Meyeniihydantoins A–C, three novel hydantoin derivatives from the roots of Lepidium meyenii Walp.

Geng, Hongya; Dongshun, Yang; Chen, Xinglian; Wang, Luxiang; Zhou, Min; Mei, Wen-Quan

doi:10.1016/j.phytol.2018.06.010

Cited by 13 publications

(9 citation statements)

References 14 publications

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“…According to Carvalho and Ribeiro (2019), 26 macamides and macaenes, 9 glucosinolates and 2 isothiocyanates were reported in the timeframe 2000-2018. In 2017-2018, a number of papers was published in which the alkaloid fraction was investigated in more detail, including pyrrole alkaloids , thiohydantoin alkaloids (Yu et al, 2017), urea alkaloids (Kitamura et al, 2017), hexahydroimidazo [1,5-c]thiazole alkaloids , hydantoin and thioamide alkaloids (Geng et al, 2018) (Tian et al, 2018). Not less than 26 alkaloids belonging to these skeleton types were reported; they can be considered as minor constituents because mostly large amounts of dried plant material (10-25 kg) were needed to obtain around 1-20 mg pure compound.…”

Section: Introductionmentioning

confidence: 99%

Alkaloids from Lepidium meyenii (Maca), structural revision of macaridine and UPLC-MS/MS feature-based molecular networking

Roy

Dendooven

et al. 2021

Phytochemistry

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Section: Introductionmentioning

confidence: 99%

Alkaloids from Lepidium meyenii (Maca), structural revision of macaridine and UPLC-MS/MS feature-based molecular networking

Roy

Dendooven

et al. 2021

Phytochemistry

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“…MS2 data showed fragments at m / z 231.0294, 184.0737, and 121.0644, indicating loss of OCH 3 , C 6 H 5 , and C 6 H 8 N 2 O 2 groups, respectively, from the molecular ion. 6 , 45 …”

Section: Results and Discussionmentioning

confidence: 99%

Lepidium meyenii (Maca) Roots: UPLC-HRMS, Molecular Docking, and Molecular Dynamics

et al. 2022

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Lepidium meyenii or Maca is widely cultivated as a health care food supplement due to its nutritional and medicinal properties. Although there are a few in-depth studies evaluating Maca antihypertensive effects, the correlations between the chemical constituents and bioactivity of the plant have not been studied before. Thus, the roots were extracted using different solvents (aqueous, methanol, 50% methanol, and methylene chloride) and investigated for their antihypertensive and antioxidant activities through several in vitro assays. The methanolic extract exhibited the best renin and angiotensin converting enzyme (ACE) inhibitory activities with IC 50 values of 24.79 ± 1.3 ng/mL and 22.02 ± 1.1 ng/mL, respectively, along with the highest antioxidant activity. In total, 120 metabolites from different classes, e.g., alkylamides, alkaloids, glucosinolates, organic acids, and hydantoin derivatives, were identified in the methanolic extract using ultrahigh-performance liquid chromatography/high-resolution mass spectrometry (UPLC/HRMS). Molecular docking simulations were used to investigate the potential binding modes and the intermolecular interactions of the identified compounds with ACE and renin active sites. Glucotropaeolin, β-carboline alkaloids, succinic acid, and 2,4-dihydroxy-3,5-cyclopentyl dienoic acid showed the highest affinity to target the ACE with high docking scores ( S ranging from −35.32 to −22.51 kcal mol –1 ) compared to lisinopril ( S = −36.64 kcal mol –1 ). Interestingly, macamides displayed the greatest binding affinity to the active site of renin with docking scores ( S ranging from −22.47 to −28.25 kcal mol –1 ). Further, β-carbolines achieved docking scores comparable to that of the native ligand ( S ranging from −13.50 to −20.06 kcal mol –1 ). Molecular dynamics simulations and MMPBSA were also carried out and confirmed the docking results. Additionally, the computational ADMET study predicted that the compounds attaining promising docking results had proper pharmacokinetics, drug-likeness characteristics, and safe toxicological profiles. Ultimately, our findings revealed that Maca roots could be considered a promising candidate as an antihypertensive drug.

