Sch 54445: A new polycyclic xanthone with highly potent antifungal activity produced by Actinoplanes sp.

Journal of Natural Products

Volumn 60, Issue 5, 1997, Pages 525-528

  Chu, Min ^a   Truumees, Imbi ^a   Mierzwa, Ronald ^a   Terracciano, Joseph ^a   Patel, Mahesh ^a   Loebenberg, David ^a   Kaminski, James J ^a   Das, Pradip ^a   Puar, Mohindar S ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; POLYCYCLIC HYDROCARBON; SCH 54445; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ANIMAL EXPERIMENT; ANTIFUNGAL ACTIVITY; ARTICLE; CIRCULAR DICHROISM; DERMATOPHYTE; DRUG ISOLATION; DRUG STRUCTURE; FERMENTATION; FUNGUS; GEL PERMEATION CHROMATOGRAPHY; INFRARED SPECTROSCOPY; INTRAVENOUS DRUG ADMINISTRATION; LD 50; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; ULTRAVIOLET SPECTROSCOPY; YEAST;

ACTINOMYCETALES; ANTIBIOTICS, ANTIFUNGAL; CARBOHYDRATE SEQUENCE; FERMENTATION; FUNGI; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; XANTHENES;

ACTINOPLANES; ACTINOPLANES SP.; ANIMALIA; ARTHRODERMATACEAE; FUNGI;

EID: 0030953723     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np960737v     Document Type: Article

References (10)

1. Greene, S. I. Treatment of Fungal Infections in the Human Immunodeficiency Virus - Infected Individual. In Antifungal Drug Therapy; Jacobs, P. H., Nall, L., Eds.; Marcel Dekker: New York, 1990; Chapter 23, p 237.
2. For a review on antifungal agents, see: Medoff, G.; Kobayashi, G. A.; Scholer, H. J.; Holt, R. J.; Davies, R. R.; Speller, D. C. E. Antifungal Agents. In Antifungal Chemotherapy; Speller, D. C. E., Ed.; John Wiley & Sons: New York, 1980; Part I, p 3.
3. Cauwenbergh, G. Acta Derm. Venerol. 1986, 121, 147-156.
4. Janssen, P. A.; Cauwenbergh, G. Antifungal Therapy of the Future. In Antifungal Drug Therapy; Jacobs, P. H., Nall, L., Eds.; Marcel Dekker: New York, 1990; Chapter 28, p 315.
5. The microorganism, Actinoplanes sp. SCC 2314, was deposited in the collection of the American Type Culture Collection (ATCC) in Rockville, MD, where it has been assigned accession no. ATCC 55600.
6. Gurevich, A. I.; Deshko, T. N.; Kogan, G. A.; Kolosov, M. N.; Kudryashova, V. V.; Onoprienko, V. V. Tetrahedron Lett. 1974, 2801-2804.
7. The CD spectrum of albofungol displayed a positive cotton effect at 220-250 nm region and two negative cotton effects at 200-220, 250-370 nm region. The similar CD spectra of 1 and albofungol could be well explained: both compounds possess the same planar chromophore, which is critical to electric dipole transition measurements in CD spectra. (Graph Presented)
8. Onoprienko, V. V.; Kozmin, Y. P.; Kolosov, M. N. Bioorg. Khim. 1978, 4, 1418-1422.
9. The value of the optical rotation of 1 should change significantly or even the sign could be changed to a positive number if the stereochemistry of the G ring versus H-9 was in the anti configuration. However, it should be noted that in order to establish stereochemistry conclusively without any ambiguity, as well as to assign the configuration of the asymmetric center at C-30 on the butyl group, an X-ray crystallographic study should be conducted. Several attempts unfortunately failed to make a crystal suitable for X-ray analysis. Different approaches, such as derivatization of 1 for X-ray crystallography, are in progress.
10. Cooper, R.; Truumees, I.; Gunnarsson, I.; Loebenberg, D.; Horan A.; Marquez, J.; Patel, M.; Gullo, V.; Puar, M.; Das, P.; Mittelman, S. J. Antibiot. 1992, 45, 444-453.