Hesseltin A, a novel antiviral metabolite from Penicillium hesseltinei

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3441-3443

  Phipps, Richard K ^a   Petersen, Bent O ^b   Christensen, Kathrine B ^a   Duus, Jens Ø ^b   Frisvad, Jens C ^a   Larsen, Thomas O ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b CARLSBERG LABORATORY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; HESSELTIN A; POLYKETIDE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PENICILLIUM; PENICILLIUM HASSELTINEI; STEREOCHEMISTRY;

ANIMALS; ANTIVIRAL AGENTS; DIPODOMYS; HERPESVIRUS 1, HUMAN; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; SESQUITERPENES;

EID: 6444241597     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048824z     Document Type: Article

References (12)

1. Larsen, T. O.; Frydenvang, K.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 1998, 61, 1154-1157.
2. Larsen, T. O.; Franzyk, H.; Jensen, S. R. J. Nat. Prod. 1999, 62, 1578-1580.
3. Culture was determined by Prof. Jens C. Frisvad to be a previously undescribed species and was assigned the name Penicillium hesseltinei (#56A = IBT 12396) and placed in Penicillium subgenus Penicillium section Viridicata series Viridicata. Subcultures have been deposited at the IBT culture collection, BioCentrum-DTU, Technical University of Denmark, Kgs. Lyngby, Denmark. The strain of P. hesseltinei was originally isolated from a cheek pouch of a live trapped kangaroo rat (Dipodomys spectabilis) in Seviletta National Wildlife Refuge, Socorro County, New Mexico, USA, in March 1988, by Lauraine Hawkins (#56A). The combination of penicillic acid, terrestric acid, cyclopeptin, dehydrocyclopeptin, cyclopenol, cyclopenin, viridicatol produced by P. hesseltinei sets this species apart from any other species in series Viridicata (Frisvad, J. C.; Samson, R. A., Stud. Mycol. (Utrecht) 2004, 49, 1-173).
4. 6, 150.9 and 201.1 MHz) δ 178.2 (C8), 161.6 (C10), 157.6 (C6), 136.7 (C2), 135.1 (C4), 130.4 (C3), 120.0 (C5), 111.2 (C7), 102.5 (C9), 96.9 (C20), 85.2 (C13), 73.6 (C16), 66.5 (C25), 57.6 (C11), 46.5 (C12), 46.2 (C21), 41.7 (C17), 35.0 (C14), 28.9 (C19), 27.3 (C18), 26.8 (C15), 21.5 (C24), 21.1 (C22), 20.2 (C23), 18.4 (C1). NOE correlations: H1/H3, H2/H4, H3/H5, H5/H7, H11/ H12, H11/H18b, H25a/H18a, OH11/H25a, H24/H25b, H25b/H22, H24/ H14b, H14a/OH16, H22/OH20, H23/OH16, H22/H15a, H25b/H15a, H19a/ OH20, H19b/OH20.
5. Zhang, Y.; Li, C.; Swenson, D. C.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Org Lett. 2003, 5, 773-776.
6. 3, 100 MHz) for the bicyclo[2,2,2]octane moiety of (2) (atoms numbered as in 1 for comparison) δ 98.1 (C20), 75.0 (C16), 67.7 (C25), 46.3 (C21), 39.6 (C17), 29.4 (C19), 28.7 (C18), 20.6 (C22), 19.2 (C23).
7. 2).
8. Roussis, V.; Pawlik, J. R.; Hay, M. E.; Fenical, W. Experientia 1990, 46, 327-329.
9. Vardaro, R. R.; Di Marzo, V.; Crispino, A.; Cimino, G. Tetrahedron 1991, 47 (29), 5569-5576.
10. Vardaro, R. R.; Di Marzo, V.; Marin, A.; Cimino, G. Tetrahedron 1992, 48 (43), 9561-9566.
11. 3, 125.8 MHz, atoms numbered as in 1 for comparison) δ 181.5 (C8), 161.9 (C10), 159.1 (C6), 135.8 (C2), 139.4 (C4), 130.9 (C3), 125.5 (C5), 117.7 (C7), 99.3 (C9), 21.6 (C1).
12. 3, 125.8 MHz, atoms numbered as in 1 for comparison) δ 181.0 (C8), 162.3 (C10), 157.2 (C6), 141.4 (C2), 139.5 (C4), 132.4 (C3), 116.5 (C5), 111.4 (C7), 102.5 (C9), 22.1 (C1).