Purealidins

Similarly, Aplysina sp.(Fig. 10.7), which show a dramatic change in color from yellow to black when exposed to air, contain cytotoxic compounds including bromotyrosine-derivative alkaloids, purealidins (Ishibashi et ah, 1991 Yagi et ah, 1993), aplysamine 2 (Xynas and Capon, 1989), and purpuramin G (Fattorusso et ah, 1970 Fig. 10.8). 

Ishibashi, M., Tsuda, M., Ohizumi, Y., Sasaki, T., and Kobayashi, J. (1991). Purealidin A, a new cytotoxic bromotyrosine-derived alkaloid from the Okinawan marine sponge Psammaplysilla purea. Experientia 47, 299-300. 

The Okinawan sponge Psammaplysilla purea that contains purealidins M-0 (2004-2006) also yields purealidins J (2078), K (2079), L (2080), P (2081), Q (2082), and R (2083) (1835). Purealidin J (2078) is the antipode of pseudocer-atinine A (2089). The Indian sponge Psammaplysilla purpurea, which is the source of purpurealidins F-H (2018-2020) and other bromotyrosines (vide supra), also contains purpurealidins A (2084), B (2085), C (2086), and D (2087) (1842). A Caribbean Pseudoceratina sponge has afforded the simple carboxylic acid 2088 (1868). The New Caledonian sponge Pseudoceratina verrucosa, which is the source of pseudoceratinine B (1990), also contains pseudo-ceratinines A (2089) and C (2090), the absolute configurations of which are shown (1829). 

A collection of the sponge Suberea aff. praetensa from the Gulf of Thailand contains 11,17-dideoxyagelorins A (2119) and B (2120) (1890), and the Fijian sponge Druinella sp. has afforded purealidin S (2121) (1861). The Malaysian crinoid Himerometra magnipinna has furnished (+)-12-hydroxyhomoaerothionin (2122) (1891). 

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... 

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

Boehlow TR, Harbum JJ, Spilling CD (2001) Approaches to the Synthesis of Some Tyrosine-Derived Marine Sponge Metabolites Synthesis of Verongamine and Purealidin N. J Org Chem 66 3111... 

Purealidin D (114) was isolated from the Okinawan sponge Psammaplysilla purea as an inhibitor of Na+, K+-ATPase. Its structure was determined using FABMS, HRFABMS, IR, UV, and one- and two-dimensional H and NMR [321]. 

Purealidin C. The structures of several bromotyrosine-derived alkaloids were reported from the Okinawan marine sponge, Psammaplysilla purea by Kobayashi et al. (1991c). Structurally, purealidin B (48) is perhaps the most... 

Long-range connectivities from an HMBC spectrum were utilized to establish the structure of the side-chain of purealidin C (49). These connectivities are shown on the structure and illustrate the ability of long-range... 

J3-Dihydro, 13-oxo (72RS)-. [167394-76-5]. Purealidin K CisHnBrjNgOs M 507.138 Alkaloid from P. purea. Shows mod. inhibition of epidermal growth factor receptor kinase. Oil (as trifluoroacetate). [a] " +26 (c, 0.38 in MeOH) (trifluoroacetate). 

Alkaloid from the Okinawan marine sponge Psammaplysilla purea. Oil (as trifluoroacetate). Deamino [167394-79-8]. Purealidin N... 

---