570411-29-9Relevant academic research and scientific papers
Ipobscurines C and D: Macrolactam-type indole alkaloids from the seeds of Ipomoea obscura
Jenett-Siems, Kristina,Weigl, Robert,Kaloga, Macki,Schulz, Jutta,Eich, Eckart
, p. 1257 - 1263 (2007/10/03)
Separation of the methanolic seed extract of Ipomoea obscura afforded five indole alkaloids, three of them (ipobscurines B-D) being new natural products of a unique structural type characterized as serotonin hydroxycinnamic acid amide-type conjugates with a second phenylpropanoid moiety forming an ether with the 5-OH position of the indole nucleus. Due to an oxidative phenolic coupling between the two phenylpropanoid moieties of the supposed precursor ipobscurine B two 21-membered macrolactams with a phenol ether partial structure are formed: the trans-cis isomers ipobscurines C and D. Their structures were established on the basis of spectral data. Moreover, total synthesis of the racemic erythro- and threo-ipobscurine B 4′,4″-dimethyl ethers and the comparison with the corresponding derivative of natural (-)-ipobscurine B proved an erythro configuration of the latter.
