Recent Synthetic Studies Leading to Structural Revisions of Marine Natural Products

Usami, Yoshihide

doi:10.3390/md7030314

Cited by 60 publications

(25 citation statements)

References 59 publications

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“…A variety of marine natural products with their specific activities, such as antimalarial, antituberculosis, anticancer, antifoulants, anti-inflammatory, anti-HIV, etc., have been reported from diverse marine organisms such as cyanobacteria, macroalgae, phytoplankton and animals [22,28]. In recent years, natural products from marine organisms have gained increasing research awareness, and a number of novel marine compounds of potential economic importance have been reported from different marine organisms [22,60,61,111,123,216,230,231].…”

Section: Introductionmentioning

confidence: 99%

Photoprotective compounds from marine organisms

Rastogi

Richa

Sinha

et al. 2010

J Ind Microbiol Biotechnol

194

139

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The substantial loss in the stratospheric ozone layer and consequent increase in solar ultraviolet radiation on the earth's surface have augmented the interest in searching for natural photoprotective compounds in organisms of marine as well as freshwater ecosystems. A number of photoprotective compounds such as mycosporine-like amino acids (MAAs), scytonemin, carotenoids and several other UV-absorbing substances of unknown chemical structure have been identified from different organisms. MAAs form the most common class of UV-absorbing compounds known to occur widely in various marine organisms; however, several compounds having UV-screening properties still need to be identified. The synthesis of scytonemin, a predominant UV-A-photoprotective pigment, is exclusively reported in cyanobacteria. Carotenoids are important components of the photosynthetic apparatus that serve both light-harvesting and photoprotective functions, either by direct quenching of the singlet oxygen or other toxic reactive oxygen species or by dissipating the excess energy in the photosynthetic apparatus. The production of photoprotective compounds is affected by several environmental factors such as different wavelengths of UVR, desiccation, nutrients, salt concentration, light as well as dark period, and still there is controversy about the biosynthesis of various photoprotective compounds. Recent studies have focused on marine organisms as a source of natural bioactive molecules having a photoprotective role, their biosynthesis and commercial application. However, there is a need for extensive work to explore the photoprotective role of various UV-absorbing compounds from marine habitats so that a range of biotechnological and pharmaceutical applications can be found.

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Section: Introductionmentioning

confidence: 99%

Photoprotective compounds from marine organisms

Rastogi

Richa

Sinha

et al. 2010

J Ind Microbiol Biotechnol

194

139

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“…59 Various aspects of the biosynthesis of marine natural products have been reviewed. 65 The MarinLit database 66 has been updated and was used as the literature source for the preparation of this present review. Recent synthetic studies leading to structural revision of marine natural products have been collated.…”

Section: Mich Ele Prinsepmentioning

confidence: 99%

Marine natural products

et al. 2011

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“…[9] While marine secondary metabolites,t hus, offer significant potential as lead structures for drug discovery, the initial research into their biochemicala nd pharmacological effectsi so ften hampered by the very limited amountso fm aterial available from the natural source.I nt his context total synthesis plays an essential role as an enabling technologyt oe stablisht he true potentialofabioactive marine secondary metabolite for drug discovery. [10] At am ore fundamental level, the availability of stereochemically defined synthetic material can be essential to confirm (or refute) the original structure assignment of an atural product, [11] notwithstanding the existence of highly sophisticated modern analytical tools forstructure elucidation.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Biological Assessment of Mandelalide A

Brütsch

Bucher

Altmann

2015

Chemistry A European J

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A new convergent total synthesis of the marine macrolide mandelalide A (1) has been developed that is based on macrocyclic ring closure by a Shiina-type macrolactonization and the construction of the requisite precursor seco acid by a highly efficient Sonogashira cross-coupling reaction between two fragments of comparable complexity. Key steps in the elaboration of the acid building block were the enantioselective, catalytic addition of a protected acetylene to crotonaldehyde and the construction of the tetrahydropyran unit that is embedded in the macrocycle by means of an acid-catalyzed Prins reaction. The synthesis of the alcohol fragment features the formation of the trisubstituted tetrahydrofuran ring through an acetal cleavage/epoxide opening cascade reaction and a rarely used radical alkynylation of a primary alkyl iodide. Intriguingly, the dihydroxylation of a terminal double bond as part of the synthesis of this building block gave the same major product for both the α- and β-AD-mix reagents, albeit with moderate or low selectivity. Synthetic mandelalide A (1) was a potent proliferation inhibitor of A549, HT460, and H1299 human lung cancer cells in vitro, but not of SK-N-SH neuroblastoma cells. However, in no case did we observe complete cell kill even at the highest compound concentration tested (5 μm).

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Recent Synthetic Studies Leading to Structural Revisions of Marine Natural Products

Cited by 60 publications

References 59 publications

Photoprotective compounds from marine organisms

Photoprotective compounds from marine organisms

Marine natural products

Total Synthesis and Biological Assessment of Mandelalide A

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