Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola:  metabolism of 1-hydroxyindolizidines

Harris, Constance M.; Schneider, Marilyn J.; Ungemach, Frank S.; Hill, James E.; Harris, Thomas M.

doi:10.1021/ja00211a039

Cited by 88 publications

(56 citation statements)

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“…The biosynthesis of swainsonine has been investigated in the fungus R. leguminicola (Harris et al . ). Swainsonine is derived from lysine which is converted into pipecolic acid.…”

Section: Endophytes Of Locoweeds and Related Taxamentioning

confidence: 97%

Bioactive alkaloids in vertically transmitted fungal endophytes

2013

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Summary1. Plants form mutualistic symbioses with a variety of microorganisms including endophytic fungi that live inside the plant and cause no overt symptoms of infection. Some endophytic fungi form defensive mutualisms based on the production of bioactive metabolites that protect the plant from herbivores in exchange for a protected niche and nutrition from the host plant. Key elements of these symbioses are vertical transmission of the fungus through seed of the host plant, a narrow host range, and production of bioactive metabolites by the fungus. 2. Grasses frequently form symbioses with endophytic fungi belonging to the family Clavicipitaceae. These symbioses have been studied extensively because of their significant impacts on insect and mammalian herbivores. Many of the impacts are likely due to the production of four classes of bioactive alkaloids -ergot alkaloids, lolines, indole-diterpenes and peraminethat are distributed in different combinations among endophyte taxa. 3. Several legumes, including locoweeds, are associated with a toxic syndrome called locoism as a result of their accumulation of swainsonine. Species in two genera were recently found to contain previously undescribed endophytic fungi (Undifilum spp., family Pleosporaceae) that are the source of that toxin. The fungi are strictly vertically transmitted and have narrow host ranges. 4. Some plant species in the morning glory family (Convolvulaceae) also form symbioses with endophytic fungi of the Clavicipitaceae that produce ergot alkaloids and, perhaps in at least one case, lolines. Other species in this plant family form symbioses with undescribed fungi that produce swainsonine. The swainsonine-producing endophytes associated with the Convolvulaceae are distinct from the Undifilum spp. associated with locoweeds and the Clavicipitaceous fungi associated with Convolvulaceae. 5. In the establishment of vertically transmitted symbioses, fungi must have entered the symbiosis with traits that were immediately useful to the plant. Bioactive metabolites are likely candidates for such pre-adapted traits which were likely useful to the free-living fungi as well. With future research, vertically transmitted fungi from diverse clades with narrow host ranges and that produce bioactive compounds are likely to be found as important mutualists in additional plants.

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“…The biosynthesis of swainsonine has been investigated in the fungus R. leguminicola (Harris et al . ). Swainsonine is derived from lysine which is converted into pipecolic acid.…”

Section: Endophytes Of Locoweeds and Related Taxamentioning

confidence: 97%

Bioactive alkaloids in vertically transmitted fungal endophytes

2013

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“…Oxidative deamination of cadaverine by copper amine oxidase (CuAO, EC 1.4.3.22) yields 5-aminopentanal, which is spontaneously cyclized to Δ 1 -piperideine Schiff base (Leistner and Spenser, 1973; Gupta et al, 1979; Golebiewski and Spenser, 1988; Saito and Murakoshi, 1995; Ma and Gang, 2004). In contrast, indolizidine alkaloids are formed from L-Lys via L-pipecolic acid which is formed via the aldehyde and Schiff base, with retention of the nitrogen of the α-amino acid group ( Figure 1 ; Harris et al, 1988a,b; Wickwire et al, 1990; Dewick, 2001). Δ 1 -Piperideine and L-pipecolic acid are universal intermediates that can be modified by condensation, hydrolysis, or methylation to produce diverse Lys-derived alkaloids ( Figure 1 ; Evans, 2009).…”

Section: Biosynthesis Of Lys-derived Alkaloidsmentioning

confidence: 99%

Quinolizidine alkaloid biosynthesis: recent advances and future prospects

Bunsupa¹,

Yamazaki²,

Saito³

2012

Front. Plant Sci.

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Lys-derived alkaloids, including piperidine, quinolizidine, indolizidine, and lycopodium alkaloids, are widely distributed throughout the plant kingdom. Several of these alkaloids have beneficial properties for humans and have been used in medicine. However, the molecular mechanisms underlying the biosynthesis of these alkaloids are not well understood. In the present article, we discuss recent advances in our understanding of Lys-derived alkaloids, especially the biochemistry, molecular biology, and biotechnology of quinolizidine alkaloid (QA) biosynthesis. We have also highlighted Lys decarboxylase (LDC), the enzyme that catalyzes the first committed step of QA biosynthesis and answers a longstanding question about the molecular entity of LDC activity in plants. Further prospects using current advanced technologies, such as next-generation sequencing, in medicinal plants have also been discussed.

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“…Supplementing medium with L-lysine boosts swainsonine production ( Table 2). There are conflicting reports on the preferred enantiomeric form of lysine for incorporation into pipecolic acid, a precursor in the swainsonine biosynthetic pathway (Harris et al, 1988). Studies on R.legummicola (Wickwire et al, 1990) indicated that L-lysine was the preferred substrate, although some L-pipecolate was also produced from D-lysine.…”

Section: Quantitative Swainsonine Analysismentioning

confidence: 99%

Production of an indolizidine alkaloid, swainsonine by the filamentous fungus, Metarhizium anisopliae

1993

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The physiology ofMetarhi~um anisophae has been studied with a view to improving swainsonine producUon. In prelimina.~" work, the stability of pure s~ainsonine in aqueous solution has been investigated under varying conditions of pH and temperature and in the presence of oxidizing agents. The effects of o.~.gen on the growth and morpholoKv of M.anisopliae and the production of swainsomne were also examined Shaken flask fermentations have been carried out in order to develop a medium suitable for production of swainsonine.

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Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines

Cited by 88 publications

References 0 publications

Bioactive alkaloids in vertically transmitted fungal endophytes

Bioactive alkaloids in vertically transmitted fungal endophytes

Quinolizidine alkaloid biosynthesis: recent advances and future prospects

Production of an indolizidine alkaloid, swainsonine by the filamentous fungus, Metarhizium anisopliae

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