4'-N-Methyl-5'-hydroxystaurosporine and 5'-Hydroxystaurosporine, New Indolocarbazole Alkaloids from a Marine Micromonospora sp. Strain.

Abstract

Two new indolocarbazole alkaloids, 4'-Af-methyl-5'-hydroxystaurosporine (2) and 5'-hydroxystaurosporine (3), were isolated together with the known staurosporine (1) from the culture broth of a marine Micromonospora sp. (strain L-31-CLCO-002). The fermentation, structural data and cytotoxic activities of these compounds against various tumorcell lines aregiven.

A comprehensive review of glycosylated bacterial natural products

“…558 Three divergent N , N ′-12,13-pyranosides have also been observed including: 4′- O -methyl-α-L-olivose ( 106 , RK-1409B); 570 3′-nitro-2′,3′,6′-trideoxy-α-L-glucose ( 143 , 4′-demethylamino-4′-nitro-staurosporine); 568 and 3′-amino-3′,6′-dideoxy-4′- O -methyl-α-L-altrose ( 147 , 5′-hydroxystaurosporine and 4′- N -methyl-5′-hydroxystaurosporine from Micromonospora ). 571 The corresponding N , N ′-12,13-fused furanoside-containing members of this group include indocarbazostatins A–D, 572–574 all of which contain a novel branched α-L pentose 145 [differing via a C-3′-side chain ethyl (A/B) or methyl (C/D) ester], and K-252a-b. 566,575,576 K-252a and K-252b contain a novel branched α-L pentose 146 [differing via the presence of a C-3′-side chain free acid (b) or methyl ester (a)] while, in N -methyl-3′-amino-3′-deoxy K-252a, the 146 C-3′-hydroxyl has been replaced with a N -methyl-amino group to afford 149 (Fig.…”

N-Carboxamido-staurosporine and Selina-4(14),7(11)-diene-8,9-diol, New Metabolites from a Marine Streptomyces sp.

“…It exhibited similar UV data in MeOH with characteristic absorption maxima [16] With respect to the tremendous number of staurosporines listed in the Chemical Abstracts, it was very unexpected that less than 10 urea derivatives like 1c are known, none of them being natural [17].…”

Cytotoxic Indolocarbazoles fromActinomadura melliauraATCC 39691

“…14,15 Indolocarbazoles including staurosporines, 51–60 K-252 derivatives, 61–63 rebeccamycins, 64,65 RK-1409B, 66 RK-286 C and D, 67,68 tjipanazoles, 69 TAN-999S and TAN-1030A analogues, 54,70 fradcarbazoles, 71 indocarba-zostatins, 72–75 ZHD-0501, 76 fluoroindolocarbazoles, 77 holy-rines, 78 MLR-52, 79 and BE-13793C 80,81 have been reported to have promising antibacterial, antifungal, antitumor, and neuroprotective activities. Thus, compounds 1 – 7 were tested against five bacterial strains ( Staphylococcus aureus ATCC 6538, Micrococcus luteus NRRL B-287, Mycobacterium smegmatis ATCC 14468, Salmonella enterica ATCC 10708, and Escherichia coli NRRL B-3708), one fungal strain ( Saccharomyces cerevisiae ATCC 204508), and three human cancer cell lines (PC-3, prostate; A549, lung; and U118, brain).…”