A New Indolinepeptide from Paecilomyces sp. J300

  • Kwon, Hak-Cheol (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University) ;
  • Kim, Kyung-Ran (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University) ;
  • Zee, Sang-Deuk (Depart-ment of Sericulture & Entomology, National Institute Agricultural Science and Technology, RDA) ;
  • Cho, Sae-Yun (Depart-ment of Sericulture & Entomology, National Institute Agricultural Science and Technology, RDA) ;
  • Lee, Kang-Ro (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University)
  • Published : 2004.06.01

Abstract

A new indolinepeptide (3) was isolated, together with two known compounds, a cerebroside (1) and an alloxazine (2), from silkworm larvae infected with Paecilomyces sp. J300. On the basis of spectroscopic data, their structures were elucidated as (4E, 8E, 25, 2'R, 3R )-N-2'-hydroxy-hexadecanoyl-1-O-$\beta$-D-glucopyranosyl-9-methyl-4, 8-sphingadienine (1), 7,8-dimethylalloxazine (2) and 3$\beta$,5-dihydroxy-1-N-methyl-indoline-2$\beta$-carbonyl amino-D-alanyl-erythro-$\beta$-hydoxyiso-leucinyl-glycine (3).

Keywords

References

  1. Bernardini, M., Carilli, A., Pacioni, G., and Santurbano, B., Isolation of beauvericin from Paecilomyces fumoso-roseus. Phytochemistry, 14, 1865(1975)
  2. Collot, V., Schmitt, M., Marwah, P, and Bourguignon, J. J., Regiospecific functionalization of indole-2-carboxylates and diastereoselective preparation of the corresponding indolines. Heterocycles, 51, 2823-2847(1999) https://doi.org/10.3987/COM-98-8315
  3. Dobson, T. A. and Vining, L. C., Synthesis of DL-threo- and DLerythro-${\beta}$-hydroxyisoleucine. Can. J. Chem., 46, 3007-3012(1968) https://doi.org/10.1139/v68-500
  4. Domenech, J., Prieto, A., Barasoain, I., Gomez-Miranda, B., Bernabe, M., and Leal, J. A., Galactomannans from the cell walls of species of Paecilomyces sect. Paecilomyces and their teleomorphs as immunotaxonomic markers. Microbiology, 145, 2789-2796 (1999) https://doi.org/10.1099/00221287-145-10-2789
  5. Higuchi R., Harano, Y, Mitsuyuki, M., Isobe, R., Yamada, K., Miyamoto, T., and Komori, T., Isolation and structure of cerebrosides from the starfish Stellaster equestris. Liebigs Annalen, 593-599(1996)
  6. Horn, W. S., Smith, J. L, Bills, G. F., Raghoobar, S. L., Helms, G. L., Kurtz, M. B., Marrinan, J. A., Frommer, B. R., Thornton, R. A., and Mandala, S. M., Sphingofungins E and F : novel serinepalmitoyl transferase inhibitors from Paecilomyces variotii. J. Antibiotics, 45, 1692-1696(1992) https://doi.org/10.7164/antibiotics.45.1692
  7. Inagaki, M., Harada, Y, Yamada, K. Isobe, R., Ryuichi, H., Matsuura, H., and Itakura, Y, Isolation and structure determination of cerebrosides from garlic, the bulbs of Allium sativum L. Chem. Pharm. Bull., 46, 1153-1156 (1998) https://doi.org/10.1248/cpb.46.1153
  8. Isobe R., Inagaki M., Harano, Y., Sakiyama H. and Higuchi R., Structural elucidation of glycosphingolipids by collisioninduced dissociation of sodium ion complex. Chem. Pharm. Bull,45, 1611-1614 (1997) https://doi.org/10.1248/cpb.45.1611
  9. Jegorov, A., Sedmera, P, Matha, V., Simek, P., Zahradnickova, Z. L., and Eyal, J., Beauverolides L and La from Beauveria tenella and Paecilomyces fumosoroseus. Phytochemistry, 37, 1301-1303 (1994) https://doi.org/10.1016/S0031-9422(00)90402-3
