Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
권호 표지
DOI QR코드

DOI QR Code

Structure elucidation of 11-epiterpestacin glycoside (11-ETG) isolated from Bipolaris sorokiniana NSDR-011

  • Lim, Chi-Hwan (Department of Bio-Environmental Chemistry, College of Agricultural Biology & Life Science, Chungnam National University) ;
  • Nihashi, Youichirou (Shionogi &Co, LTD)
  • Received : 2018.02.08
  • Accepted : 2018.02.26
  • Published : 2018.03.31
Download PDF
⟨ Previous Next ⟩

Abstract

An ${\alpha}-{\text\tiny{D}}-glucoside$ of sesterterpene, 11-epiterpestacin, was isolated from the culture of a filamentous fungus Bipolaris sorokiniana NSDR-011. The structure was elucidated by chemical studies and spectroscopic methods including NMR and ESI-MS. 11-ETG (1) named arbitrarily did not inhibit the root growth of Italian ryegrass seedlings even at the level of 200 ppm, while its aglycone 11-ET (2) completely inhibited root growth at level of 100 ppm.

Keywords

References

  1. Ballio A, Chain EB, De Leo P, Erlanger BF, Mauri M, Tonolo A (1964) Fusicoccin: a new wilting toxin produced by Fusicoccum amygdali. Nature 203 (4942): 297 https://doi.org/10.1038/203297a0
  2. Lim CH, Miyagawa H, Ueno T, Takenaka H, Sung ND (1996) Siccanol: sesterterpene isolated from pathogenic fungus Drechslera siccans. Agric Chem Biotechnol 39: 241-244
  3. Lim CH, Miyagawa H, Ueno T, Takenaka H, Tsurushima T (1995) Isolation and structure elucidation of terpenoid phytotoxins produced by the plant pathogenic fungus Bipolaris cynodontis. In abstracts of Papers of 37th Symposium on the Chemistry of Natural Products, Tokushima, Japan, 325-330
  4. Nihashi Y, Lim CH, Tanaka C, Miyagawa H, Tamio U (2002) Phytotoxic Sesterterpene, 11-Epiterpestacin, from Bipolaris sorokiniana NSDR-011. Biosci Biotechnol Biochem 66(3): 685-688 https://doi.org/10.1271/bbb.66.685
  5. Oka M, Iimura S, Tenmyo O, Yamamoto H, Kawano K, Hu SL, Fukagawa Y, Oka T (1993) Terpestacin, a new syncytium formation inhibitor from Arthrinium sp.. J Antibiot 46: 367-373 https://doi.org/10.7164/antibiotics.46.367
  6. Santini A, Ritieni A, Fogriano V, Randazzo G, Manniana L, Benedetti E (1996) Structure and absolute stereochemistry of fusaproliferin, a toxic metabolite from Fusarium proliferatum. J Nat Prod 59: 109-112 https://doi.org/10.1021/np960023k
  7. Scheffer RP, Daly JM, Deverall BJ (1983) Toxins and plant pathogenesis, Academic Press, New York
  8. Shimizu K, Tanaka C, Tsuda M (1997) Cloning of Brnl, a reductase gene involved in melanin biosynthesis in Cochliobolis heterostrophus. J Gen Appl Microbiol 43: 145-150 https://doi.org/10.2323/jgam.43.145
  9. Toyomasu T, Tsukahara M, Kaneko A, Niida R, Mitsuhashi W, Dairi T, Kato N, Sassa T (2007) Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi. PNAS 104 (9): 3084-3088 https://doi.org/10.1073/pnas.0608426104