Psammaplysilla purealidins

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). 

Kobayashi J, Honma K, Tsuda M, Kosaka T (1995) Lipopurealins D and E and Purealidin H, New Bromotyrosine Alkaloids from the Okinawan Marine Sponge Psammaplysilla purea. J Nat Prod 58 467... 

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... 

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

Different iV-methylation derivatives of moloka iamine, aplysamine 1 (54) 44), purealidin F (55), and G (56) 45), were obtained from an Australian sponge Aplysina sp. and the Okinawan sponge Pscanmaplysilla purea, respectively. 3,5-Dibromo-4-(3-dimethylaminopropoxy)phenethyl carbamic acid methyl ester (57) and its salt 58 were obtained as the first bromotyrosine derivatives containing a carbamate group from an Indian sample of Psammaplysilla purpurea 46), along with 59 47,48). 

Psammaplysilla purea and was named as purealidin R (79). Alkaloid 98 was isolated from a Caribbean sponge Pseudoceratina sp. as a major brominated metabolite (80). 

Purealidins J (116) and K (117) were isolated from the Okinawan sponge Psammaplysilla purea by Kobayashi et al. (7P). The absolute stereochemistry of the spirocyclohexadienylisoxazoline was determined by the positive Cotton effects at 248 and 184 nm in the CD spectra. Purealidin K was subjected to ozonolysis, followed by oxidation with H2O2, and subsequently acid hydrolysis. Chiral HPLC analysis of the hydrolysate revealed D- and L-2,4-diaminobutyric acids in the ratio of 1 1, suggesting that C-12 of purealidin K is racemic. A similar alkaloid, 14-oxo-aerophobin-2 (118), was identified from the Caribbean sponge Aplysina insularis 88). The stereochemistry of C-13 was not determined. 

Compound 199 and purealidin O (200) are two oxime-type bromotyrosine-derived metabolites containing an agmatine moiety, isolated from Psammaplysilla purea and Oceanapia sp., respectively (79,90). Alkaloids 201, 202, and 203 were iodinated tyrosine derivatives isolated from the ascidian Aplidium sp. (127). 

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