(1S,2R,8aS)-1,2-Dihydroxyindolizidine formation by Rhizoctonia leguminicola, the fungus that produces slaframine and swainsonine

Harris, Thomas M.; Harris, Constance M.; Hill, James E.; Ungemach, Frank S.; Broquist, Harry P.; Wickwire, Brian M.

doi:10.1021/jo00390a024

Cited by 48 publications

(21 citation statements)

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“…In SW biosynthetic pathway of fungus, saccharopine reductase 9–11 catalyzes the transformation of lysine and saccharopine to form alpha-aminohexanedioichemialdehyde, which is one of the precursors of SW biosynthesis. So saccharopine reductase is also a key enzyme in SW biosynthesis 11 .…”

Section: Discussionmentioning

confidence: 99%

Transcriptome Profiles of Alternaria oxytropis Provides Insights into Swainsonine Biosynthesis

2019

Sci Rep

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Swainsonine (SW) is a toxic alkaloid biosynthesized by the endophytic fungus Alternaria oxytropis in Oxytropis glabra . The biosynthetic pathway of SW is poorly understood. Saccharopine reductase/dehydrogenase of fungus plays an important role in this pathway. The gene knocked out mutant M1 in A. oxytropis was constructed in our previous work. In this study, the transcriptome of wild-strain OW7.8 and M1 was firstly sequenced to understand the biosynthetic pathway and molecular mechanism of SW in A. oxytropis . A total of 45,634 Unigenes were annotated. 5 genes were up-regulated and 11,213 genes were down-regulated. 41 Unigenes possibly related to the biosynthesis of SW were identified by data analyzing. The biosynthesis pathway of SW in the fungus was speculated, including two branches of P6C and P2C. Delta1-piperidine-2-carboxylate reductase, lysine 6-dehydrogenase, and saccharopine oxidase/L-pipecolate oxidase were involved in P6C. 1-piperidine-2-carboxylate/1-pyrroline-2- carboxylate reductase [NAD(P)H] and delta1-piperidine-2-carboxylate reductase were involved in P2C. Saccharopine reductase was involved in both. In addition, 1-indolizidineone was considered to be the direct precursor in the synthesis of SW, and the hydroxymethylglutaryl-CoA lyase catalyzed the synthesis of SW. Here we analyzed details of the metabolic pathway of A. oxytropis SW, which is of great significance for the follow-up research.

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Section: Discussionmentioning

confidence: 99%

Transcriptome Profiles of Alternaria oxytropis Provides Insights into Swainsonine Biosynthesis

2019

Sci Rep

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“…In particular, several biosynthetic pathways involving epimerization have been suggested for different natural products. For example, epimerization has also been suggested to account for the different configuration at C‐8a of swainsonine ( 30 ), relative to 2‐ epi ‐lentiginosine ( 28 ) and slaframine ( 29 ), all of which are produced by the fungus Rhizoctonia leguminicola 46a. In addition, 2‐ epi ‐lentiginosine ( 28 ) has been reported to be a late intermediate in the biosynthesis of slaframine ( 29 ) and swainsonine ( 30 ) by Harris and co‐workers 46b.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Syntheses of Rigidiusculamides A and B: Revision of the Relative Stereochemistry of Rigidiusculamide A

Chen

Huang

et al. 2012

Chemistry An Asian Journal

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The first enantioselective synthesis of cytotoxic natural products rigidiusculamides A (ent-21) and B (8) has been achieved by two synthetic routes. The first one is convergent based on the common intermediate 11, obtained through a high yielding SmI(2) -mediated Reformatsky-type reaction. A highly diastereoselective one-pot Dess-Martin periodinane-mediated bis-oxidation allowed the direct conversion of the diastereomeric mixture of 11 into rigidiusculamide B (8). Isolation of minor diastereomer 21, in combination with computational work, allowed us to suggest the structure of the natural rigidiusculamide A to be ent-21, as synthesized by the second route. Four diastereomers (7, ent-7, 22a, and 22b) and an enantiomer (21) of rigidiusculamide A (ent-21) have been synthesized. On the basis of literature precedents and computational work, a biosynthetic pathway for rigidiusculamides A and B was proposed to account for the opposite configuration at C-5 of those two congeners.

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“…(1 S ,2 R ,8a S )‐Octahydroindolizine‐1,2‐diol (18) : Based on a modified procedure by Harris11, a solution of bicyclic piperidine (27.0 mg, 0.12 mmol) in a 1:3 mixture of 10 % H 2 SO 4 and MeOH (2 mL) was stirred at 50 °C for 12 h and cooled to RT. Flash column chromatography (MeOH/CH 2 Cl 2 =50:50) afforded 17 (17.5 mg, 92.8 %) as a colorless oil.…”

Section: Methodsmentioning

confidence: 99%

Access to trans‐3,4‐Dihydroxy‐2‐alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O‐Acetals as a Diversity‐Generating Element

Kang

Kim

Rhee

2014

Chemistry A European J

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(1S,2R,8aS)-1,2-Dihydroxyindolizidine formation by Rhizoctonia leguminicola, the fungus that produces slaframine and swainsonine

Cited by 48 publications

References 0 publications

Transcriptome Profiles of Alternaria oxytropis Provides Insights into Swainsonine Biosynthesis

Transcriptome Profiles of Alternaria oxytropis Provides Insights into Swainsonine Biosynthesis

Enantioselective Syntheses of Rigidiusculamides A and B: Revision of the Relative Stereochemistry of Rigidiusculamide A

Access to trans‐3,4‐Dihydroxy‐2‐alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O‐Acetals as a Diversity‐Generating Element

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