Amaryllidaceae and Sceletium alkaloids

Jin, Zhong

doi:10.1039/c0np00073f

Cited by 104 publications

(40 citation statements)

References 119 publications

(175 reference statements)

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“…We minimized methodological artefacts by using the same plant accessions for both phylogenetic, chemical, and bioactivity studies, and by analysing our data with consistent methods. Chemical profiles were based on types deducted from hypothetical pathways and could be an oversimplification of the chemical diversity contained by over 500 individual alkaloid structures known from the subfamily [45,47]. …”

Section: Discussionmentioning

confidence: 99%

“…The traditional use of plants of Amaryllidoideae has been related to their unique and subfamily specific alkaloid chemistry (Figure 1). Over 500 alkaloids have been described from various species and have been subdivided into 18 major types based on hypothetical biosynthetic pathways [45-47]. Extracts or isolated alkaloids of Amaryllidaceae species have shown activity in vitro in a range of assays related to disorders of the central nervous system, primarily Alzheimers disease (inhibition of acetylcholinesterase, AChE) [21,48-51], and anxiety and depression (affinity to the serotonin re-uptake transporter, SERT) [21,52,53].…”

Section: Introductionmentioning

confidence: 99%

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Can phylogeny predict chemical diversity and potential medicinal activity of plants? A case study of amaryllidaceae

et al. 2012

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BackgroundDuring evolution, plants and other organisms have developed a diversity of chemical defences, leading to the evolution of various groups of specialized metabolites selected for their endogenous biological function. A correlation between phylogeny and biosynthetic pathways could offer a predictive approach enabling more efficient selection of plants for the development of traditional medicine and lead discovery. However, this relationship has rarely been rigorously tested and the potential predictive power is consequently unknown.ResultsWe produced a phylogenetic hypothesis for the medicinally important plant subfamily Amaryllidoideae (Amaryllidaceae) based on parsimony and Bayesian analysis of nuclear, plastid, and mitochondrial DNA sequences of over 100 species. We tested if alkaloid diversity and activity in bioassays related to the central nervous system are significantly correlated with phylogeny and found evidence for a significant phylogenetic signal in these traits, although the effect is not strong.ConclusionsSeveral genera are non-monophyletic emphasizing the importance of using phylogeny for interpretation of character distribution. Alkaloid diversity and in vitro inhibition of acetylcholinesterase (AChE) and binding to the serotonin reuptake transporter (SERT) are significantly correlated with phylogeny. This has implications for the use of phylogenies to interpret chemical evolution and biosynthetic pathways, to select candidate taxa for lead discovery, and to make recommendations for policies regarding traditional use and conservation priorities.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Can phylogeny predict chemical diversity and potential medicinal activity of plants? A case study of amaryllidaceae

et al. 2012

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“…More than 500 Amaryllidaceae alkaloids representing 18 skeletal types have been isolated and reported to have acetylcholinesterase (AChE) inhibitory, analgesic, antibacterial, antifungal, antimalarial, antitumor, antiviral, and cytotoxic activities. 1 Zephyranthes candida (Lindl.) Herb.…”

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confidence: 99%

Cytotoxic Alkaloids from the Whole Plants of Zephyranthes candida

et al. 2012

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Seven new alkaloids, N-methylhaemanthidine chloride (1), N-methyl-5,6-dihydroplicane (5), O-methylnerinine (6), N-ethoxycarbonylethylcrinasiadine (7), N-ethoxycarbonylpropylcrinasiadine (8), N-phenethylcrinasiadine (9) and N-isopentylcrinasiadine (10), together with eight known alkaloids, haemanthamin (2), 3-epimacronine (3), (+)-tazettine (4), N-methylcrinasiadine (11), trisphaeridine (12), 5,6-dihydrobicolorine (13), lycorine (14), and nigragillin (15), were isolated from the whole plants of Zephyranthes candida. The structures of the new compounds were established by spectroscopic data interpretation, with single-crystal X-ray diffraction analysis performed on 1. The absolute configuration of 3-epimacronine (3) was determined by single-crystal X-ray diffraction analysis with CuKα irradiation. Compounds 1–15 were evaluated for their in vitro cytotoxicity against five human cancer cell lines and the Beas-2B immortalized (non-cancerous) human bronchial epithelial cell line. Compounds 1, 2, 9, and 14 exhibited cytotoxicity with IC50 values ranging from 0.81 to 13 μM with selectivity indices as high as 10 when compared to the Beas-2B cell line.

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“…Especially, galantamine and lycorine types exhibited significant usefulness in healing Alzheimer's disease [3]. Lycoris sprengeri Comes ex Baker is mainly distributed in the lower reaches of the Yangtze River, and its bulbs have been used as traditional Chinese medicine for the treatment of various diseases, such as sore throats, furuncle carbuncle swollen in skin and scrofula [4,5]. However, the chemical constituents of the plant have never been studied before.…”

Section: Introductionmentioning

confidence: 99%

Two new alkaloids from the bulbs of Lycoris sprengeri

Zhu

et al. 2013

Journal of Asian Natural Products Research

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Two new alkaloids, lycosprenine (1) and 2α-methoxy-6-O-methyllycorenine (2), along with 22 known alkaloids (3-23b), were isolated from the bulb of Lycoris sprengeri. Their structures were elucidated on the basis of spectral analysis and by comparison of the spectroscopic data with those of known compounds. Selected compounds (1-3 and 6-9) were tested for their neuroprotective activities against H2O2-, CoCl2- and Aβ25-35-induced SH-SY5Y cell injury, most of which exhibited neuroprotective effects of different degrees.

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Amaryllidaceae and Sceletium alkaloids

Cited by 104 publications

References 119 publications

Can phylogeny predict chemical diversity and potential medicinal activity of plants? A case study of amaryllidaceae

Can phylogeny predict chemical diversity and potential medicinal activity of plants? A case study of amaryllidaceae

Cytotoxic Alkaloids from the Whole Plants of Zephyranthes candida

Two new alkaloids from the bulbs of Lycoris sprengeri

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