Indolizidine and quinolizidine alkaloids

Quinolizidine-Type Alkaloids: Chemodiversity, Occurrence, and Bioactivity

“…The other four ormosanine-like diastereomers have been reported due to the configuration of six chiral carbons (i.e., C-5, C-7, C-9, C-10, C-17, and C-18) ( 261 , 263 , 265 , and 266 ). Finally, a Δ 5(6) -containing structural variant of 264 was also reported ((−)-podopetaline, 262 ) . On the other hand, the homoormosanine-type QAs are based on a singular triazahexacyclic structure ( 267 – 271 ) involving an aloperine moiety fused with an additional azabicyclic fragment bonded at N-1 and C-9 of the aloperine moiety (Figure , Figure S13).…”

“…Finally, a Δ 5(6) -containing structural variant of 264 was also reported ((−)-podopetaline, 262 ). 24 On the other hand, the homoormosanine-type QAs are based on a singular triazahexacyclic structure ( 267 – 271 ) involving an aloperine moiety fused with an additional azabicyclic fragment bonded at N-1 and C-9 of the aloperine moiety ( Figure 14 , Figure S13 ). The additional azabicyclic moiety can be formed through a methylenediaza bridge ( 267 – 270 ) or an N-1–C-20 linking ( 271 ).…”

“…Considering that these most-known QA types are mainly associated with Fabaceae-related taxa, the present compilation was organized on the basis of three motivations: (1) lack of exclusive and comprehensive information on QAs reported to date from diversified sources, even incorporating animal sources such as sponges and frogs, since the available reviews on QAs are emphasized on occurrence in particular taxa, e.g., Sophora , ,, their bioactivities, biosynthesis, − and diversity; − (2) classification of QA structures beyond the plant-derived QAs; and (3) recognition of structural diversity and substituent variations within common QA skeletons to be described in light of their chemodiversity. Hence, this review provides comprehensive background information on the chemodiversity of QAs, focusing on their structural variants, substitutions, occurrences, and reported biological activities, harmonizing previous reviews.…”