Hesseltins B-G, novel meroterpenoids from a new Penicillium species

Tetrahedron Letters

Volumn 52, Issue 5, 2011, Pages 598-601

  Phipps, Richard K ^a   Gotfredsen, Charlotte H ^a   Paludan, Søren R ^b   Frisvad, Jens C ^a   Eriksen, Kathrine ^a   Petersen, Bent O ^c   Duus, Jens Ø ^c   Larsen, Thomas O ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b Technical University of Denmark ^*  (Denmark)

^c CARLSBERG LABORATORY   (Denmark)

Author keywords

Antiviral; Hesseltin; Meroterpenoid; Penicillium; Photoisomerism

Indexed keywords

HESSELTIN A; HESSELTIN B; HESSELTIN C; HESSELTIN D; HESSELTIN E; HESSELTIN F; HESSELTIN G; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; HERPES SIMPLEX VIRUS 2; ISOMER; NONHUMAN; PENICILLIUM; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; VIRUS STRAIN; VIRUS TYPING;

HUMAN HERPESVIRUS 2; PENICILLIUM;

EID: 78651099505     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.140     Document Type: Article

References (18)

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2. 2O (500 mL), in 10% steps. Hesseltins were detected in the 70-90% MeOH fractions. The 70% MeOH fraction was shown to contain five compounds (1-3, 5-6) all showing almost identical UV-vis spectra as well as a sixth compound (4) showing a slightly different chromophore to that seen in the others. A seventh compound with an almost identical UV-vis spectrum to that of 1 was seen in the 90% MeOH fraction. The 70% MeOH fraction was purified by semi-preparative HPLC on a Waters Delta Pak C18 column (15 μm, 300 mm × 19 mm), at 20 mL/min, starting at 40% MeCN (50 ppm TFA) and increasing in a linear gradient to 53% over 20 min. The 90% MeOH fraction was purified on the same column, but with a gradient starting at 59% MeCN and increasing to 72% over 20 min.
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4. 13C. Preparative HPLC was performed with a Waters 600 chromatograph attached to a Waters 600 DAD, on a Waters Delta Pak C18 column (15 μm, 300 mm × 19 mm).
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7. ++H] 413.2328; found: 413.2311.
8. ++H] 427.2120; found: 427.2127.
9. ++H] 427.2120; found: 427.2174.
10. ++H] 397.2379; found: 397.2332.
11. ++H] 429.2277; found: 429.2274.
12. ++H] 399.2535; found: 399.2527.
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18. Viral plaque assay: Vero cells were seeded in MEM supplemented with 5% FCS at a density of 1.2 × 105 cells in 24-well tissue culture plates and left overnight to settle. Serial dilutions of samples to be analysed for antiviral activity were mixed with 104 plaque-forming units of herpes simplex virus type 2 (strain MS) and incubated for 15 min prior to addition to the cells. After 1 h post-infection, the growth medium was supplemented with 0.2% human Ig. The cells were incubated at 37 °C for 2 d, stained with 0.03% methylene blue and the plaques were counted. All the samples were analysed in triplicate.