Eight-Membered Cyclic 1,2,3-Trithiocane Derivatives from Perophora viridis, an Atlantic Tunicate

Abstract

Two novel sulfur derivatives, one of which is a glycoside, containing substituted 1,2,3‐trithiocane cycles were isolated from Perophora viridis which was collected off the Atlantic coast of North Carolina. They were characterized by spectroscopic methods, mainly 1H NMR, 13C NMR, IR and UV spectroscopy and mass spectrometry. The compounds gave positive results in the brine shrimp toxicity assay and the sea urchin test. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Neogrisemycin, a Trisulfide-Bridged Angucycline, Produced upon Expressing the Thioangucycline Biosynthetic Gene Cluster in Streptomyces albus J1074

“…Natural products bearing a trisulfide bridge have been attractive and challenging targets for synthetic campaigns, 6 exemplified by the total synthesis of calicheamicin γ 1 (2) by Nicolaou and co-workers in 1992 7 and of luteoalbusins by Movassaghi and co-workers in 2015. 8 Trisulfide bridgecontaining natural products, such as luteoalbusin B (3), 9 (2E,4′R,5′S,6′S,7′R)-3-{7′-hydroxy-4′,6′-dimethyl-4′-(3″methylenepent-4″-enyl)[1′,2′,3′]trithiocan-5′-yl} acrylic acid (4), 10 cis-5-hydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-4-(2″imidazolyl)-1,2,3-trithiane (5), 11 and a psammaplin congener (6) 12 (Figure 1), therefore continue to inspire innovations in synthetic organic chemistry. [6][7][8]13 We recently reported the isolation of a group of sulfurbridged angucyclines, the thioangucyclines (TACs), from Streptomyces sp.…”

Neogrisemycin, a Trisulfide-Bridged Angucycline, Produced upon Expressing the Thioangucycline Biosynthetic Gene Cluster in Streptomyces albus J1074

“…Natural products bearing a trisulfide bridge have been attractive and challenging targets for synthetic campaigns, 6 exemplified by the total synthesis of calicheamicin γ 1 (2) by Nicolaou and co-workers in 1992 7 and of luteoalbusins by Movassaghi and co-workers in 2015. 8 Trisulfide bridgecontaining natural products, such as luteoalbusin B (3), 9 (2E,4′R,5′S,6′S,7′R)-3-{7′-hydroxy-4′,6′-dimethyl-4′-(3″methylenepent-4″-enyl)[1′,2′,3′]trithiocan-5′-yl} acrylic acid (4), 10 cis-5-hydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-4-(2″imidazolyl)-1,2,3-trithiane (5), 11 and a psammaplin congener (6) 12 (Figure 1), therefore continue to inspire innovations in synthetic organic chemistry. [6][7][8]13 We recently reported the isolation of a group of sulfurbridged angucyclines, the thioangucyclines (TACs), from Streptomyces sp.…”

Evolution of probiotics in aquatic world: Potential effects, the current status in Egypt and recent prospectives

“…Acebal et al [113] , [114] detected large numbers of antibiotics from marine bacteria as lotoatins from Bacillus spp., agrochelin and sesbanimides from Agro-bacterium , 5-indomycinone and dihydrophenomycin methyl ester from Streptomyces spp. Rezanka and Dembitsky [115] recorded that antibiotic production has recently been found to be produced by a variety of organisms present in the marine surface environment as tunicates, sponge and bacteria.…”

Disulfide- and Multisulfide-Containing Metabolites from Marine Organisms

“…Two unusual eight-membered cyclic 1,2,3-trithiocane derivatives 25 and 26 , one of them a glycoside, were isolated from tunicate Perophora viridis collected from the Atlantic coast of North Carolina Their structures including relative stereochemistries were deduced from analyses of their 2D NMR spectra (COSY, HMQC, HMBC, and NOESY), while methylthiopropionate (MTPA) derivation of the hydroxyl groups on their eight-membered rings helped to secure their absolute configurations.…”

Neogrisemycin, a Trisulfide-Bridged Angucycline, Produced upon Expressing the Thioangucycline Biosynthetic Gene Cluster in Streptomyces albus J1074

