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Planta Med 2018; 84(03): 201-207
DOI: 10.1055/s-0043-119888
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Grincamycins I – K, Cytotoxic Angucycline Glycosides Derived from Marine-Derived Actinomycete Streptomyces lusitanus SCSIO LR32

Zhenzhu Lai
1   School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, China
2   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
,
Jianchen Yu
3   Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, China
,
Huiping Ling
1   School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, China
,
Yongxiang Song
2   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
,
Jie Yuan
3   Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, China
,
Jianhua Ju
2   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
,
Yiwen Tao
1   School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, China
4   The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, China
,
Hongbo Huang
2   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
› Author Affiliations
Further Information

Publication History

received 02 July 2017
revised 04 September 2017

accepted 14 September 2017

Publication Date:
26 September 2017 (online)

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Abstract

Three new angucycline glycosides, designated grincamycin I (1), J (2), and K (3), together with the known congener A-7884 (4), were isolated from marine-derived actinomycete Streptomyces lusitanus SCSIO LR32. The structures of the new compounds were elucidated by comprehensive spectral data analysis. Compounds 2 and 4 exhibited antitumor activity against human cancer cells MDA-MB-435, MDA-MB-231, NCI-H460, HCT-116 and HepG2, and human normal breast epithelial cell MCF10A with IC50 values ranging from 0.4 to 6.9 µM. In addition, A-7884 (4) demonstrated antimicrobial activity against Micrococcus luteus with an MIC value of 1.95 µg/mL.

Key words

angucycline glycoside - naphthacenequinone - cytotoxicity - marine actinomycete - Streptomyces lusitanus - Streptomycetaceae

Supporting Information

    HR-ESI-MS and NMR spectra of grincamycins I (1), J (2), and K (3) are available as Supporting Information.

  • Supporting Information
 

  • References

  • 1 Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. J Antibiot 2009; 62: 5-16
    CrossrefPubMedGoogle Scholar
  • 2 Berdy J. Bioactive microbial metabolites. J Antibiot 2005; 58: 1-26
    CrossrefPubMedGoogle Scholar
  • 3 Adegboye MF, Babalola OO. Actinomycetes: a yet inexhaustive Source of bioactive secondary Metabolites. In: Mendez-Vilas A. ed. Microbial Pathogens and Strategies for combating Them: Science, Technology and Education. Badajoz, Spain: Formatex Research Center; 2013: 786-795
    Google Scholar
  • 4 Baltz RH. Antimicrobials from actinomycetes: back to the future. Microbe 2007; 2: 125-131
    PubMedGoogle Scholar
  • 5 Naine SJ, Srinivasan VM, Devi CS. Novel anticancer compounds from marine actinomycetes: a review. J Pharm Res 2011; 4: 1285-1287
    PubMedGoogle Scholar
  • 6 Gerwick WH, Moore BS. Lessons from the past and charting the future of marine natural products drug discovery and chemical biology. Chem Biol 2012; 19: 85-98
    CrossrefPubMedGoogle Scholar
  • 7 Huang H, Yang T, Ren X, Liu J, Song Y, Sun A, Ma J, Wang B, Zhang Y, Huang C, Zhang C, Ju J. Cytotoxic angucycline class glycosides from the deep sea actinomycete Streptomyces lusitanus SCSIO LR32. J Nat Prod 2012; 75: 202-208
    CrossrefPubMedGoogle Scholar
  • 8 Zhu X, Duan Y, Cui Z, Wang Z, Li Z, Zhang Y, Ju J, Huang H. Cytotoxic rearranged angucycline glycosides from deep sea-derived Streptomyces lusitanus SCSIO LR32. J Antibiot 2017; 70: 819-822
    CrossrefPubMedGoogle Scholar
  • 9 Alvi KA, Baker DD, Stienecker V, Hosken M, Nair B. Identification of inhibitors of inducible nitric oxide synthase from microbial extracts. J Antibiot 2000; 53: 496-501
    CrossrefPubMedGoogle Scholar
  • 10 Ding B, Yuan J, Huang X, Wen W, Zhu X, Liu Y, Li H, Lu Y, He L, Tan H, She Z. New dimeric members of the phomoxanthone family: phomolactonexanthones A, B and deacetylphomoxanthone C isolated from the fungus Phomopsis sp. Mar Drugs 2013; 11: 4961-4972
    CrossrefPubMedGoogle Scholar
  • 11 Zhang Y, Huang H, Chen Q, Luo M, Sun A, Song Y, Ma J, Ju J. Identification of the grincamycin gene cluster unveils divergent roles for GcnQ in different hosts, tailoring the L-rhodinose moiety. Org Lett 2013; 15: 3254-3257
    CrossrefPubMedGoogle Scholar
  • 12 Zhou X, Huang H, Li J, Song Y, Jiang R, Liu J, Zhang S, Hua Y, Ju J. New anti-infective cycloheptadepsipeptide congeners and absolute stereochemistry from the deep sea-derived Streptomyces drozdowiczii SCSIO 10141. Tetrahedron 2014; 70: 7795-7801
    CrossrefPubMedGoogle Scholar