Korean Journal of Microbiology (미생물학회지)

The Microbiological Society of Korea (한국미생물학회)
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Chemical constituents from the culture filtrate of a Himalayan soil fungus, Preussia sp. and their anti-inflammatory activity

히말라야의 토양 곰팡이, Preussia sp. 배양액으로부터 추출된 화학 성분들 및 항 염증 활성

  • Youn, Ui Joung (Division of Life Sciences, Korea Polar Research Institute, KIOST) ;
  • Seo, Seung Suk (Division of Life Sciences, Korea Polar Research Institute, KIOST) ;
  • Yim, Jung Han (Division of Life Sciences, Korea Polar Research Institute, KIOST) ;
  • Kim, Il Chan (Division of Life Sciences, Korea Polar Research Institute, KIOST) ;
  • Han, Se Jong (Division of Life Sciences, Korea Polar Research Institute, KIOST)
  • 윤의중 (극지연구소 극지생명과학연구부) ;
  • 서승석 (극지연구소 극지생명과학연구부) ;
  • 임정한 (극지연구소 극지생명과학연구부) ;
  • 김일찬 (극지연구소 극지생명과학연구부) ;
  • 한세종 (극지연구소 극지생명과학연구부)
  • Received : 2017.10.26
  • Accepted : 2018.02.19
  • Published : 2018.03.31
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Abstract

A new naturally occurring benzoic acid derivative, benzyl 2,4-di(benzyloxy)benzoate (1) and six known compounds (2-7) were isolated from the fungus, Preussia sp. found in frozen soil of the Himalaya Mountain. The structures of the new compound, together with the known compounds were determined by 1D-and 2D-NMR experiments, as well as comparison with published values. In addition, to the best of our knowledge, the known compounds 2-7 were isolated for the first time from the genus Preussia and the family Sporormiaceae. The isolates were evaluated for cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in mouse macrophage RAW 264.7 cells in vitro. Compounds 1 and 2 inhibited NO production by 50.7% and 88.5% at a concentration of 100 mg/ml, respectively.

히말라야산의 동토에서 발견된 Preussia sp.로부터 신규 벤조산 유도체 benzyl 2,4-di(benzyloxy)benzoate (1)와 6개의 알려진 화합물들(2-7)이 분리되었다. 신규물질 및 다른 화합물들의 구조는 1D-와 2D NMR실험 및 문헌값과의 비교에 의하여 결정되었다. 화합물 2-7은 동 속 및 Sporormiaceae과에서 처음으로 얻어졌다. 분리된 물질들은 쥐의 대식세포 RAW 264.7 cells에서 lipopolysaccharide (LPS) 처리에 의하여 유도된 nitric oxide (NO)의 생성량 억제를 측정하였다. 화합물 1번과 2번은 100 mg/ml의 농도로 처리했을 때 LPS에 의하여 유도된 NO 생성량을 각각 50.7% 및 88.5%까지 억제하는 것을 보였다.

