Indolizidine and quinolizidine alkaloids

Michael, J. P.

doi:10.1039/np9900700485

Cited by 34 publications

(5 citation statements)

References 58 publications

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“…The authors also studied the glycosidase inhibitory activity of these compounds. [72,73] Compounds 111a and 111b showed no glycosidase inhibitory activity. Compound 115b was a selective β-glucosidase inhibitor (μm range), and compounds 115a and 114a·HCl were selective β-glucosidase inhibitors (mm range).…”

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 98%

“…[72,73] Compounds 111a and 111b showed no glycosidase inhibitory activity. [72,73] Compounds 111a and 111b showed no glycosidase inhibitory activity.…”

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 99%

“…Dhavale and co-workers [72] reported the synthesis of tetrahydroxyperhydroaza-azulenes 111a and 111b (Scheme 24) through Johnson-Claisen rearrangement of sugar-derived allyl alcohols. These compounds were of interest as higher ring homologues of polyhydroxylated indolizidine alkaloids [73] such as castanospermine (112). The Johnson-Claisen rearrangement of d-glucose-derived allyl alcohol 108 afforded unsaturated ester 109, which was elaborated to diastereomeric azido epoxides 110a and 110b (Scheme 24).…”

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 99%

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The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

2013

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The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration.

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Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 98%

“…[72,73] Compounds 111a and 111b showed no glycosidase inhibitory activity. [72,73] Compounds 111a and 111b showed no glycosidase inhibitory activity.…”

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 99%

Section: Applications In Synthesis Of Bioactive Molecules Natural Prmentioning

confidence: 99%

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The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

2013

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“…Quinolizidine alkaloids (QA) ( Figure ) are toxic compounds ( − ) present in plants, mainly within the Leguminosae ( − ). In particular, QA are present throughout plants of the genus Lupinus , imparting a bitter taste and constituting a defense mechanism against herbivory of high protein tissue ( − ).…”

Section: Introductionmentioning

confidence: 99%

Bacterial Removal of Quinolizidine Alkaloids and Other Carbon Sources from a Lupinus albus Aqueous Extract

Santana¹,

Pinto²,

Fialho³

et al. 2002

J. Agric. Food Chem.

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Two Gram-negative bacterial strains capable of using lupanine, the predominant quinolizidine alkaloid in Lupinus albus, as a sole carbon source were isolated from soil in which L. albus and L. luteus had been grown [Santana, F. M. et al. J. Ind. Microbiol. 1996, 17, 110-115]. In the present study, we present results suggesting that these isolates are of potential interest for removing lupanine and other quinolizidine alkaloids (QA) from the effluent resulting from the wet processing of Lupinus seeds, at temperatures within the range 20-34 degrees C. Growth in L. albus aqueous extract was diauxic, with a first period of rapid growth leading to the simultaneous consumption of a significant part of the initial concentration of QA (3 g L(-1), being 2 g L(-1) lupanine) and amino acids (1.5 g L(-1)). This period was followed by a second period of slower growth corresponding to the subsequent partial utilization (25%) of the carbohydrates (initial concentration of 20 g L(-1)) together with further removal of QA and amino acids. Despite the differences detected in the susceptibility of the two strains to lupanine toxicity, in particular at supraoptimal temperatures, and in the efficiency of lupanine catabolism, their performance on L. albus extract did not vary significantly.

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“…Among azasugars, (+)-castanospermine 1a (Figure ) was isolated from the seeds of the Australian legume Castanospermum australe ,13a as well as from the dried pod of Alexa leiopetala ,13b known to have a significant glycosidase inhibitory activity . In the search for a structure−activity relationship, a number of natural and unnatural analogues of 1a , with variation in the number/position and stereochemistry of the hydroxyl groups at each carbon atom in the indolizidine ring skeleton, have been synthesized 12c, and evaluated for the glycosidase inhibition in the treatment of various diseases such as diabetes, cancer, and multiple scelerosis, as well as viral infections including AIDS, hepatitis C, and HSV-1 .…”

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confidence: 99%

Intramolecular 5-endo-Trig Aminomercuration of β-Hydroxy-γ-alkenylamines: Efficient Route to a Pyrrolidine Ring and Its Application for the Synthesis of (+)-Castanospermine and Analogues

et al. 2006

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The intramolecular aminomercuration reaction of sugar-derived beta-hydroxy-gamma-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidine alkaloids, namely, castanospermine 1a, 1-epi-castanospermine 1b, and 8a-epi-castanospermine 1c, having promising glycosidase inhibitory activities.

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Indolizidine and quinolizidine alkaloids

Cited by 34 publications

References 58 publications

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

Bacterial Removal of Quinolizidine Alkaloids and Other Carbon Sources from a Lupinus albus Aqueous Extract

Intramolecular 5-endo-Trig Aminomercuration of β-Hydroxy-γ-alkenylamines: Efficient Route to a Pyrrolidine Ring and Its Application for the Synthesis of (+)-Castanospermine and Analogues

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