  10. Kang, S. S., Kim, J. S., Xu, Y. N., and Kim, Y. H., Isolation of a new cerebroside from the root bark of Aralia elata. J. Nat. Prod., 62, 1059-1060 (1999) https://doi.org/10.1021/np990018r
  11. Kim, W. G., Kim, J. P, Koshino, H., Shin-Ya, K., Seto, H., and Yoo, I. D., Benzastatins E. F., and G: New indoline alkaloids with neuronal cell protecting activity from Streptomyces nitrosporeus. Tetrahedron, 53, 4309-4316 (1997) https://doi.org/10.1016/S0040-4020(97)00157-9
  12. Kwon, H. C., Zee, S. D., Cho, S. Y, Choi, S, U., and Lee, K. R., Cytotoxic Ergosterols from Paecilomyces sp. J300. Arch. Pharm. Res., 25, 851-855(2002) https://doi.org/10.1007/BF02977003
  13. Li, S. P, Li, P, Dong, T. T., and Tsim, K. W., Anti-oxidation activity of different types of natural Cordyceps sinensis and cultured Cordyceps mycelia. Phytomedicine, 8, 207-212 (2001 ) https://doi.org/10.1078/0944-7113-00030
  14. Lee, J. S., Lee, I. S., Chung, K. S., Kim, Y. H., Han, Y. H., and Lee, M. H., Flow cytometrical investigation on antitumor acitivity of mycelial culture of insect-born fungus Paecilomyces japonica DGUM32001. Yakhak Hoechi, 45, 64-70 (2001)
  15. Mori, K. and Fumaki, Y, Synthesis of (4E, 8E, 2S, 3R, 2R)-N-2 hydroxyhexadecanoyl- 9-methyl-4,8-spingadienine. The ceramide portion of the fruiting-inducing cerebroside in a basidiomycete Schizophyllum commune and its (2R, 3S)isomer. Tetrahedron, 41, 2369-2377 (1985) https://doi.org/10.1016/S0040-4020(01)96632-3
  16. Nam, K. S., Jo, Y. S., Kim, Y. H., Hyun, J. W., and Kim, H. W., Cytotoxic activities of acetoxyscirpenediol and ergosterol peroxide from Paecilomyces tenuipes. Life Sci., 69, 229-237 (2001) https://doi.org/10.1016/S0024-3205(01)01125-0
  17. Pemberton, R. W., Insects and other arthropods used as drugs in Korean traditional medicine. J. Ethnopharm, 65, 207-216 (1999) https://doi.org/10.1016/S0378-8741(98)00209-8
  18. Rossi, C., Tuttobello, L, Ricci, M. Casinovi, C. G., and Radics, L., Leucinostatin D, a novel peptide antibiotic from Paecilomyces marquandii. J. Antibiotics, 40, 130-133 (1987) https://doi.org/10.7164/antibiotics.40.130
  19. Shanghai Science and Technologic Publisher and JungDam Publisher, The Dictionary of Chinese Drugs, JungDam Publisher, Seoul, pp. 1427-1430 (1997)
  20. Shim, J. Y, Lee, Y. S., Lim, S. S., Shin, K. H., Hyun, J. E., Kim, S. Y, and Lee, E. B., Pharmacological activities of Paecilomyces japonica, A new type Cordyceps sp. Kor. J. Pharmacogn., 31,163-167 (2000)
  21. Sikorski, M., Sikorska, E., Wilkinson, F., and Steer, R. P., Studies of the photophysics and spectroscopy of alloxazine and related compounds in solution and in the solid state. Can. J. Chem., 77, 472-480 (1999) https://doi.org/10.1139/cjc-77-4-472
  22. Toledo, M. S., Levery, S. B., Straus, A. H., Suzuki, E., Momany, M., Glushka, J., Moulton, J. M., and Takahashi, H. K., Characterization of sphingolipids from Mycopathogens: Factors correlating with expression of 2-hydroxy fatty acyl (E)-${\Delta}^3$-unsaturation in cerebrosides of Paracoccidioides brasiliensis and Aspergillus fumigatus. Biochemistry, 38, 7294-7306 (1999) https://doi.org/10.1021/bi982898z
  23. Yamashita, Y, Saitoh, Y, Ando, K., Takahashi, K., Ohno, H., and Nakano, H., Saintopin, A new antitumor antibiotic with topoisomerase dependent DNA cleavage activity, from Paecilomyces. J. Antibiotics, 43, 1344-1346 (1990) https://doi.org/10.7164/antibiotics.43.1344