Biosynthesis of polyketides by trans-AT polyketide synthases

Deep Sea Adriana Lorente,†,‡ Janire Lamariano-Merketegi,†,‡ Fernando Albericio,†,‡,§,# and Mercedes Álvarez*,†,‡,⊥ †Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain ‡CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain School of Chemistry, University of KwaZulu-Natal, 4001-Durban, South Africa Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain

Tetrahydrofuran-containing macrolides: a fascinating gift from the deep sea.

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon–carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.

/pdf/palladium-catalyzed-1-4-difunctionalization-of-butadiene-to-4osy5t6b2m.pdf

Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Chlorinated macrolides, haterumalide NA, B and NE, and a new haterumalide X, were produced by the soil bacterium Serratia plymuthica. Haterumalides NA, B and NE caused complete suppression of apothecial formation in sclerotia of Sclerotinia sclerotiorum at a concentration of 0.5 μg ml−1. Ascospore germination of this fungus was inhibited in the concentration range 0.8–3.0 μg ml−1. Haterumalides NA, B and NE prevented spore germination of several other filamentous fungi as well as Oomycetes at concentrations ranging from 0.4 to 40 μg ml−1, but did not show any effect against the yeast Candida albicans. Inhibition data could not be collected for haterumalide X due to its rapid conversion to haterumalide NA. The bacterium also produced two other antifungal metabolites: pyrrolnitrin and 1-acetyl-7-chloro-1-H-indole, which in contrast to the haterumalides, did not inhibit the apothecial formation on sclerotia. Pyrrolnitrin, and haterumalide NA, B and NE effectively inhibited spore germination of tested filamentous fungi at concentrations ranging from 0.06 to 50 μg ml−1, whereas 1-acetyl-7-chloro-1-H-indole inhibited spore germination only at concentrations above 50 μg ml−1. The minimal inhibitory concentrations of the respective compounds needed for total inhibition of spore germination varied for the fungal species tested.

Broad-spectrum antifungal metabolites produced by the soil bacterium Serratia plymuthica A 153

Total synthesis of (+)-oocydin A: application of the Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl 9-BBN.

Haterumalide B: A new cytotoxic macrolide from an Okinawan ascidian Lissoclinum sp.

Flag leaf cell wall functional groups and components play a crucial role in the accumulation and translocation of Cd in rice grain via foliage application of humic acid.

Haterumalide B (1), a new cytotoxic macloride, was isolated from an Okinawan ascidian Lissoclinum sp. and its structure of 1 determined by spectroscopic investigation. Haterumalide B completely inhibited the first cleavage of fertilized sea urchin eggs at a concentration of 0.01 μg/ml.

Haterumalide B: A New Cytotoxic Macrolide from an Okinawan Ascidian Lissoclinum sp.

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Haterumalide B: A new cytotoxic macrolide from an Okinawan ascidian Lissoclinum sp.

Flag leaf cell wall functional groups and components play a crucial role in the accumulation and translocation of Cd in rice grain via foliage application of humic acid.

Haterumalide B: A New Cytotoxic Macrolide from an Okinawan Ascidian Lissoclinum sp.