Keywords

References

  1. Anggard, E. 1994. Nitric oxide: mediator, murderer, and medicine. Lancet 343, 1199-1206. https://doi.org/10.1016/S0140-6736(94)92405-8
  2. Arenal, F., Platas, G., and Pelaez, F. 2004. Variability of spore length in some species ofthe genus Preussia (Sporormiella). Mycotaxon 89, 137-151.
  3. Arx von, J.A. and Van der Aa, H.A. 1987. Spororminula tenerifae gen. et sp. nov. Mycol. Soc. 89, 117-120. https://doi.org/10.1016/S0007-1536(87)80068-2
  4. Chen, X., Shi, Q., Lin, G., Guo, S., and Yang, J. 2009. Spirobisnaphthalene analogs from the endophytic fungus Preussia sp. J. Nat. Prod. 72, 1712-1715. https://doi.org/10.1021/np900302w
  5. Du, L., Robles, A.J., King, J.B., Mooberry, S.L., and Cichewicz, R.H. 2014. Cytotoxic dimeric epipolythiodiketopiperazines from the ascomycetous fungus Preussia typharum. J. Nat. Prod. 77, 1459-1466. https://doi.org/10.1021/np5002253
  6. Guarro, J., Abdullah, S.K., Gene, J., and Al-Saadoon, A.H. 1997. A new species of Preussia from submerged plant debris. Mycol. Res. 101, 305-308. https://doi.org/10.1017/S0953756296002638
  7. Kawada, M., Someno, T., Inoue, H., Ohba, S., Masuda, T., Kato, T., and Ikeda, D. 2010. NBRI16716A, a new antitumor compound against human prostate cancer cells, produced by Perisporiopsis melioloides Mer-f16716. J. Antibiot. 63, 319-323. https://doi.org/10.1038/ja.2010.42
  8. Kitajima, J., Ishikawa, T., Tanaka, T., and Ida, Y. 1999. Water-soluble constituents of fennel. IX. Glucides and nucleosides. Chem. Pharm. Bull. 47, 988-992. https://doi.org/10.1248/cpb.47.988
  9. Krasnoff, S.B., Keresztes, I., Donzelli, B.G.G., and Gibson, D.M. 2014. Metachelins, mannosylated and N-oxidized coprogen-type siderophores from Metarhizium robertsii. J. Nat. Prod. 77, 1685-1692. https://doi.org/10.1021/np500300s
  10. Lee, B.H. and Pan, T.M. 2013. Dimerumic acid, a novel antioxidant identified from Monascus-fermented products exerts chemoprotective effects: Mini review. J. Funct. Foods 5, 2-9. https://doi.org/10.1016/j.jff.2012.11.009
  11. Mapperson, R.R., Kotiw, M., Davis, R.A., and Dearnaley, J.D. 2014. The diversity and antimicrobial activity of Preussia sp. endophytes isolated from Australian dry rainforests. Curr. Microbiol. 68, 30-37. https://doi.org/10.1007/s00284-013-0415-5
  12. Moncada, S., Palmer, R.M.J., and Higgs, E.A. 1991. Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 43, 109-142.
  13. Saladino, R., Crestini, C., Neri, V., Ciciriello, F., Costanzo, G., and Mauro, E.D. 2006. Origin of informational polymers: The concurrent roles of formamide and phosphates. Chembiochem 7, 1707-1714. https://doi.org/10.1002/cbic.200600139
  14. Talontsi, F.M., Lamshoft, M., Douanla-Meli, C., Kouam, S.F., and Spiteller, M. 2014. Antiplasmodial and cytotoxic dibenzofurans from Preussia sp. harboured in Enantia chlorantha Oliv. Fitoterapia 93, 233-238. https://doi.org/10.1016/j.fitote.2014.01.003
  15. Tang, F., Wang, Y., and Hou, A.J. 2014. Total syntheses of Nigrasin I and Kuwanon C. Tetrahedron 70, 3963-3970. https://doi.org/10.1016/j.tet.2014.04.089
  16. Tseng, W.T., Hsu, Y.W., and Pan, T.M. 2016. Neuroprotective effects of dimerumic acid and deferricoprogen from Monascus purpureus NTU 568-fermented rice against 6-hydroxydopamine-induced oxidative stress and apoptosis in differentiated pheochromocytoma PC-12 cells. Pharm. Biol. 54, 1434-1444. https://doi.org/10.3109/13880209.2015.1104698
  17. Uemoto, H., Tsuda, M., and Kobayashi, J. 1999. Mukanadins A-C, new bromopyrrole alkaloids from marine sponge Agelas nakamurai. J. Nat. Prod. 62, 1581-1583. https://doi.org/10.1021/np9902542
  18. Yamashiro, J., Shiraishi, S., Fuwa, T., and Horie T. 2008. Dimerumic acid protected oxidative stress-induced cytotoxicity in isolated rat hepatocytes. Cell Biol. Toxicol. 24, 283-290. https://doi.org/10.1007/s10565-007-9037-7