The structure of lobinaline

Robison, Michael M.; Pierson, William G.; Dorfman, Leon M.; Lambert, Bernard; Lucas, Robert A.

doi:10.1016/0040-4039(64)83045-8

Cited by 6 publications

(4 citation statements)

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“…[1][2][3][4][5] are consistent with the view that an intact C6-C2 unit, derived from phenylalanine, is incorporated into each of the two "halves" of lobinaline, in analogy with the mode of entry of the phenylalanine-derived fragment into sedamine (Scheme 1).…”

Section: Discussionsupporting

confidence: 61%

“…ref. 3), sustained attempts to devise reactions capable of yielding degradation products representing C-6, -8, -8a, and -2' failed to give useful results. Even though the interpretation of some of the incorporation data therefore rests on indirect argument, the conclusions are, for the most part, unambiguous.…”

Section: Discussionmentioning

confidence: 99%

“…Lobinaline (I), the major alkaloid of this plant species, was isolated by Manske (2) in 1938. Its structure was determined some 30 years later (3,4,5).…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of Lobinaline

Gupta¹,

Spenser²

1971

Can. J. Chem.

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The biosynthesis of lobinaline (1) in intact plants of Lobelia cardinalis L. was studied by tracer methods. The incorporation data are consistent with the view that the alkaloid is formed by dimerization of α-phenacylpiperidine (3), whose piperidine nucleus is derived from lysine via a nonsymmetrical intermediate, and whose sidechain originates, as an intact C6–C2 unit, from phenylalanine via cinnamic acid.

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Section: Discussionsupporting

confidence: 61%

Section: Discussionmentioning

confidence: 99%

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Biosynthesis of Lobinaline

Gupta¹,

Spenser²

1971

Can. J. Chem.

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“…This homology makes them valuable as lead compounds in degeneration of dopaminergic neurons in the human brain (Rudnick et al 2014, Segura-Aguilar & Kostrzewa 2015). However, lobinaline, is a complex binitrogenous decahydroquinoline alkaloid (Manske 1938, Robison & Pierson 1964) with 5 chiral centers. Chemical synthesis is difficult, and lobinaline is present in low yields in the wild type plant.…”

Section: Introductionmentioning

confidence: 99%

Target-directed discovery and production of pharmaceuticals in transgenic mutant plant cells

Brown

Rogers

Gunjan

et al. 2016

Journal of Biotechnology

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Plants are a source of complex bioactive compounds, with value as pharmaceuticals, or leads for synthetic modification. Many of these secondary metabolites have evolved as defenses against competing organisms. and their pharmaceutical value is “accidental”, resulting from homology between target proteins in these competitors, and human molecular therapeutic targets. Here we show that it is possible to use mutation and selection of plant cells to re-direct their “evolution” toward metabolites that interact with the therapeutic target proteins themselves. This is achieved by expressing the human target protein in plant cells, and selecting mutants for survival based on the interaction of their metabolome with this target. This report describes the successful evolution of hairy root cultures of a Lobelia species toward increased biosynthesis of metabolites that inhibit the human dopamine transporter protein. Many of the resulting selected mutants are overproducing the active metabolite found in the wild-type plant, but others overproduce active metabolites that are not readily detectable in non-mutants. This technology can access the whole genomic capability of a plant species to biosynthesize metabolites with a specific target. It has potential value as a novel platform for plant drug discovery and production, or as a means of optimizing the therapeutic value of medicinal plant extracts.

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Lobeliaceae

Hegnauer¹

1966

Chemotaxonomie Der Pflanzen

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The structure of lobinaline

Cited by 6 publications

References 1 publication

Biosynthesis of Lobinaline

Biosynthesis of Lobinaline

Target-directed discovery and production of pharmaceuticals in transgenic mutant plant cells

Lobeliaceae

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