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Chemical constitutes from endophytic Streptomyces sp. W5 isolated from Trewia nudiflora L.

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Abstract

Strain W5 was isolated from stem of Trewia nudiflora L. and identified as a member of Streptomyces according to its 16S rDNA partial sequence. From extracts of fermentation medium of W5, a new γ-butyrolactone (1), together with nine known compounds [2-methyl-2,5-bornandiol (2), dimeric dinactin (3), (R)-2-((2R,5S)-tetrahydro-5-(2-oxopropyl)furan-2-yl)propanoic acid (4), 2-(5-(2-acetoxypropyl)-tetrahydrofuran-2-yl)propanoic acid (5/6), (±)-homononactic acid (7/8), (±)-nonactic acid (9/10)] was isolated. Their structures were elucidated on the basis of extensive spectroscopic data.

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References

  • Arco MJ, Trammell MH, White JD (1976) Synthesis of (+/−)-nonactic acid. J Org Chem 41:2075–2083

    Article  CAS  PubMed  Google Scholar 

  • Gombos J, Haslinger E, Zak H, Schmidt U (1975) Gezielte synthese des nonactins. Tetrahedron Lett 16:3391–3394

    Article  Google Scholar 

  • Higashide E, Asai M, Ootsu K, Tanida S, Kozai Y, Hasegawa T, Kishi T, Sugino Y, Yoneda M (1977) Ansamitocin, a group of novel maytansinoid antibiotics with antitumour properties from Nocardia. Nature 270:721–722

    Article  CAS  PubMed  Google Scholar 

  • Kondo K, Higuchi Y, Sakuda S, Nihira T, Yamada Y (1989) New virginiae butanolides from Streptomyces virginiae. J Antibiot 42:1873–1876

    CAS  PubMed  Google Scholar 

  • Lane DJ, Pace B, Olsen GJ, Stahl DA, Sogin ML, Pace NR (1985) Rapid determination of 16S ribosomal RNA sequences for phylogenetic analyses. Proc Natl Acad Sci USA 82:6955–6959

    Article  CAS  PubMed  Google Scholar 

  • Nihira T, Shimizu Y, Kim HS, Yamada Y (1988) Structure–activity relationships of virginiae butanolide C, an inducer of virginiamycin production in Streptomyces virginiae. J Antibiot 41:1828–1837

    CAS  PubMed  Google Scholar 

  • Owen NL, Hundley N (2004) Endophytes—the chemical synthesizers inside plants. Sci Prog 87:79–99

    Article  CAS  PubMed  Google Scholar 

  • Powell RG, Weisleder D, Smith CR, Kozlowski J, Rohwedder WK (1982) Treflorine, trenudine, and N-methyltrenudone: Novel maytansinoid tumor inhibitors containing two fused macrocyclic rings. J Am Chem Soc 104:4929–4934

    Article  CAS  Google Scholar 

  • Powell RG, Smith CR, Plattner RD, Jones BE (1983) Additional new maytansinoids from Trewia nudiflora: 10-Epitrewiasine and nortrewiasine. J Nat Prod 46:660–666

    Article  CAS  Google Scholar 

  • Prikrylova V, Beran M, Sedmera P, Jizba J (1994) Isolation of nonactic acids from Streptomyces griseus fermentation broth by thin-layer and high-performance liquid-chromatography. Folia Microbiol 39:191–196

    Article  CAS  Google Scholar 

  • Pullen CB, Schmitz P, Hoffmann D, Meurer K, Boettcher T, Bamberg D, Pereira AM, Franca SC, Hauser M, Geertsema H, Wyk A, Mahmud T, Floss HG, Leistner E (2003) Occurrence and non-detectability of maytansinoids in individual plants of the genera Maytenus and Putterlickia. Phytochemistry 62:377–387

    Article  CAS  PubMed  Google Scholar 

  • Ryan RP, Germaine K, Franks A, Ryan DJ, Dowling DN (2008) Bacterial endophytes: recent developments. FEMS Microbiol Lett 278:1–9

    Article  CAS  PubMed  Google Scholar 

  • Sambrook J, Russell DW (2001) Molecular cloning: a laboratory manual, 3rd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY

    Google Scholar 

  • Snipes CE, Duebelbeis DO, Olson M, Hahn DR, Dent WH 3rd, Gilbert JR, Werk TL, Davis GE, Lu RL, Graupner PR (2007) The ansacarbamitocins: polar ansamitocin derivatives. J Nat Prod 70:1578–1581

    Article  CAS  PubMed  Google Scholar 

  • Sturz AV, Christie BR, Nowak J (2000) Bacterial endophytes: Potential role in developing sustainable systems of crop production. Crit Rev Plant Sci 19:1–30

    Article  Google Scholar 

  • Tan RX, Zou WX (2001) Endophytes, a rich source of functional metabolites. Nat Prod Rep 18:448–459

    Article  CAS  PubMed  Google Scholar 

  • Tang YQ, Sattler I, Thiericke R, Grabley S, Feng XZ (2000) Parallel chromatography in natural products chemistry: Isolation of new secondary metabolites from Streptomyces sp. ECSOC-4. Proceedings of the Fourth International Electronic Conference on Synthetic Organic Chemistry, pp 1605–1622

  • Yamada Y, Sugamura K, Kondo K, Yanagimoto M, Okada H (1987) The structure of inducing factors for virginiamycin production in Streptomyces virginiae. J Antibiot 40:496–504

    CAS  PubMed  Google Scholar 

  • Yu TW, Bai LQ, Clade D, Hoffmann D, Toelzer S, Trinh KQ, Xu J, Moss SJ, Leistner E, Floss HG (2002) The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum. Proc Natl Acad Sci USA 99:7968–7973

    Article  CAS  PubMed  Google Scholar 

  • Zhao PJ, Fan LM, Li GH, Zhu N, Shen YM (2005) Antibacterial and antitumor macrolides from Streptomyces sp Ls9131. Arch Pharm Res 28:1228–1232

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

This work was partly supported by the Natural Science Foundation of Yunnan Province (2007C096M), and the Chinese Academy of Sciences projects (XiBuZhiGuang to Peiji Zhao), and grants from the Young Academic and Technical Leader Raising Foundation of Yunnan Province (2009CI071).

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Authors and Affiliations

  1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, People’s Republic of China

    Guozhu Wei, Na Zhu, Ying Zeng, Yuemao Shen & Peiji Zhao

  2. Graduate University of the Chinese Academy of Sciences, Beijing, 100039, People’s Republic of China

    Guozhu Wei

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  1. Guozhu Wei
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  2. Na Zhu
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  3. Ying Zeng
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  4. Yuemao Shen
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  5. Peiji Zhao
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Correspondence to Peiji Zhao.

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Wei, G., Zhu, N., Zeng, Y. et al. Chemical constitutes from endophytic Streptomyces sp. W5 isolated from Trewia nudiflora L.. Ann Microbiol 60, 249–253 (2010). https://doi.org/10.1007/s13213-010-0034-3

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  • DOI: https://doi.org/10.1007/s13213-010-0034-3

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