Yuremamine is a phytoindolealkaloid which was isolated from the bark of Mimosa tenuiflora in 2005, and erroneously assigned a pyrrolo[1,2-a]indole structure that was thought to represent a new class of indole alkaloids.[2] However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative.[3] It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, but total synthesis revealed that yuremamine as a free base is colorless, and the formation of a trifluoroacetate salt during HPLC purification is what led to the purple appearance.[3]
Originally proposed chemical structure of yuremamine
^Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (26 January 2010). Dictionary of Alkaloids with CD-ROM. CRC Press. p. 2033. ISBN 978-1-4200-7770-4.
^Vepsäläinen, J. J.; Auriola, S.; Tukiainen, M.; Ropponen, N. & Callaway, J. (2005). "Isolation and characterization of Yuremamine, a new phytoindole". Planta Medica. 71 (11): 1049–1053. doi:10.1055/s-2005-873131. PMID16320208. S2CID260250347.
^ abCalvert, Matthew B.; Sperry, Jonathan (2015). "Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora". Chemical Communications. 51 (28): 6202–6205. doi:10.1039/c5cc00380f. PMID25756921.
