Isolation and Total Synthesis of Beru’amide, an Antitrypanosomal Polyketide from a Marine Cyanobacterium <i>Okeania</i> sp.
Raimu Taguchi, Arihiro Iwasaki, Akira Ebihara, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga
Abstract
A 68 μg amount of an acyclic polyketide, named beru’amide, was isolated from a marine cyanobacterium Okeania sp. Beru’amide contains six unique moieties in its relatively small skeleton. By applying several cutting-edge techniques, including DFT-based chemical shift calculations, we achieved the structure determination and the total synthesis of this highly functionalized scarce natural product. Furthermore, beru’amide was shown to have strong antitrypanosomal activity.
Topics & Concepts
PolyketideAmideChemistryIsolation (microbiology)StereochemistryTotal synthesisSpongeCombinatorial chemistryBotanyOrganic chemistryBiochemistryMicrobiologyBiologyBiosynthesisGeneChemical synthesis and alkaloidsTraditional and Medicinal Uses of AnnonaceaeMicrobial Natural Products and Biosynthesis