Download PDF
Planta Med 2012; 78(10): 988-994
DOI: 10.1055/s-0031-1298592
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Actinotetraoses A–H: Tetrasaccharide Derivatives from a Grasshopper-Associated Amycolatopsis sp. HCa1

Zhi Kai Guo
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
2   Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, and Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Haikou, Peopleʼs Republic of China
,
Gao Fei Zhang
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
,
Rui Hua Jiao
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
,
Yan Shen
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
,
Qiang Xu
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
,
Ren Xiang Tan
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
,
Hui Ming Ge
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 20 February 2012
revised 24 April 2012

accepted 27 April 2012

Publication Date:
22 May 2012 (online)

Also available at
    Permissions and Reprints

Abstract

Chemical investigation of the insect-derived actinomycete Amycolatopsis sp. HCa1 with NMR-guided fractionation led to the isolation of eight new tetrasaccharide derivatives containing an unusual nonreducing glucotetraose skeleton, named actinotetraoses A–H (1–8), and one known compound, tigloside (9). The structures of these compounds were determined on the basis of analyses of their spectroscopic data. The in vitro immunosuppressive activity and cytotoxicity of these compounds were evaluated by T cell viability and MTT assays, respectively. Only actinotetraose E (5) displayed weak immunosuppressive activity.

Key words

Amycolatopsis - Pseudonocardiaceae - insect-derived actinomycete - tetrasaccharide derivatives

Supporting Information

 

  • References

  • 1 Iwai K, Iwamoto S, Aisaka K, Suzuki M. Isolation of novel actinomycetes from spider materials. Actinomycetologica 2009; 23: 8-15
    CrossrefPubMedSearch in Google Scholar
  • 2 Patil PB, Zeng Y, Coursey T, Houston P, Miller I, Chen S. Isolation and characterization of a Nocardiopsis sp. from honeybee guts. FEMS Microbiol Lett 2010; 312: 110-118
    CrossrefPubMedSearch in Google Scholar
  • 3 Zhang YL, Ge HM, Zhao W, Dong H, Xu Q, Li SH, Li J, Zhang J, Song YC, Tan RX. Unprecedented immunosuppressive polyketides from Daldinia eschscholzii, a mantis-associated fungus. Angew Chem Int Ed 2008; 47: 5823-5826
    CrossrefPubMedSearch in Google Scholar
  • 4 Zhang YL, Zhang J, Jiang N, Lu YH, Wang L, Xu SH, Wang W, Zhang GF, Xu Q, Ge HM, Ma J, Song YC, Tan RX. Immunosuppressive polyketides from mantis-associated Daldinia eschscholzii . J Am Chem Soc 2011; 133: 5931-5940
    CrossrefPubMedSearch in Google Scholar
  • 5 Zhang YL, Ge HM, Li F, Song YC, Tan RX. New phytotoxic metabolites from Pestalotiopsis sp. HC02, a fungus residing in Chondracris rosee gut. Chem Biodivers 2008; 5: 2402-2407
    CrossrefPubMedSearch in Google Scholar
  • 6 Scott JJ, Oh DC, Yuceer MC, Klepzig KD, Clardy J, Currie CR. Bacterial protection of beetle-fungus mutualism. Science 2008; 322: 63
    CrossrefPubMedSearch in Google Scholar
  • 7 Oh DC, Scott JJ, Currie CR, Clardy J. Mycangimycin, a polyene peroxide from a mutualist Streptomyces sp. Org Lett 2009; 11: 633-636
    CrossrefPubMedSearch in Google Scholar
  • 8 Oh DC, Poulsen M, Currie CR, Clardy J. Dentigerumycin: a bacterial mediator of an ant-fungus symbiosis. Nat Chem Biol 2009; 5: 391-393
    CrossrefPubMedSearch in Google Scholar
  • 9 Oh DC, Poulsen M, Currie CR, Clardy J. Sceliphrolactam, a polyene macrocyclic lactam from a wasp-associated Streptomyces sp. Org Lett 2011; 13: 752-755
    CrossrefPubMedSearch in Google Scholar
  • 10 Guo ZK, Wang T, Guo Y, Song YC, Tan RX, Ge HM. Cytotoxic angucyclines from Amycolatopsis sp. HCa1, a rare actinobacteria derived from Oxya chinensis . Planta Med 2011; 77: 2057-2060
    Thieme ConnectPubMedSearch in Google Scholar
  • 11 Rickards RW, Rothschild JM, Lacey E. Structure of actinotetraose hexatiglate, a unique glucotetraose from an actinomycete bacterium. J Antibiot 1998; 51: 1093-1098
    CrossrefPubMedSearch in Google Scholar
  • 12 Breinholt J, Kulik A, Gürtler H, Fiedler HP. Tigloside: a new tigloylated tetrasaccharide from Amycolatopsis sp. Acta Chem Scand 1998; 52: 1239-1242
    CrossrefPubMedSearch in Google Scholar