Cyclo(Pro-DOPA), a third identified bioactive metabolite produced by Streptomyces sp. 8812

Abstract

A new metabolite, cyclic dipeptide, cis-(3S,8aS)-3-(3,4-dihydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione, named JS-3 was isolated from Streptomyces sp. 8812 fermentation broth. Its chemical structure was established by means of spectroscopic analysis. A wide-range-screening study, which included inhibition assay of DD-carboxypeptidase/transpeptidase activity, determination of antibacterial, antifungal, and antiproliferative activities as well as free-radical scavenging was performed. To authors knowledge, this is the first isolation of such compound from natural sources and the first one from bacteria, Streptomyces.

Catecholamine Derivatives: Natural Occurrence, Structural Diversity, and Biological Activity

“…154 These conjugates were recognized and transported by outer membrane transporters FepA and/or IroN and displayed a 10-to 1,000-fold potency over the parent antibiotics against both serovars Typhimurium and Enteritidis under iron-limiting conditions. 154 Siderophore-antibiotic conjugates provide a promising strategy to tackle antibiotic resistance which has As summarized in Table 2, several other CAs with potential metal-binding capacities, such as 25, 32 27, 35 64b, 63,60 76, 73 84, 73 85, 73 213, 139 and 230 145 have also demonstrated moderate to potent antibacterial activities (including some MDR bacteria). Whether or not these antibacterial activities are related to iron competition within bacteria is of an interesting question that might be explored by future research.…”

“…Cis -cyclo-( l -Pro-L-DOPA) ( 25 ) together with N -acetyl-3,4-dihydroxy- l -phenylalanine ( 26 ) (Figure ) were isolated from the Gram-positive actinomycete Streptomyces sp.8812, while 25 was also isolated from Streptomyces sp. HDa1, an actinomycete derived from the gut of a sea urchin Anthocidaris crassispina .…”

“…As summarized in Table , several other CAs with potential metal-binding capacities, such as 25 , 27 , 64b , , 76 , 84 , 85 , 213 , and 230 have also demonstrated moderate to potent antibacterial activities (including some MDR bacteria). Whether or not these antibacterial activities are related to iron competition within bacteria is of an interesting question that might be explored by future research.…”

“…Polyphenol-rich diets have been linked to many health benefits because of their potential antioxidant and radical scavenging activities . CAs derivatives (such as 25 , 38 , 63 , 102 , 120 - 135 , 141 – 142 , 148 , and 153 ) (Table ) bearing two adjacent phenols contain electronic effects desirable for antioxidant activity. CA derivatives may be beneficial in preventing diseases caused by oxidative stress, an area of research requiring further in vivo examination in the future.…”

“…Polyphenol-rich diets have been linked to many health benefits because of their potential antioxidant and radical scavenging activities. 168 CAs derivatives (such as 25, 32 38, 48 63, 59 102, 48 120-135, 97 141−142, 105 148, 59 and 153 48 ) (Table 2) bearing two adjacent phenols Effect on Nervous System. In addition to being present in plants, salsolinol (55) has also been found in humans and was first detected in the urine of Parkinsonian patients prescribed L-DOPA medication in 1973.…”