Abstract
Two new C-glycoside angucyclines, marangucycline A (1) and marangucycline B (2), along with three known compounds, dehydroxyaquayamycin (3), undecylprodigiosin (4) and metacycloprodigiosin (5), have been identified as products of the deep-sea sediment strain Streptomyces sp. SCSIO 11594. New structures were elucidated on the basis of HRESIMS, 1D and 2D NMR analyses and comparisons to previously reported datasets. Compounds 2 and 4 displayed in vitro cytotoxicity against four cancer cell lines A594, CNE2, HepG2, MCF-7 superior to those obtained with cisplatin, the positive control. Notably, compound 2 bearing a keto-sugar displayed significant cytotoxicity against cancer cell lines with IC50 values ranging from 0.24 to 0.56 μM; An IC50 value of 3.67 μM was found when using non-cancerous hepatic cell line HL7702, demonstrating the cancer cell selectivity of 2. Compounds 1-3 were proved to have weak antibacterial activities against Enterococcus faecalis ATCC29212 with an MIC value of 64.0 μg/mL. Moreover, 3 displayed selective antibacterial activity against methicillin-resistant Staphylococcus epidermidis shhs-E1 with an MIC value of 16.0 μg/mL.
References
Aug 1, 1979·The Journal of Antibiotics·T OkiH Umezawa
Nov 1, 1977·The Journal of Antibiotics·S OmuraK Tanaka
Apr 1, 1992·Natural Product Reports·J Rohr, R Thiericke
Nov 1, 1970·Tetrahedron·M SezakiM Ono
Sep 1, 1966·The Journal of Organic Chemistry·M P Kuntsmann, L A Mitscher
Dec 16, 1983·Journal of Immunological Methods·T Mosmann
May 1, 1982·The Journal of Antibiotics·N ImamuraS Omura
Nov 1, 1981·The Journal of Antibiotics·N ImamuraS Omura
Apr 9, 2005·The Journal of Antibiotics·János Bérdy
Jan 6, 2006·Archives of Pharmacal Research·Rui LiuWei-Ming Zhu
May 6, 2006·Current Opinion in Microbiology·Kin S Lam
Jun 16, 2006·Organic Letters·Gillian E Morton, Anthony G M Barrett
Aug 1, 2008·Journal of Natural Products·Mohamed S AbdelfattahJürgen Rohr
Sep 13, 2008·Organic Letters·Xiaomei Yu, George A O'Doherty
Nov 26, 2008·Natural Product Reports·Danielle Skropeta
Jun 21, 2011·Journal of Biotechnology·Sergey B Zotchev
Oct 8, 2011·Journal of Natural Products·Hongbo HuangJianhua Ju
Feb 7, 2012·Journal of Natural Products·Hongbo HuangJianhua Ju
Jul 17, 2012·Microbiological Research·Ramesh Subramani, William Aalbersberg
Dec 12, 2012·Journal of Natural Products·Xiao ZhouJianhua Ju
Mar 27, 2013·Marine Drugs·Zhi-Qiang XiongYong Wang
May 4, 2013·Applied Microbiology and Biotechnology·Sung-Hwan EomSe-Kwon Kim
Jul 3, 2013·International Journal of Systematic and Evolutionary Microbiology·Zhi-Qing YouSi Zhang
Nov 21, 2013·Journal of Natural Products·Yongxiang SongJianhua Ju
Feb 25, 2014·Applied Microbiology and Biotechnology·Randy Chi Fai CheungTzi Bun Ng
May 30, 2014·Natural Product Reports·Danielle Skropeta, Liangqian Wei
Jul 30, 2014·Journal of Natural Products·Yongxiang SongJianhua Ju
Citations
Dec 30, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yong-Qi TianYonghong Liu
Jan 12, 2017·The Journal of Antibiotics· YixizhuomaMasami Ishibashi
May 11, 2017·Journal of Natural Products·Chun GuiJianhua Ju
Mar 23, 2017·Natural Product Reports·Sylvia Soldatou, Bill J Baker
Jan 4, 2017·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Syed Shams Ul Hassan, Abdul Lateef Shaikh
Jul 4, 2017·International Journal of Molecular Sciences·Shian-Ren LinChing-Feng Weng
Jul 18, 2017·Marine Drugs·Ming-Fang ChengChing-Feng Weng
Nov 10, 2017·Microbial Ecology·Douglas C WoodhamsKevin P C Minbiole
Nov 18, 2018·Natural Product Research·Shanwen ZhangJianhua Ju
Feb 6, 2020·Marine Drugs·Stefano VarrellaCinzia Corinaldesi
Mar 4, 2020·Marine Drugs·Justus Amuche NwezeDengfeng Yang
Jan 15, 2020·Current Medicinal Chemistry·Dario MatuljaDean Marković
Jun 13, 2019·Journal of Hematology & Oncology·Qing XieJunying Ma
Mar 16, 2017·Natural Product Reports·John W BluntMichèle R Prinsep
Sep 1, 2017·Nature Communications·Junying MaJianhua Ju
Oct 24, 2018·Journal of Clinical Medicine·Shian-Ren Lin, Ching-Feng Weng
May 31, 2018·Marine Drugs·Chun GuiJianhua Ju
Nov 7, 2019·International Journal of Molecular Sciences·Kai ZhaoXiujun Fan
Nov 7, 2015·Marine Drugs·Sergey A Dyshlovoy, Friedemann Honecker
Jun 14, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natalia QuiñonesMauricio A Cuellar
May 26, 2018·Chembiochem : a European Journal of Chemical Biology·Ozkan FidanJixun Zhan
Jul 30, 2019·International Journal of Microbiology·Periyasamy SivalingamKandasamy Prabakar
Nov 30, 2018·Marine Drugs·Aihong PengWeidong Xie
Apr 26, 2020·The Journal of Antibiotics·Yongxiang SongJianhua Ju
May 17, 2017·Frontiers in Microbiology·Manita KamjamKui Hong
Jul 16, 2017·Scientific Reports·Andrés M Caraballo-RodríguezMonica T Pupo
Nov 8, 2018·International Journal of Molecular Sciences·Dan LiKai Zhao
May 10, 2019·Current Microbiology·Gyana Prakash MahapatraJayanta Kumar Patra
Oct 27, 2020·Journal of Basic Microbiology·Ravi LokeshKrishnan Kannabiran
Dec 31, 2020·Microorganisms·Ali NawazIkram Ul Haq
Jun 3, 2021·Marine Drugs·Giulia GrecoCarmela Fimognari
Mar 17, 2020·ACS Omega·Edi SetiyonoTatas Hardo Panintingjati Brotosudarmo
Jan 10, 2018·The Journal of Organic Chemistry·Andrew W RobertsonDavid L Jakeman