Biosynthesis of lambertellols based on the high specific incorporation of the 13C-labeled acetates and their biological properties

Journal of the American Chemical Society

Volumn 126, Issue 30, 2004, Pages 9214-9220

  Murakami, Takanori ^a   Takahashi, Yukiko ^a   Fukushi, Eri ^b   Kawabata, Jun ^b   Hashimoto, Masaru ^a   Okuno, Toshikatsu ^a   Harada, Yukio ^a  

^a HIROSAKI UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; BIOASSAY; CARBON; ISOTOPES;

GERMINATION; LAMBERTELLOLS;

BIOSYNTHESIS;

ACETIC ACID; ANTIFUNGAL AGENT; CARBON 13; LAMBERTELLIN; LAMBERTELLOL A; LAMBERTELLOL B; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONIDIUM; CONTROLLED STUDY; FUNGUS; FUNGUS HYPHAE; FUNGUS SPORE; ISOTOPE LABELING; MASS SPECTROMETRY; MONILINIA FRUCTICOLA; MONILINIA FRUCTIGENA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ACETATES; ANTIFUNGAL AGENTS; ASCOMYCOTA; CARBON ISOTOPES; NAPHTHALENES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPIRO COMPOUNDS;

EID: 3343020681     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048345v     Document Type: Article

References (37)

1. Harada, Y.; Sasaki, M. Rep. Tottori Mycol. Inst. 1990, 28, 275-285.
2. Byrde, R. J. W.; Willetts, H. J. The Brown Rot Fungi of Fruit: Their Biology and Control; Pergamon Press: Oxford, 1977.
3. Jeffries, P.; Young, T. W. K. Interfungal Parasitic Relationships; CAB International: Wallingford, U.K., 1994.
4. Joshi, B. K.; Gloer, J. B.; Wicklow, D. T. J. Nat. Prod. 1999, 62, 730-733.
5. Soman, A. G.; Gloer, J. B.; Wicklow, D. T. J. Nat. Prod. 1999, 62, 386-388.
6. Wicklow, D. T.; Hirschfield, B. J. Can. J. Microbiol. 1979, 25, 855-858.
7. Murakami, T.; Morikawa, Y.; Hashimoto, M. H.; Okuno, T.; Harada, Y. Org. Lett. 2004, 6, 157-160.
8. Armstrong, J. J.; Turner, W. B. J. Chem. Soc. 1965, 5927-5930.
9. Brown, P. M.; Krishnamoothy, V.; Mathieson, J. W.; Thomson, R. H. J. Chem. Soc. C 1970, 109-110.
10. Trossell, K. B. G. Natural Products Chemistry; Apotekarsocieteten-Swedish Pharmaceutical Society, Swedish Pharmaceutical Press: Stockholm, 1997.
11. Garson, M. J.; Staunton, J. Chem. Soc. Rev. 1979, 8, 539.
12. Paulick, R. C.; Casey, M. L.; Hillenbrand, D. F.; Whitlock, H. W. J. Am. Chem. Soc. 1975, 97, 5303-5305.
13. Bradshaw, A. P. W.; Hanson, J. R.; Siverns, M. J. Chem. Soc., Chem. Commun. 1977, 819.
14. Lunnon, M. W.; MacMillan, J.; Simpson, T. J. J. Chem. Soc., Perkin Trans. I 1979, 931.
15. Simpson, T. J.; Holkler, J. S. E. Phytochemistry 1977, 16, 229-233.
16. Simpson, T. J. Tetrahedron Lett. 1975, 175-178.
17. Simpson, T. J.; Lunnon, M. W.; MacMillan, J. J. Chem. Soc., Perkin Trans. I 1979, 931-934.
18. Bax, A.; Freeman, R.; Kempsell, S. P. J. Am. Chem. Soc. 1980, 102, 4849-4851.
19. Turner, D. L. J. Magn. Reson. 1982, 175.
20. Shaka, A. J.; Pines, A. J. Magn. Reson. 1987, 71, 495.
21. Moore, R. N.; Bigam, G.; Chan, J. K.; Hogg, A. M.; Nakashima, T. T.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 3694-3701.
22. Bringmann, G.; Wohlfarth, M.; Rischer, H.; Grune, M.; Schlauer, J. Angew. Chem., Int. Ed. 2000, 39, 1464-1466.
23. Buddrums, J.; Bauer, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 625-642.
24. van Eijk, G. W.; Roeymans, H. Phytochemistry 1978, 17, 1804-1805.
25. Batra, L. R.; Harada, Y. Mycologia 1986, 78, 913-917.
26. The expected ratio was estimated as follows: intensity of minor double - doublet/intensity of main doublet × 100 = probability of sequentially labeled acetate unit/probability of isolately labeled acetate unit × 100 = 0.07 × 0.07/0.07 × (1-0.07) × 100 ≅ 7 (%)
27. The intensity of the minor double doublet can be estimated roughly as 4 times intensity of the rightmost (or leftmost) small peak because of the double doublet.
28. Since isolation was performed before fully growing the number of fungi, their yields depended much on the number of hyphae inoculated. Their yield varied because of the difficulty of implanting the same number of hyphae.
29. 3 (cat no. CMS-0025) was employed. Shigemi, Inc. Home Page. http://www.geocities.com/ ~shigemi/index.html.
30. 3 solution during measurement of the spectrum. Lambertellol A (1) was gradually decomposed in methanol, which dissolves 1 well to lambertellin (3) after 12 h.
31. 13C in corresponding isotopomer)]/total number of isotopomers
32. Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Tables of Spectral Data; Springer-Verlag: Berlin, 2000.
33. Terui, M.; Harada, Y. Ann. Phytopathol. Soc. Jpn. 1966, 32, 291-294.
34. Monilinia fructigana produces spores in limited conditions. It requires a rather long time cultivation in vitro.
35. Ulloa, M.; Hanlin, R. Illustrated Dictionary of Mycology; APS Press: St. Paul, MN, 2000.
36. Nihei, K.; Itoh, H.; Hashimoto, K.; Miyairi, K.; Okuno, T. Biosci. Biotechnol. Biochem. 1998, 62, 852-857.
37. 13C]acetate (32.3%). However, they used exogenous acetate in much higher concentration (450 mg/900 mL of media). We kept a low concentration of the acetate to not disturb the biosynthetic system of L. 1346.