Structure elucidation of fungal sespendole, an inhibitor of lipid droplet synthesis in macrophages

Journal of Antibiotics

Volumn 59, Issue 6, 2006, Pages 338-344

  Uchida, Ryuji ^a   Kim, Yong Pil ^a   Nagamitsu, Tohru ^a   Tomoda, Hiroshi ^a   Ömura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Fungal metabolites; Indolosesquiterpene; Sespendole; Structure elucidation

Indexed keywords

FAT DROPLET; ISOPRENE; PROBIOTIC AGENT; SESPENDOLE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL CELL CULTURE; LIPOGENESIS; MACROPHAGE; METABOLITE; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SPECTROSCOPY; STEREOCHEMISTRY;

ANIMALS; DITERPENES; INDOLES; LIPID METABOLISM; MACROPHAGES; MICE; MOLECULAR CONFORMATION;

PSEUDOBOTRYTIS;

EID: 33746907828     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2006.47     Document Type: Article

References (20)

1. Yamaguchi Y, Masuma R, Kim YP, Uchida R, Tomoda H, Ömura S. Taxonomy and secondary metabolites of Pseudobotrytis sp. FKA-25. Mycoscience 45: 9-16 (2004)
2. Uchida R, Kim YP, Namatame I, Tomoda H, Ömura S. Sespendole, a new inhibitor of lipid droplet synthesis in macrophages, produced by Pseudobotrytis terrestris FKA-25. J Antibiot 59: 93-97 (2006)
3. 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)
4. Springer JP, Clardy J. Paspaline and paspalicine, two indolemevalonate metabolites from Claviceps paspali. Tetrahedron Lett 21: 231-234 (1980)
5. 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)
6. 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)
7. 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)
8. 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)
9. Gallagher RT A. D. HAWKES 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)
10. 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)
11. 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)
12. 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)
13. Huang XH, Tomoda H, Nishida H, Masuma R, Ömura S. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. I. Production, isolation and biological properties. J Antibiot 48: 1-4 (1995)
14. Huang XH, Tomoda H, Nishida H, Masuma R, Ömura 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)
15. Tomoda H, Tabata N, Yang DJ, Takayanagi H, Ömura S. Terpendoles, novel ACAT inhibitors produced by Albophoma yamanashiensis. III. Production, isolation and structure elucidation of new components. J Antibiot 48: 793-804 (1995)
16. Uchida R, Tomoda H, Ömura S. Biosynthesis of sespendole, having an indolosesquiterpene skeleton, produced by Pseudobototytis terrestris FKA-25. J Antibiot 59: 298-302 (2006)
17. Mitchell S, Veitch J. Rotatory-dispersion measurements with a Unicam spectrophotometer. Nature 168: 662-663 (1951)
18. 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)
19. 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)
20. Imai H. Shift reagents of NMR signals (in Japanese). The Chemical Times (Kanto Chemical Co., Inc.) 156: 14-20 (1995)