Alkaloids bromotyrosine

While there exist too many syntheses of bromotyrosine alkaloids to delineate here, two illustrative examples are those of moloka iamine (1865) and the mycothiol-S -conjugate amidase inhibitor 2068 (1866). 

Benharref A, Pais M, Debitus C (1996) Bromotyrosine Alkaloids from the Sponge Pseudoceratina verrucosa. J Nat Prod 59 177... 

Kobayashi J, Honma K, Sasaki T, Tsuda M (1995) Purealidins J-R, New Bromotyrosine Alkaloids from the Okinawan Marine Sponge Psammaplysillapurea. Chem Pharm Bull 43 403... 

Tsuda M, Endo T, Watanabe K, Fromont J, Kobayashi J (2002) Nakirodin A, a Bromotyrosine Alkaloid from a Verongid Sponge. J Nat Prod 65 1670... 

Tsuda M, Sakuma Y, Kobayashi J (2001) Subserediamines A and B, New Bromotyrosine Alkaloids from a Sponge Subera Species. J Nat Prod 64 980... 

Nicholas GM, Newton GL, Fahey RC, Bewley CA (2001) Novel Bromotyrosine Alkaloids Inhibitors of Mycothiol S-Conjugate Amidase. Org Lett 3 1543... 

Tabudravu JN, Jaspars M (2002) Purealidin S and Purpuramine J, Bromotyrosine Alkaloids from the Fijian Marine Sponge Druinella sp. J Nat Prod 65 1798... 

Assmann M, Wray V, van Soest RWM, Proksch P (1998) A New Bromotyrosine Alkaloid from the Caribbean Sponge Aiolochroia crassa. Z Naturforsch 53c 398... 

Crews has also formulated a biosynthetic pathway for the disulfide bromotyrosine psammaplins from the sponge Pseudoceratina purpurea [64,126]. The structurally unique ma edamines (80, 81) may be derived from a dehydro derivative of aplysa-mine-2 or purpuramine H via cyclization and dehydroxylation [69]. The numerous bromotyrosine alkaloids that contain an aminopropanol unit, such as nakirodin A (71), may be derived from a homoserine unit through decarboxylation [60]. The... 

Characterization of Ceratinadin A—A Quinoline-Containing Bromotyrosine Alkaloid from an Okinawan Marine Sponge... 

Kobakyashi and coworkers [82] reported the isolation and characterization of three bromotyrosine alkaloids isolated from an Okinawan marine sponge, Pseudoceratina sp. Two of the three alkaloids contained 4-quinolone moieties in the structures, which provides the basis for the present categorization. It is quite common for spectroscopists working with families of compounds to fingerprint them using, for example, and shifts obtained from multiplicity-edited HSQC spectra. Kobakyashi s group extended this idea further to include the diagnostic H7—N9 correlation of ceratinadin-A, which resonates quite far downfield at 384.2 ppm. It should also be noted... 

Y. Kon, T. Kubota, A. Shibazaki, T. Goni, J. Kobakyashi, Ceratinadins A-C, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp, Bioorg. Med. Chem. Lett. 20 (2010) 4569-4572. 

Nicholas, G.M., Newton, G.L., Fahey, R.C., and Bewley, C.A, (2001) Novel bromotyrosine alkaloids inhibitors of mycothiol S-conjugate amidase. Org, Lett., 3, 1543-1545. 

Hirano, K., Kubota. T, Tsuda, M., Watanabe, K., Fromont, J., and Kobayashi, J. (2000b) Ma edamines A and B, cytotoxic bromotyrosine alkaloids with a imique 2(lH)-pyiazinone ring from sponge Suberea sp. Tetrahedron, 56,8107-8110. 

Kobayashi, (., Honma, K., Sasaki, T, and Tsuda, M. (1995c) Purealidins (-R, new bromotyrosine alkaloids from the Okinawan marine sponge Psammaplysilla purea. Chem. Pharm. Butt., 43,403-407. 

Tabudravu, J.N. and Jaspars, M. (2002) Purealidin S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinella sp. J. Nat Prod., 65, 1798-1801. 

Tdvi, S., Rodrigues, C., Naik, C.G., Parameswaran, P.S., and WahiduUa, S. (2004) New bromotyrosine alkaloids from the marine sponge PsammaplysSla purpurea. Tetrahedron, 60,10207—10215. 

Yoshida, M. and Yamaguchi, K. (2009) Total synthesis of the marine bromotyrosine alkaloid moloka iakitamide. Chem. Pharm. Bull., 57, 1147-1149. 

Pseudoceratinine B (151), in which the oxime is reduced and tri-methylated, was isolated from Pseudoceratina verrucosa (89). The absolute configuration of tyrosine was deduced from the positive Cotton effect at 212 nm, corresponding to an 5-configuration (106). Pseudoceratinine B (151) is the second bromotyrosine alkaloid containing a non-oxidized amino group. 

Bromotyrosine derivatives were first isolated in the process of searching for antibiotics from marine sources. The dienone 1, aeroplysinin-1 (14), and aerothionin (68) are the earliest antimicrobial bromotyrosine derivatives (2,14,58). The antibacterial and antifungal activities of the bromotyrosine alkaloids are summarized in Table IV and... 

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