“…Natural products bearing a trisulfide bridge have been attractive and challenging targets for synthetic campaigns, 6 exemplified by the total synthesis of calicheamicin γ 1 (2) by Nicolaou and co-workers in 1992 7 and of luteoalbusins by Movassaghi and co-workers in 2015. 8 Trisulfide bridgecontaining natural products, such as luteoalbusin B (3), 9 (2E,4′R,5′S,6′S,7′R)-3-{7′-hydroxy-4′,6′-dimethyl-4′-(3″methylenepent-4″-enyl)[1′,2′,3′]trithiocan-5′-yl} acrylic acid (4), 10 cis-5-hydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-4-(2″imidazolyl)-1,2,3-trithiane (5), 11 and a psammaplin congener (6) 12 (Figure 1), therefore continue to inspire innovations in synthetic organic chemistry. [6][7][8]13 We recently reported the isolation of a group of sulfurbridged angucyclines, the thioangucyclines (TACs), from Streptomyces sp.…”

Evolution of probiotics in aquatic world: Potential effects, the current status in Egypt and recent prospectives

“…Acebal et al [113] , [114] detected large numbers of antibiotics from marine bacteria as lotoatins from Bacillus spp., agrochelin and sesbanimides from Agro-bacterium , 5-indomycinone and dihydrophenomycin methyl ester from Streptomyces spp. Rezanka and Dembitsky [115] recorded that antibiotic production has recently been found to be produced by a variety of organisms present in the marine surface environment as tunicates, sponge and bacteria.…”

Disulfide- and Multisulfide-Containing Metabolites from Marine Organisms

“…Two unusual eight-membered cyclic 1,2,3-trithiocane derivatives 25 and 26 , one of them a glycoside, were isolated from tunicate Perophora viridis collected from the Atlantic coast of North Carolina Their structures including relative stereochemistries were deduced from analyses of their 2D NMR spectra (COSY, HMQC, HMBC, and NOESY), while methylthiopropionate (MTPA) derivation of the hydroxyl groups on their eight-membered rings helped to secure their absolute configurations.…”

Neogrisemycin, a Trisulfide-Bridged Angucycline, Produced upon Expressing the Thioangucycline Biosynthetic Gene Cluster in Streptomyces albus J1074

“…Natural products bearing a trisulfide bridge have been attractive and challenging targets for synthetic campaigns, 6 exemplified by the total synthesis of calicheamicin γ 1 (2) by Nicolaou and co-workers in 1992 7 and of luteoalbusins by Movassaghi and co-workers in 2015. 8 Trisulfide bridgecontaining natural products, such as luteoalbusin B (3), 9 (2E,4′R,5′S,6′S,7′R)-3-{7′-hydroxy-4′,6′-dimethyl-4′-(3″methylenepent-4″-enyl)[1′,2′,3′]trithiocan-5′-yl} acrylic acid (4), 10 cis-5-hydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-4-(2″imidazolyl)-1,2,3-trithiane (5), 11 and a psammaplin congener (6) 12 (Figure 1), therefore continue to inspire innovations in synthetic organic chemistry. [6][7][8]13 We recently reported the isolation of a group of sulfurbridged angucyclines, the thioangucyclines (TACs), from Streptomyces sp.…”

Evolution of probiotics in aquatic world: Potential effects, the current status in Egypt and recent prospectives

“…Acebal et al [113] , [114] detected large numbers of antibiotics from marine bacteria as lotoatins from Bacillus spp., agrochelin and sesbanimides from Agro-bacterium , 5-indomycinone and dihydrophenomycin methyl ester from Streptomyces spp. Rezanka and Dembitsky [115] recorded that antibiotic production has recently been found to be produced by a variety of organisms present in the marine surface environment as tunicates, sponge and bacteria.…”

Disulfide- and Multisulfide-Containing Metabolites from Marine Organisms

“…Two unusual eight-membered cyclic 1,2,3-trithiocane derivatives 25 and 26 , one of them a glycoside, were isolated from tunicate Perophora viridis collected from the Atlantic coast of North Carolina Their structures including relative stereochemistries were deduced from analyses of their 2D NMR spectra (COSY, HMQC, HMBC, and NOESY), while methylthiopropionate (MTPA) derivation of the hydroxyl groups on their eight-membered rings helped to secure their absolute configurations.…”