Streamlined targeting of Amaryllidaceae alkaloids from the bulbs of Crinum scillifolium using spectrometric and taxonomically-informed scoring metabolite annotations

N'Tamon, Amon Diane; Timothée, Okpekon Aboua; Bony, Nicaise F.; Bernadat, Guillaume; Gallard, Jean‐François; Kouamé, Tapé; Seon-Méniel, Blandine; Leblanc, Karine; Rharrabti, Somia; Mouray, Elisabeth; Grellier, Philippe; Aké, Michèle; Amin, N'Cho Christophe; Champy, Pierre; Beniddir, Mehdi A.; Pogam, Pierre Le

doi:10.1016/j.phytochem.2020.112485

Cited by 9 publications

(14 citation statements)

References 69 publications

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“…Several of these novel AAs belong to known structural types, while others harbor new structures. The 91 AAs were classified in this manuscript as I) norbelladine-type (1-6), II) cherylline-type (7, 8), III) galantamine-type (9-16), IV) lycorine-type (17-25), V) homolycorine-type (26)(27)(28)(29)(30), VI) crinine-type (31-50), VII) narciclasine-type (51), VIII) pretazettine-type (52-54), IX) montanine-type (55), and X) other types including AAs related to plicamine (56)(57)(58)(59)(60)(61)(62)(63)(64)(65)(66)(67), seco-plicamine (68-70), cripowellin (71)(72)(73)(74)(75)(76), mesembrine (77,78), and various others AAs (79)(80)(81)(82)(83)(84)(85)(86)(87)(88)(89)(90)(91). Structures of novel AAs belonging to the I to III scaffold types (norbelladine-, cherylline-, and galantamine-type) are depicted in Figure 3, whereas types IV and V (lycorine-and homolycorine-type) are represented in Figure 4.…”

Section: Occurrence Of Amaryllidaceae Alkaloidsmentioning

confidence: 99%

“…Their structure was elucidated using various spectroscopic methods (1D and 2D 1 H and 13 C NMR and HR-ESIMS). Their relatives and absolute configurations were determined by DFT-NMR and ECD calculations [61].…”

Section: Antitumoral Cytotoxic Activitymentioning

confidence: 99%

“…Scillitazettine (53) and scilli-N-desmethylpretazettine (54) were evaluated against the chloroquineresistant strain P. falciparum FcB1 and displayed antiparasitic activity with IC 50 values of 77.0 ± 2.0 and 46.5 ± 2.0 µM, respectively [61].…”

Section: Anti-inflammatory and Antioxidant Activitymentioning

confidence: 99%

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Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

Koirala

Mérindol

et al. 2020

Molecules

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Alkaloids are an important group of specialized nitrogen metabolites with a wide range of biochemical and pharmacological effects. Since the first publication on lycorine in 1877, more than 650 alkaloids have been extracted from Amaryllidaceae bulbous plants and clustered together as the Amaryllidaceae alkaloids (AAs) family. AAs are specifically remarkable for their diverse pharmaceutical properties, as exemplified by the success of galantamine used to treat the symptoms of Alzheimer’s disease. This review addresses the isolation, biological, and structure activity of AAs discovered from January 2015 to August 2020, supporting their therapeutic interest.

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Section: Occurrence Of Amaryllidaceae Alkaloidsmentioning

confidence: 99%

Section: Antitumoral Cytotoxic Activitymentioning

confidence: 99%

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Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

Koirala

Mérindol

et al. 2020

Molecules

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“…In the adjoining biological evaluation, negligible effects were observed for all 3 compounds (at 1 µM) on the HCT116 colon carcinoma cell line where cell viabilities were high (> 90 %) [11]. However, there was some modulation in activity (75 % viability) for 4-O,N-dimethylnorbelladine-N-oxide (20) when its concentration was increased to 10 µM [11]. The Ismine Group…”

Section: The Belladine Groupmentioning

confidence: 99%

Cytotoxic Agents in the Minor Alkaloid Groups of the Amaryllidaceae

Nair

Staden

2021

Planta Med

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Over 600 alkaloids have to date been identified in the plant family Amaryllidaceae. These have been arranged into as many as 15 different groups based on their characteristic structural features. The vast majority of studies on the biological properties of Amaryllidaceae alkaloids have probed their anticancer potential. While most efforts have focused on the major alkaloid groups, the volume and diversity afforded by the minor alkaloid groups have promoted their usefulness as targets for cancer cell line screening purposes. This survey is an in-depth review of such activities described for around 90 representatives from 10 minor alkaloid groups of the Amaryllidaceae. These have been evaluated against over 60 cell lines categorized into 18 different types of cancer. The montanine and cripowellin groups were identified as the most potent, with some in the latter demonstrating low nanomolar level antiproliferative activities. Despite their challenging molecular architectures, the minor alkaloid groups have allowed for facile adjustments to be made to their structures, thereby altering the size, geometry, and electronics of the targets available for structure-activity relationship studies. Nevertheless, it was seen with a regular frequency that the parent alkaloids were better cytotoxic agents than the corresponding semisynthetic derivatives. There has also been significant interest in how the minor alkaloid groups manifest their effects in cancer cells. Among the various targets and pathways in which they were seen to mediate, their ability to induce apoptosis in cancer cells is most appealing.

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“…Especially in the field of cancer, more than 60% of drugs are derived from natural products. Plants in the Amaryllidaceae family are known for their medicinal effects and toxicity [1][2][3][4]. The role has been known for a long time.…”

Section: Introductionmentioning

confidence: 99%

Determination of narciclasine in mouse blood by UPLC-MS/MS and its application to a pharmacokinetic study

Ren

Feng

Shi

et al. 2021

AChrom

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Narciclasine is a 7-hydroxy derivative of lycorisidine. It was the first alkaloid isolated from the stem of narcissus (Amaryllidaceae) in 1967. Six mice were given narciclasine (5 mg/kg) by intravenous administration. A UPLC-MS/MS method was developed to determine narciclasine in mouse blood. Tectorigenin (internal standard, IS) and narciclasine were gradient eluted by mobile phase of methanol and 0.1% formic acid in a BEH C18 column. The multiple reaction monitoring (MRM) of m/z 308.1→248.1 for narciclasine and m/z 301.1→286.0 for IS with an electrospray ionization (ESI) source was used for quantitative determination. The calibration curve ranged from 1 to 6,000 ng/mL. The accuracy was from 92.5 to 107.3%, and the matrix effect was between 103.6 and 107.4%. The developed UPLC-MS/MS method was successfully applicated to a pharmacokinetic study of narciclasine in mice after intravenous administration (5 mg/kg).

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Streamlined targeting of Amaryllidaceae alkaloids from the bulbs of Crinum scillifolium using spectrometric and taxonomically-informed scoring metabolite annotations

Cited by 9 publications

References 69 publications

Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

Biosynthesis and Biological Activities of Newly Discovered Amaryllidaceae Alkaloids

Cytotoxic Agents in the Minor Alkaloid Groups of the Amaryllidaceae

Determination of narciclasine in mouse blood by UPLC-MS/MS and its application to a pharmacokinetic study

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