
Zhou, Z. Y. et al. Gallicynoic acids A–I, acetylenic acids from the Basidiomycete Coriolopsis gallica. J. Nat. Prod. 71, 223–226 (2008).
Zhang, L., Wang, F., Dong, Z. J., Steglich, W. & Liu, J. K. A new butenolide-type fungal pigment from the mushroom Pulveroboletus ravenelii. Heterocycles 68, 1455–1458 (2006).
Yang, H. Y., Dou, W., Lou, J., Leng, Y. & Shen, J. H. Discovery of novel inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 by docking and pharmacophore modeling. Bioorg. Med. Chem. Lett. 18, 1340–1345 (2008).
Liu, D. Z. et al. Vibralactone: a lipase inhibitor with an unusual fused beta-lactone produced by cultures of the basidiomycete Boreostereum vibrans. Org. Lett. 8, 5749–5752 (2006).
Amos, R. D. Electric and magnetic properties of CO, HF, HCI, and CH3F. Chem. Phys. Lett. 87, 23–26 (1982).
Polavarapu, P. L. Ab initio molecular optical rotations and absolute configurations. Mol. Phys. 91, 551–554 (1997).
Kuschinsky, G., Lange, G., Scholtissek, C. h. & Turba, F. Reaction mechanism of digitalis constituents. Biochem. Z. 327, 314–330 (1955).
Bonini, C., Chiummiento, L., Funicello, M., Lupattelli, P. & Pullez, M. New functionalized hydroxymethyl ketones from the mild and chemoselective KMnO4 oxidation of chiral terminal olefins. Eur. J. Org. Chem. 80–83 (2006).
Dale, J. A. & Mosher, H. S. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 95, 512–519 (1973).
Ohtani, I., Kusumi, T., Kashman, Y. & Kakisawa, H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 113, 4092–4096 (1991).
Zhu, H. J., Ren, J. & Pittman, C. U. Matrix model to predict specific optical rotations of acyclic chiral molecules. Tetrahedron 63, 2292–2314 (2007).
Yiotakis, A., Magriotisb, P. A. & Vassiliou, S. A simple synthesis of the metabotropic receptor ligand (2S)-α-(hydroxymethyl)-glutamic acid and its Fmoc protected derivatives. Tetrahedron: Asymmetry 18, 873–877 (2007).
Stewart, P. M. & Draper, N. 11β-hydroxysteroid dehydrogenase and the pre-receptor regulation of corticosteroid hormone action. J. Endocrinol. 186, 251–271 (2005).
Seckl, J. R. & Walker, B. R. Minireview: 11beta-hydroxysteroid dehydrogenase type 1-a tissue-specific amplifier of glucocorticoid action. Endocrinology 142, 1371–1376 (2001).
Acknowledgements
This project was supported by National Basic Research Program of China (973 Program, 2009CB522300), National Natural Science Foundation of China (30830113) and Chinese Academy of Sciences (KSCX1-YW-R-24; KSCX2-YW-G-025).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Zhang, L., Shen, Y., Zhu, HJ. et al. Pentanol derivatives from basidiomycete Catathelasma imperiale and their 11β-hydroxysteroid dehydrogenases inhibitory activity. J Antibiot 62, 239–242 (2009). https://doi.org/10.1038/ja.2009.17
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/ja.2009.17
