Cytotoxic and Antibacterial Angucycline- and  Prodigiosin- Analogues from the Deep-Sea Derived  Streptomyces sp. SCSIO 11594

Song, Yongxiang; Liu, Guangfu; Li, Jie; Huang, Hongbo; Zhang, Xing; Zhang, Hua; Ju, Jianhua

doi:10.3390/md13031304

Cited by 69 publications

(52 citation statements)

References 31 publications

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“…Data consistent with β-D-olivose and L-Rhodinose (Oki et al, 1979;Song et al, 2015). *Not observed, chemical shift assumed from Song et al, 2015. Compound (7) (Figure 13, Appendix W): colorless oil, this compound was identified by NMR data: 1 H NMR (500 MHz, CDCl3) δ 7.73 (1H, m), 7.54 (1H, m), 4.09 (2H, d, J = 6.7 Hz), 2.04 (1H, non, J = 6.7 Hz), 0.99 (6H, d, J = 6.7 Hz). NMR data supports the attribution of diisobutyl phthalate (7).…”

Section: Measurement Of Colony Areassupporting

confidence: 60%

“…Compound 6: brownish solid and similar UV pattern observed for compounds (4) and (5), suggesting the presence of an additional angucycline derivative (Figure 12); HR-ESI-MS m/z 549.2115 (calcd for C31H33O9, 549.2119, error 0.7 ppm). Search in literature showed similarity to a C-glycoside angucycline from a marine actinobacteria named marangucycline A (Song et al, 2015). By comparison of NMR data, the isolated compound (6) differs from marangucycline A in one of the units of the disaccharide moiety.…”

Section: Measurement Of Colony Areasmentioning

confidence: 95%

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Elicitation of natural products biosynthesis from endophytic microorganisms´ interactions

Rodríguez¹,

Mauricio²

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CARABALLO-RODRÍGUEZ, A. M. Elicitation of natural products biosynthesis from endophytic microorganisms´ interactions. 2016. 169 p. Doctoral Dissertation. School of Pharmaceutical Sciences of Ribeirão Preto -University of São Paulo, Ribeirão Preto, 2016. In order to continue with the study of natural products from previously isolated endophytes of the Brazilian medicinal plant Lychnophora ericoides, the main goal of this work focused on the metabolic exchange of endophytic microorganisms from this plant. As it has been demonstrated during the last years, elicitation of different molecules is consequence of microbial interactions, mainly due to the need to compete, survive and establish microbial communities in shared environments. Recent mass spectrometry related approaches, such as imaging and molecular networking, in combination with purification and structural elucidation were applied to the current study of the microbial interactions of endophytes. During this study, several chemical families were identified, such as polyene macrocycles, pyrroloindole alkaloids, leupeptins, angucyclines, siderophores, amongst others. Amongst the polyene macrocycles, the well-known antifungal amphotericin B was identified as a biosynthetic product of the endophytic actinobacteria Streptomyces albospinus RLe7. When S. albospinus RLe7 interacted with an endophytic fungus, Coniochaeta sp. FLe4, a red pigmentation was observed. A new fungal compound was detected from microbial interactions. Isolation and structure elucidation of this new compound enabled to demonstrate the elicitation of fungal secondary metabolites by amphotericin B, an actinobacterial metabolite. It was also demonstrated the elicitation of griseofulvin and its analogue dechlorogriseofulvin from another endophytic fungus, FLe9, as a consequence of exposition to amphotericin B. In addition, investigation of the chemical profile of another endophytic actinobacteria, S. mobaraensis RLe3, led to reveal this strain as angucycline-derivatives producer. Besides that, coculturing of this actinobacteria against Coniochaeta sp. FLe4 also demonstrated elicitation of angucycline analogues. In conclusion, this study demonstrated elicitation of natural products from microbial interactions as well as new compounds from endophytes from L. ericoides and contributed to the identification of microbial metabolites. RESUMO CARABALLO-RODRÍGUEZ, A. M. Eliciação da biossíntese de produtos naturais a partir da interação de microorganismos endofíticos. 2016. 169 f. Tese de doutorado, Faculdade de Ciências Farmacêuticas de Ribeirão Preto -Universidade de São Paulo, Ribeirão Preto, 2016. Com o propósito de continuar com os estudos de produtos naturais de microorganismos endofíticos da planta medicinal Brasileira Lychnophora ericoides, o principal objetivo desse trabalho focou-se no estudo da troca metabólica de microorganismos endofíticos dessa planta. Como tem sido demonstrado durante os últimos anos, a elicitação de diferentes compostos é consequência das interações microbianas, principalm...

