Abstract
A new fungal metabolite named sespendole was isolated as an inhibitor of lipid droplet synthesis in mouse macrophages from the culture broth of the fungal strain Pseudobotrytis terrestris FKA-25. The structure and stereochemistry of sespendole were elucidated by spectroscopic studies including various NMR spectral analyses, exciton chirality experiments and the modified Mosher method. Sespendole was found to possess a new indolosesquiterpene skeleton modified with two isoprenes.
Similar content being viewed by others
Article PDF
References
Yamaguchi Y, Masuma R, Kim YP, Uchida R, Tomoda H, Ōmura S . Taxonomy and secondary metabolites of Pseudobotrytis sp. FKA-25. Mycoscience 45: 9–16 ( 2004)
Uchida R, Kim YP, Namatame I, Tomoda H, Ōmura S . Sespendole, a new inhibitor of lipid droplet synthesis in macrophages, produced by Pseudobotrytis terrestris FKA-25. J Antibiot 59: 93–97 ( 2006)
Nozawa K . Biologically active indoloditerpenes from Aspergillus and Penicillium. In Proceeding of the 38th Annual Meeting of the Mycological Society of Japan. pp. 10–11 ( 1994)
Springer JP, Clardy J . Paspaline and paspalicine, two indole-mevalonate metabolites from Claviceps paspali. Tetrahedron Lett 21: 231–234 ( 1980)
Nozawa K, Nakajima S, Kawai K, Udagawa S . Isolation and structures of indoloditerpenes. Possible biosynthetic intermediates to the tremogenic mycotoxin, paxilline, from Emericella striata. J Chem Soc Perkin Trans I 2607–2610 ( 1988)
Springer JP, Clardy J, Wells M, Cole RJ, Kirksey JW . The structure of paxilline, a tremorgenic metabolite of Penicillium paxilli Bainier. Tetrahedron Lett 16: 2531–2534 ( 1975)
Gallagher RT, Latch GCM, Keogh RG . The janthitrems: Fluorescent tremogenic toxin produced by Penicillium janthinellum isolated from ryegrass pastures. Appl Environ Microbial 39: 272–273 ( 1980)
de Jesus AE, Steyn PS, Van Heerden FR, Vleggaar R . Structure elucidation of the janthitrems, novel tremorgenic mycotoxins from Penicillium janthinellum. J Chem Soc Perkin Trans I 697–701 ( 1984)
Gallagher RT, Hawkes AD, Steyn PS, Vleggaar R . Tremorgenic neurotoxins from perennial ryegrass causing ryegrass staggers disorder of livestock: Structure elucidation of the lolitrem B. J Chem Soc Chem Commun 614–616 ( 1984)
de Jesus AE, Steyn PS, Van Heerden FR, Vleggaar R, Wessels PL, Hull WE . Structure and biosynthesis of the penitrems A~F, six novel tremorgenic mycotoxins from Penicillium crustosum. J Chem Soc Chem Commun 289–291 ( 1981)
de Jesus AE, Steyn PS, Van Heerden FR, Vleggaar R, Wessels PL, Hull WE . Tremorgenic mycotoxins from Penicillium crusotosum: Isolation of penitrem A~F and the structure elucidation and absolute configuration of penitrem A. J Chem Soc Perkin Trans I 1847–1856 ( 1983)
de Jesus AE, Steyn PS, Van Heerden FR, Vleggaar R, Wessels PL, Hull WE . Tremorgenic mycotoxins from Penicillium crusotosum: Isolation of penitrem A~F and the structure elucidation and absolute configuration of penitrem B~F. J Chem Soc Perkin Trans I 1857–1861 ( 1983)
Huang XH, Tomoda H, Nishida H, Masuma R, Ōmura S . Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. I. Production, isolation and biological properties. J Antibiot 48: 1–4 ( 1995)
Huang XH, Tomoda H, Nishida H, Masuma R, Ōmura S . Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. II. Structure elucidation of terpendoles A, B, C and D. J Antibiot 48: 5–10 ( 1995)
Tomoda H, Tabata N, Yang DJ, Takayanagi H, Ōmura S . Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. III. Production, isolation and structure elucidation of new components. J Antibiot 48: 793–804 ( 1995)
Uchida R, Tomoda H, Ōmura S . Biosynthesis of sespendole, having an indolosesquiterpene skeleton, produced by Pseudobototytis terrestris FKA-25. J Antibiot 59: 298–302 ( 2006)
Mitchell S, Veitch J . Rotatory-dispersion measurements with a Unicam spectrophotometer. Nature 168: 662–663 ( 1951)
Adachi K, Naemura K, Nakazaki M . The synthesis and the absolute configuration of optically active tricyclo[4.4.0.03.8]decane. Tetrahedron Lett 9: 5467–5470 ( 1968)
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)
Imai H . Shift reagents of NMR signals (in Japanese). The Chemical Times (Kanto Chemical Co., Inc.) 156: 14–20 ( 1995)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Uchida, R., Kim, YP., Nagamitsu, T. et al. Structure Elucidation of Fungal Sespendole, an Inhibitor of Lipid Droplet Synthesis in Macrophages. J Antibiot 59, 338–344 (2006). https://doi.org/10.1038/ja.2006.47
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2006.47