12T061A and 12T061C, two new julichrome family compounds, as radical scavengers from <i>Streptomyces</i> sp.

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q3 ⋅ 5 and Q3 ⋅ 3

“…Julichrome compounds display a wide array of biological activities including, but not limited to antimicrobial, antitumor, antioxidant and anti-phytodevelopmental activities. [4][5][6] Key to the biosynthesis of the julichromes is a cytochrome P450 monooxygenase that carries out a regioselective intermolecular oxidative phenol-coupling reaction manner to install a unique biaryl linkage characteristic of the dimeric julichromes. [7] The monomer julichrome Q 6 , derived from a common nonaketide precursor, serves a vital role in the production of many dimer-based julichromes by virtue of its use as a monomer.…”

Dimeric Tetrahydroanthracene Regioisomers and Their Monomeric Precursor Produced by Streptomyces fumigatiscleroticus HDN10255

“…Dimeric preanthraquinones, which have mainly been isolated from bacteria, have exhibited antibacterial, antifungal, cytotoxic, antiviral, radical-scavenging, and plant transformation inhibiting activities. ,,,,, Compounds 1 – 5 were evaluated in vitro for their cytotoxicity against HTC-116 and HeLa cells by the SRB method, and the K562 and HL-60 cells by the MTT method . As a result, both 2 and 4 displayed cytotoxic activity with the best IC 50 values of 1.8 and 5.1 μM, respectively, against HeLa cells, while 1 , 3 , and 5 were inactive (IC 50 > 10 μM) (Table ).…”

“…Chemical investigation of the extract resulted in the isolation of four new tetrahydroanthracene derivatives ( 1 , 3 – 5 ) and a known antibiotic, A-39183A ( 2 ). Among them, compound 1 is a monomeric julichrome derivative, which is rare, with only six structures (julichromes Q 6 , Q 10 , Q 11 and Q 12 , 12T061A, and 12T061C) discovered so far. − Compounds 2 – 5 are dimeric forms featuring diverse coupling positions, and atroposelective homodimers produced by a single bacterial strain have never been reported. The cytotoxicities of compounds 1 – 5 were evaluated against four human cancer cell lines.…”

Elucidation of the Tailoring Steps in Julichrome Biosynthesis by Marine Gastropod Mollusk-Associated Streptomyces sampsonii SCSIO 054

“…7−17 Julichrome derivatives display moderate cytotoxic activity against a range of human tumor cell lines, 17 as well as radical-scavenging activity. 15 Julichrome representatives have also displayed significant inhibitory effects on crown gall formation and have potential as agricultural antibiotics and inhibitors of plant transformation. 12 To date, however, reports of julichrome biosynthetic pathway(s) have remained scarce.…”

“…To date, 28 julichrome derivatives, including 20 dimeric species, have been reported (Figure S1). − Julichrome derivatives display moderate cytotoxic activity against a range of human tumor cell lines, as well as radical-scavenging activity . Julichrome representatives have also displayed significant inhibitory effects on crown gall formation and have potential as agricultural antibiotics and inhibitors of plant transformation .…”