Benzodiazepine Derivatives from Marine-Derived Streptomyces cacaoi 14CM034

Abstract

7-methoxy-8-hydroxy cycloanthranilylproline (2), a new natural product with pyrrolobenzodiazepine (PBD) framework, was isolated from marine-derived actinobacterium Streptomyces cacaoi 14CM034, together with cycloanthranilylproline (1). Structural elucidation of the compounds was based on FTIR, 1D- (1H and 13C NMR), 2D-NMR (COSY, HMBC and NOESY) and HR-MS analyses. Compounds 1 and 2 exhibited notable antimicrobial activity. The presence of PBD derivatives in S. cacaoi was first demonstrated with this study.

Actinoquinazolinone, a New Quinazolinone Derivative from a Marine Bacterium Streptomyces sp. CNQ-617, Suppresses the Motility of Gastric Cancer Cells

“…The 13 C NMR spectrum of 3 showed twelve carbons at δ C 171.2 (C-11), 166.6 (C-5), 151.1 (C-8), 145.4 (C-7), 131.4 (C-9a), 117.9 (C-5a), 111.8 (C-6), 107.7 (C-9), 57.2 (C-11a), 47.1 (C-3), 25.8 (C-1), 23.4 (C-2), and one methoxy group at δ C 55.4 (7-Ome) ( Figure S9 ). The chemical structure of 3 was determined as 7-methoxy-8-hydroxy cycloanthranilylproline based on the comparison of NMR data to those of previously reported ones [ 25 ].…”

“…Therefore, marine-derived Streptomyces and other actinobacteria are regarded as a valuable resource for the discovery of novel bioactive compounds with potential therapeutic applications [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. Marineosins A and B are two structurally related compounds that were first discovered from this strain.…”

Marine Streptomyces-Derived Novel Alkaloids Discovered in the Past Decade

“…Compound 70 had antiproliferative effects against MDA-MB-231 cells and A549 cells at 10 µM, with growth inhibition rates of 10.2% and 7.3%. An unusual PBD derivative, 7methoxy-8-hydroxy cycloanthranilylproline (71), along with a known analogue (72), was isolated from marine S. cacaoi 14CM034 and displayed antimicrobial effects on E. coli, MRSA, E. faecium, P. aeruginosa and C. albicans, with MIC values ranging from 8.75 to 32 µg/mL [54]. It seems that methoxy substitution on the benzene ring of PBD diminished the antimicrobial effect.…”

“…Mar. Drugs 2024, 22, x 9 of 30 8.75 to 32 µg/mL[54]. It seems that methoxy substitution on the benzene ring of PBD diminished the antimicrobial effect.…”

Unique Cyclized Thiolopyrrolones from the Marine-Derived Streptomyces sp. BTBU20218885

“…With the detailed investigation on marine microorganisms, marine-derived actinomycetes have proven to be an inexhaustible source for bioactive secondary metabolites [ 9 ]. A number of new bioactive compounds were characterized from marine-derived Streptomyces , such as isoquinolinequinones [ 10 ], terpenoid derivatives [ 11 , 12 ], angucycline derivatives [ 13 , 14 , 15 ], glycosylated aromatic polyketides [ 16 ], bicyclic peptides [ 17 ], depsipeptides [ 18 ], benzodiazepines [ 19 ], and piericidin derivatives [ 20 ].…”