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“…Natural products containing urea and hydantoin alkaloids derived from L-proline have recently been isolated from the roots of Lepidium meyenii, , better known as maca, a crop and medicinal plant cultivated in Peru . Macaurea A 17 was accessed in 96% yield from the Boc proline and CDI derived compound 16 via an initial Boc group deprotection using HCl (10.0 equiv) in dioxane and dichloromethane followed by reaction with 8m and triethylamine (1.0 equiv) (Scheme a).…”

Section: Resultsmentioning

confidence: 99%

“…The use of 8m in an analogous fashion using overnight reaction with L-proline methyl ester followed by microwave-assisted cyclization gave macahydantoin D 20d in quantitative yield after isolation by flash column chromatography (Scheme a). Reaction of 3-methoxybenzylamine with HCl followed by treatment with CDI 9 and subsequent treatment of the resultant carbamoylimidazole afforded (+)-meyeniihydantoin A 20e in 91% yield after isolation by flash column chromatography (Scheme b). Analogous reaction of phenethylamine led to the formation of hydantoin 20f , an alkaloid originating from horseradish (Armoracia rusticana), in quantitative yield (Scheme b)…”

Section: Resultsmentioning

confidence: 99%

N-Alkyl Carbamoylimidazoles as Isocyanate Equivalents: Exploration of the Reaction Scope for the Synthesis of Ureas, Hydantoins, Carbamates, Thiocarbamates, and Oxazolidinones

et al. 2022

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The reaction of the HCl or trifluoroacetic acid salts of primary amines with carbonyldiimidazole (CDI) is shown to be a preparatively useful method for forming monosubstituted carbamoylimidazoles (28 examples) without the formation of symmetrical urea side products. The utility of these air-and water-stable crystalline carbamoylimidazole reagents was demonstrated by their reactions as blocked or masked isocyanate equivalents. Reaction with various classes of nucleophiles provides access to useful functional groups including ureas, carbamates, thiocarbamates, hydantoins, and oxazolidinones. A parallel synthesis library of 30 ureas was generated by the reaction of 6× carbamoylimidazole intermediates with 5× amines and triethylamine. The unsymmetrical urea-containing natural products macaurea A and pygmaniline A were also prepared in good yields (95% over four steps and 79% over three steps, respectively) using this approach. The reaction of carbamoylimidazoles with amino acid methyl esters followed by microwave irradiation in aqueous media gives hydantoins in high yields, further demonstrating the ability of carbamoylimidazoles as isocyanate surrogates. Three hydantoin-containing natural products including macahydantoin D and meyeniihydantoin A were prepared in nearly quantitative yields from proline methyl ester and carbamoylimidazoles. The reaction of carbamoylimidazoles with alcohols and thiols under basic conditions affords carbamates and thiocarbamates, respectively, in good yields. Lastly, a method for the preparation of chiral oxazolidinone heterocycles from chiral epoxy alcohols is demonstrated using a double displacement approach. The reactions occur with high regio-and stereoselectivity (dr ≥ 15:1 by 1 H NMR) via a domino attack of the corresponding alkoxides with carbamoylimidazoles followed by an intramolecular attack of the in situ generated urea anion at the proximal position of the epoxide group.

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Meyeniihydantoins A–C, three novel hydantoin derivatives from the roots of Lepidium meyenii Walp.

Cited by 13 publications

References 14 publications

Alkaloids from Lepidium meyenii (Maca), structural revision of macaridine and UPLC-MS/MS feature-based molecular networking

Alkaloids from Lepidium meyenii (Maca), structural revision of macaridine and UPLC-MS/MS feature-based molecular networking

Lepidium meyenii (Maca) Roots: UPLC-HRMS, Molecular Docking, and Molecular Dynamics

N-Alkyl Carbamoylimidazoles as Isocyanate Equivalents: Exploration of the Reaction Scope for the Synthesis of Ureas, Hydantoins, Carbamates, Thiocarbamates, and Oxazolidinones

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