Angucyclines and Angucyclinones from Streptomyces sp. CB01913 Featuring C-Ring Cleavage and Expansion.
Angucyclines and angucyclinones are aromatic polyketides with a tetracyclic benz[a]anthracene skeleton. The benz[a]anthracene scaffold is biosynthesized by type II polyketide synthases that catalyze the decarboxylative condensation of a short acyl-CoA starter and nine extender units. Angucyclines and angucyclinones, the largest group of polycyclic aromatic polyketides, achieve structural diversity via subsequent oxidation, ring cleavage, amino acid incorporation, and glycosylation. We here report the discovery of 14 angucyclinones and two angucyclines (1-16) from Streptomyces sp. CB01913, identifying 12 new compounds featuring various oxidations on rings A and C (1, 2, and 4), different sugar moieties attached to rings A and B (3 and 6), and C-ring cleavage (5 and 10-14) and expansion (8). These new structural features, highlighted by C-ring cleavage and expansion, enrich the structural diversity of angucyclines and angucyclinones. All compounds were tested for cytotoxicity and antibacterial activities, with 1, 5, 15, and 16 showing moderate activities against selected cancer cell lines or bacterial strains.
Ming
M
Ma
Mostafa E
ME
Rateb
Qihui
Q
Teng
Dong
D
Yang
Jeffrey D
JD
Rudolf
Xiangya International Academy of Translational Medicine, Central South University , Changsha, Hunan 410013, People's Republic of China.|Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery , Changsha, Hunan 410329, People's Republic of China.
Xiangcheng
X
Zhu
Xiangya International Academy of Translational Medicine, Central South University , Changsha, Hunan 410013, People's Republic of China.
Yong
Y
Huang
Yunnan Institute of Microbiology, Yunnan University , Kunming, Yunnan 650091, People's Republic of China.
Li-Xing
LX
Zhao
Yunnan Institute of Microbiology, Yunnan University , Kunming, Yunnan 650091, People's Republic of China.
Yi
Y
Jiang
Xiuling
X
Li
Christoph
C
Rader
Xiangya International Academy of Translational Medicine, Central South University , Changsha, Hunan 410013, People's Republic of China.|Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery , Changsha, Hunan 410329, People's Republic of China.
Yanwen
Y
Duan
Ben
B
Shen
D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013302:Streptomyces / Q000737:chemistry*
D000880:Anthraquinones; D000970:Antineoplastic Agents; C510997:angucyclinone