Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

AC1O3DLL [(7R,8S)-7-hydroxy-5,6,7,8- tetrahydro-3H...

Synonyms:

Frölich, C. et al., Honda, Y. et al., Hartmann, T. et al., Haberer, W. et al.

Hartmann, Theuring, Witte, Pasteels,

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High impact information on Lycopsamine

In roots and rhizomes PAs of the lycopsamine type typical for the Boraginaceae could be detected, e. g. intermedine, lycopsamine, and their O(7)-derivatives [1].
Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species [2].
Firstly, the necine bases are structurally modified and either before or after this modification are converted into their O(9)-esters by esterification with one of the stereoisomers of 2,3-dihydroxy-2-isopropylbutyric acid, the unique necic acid of PAs of the lycopsamine type [2].
Platyphora boucardi leaf-beetles sequester tertiary pyrrolizidine alkaloids of the lycopsamine type acquired from their host-plant Prestonia portobellensis (Apocynaceae) and synthesize their own alkaloids from exogenous retronecine and aliphatic 2-hydroxy acids [3].

Associations of Lycopsamine with other chemical compounds

Since VL was suspected to be derived from pyrrolizidine alkaloids (PAs) acquired as an adult, tests for feeding response to and oral administration of four PAs (a 4:1 mixture of intermedine/lycopsamine, heliotrine, monocrotaline, and retronecine) were conducted [4].

Analytical, diagnostic and therapeutic context of Lycopsamine

In behavioral bioassays to test the attractivity of PAs to males, all individuals tested were attracted exclusively to intermedine/lycopsamine [4].

References

Pyrrolizidine alkaloids in Pulmonaria obscura. Haberer, W., Witte, L., Hartmann, T., Dobler, S. Planta Med. (2002) [Pubmed]
Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. Frölich, C., Ober, D., Hartmann, T. Phytochemistry (2007) [Pubmed]
Sequestration, metabolism and partial synthesis of tertiary pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. Hartmann, T., Theuring, C., Witte, L., Pasteels, J.M. Insect Biochem. Mol. Biol. (2001) [Pubmed]
Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): Their origins and male behavioral responses to pyrrolizidine alkaloids. Honda, Y., Honda, K., Omura, H. J. Insect Physiol. (2006) [Pubmed]

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