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Section: Measurement Of Colony Areassupporting

confidence: 60%

Section: Measurement Of Colony Areasmentioning

confidence: 95%

Elicitation of natural products biosynthesis from endophytic microorganisms´ interactions

Rodríguez¹,

Mauricio²

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“…Angucycline antibiotics are a group of biologically active natural products synthesized by type II polyketide synthase (PKS) complexes through a sequence of reactions . Angucyclines exhibit diverse biological activities, including antiviral (SM 196 B), antibacterial (marangucycline A, vineomycin A 1 ), antitumor (landomycin A, urdamycin A, and marangucycline B), and antifungal properties (Sch47554 ( 1 ) and Sch47555 ( 2 ) ) . Compounds 1 and 2 are produced by Streptomyces sp.…”

Section: Introductionmentioning

confidence: 99%

New Insights into the Glycosylation Steps in the Biosynthesis of Sch47554 and Sch47555

et al. 2018

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Sch47554 and Sch47555 are antifungal compounds from Streptomyces sp. SCC-2136. The availability of the biosynthetic gene cluster made it possible to track genes that encode biosynthetic enzymes responsible for the structural features of these two angucyclines. Sugar moieties play important roles in the biological activities of many natural products. An investigation into glycosyltransferases (GTs) might potentially help to diversify pharmaceutically significant drugs through combinatorial biosynthesis. Sequence analysis indicates that SchS7 is a putative C-GT, whereas SchS9 and SchS10 are proposed to be O-GTs. In this study, the roles of these three GTs in the biosynthesis of Sch47554 and Sch47555 are characterized. Coexpression of the aglycone and sugar biosynthetic genes with schS7 in Streptomyces lividans K4 resulted in the production of C-glycosylated rabelomycin, which revealed that SchS7 attached a d-amicetose moiety to the aglycone core structure at the C-9 position. Gene inactivation studies revealed that subsequent glycosylation steps took place in a sequential manner, in which SchS9 first attached either an l-aculose or l-amicetose moiety to 4'-OH of the C-glycosylated aglycone, then SchS10 transferred an l-aculose moiety to 3-OH of the angucycline core.

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“…3,4 An increasing number of angucycline derivatives with different activities have been isolated from natural sources, predominantly Streptomyces sps. 1,5,6 Their structures are mainly based on the tetracyclic benz[a]anthracene skeleton. 7,8 In the continuation of our search for new bioactive natural products from actinomycetes, 9 we collected sea water and soil samples from different areas in Japan.…”

Section: Introductionmentioning

confidence: 99%

Elmenols C-H, new angucycline derivatives isolated from a culture of Streptomyces sp. IFM 11490

et al. 2017

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Cytotoxic and Antibacterial Angucycline- and Prodigiosin- Analogues from the Deep-Sea Derived Streptomyces sp. SCSIO 11594

Cited by 69 publications

References 31 publications

Elicitation of natural products biosynthesis from endophytic microorganisms´ interactions

Elicitation of natural products biosynthesis from endophytic microorganisms´ interactions

New Insights into the Glycosylation Steps in the Biosynthesis of Sch47554 and Sch47555

Elmenols C-H, new angucycline derivatives isolated from a culture of Streptomyces sp. IFM 11490

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