The structures of lythranine, lythranidine, and lythramine, novel alkaloids from

Metabolomic profiling reveals shifts in defenses of an invasive plant

“…The SDH predicts that invasive genotypes evolve increased levels of toxic defense compounds as a defense against generalist herbivores, while costly digestibility reducers that are effective against specialist herbivores decrease. In our non-admixed baseline populations, we detected quinolizidine alkaloids in L. salicaria, which were not detected in previous phytochemical studies on L. salicaria (Fujita et al 1972;Willis et al 1999) but were found in other Lythrum species (Lythrum anceps) (Fujita et al 1967). Quinolizidine alkaloids have been demonstrated to play a role in plant-insect interactions as toxins or deterrents to generalists (Wink 1992).…”

“…: (0123456789) genetic introgression between L. salicaria and the native Lythrum alatum (Houghton- Thompson et al 2005). Thus far, little is known about the chemistry of L. alatum, but other Lythrum species are known to contain Lythrancine type alkaloids (Fujita et al 1967). A third possibility is that invasive genotypes formed associations with novel endophytes in the introduced range, producing these compounds (Kowalski et al 2015).…”

Synthesis of biphenyl portion of decinine

“…( 16) Shishido, K., Udo, Y., Nakamura, T., Nozaki, H., ibid., 26, 1368 (1961). (17) For complete versions of Tables I through VII, order NAPS Document No. 01244 from ASIS National Auxiliary Publications Service, % CCM Information Sciences, Inc., 909 Third Avenue, New York, N. Y.…”

“…In recent years (3,10,14,16,17,21,37), not only have the structures of several of these quinolizidine alkaloids been elucidated, but Ferris et al (15) have proposed a possible biogenetic route for their syntheses. Subsequently, Matsunaga et al (26) demonstrated the chemical feasibility of forming 2-oxo-4-quinolizidines from benzaldehyde and isopelletierine.…”