Isoprenoids sponges

Chemical bias toward certain molecular arrangements may also determine the commonness of certain metabolites (Pietra 1995), such as the aplysinopsins (indole alkaloids of many sponges, cnidarians, and mollusks. Chart 8.2. A), bis-indole and guanidine alkaloids (Chart 8.2.A), isoprenoids (Pietra 1995, Chart 8.2.1), and polypropionates of mollusks, sponges, and fungi (Chart 8.2.FA/PO). 

Rudi, A. Yosief, T. Schl er, M. Kashman, Y. (1999B) Several new isoprenoids from two marine sponges of the family Axinellidae. Tetrahedron, 55, 5555-66. 

Metabolites of the phylum Porifera account for almost 50% of the natural products reported from marine invertebrates. Of the 2609 poriferan metabolites, 98% are derived from amino acid, acetogenin, or isoprenoid pathways. Isoprenoids account for 50% of all sponge metabolites, while amino acid and polyketide pathways account for 26% and 22%, respectively. A significant number of sponge metabolites appear to be derived from mixed biosynthetic pathways. Most structures reported containing carbohydrate moieties were glycosides. 

Garson, M. J., Partali, V., Liaaen-Jensen, S., and Stoilov, I. L., Isoprenoid biosynthesis in a marine sponge of the Amphimedon genus incorporation studies with [l-14C]cholesterol and [2-14C]meva-lonate, Comp. Biochem. Physiol., 91B, 293, 1988. 

The synthesis of tedanin 589, an isoprenoid pigment of the marine sponge Tedanis digitata, starts with the Wittig reaction of phosphorane 506 with the carbonyl compound 587, giving 588. Bromination of the latter followed by treatment with KOH/methanol and twofold oxidation yield tedanin 589 280) (Scheme 99). 

Polyterpenoids.— C N.m.r. has been used to investigate the structure of the C55 polyprenol moraprenol-11 (190) from leaves of Moms alba. The main component has the trans-trans-trans-cis-cis-cis-cis-cis-cis-cis-OH configuration. The monophosphate of this compound was prepared in 34% yield by treatment with o-phenylenephosphorochloridate. Biosynthetic studies have provided evidence for the formation of 2,3-dehydrodolichyl phosphate (191) as an intermediate in dolichyl phosphate (192) biosynthesis. Most of the members of a series of C2S—C40 acyclic hydrocarbons obtained from crude oil have isoprenoid or degraded isoprenoid structures. The mokupalides from a marine sponge have been shown to be hexaprenoids with structures (193)—(195). ... 

A new class of sesterterpenes in which the middle three units of a penta-isoprenoid chain cyclised into a bicyclic system, leaving the first and the last isoprenoids to substitute the decaline moiety, was isolated from sponges of genus Dysidea and Ircinia. From the Palauan Dysidea sp. was isolated dysideapalaunic acid (107) that inhibited the aldose reductase [124]. An inhibitor of aldose reductase is expected to prevent neuropathy or cataract as a complication of diabetes. These diseases are caused by the accumulation of sorbitol in the peripheral nerve or the crystalline lens, as a result of enzymatic reduction of glucose by the aldose reductase in the sorbitol cycle [125,126]. The absolute stereochemistry of dysideapalaunic acid was established by its total synthesis [127,128],... 

The isoprenoid fatty acid 5,9,13-trimethyltetradecanoic acid (4) is a rather intriguing fatty acid, which has been isolated from several sponges... 

The non-isoprenoid aromatic ester methyl nidorellaurinate (684) has been synthesized. Another non-isoprenoid compound is upial (685), which has been isolated from the marine sponge Dysidea fragilis. It possesses the rare bicyclo[3.3.1]octyl system and possibly it is related to microcionin-4 (686),... 

Invertebrates comprise about 60% of all marine animal diversity [12], the phyla Porifera and Cnidaria are the two dominant sources of NMNPI worldwide together responsible for 72% of the compounds, and 77% of the compounds are isolated from marine invertebrates. Within each phylum above the majority of substances belong to a single class of sponges (Porifera Demospongiae) and one class of corals (Cnidaria Anthozoa Fig. 1) [5,13-15]. The majority of coral compounds are derived from the isoprenoid... 

Izumikawa, M., Khan, S.T., Takagi, M., and Shin-ya, K. (2010) Sponge-derived Streptomyces produdng isoprenoids via the mevalonate pathway,/, Nat. Prod., 73, 208-212. 

Bamathan, G. and Kornprobst, J.M. (1998) Isoprenoid 6tty adds in sponge phospholipids. A review. Recent Res. Dev. Lipids Res., 2,235-248. 

Bamathan, G., Miralles, J., and Kornprobst, J.-M. (1993a) Sponge fatty adds. 4. Co-occurrence of two isoprenoid fatty adds (4,8,12-trimethyltridecanoic and 5,9,13-trimethyltetradecanoic) in phospholipids of marine sponges from the genus Cmachyrella. Nat. Prod. Letters., 3,113-118. 

CarbaHerra. N.M.. Maldonado, L, and Porras, B. (1987) Isoprenoid fatty adds from marine sponges. Are sponges selective Lipids, 22, 767-769. 

Rezanka, T. and Dembitsky, VM. (1993) Isoprenoid polyunsaturated fatty acids from freshwater sponges, f. Nat. Prod., 56,1898-1904. 

Silva, C.J., Wiinsche, L., and Djerassi, C. (1991) Biosynthetic studies of marine lipids 35. The demonstration of de novo sterol biosynthesis in sponges using radiolabelled isoprenoid precursors. Comp. Biochem. Physiol, 99B, 763-773. 

By working with a very small amounts of material Walton and Pennock 182) observed that the sponge Grantia compressa utilized " C-mevalonate for the biosynthesis of isoprenoids (squalene, steroids and ubiquinones) in direct contrast with the complete absence of radioactivity in the terpenoids of Suberites domuncula incubated with C-mevalonate. 

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