Marine natural products

Abstract

Covering: 2010. Previous review: Nat. Prod. Rep., 2011, 28, 196. This review covers the literature published in 2010 for marine natural products, with 895 citations (590 for the period January to December 2010) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1003 for 2010), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

“…Recently, Blunt and co-workers indicated that the structures for the highly brominated derivatives 695−697 should be re-examined because of inconsistencies in the published NMR data for these compounds. 401 …”

“…Compounds of this class are generally brominated, with three of them chlorinated (407−409) 258 and four bromochlorinated (410, 411, 258 415, 72 and 416). 264 The first halogenated THF ACG to be reported was laureepoxide (401), which was isolated from L. nipponica collected from Hokkaido, Japan. 260 This compound is also the first example of a brominated ACG derivative containing both oxolane and oxirane rings.…”

Induced Production of Methyl Bromodihydroxyphenyl Acetates by the Marine-Derived Fungus Aspergillus sp.

“…1,2) When marine-derived microorganisms are cultured under saline conditions, they rarely produce interesting biological halogenated metabolites (e.g., salinosporamide A, 3) a highly potent inhibitor of the 20S proteasome, and its halogenated derivatives 4) ; cytotoxic halogenated polyenyl pyrroles, isorumbrin and bromoisorumbrin 5) ; the nematicidal and antimicrobial lachnumon and mycorrhizin A derivatives 6) ; bromomyrothenone B 7) ; and the antibacterial chlorohydroaspyrones A and B 8) ). Encouraged by the detection of bioactive halogenated marine analogs, and in an effort to gain access to a wider cross-section of halogenated secondary metabolites, we manipulated fermentation of the marine-derived fungi Phoma herbarum, Penicilliun chrysogenum, Fusarium tricinctum, and Dothideomycete sp.…”

Marine biodiversity: exploring bioactive chemical space

“…The triturated fractions were subjected to HPLC-DAD-ESI-MS analysis. Further confirmation about the structure was achieved with 13 C NMR data comparison to that in literature ( Carduusynes can undergo solvolysis in EtOH to generate the respective ethyl esters as evident from the isolation and characterisation of carduusynes A-E. 173 In the current study, we isolated a new analogue, carduusyne F ethyl ester, further indicating the existence of its acetylenic acid natural product carduusyne F (2.04). conditions at 30 µM but did not show any activity at lower concentrations.…”

“…NMR (DMSO-d 6 ) data for 3.02 revealed similarities with that of 3.01, with the key differences apparent in the 13 to C-7a'') with a sp 3 methine (C-6'''), a primary methyl (C-7'''), and a C-2'''-imidazole moiety in required NH-1 and the H 3 -7 to be on the same plane, and established a relative stereochemistry in common with dragmacidin E (3.02). Furthermore, a similar cotton effect in the CD spectra of 3.02 and 3.03 (Figure 3.11) strongly supported the proposed stereochemistry.…”