Kiamycins B and C, unusual bridged angucyclinones from a marine sediment-derived Streptomyces sp.

Guo, Lin; Xie, Zeping; Yang, Qin; Feng, Lingling; Zhang, Lu; Zhang, Yue-zhi; Li, Xiaonian; Zhang, Shumin

doi:10.1016/j.tetlet.2018.04.063

Cited by 12 publications

(8 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Angucyclines were mainly separated from terrestrial actinomycetes, though in recent years an increasing number of them have been identified from marine actinomycetes associated with seafloor sediments [4,8,16,17,18,19], sponges [7], and mangrove forests [20]. We also initiated a screening for angucycline-producing strains employing PCR amplification of the β-ketoacyl synthase (KSα) gene from marine actinomycetes, and a Streptomyces sp.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic, Anti-Migration, and Anti-Invasion Activities on Breast Cancer Cells of Angucycline Glycosides Isolated from a Marine-Derived Streptomyces sp.

Ren

Peng

et al. 2019

Marine Drugs

View full text Add to dashboard Cite

Four angucycline glycosides were previously characterized from marine-derived Streptomyces sp. OC1610.4. Further investigation of this strain cultured on different fermentation media from that used previously resulted in the isolation of two new angucycline glycosides, vineomycins E and F (1–2), and five known homologues, grincamycin L (3), vineomycinone B2 (4), fridamycin D (5), moromycin B (7), and saquayamycin B1 (8). Vineomycin F (2) contains an unusual ring-cleavage deoxy sugar. All the angucycline glycosides isolated from Streptomyces sp. OC1610.4 were evaluated for their cytotoxic activity against breast cancer cells MCF-7, MDA-MB-231, and BT-474. Moromycin B (7), saquayamycin B1 (8), and saquayamycin B (9) displayed potent anti-proliferation against the tested cell lines, with IC50 values ranging from 0.16 to 0.67 μM. Saquayamycin B (9) inhibited the migration and invasion of MDA-MB-231 cells in a dose-dependent manner, as detected by Transwell and wound-healing assays.

show abstract

Section: Introductionmentioning

confidence: 99%

Cytotoxic, Anti-Migration, and Anti-Invasion Activities on Breast Cancer Cells of Angucycline Glycosides Isolated from a Marine-Derived Streptomyces sp.

Ren

Peng

et al. 2019

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…CB00072 and S. albus recombinant strains SB4051 and SB4061 in this study.C ompounds 1 and 2 were isolatedf rom S. sp. CB00072;compounds 6,8 -O-methylrabelomycin (10), [9] tetrangomycin (11), [10] X-14881 E (12), [11] 13, [12] 14, [13] and oleaceran (15) [14] were isolated from strain SB4051;a nd the remainingcompounds were isolatedf rom SB4061. The crystal structure of 9 is shown for reference.…”

Section: Discovery Of Tacs and Congeners From Streptomyces Sp Cb00072mentioning

confidence: 99%

Cryptic Sulfur Incorporation in Thioangucycline Biosynthesis

et al. 2021

View full text Add to dashboard Cite

Sulfur incorporation into natural products is a critical area of biosynthetic studies. Recently, a subset of sulfur‐containing angucyclines has been discovered, and yet, the sulfur incorporation step is poorly understood. In this work, a series of thioether‐bridged angucyclines were discovered, and a cryptic epoxide Michael acceptor intermediate was revealed en route to thioangucyclines (TACs) A and B. However, systematic gene deletion of the biosynthetic gene cluster (BGC) by CRISPR/Cas9 could not identify any gene responsible for the conversion of the epoxide intermediate to TACs. Instead, a series of in vitro and in vivo experiments conclusively showed that the conversion is the result of two non‐enzymatic steps, possibly mediated by endogenous hydrogen sulfide. Therefore, the TACs are proposed to derive from a detoxification process. These results are expected to contribute to the study of both angucyclines and the utilization of inorganic sulfur in natural product biosynthesis.

show abstract

“…In this work, we turn our attention to the chemistry of another intermediate 2 [17] (Scheme 1), which function is still virtually unknown. Regarding that its chemical synthesis could be overcomplicated and that 2 has a potential tendency for rearrangement, we have focused on the products of such transformation, isobenzofurans 3 , [18,19] 4 (elmenols A and B) [20] and 5 [21] .…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Elmenols A and B and Related Rearranged Angucyclinones

et al. 2021

View full text Add to dashboard Cite

A synthetic approach towards rearranged angucyclinones related to Elmenols A and B and their synthetic derivatives has been developed. Carbon skeleton is constructed in a straightforward manner by directed o‐lithiation of m‐anisaldehyde dimethyl acetal and its further nucleophilic addition to properly substituted naphthalene carbaldehydes. The latter can be achieved via several alternative synthetic schemes, the most efficient of them are discussed herein.

show abstract

Kiamycins B and C, unusual bridged angucyclinones from a marine sediment-derived Streptomyces sp.

Cited by 12 publications

References 19 publications

Cytotoxic, Anti-Migration, and Anti-Invasion Activities on Breast Cancer Cells of Angucycline Glycosides Isolated from a Marine-Derived Streptomyces sp.

Cytotoxic, Anti-Migration, and Anti-Invasion Activities on Breast Cancer Cells of Angucycline Glycosides Isolated from a Marine-Derived Streptomyces sp.

Cryptic Sulfur Incorporation in Thioangucycline Biosynthesis

Total Synthesis of Elmenols A and B and Related Rearranged Angucyclinones

Contact Info

Product

Resources

About