Unveiling Amaryllidaceae alkaloids: from biosynthesis to antiviral potential – a review

Jayawardena, Thilina U.; Merindol, Natacha; Liyanage, Nuwan Sameera; Desgagné-Penix, Isabel

doi:10.1039/d3np00044c

Cited by 10 publications

(1 citation statement)

References 137 publications

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“…[45][46][47] More recently, genomic studies have identied several biosynthetic genes that encode enzymes involved in these steps. 48,49 2.2 Previous results of oxidative phenol coupling Barton and Kirby were the rst to report the biomimetic intramolecular oxidative coupling of 11a with potassium ferricyanide (K 3 Fe(CN) 6 ) as the oxidant, resulting in the desired product 12a, albeit in very low yield (Scheme 2). Subsequent ketone reduction with lithium aluminium hydride (LiAlH 4 ) led to a mixture of (±)-galantamine and (±)-epigalantamine.…”

Section: Biomimetic Oxidative Coupling Reactionsmentioning

confidence: 99%

Recent advances in the total synthesis of galantamine, a natural medicine for Alzheimer's disease

Cheng,

Wang,

et al. 2024

Nat. Prod. Rep.

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Section: Biomimetic Oxidative Coupling Reactionsmentioning

confidence: 99%

Recent advances in the total synthesis of galantamine, a natural medicine for Alzheimer's disease

Cheng,

Wang,

et al. 2024

Nat. Prod. Rep.

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Chemical and metabolic profiling of Amaryllidaceae alkaloids in the bulbs of Narcissus tazetta L. var. chinensis Roem using liquid chromatography–tandem mass spectrometry with data mining strategy

Huang,

Tan,

Luo

2024

Rapid Comm Mass Spectrometry

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RationaleThe bulbs of Narcissus tazetta L. var. chinensis Roem (BNTCR) has been used as an herbal medicine for the treatment of carbuncles in China. The previous phytochemical studies indicated that the main active components of BNTCR were Amarllidaceae alkaloids (AAs). However, the comprehensive chemical and metabolic profiling of AAs in BNTCR remains underexplored. Therefore, it is necessary to establish an accurate and rapid approach for chemical characterization and metabolic profiling of AAs in BNTCR.MethodsThe structural elucidation of natural products by ultra‐high performance liquid chromatography coupled to quadrupole time of flight tandem mass spectrometry (UHPLC‐QTOF‐MS/MS) with outstanding properties is still limited due to complex mixtures that contain hundreds of compounds. In this study, we employed UHPLC‐QTOF‐MS/MS with a data mining strategy, including diagnostic fragment ions (DFIs) and neutral loss (NL), for rapid classifying and identifying AAs in BNTCR and prototypes absorbed into the blood of mice after oral administration of BNTCR extract.ResultsAs a result, 87 AAs, including 13 narciclasine type, 13 homolycorine type, 17 lycorine type, 12 galanthamine type, 25 haemanthamine type, and 7 tazettine type, were tentatively characterized (6 verified with authentic standards). In addition, a total of 44 prototypes were identified in mice plasma, urine, and fecal samples. Among them, 8 prototypes were found in plasma, 36 in urine, and 40 in feces, respectively. Lycorine, pseudolycorine, homolycorine, 8‐O‐demetylhomolycorine, and tazettine, as major AAs in BNTCR, were absorbed into the blood.ConclusionsOur findings provided a crucial step for the elucidation of the active compounds in BNTCR for treatment of carbuncles. In the future, the developed strategy could also be applied for identifying AAs in other herbal medicines from Amarllidaceae.

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Multiple NADPH-cytochrome P450 reductases from Lycoris radiata involved in Amaryllidaceae alkaloids biosynthesis

Wu,

Zhang,

Fan

et al. 2024

Plant Mol Biol

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Unveiling Amaryllidaceae alkaloids: from biosynthesis to antiviral potential – a review

Abstract: Amaryllidaceae alkaloids (AAs) are a unique class of specialized metabolites containing heterocyclic nitrogen bridging that play a distinct role in higher plants.

Cited by 10 publications

References 137 publications

Recent advances in the total synthesis of galantamine, a natural medicine for Alzheimer's disease

Recent advances in the total synthesis of galantamine, a natural medicine for Alzheimer's disease

Chemical and metabolic profiling of Amaryllidaceae alkaloids in the bulbs of Narcissus tazetta L. var. chinensis Roem using liquid chromatography–tandem mass spectrometry with data mining strategy

Multiple NADPH-cytochrome P450 reductases from Lycoris radiata involved in Amaryllidaceae alkaloids biosynthesis

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