Lepidiline C and D: Two new imidazole alkaloids from Lepidium meyenii Walpers (Brassicaceae) roots

Jin, Wenwen; Chen, Xuemin; Dai, Pengfei; Yu, Liang

doi:10.1016/j.phytol.2016.07.001

Cited by 32 publications

(26 citation statements)

References 18 publications

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“…Four imidazole alkaloids unique to maca have been identified. They are Lepidiline A, Lepidiline B, isolated from a concentrated lipid extract of maca (Cui et al, 2003) and lepidiline C and Lepidiline D, isolated from 95% ethanolic extract of maca (Jin et al, 2016). So far, no information is available about their possible biological properties.…”

Section: Imidazole Alkaloidsmentioning

confidence: 99%

Is the hype around the reproductive health claims of maca (Lepidium meyenii Walp.) justified?

Beharry¹,

Heinrich²

2018

Journal of Ethnopharmacology

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To date, the health claims of maca cannot be fully supported from a scientific standpoint and more research is needed. It appears that the indigenous local knowledge about the health benefits of maca has been dragged out of context to fit the demands of a growing market for herbal remedies. This globalisation (or hype esp. in China) also has had serious consequences for the local producers in Peru. The lack of protocols to regulate the production and marketing of maca during this rapid expansion, poses a threat to both the safety of consumers and the sustainability of supply.

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Section: Imidazole Alkaloidsmentioning

confidence: 99%

Is the hype around the reproductive health claims of maca (Lepidium meyenii Walp.) justified?

Beharry¹,

Heinrich²

2018

Journal of Ethnopharmacology

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“…In addition, it is worth mentioning that 1,3-dibenzyl-4,5-dimethylimidazolium chloride as well as its 2-methyl-substituted analogue are well known imidazole alkaloids, which found wide application in some regions as food-stuff and medical supply [33]. The method described in the present study opens a straightforward access to their benzyloxy analogues, potentially bioactive compounds, which have not been known yet.…”

Section: Resultsmentioning

confidence: 98%

Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

Mlostoń¹,

Celeda²,

Urbaniak³

et al. 2019

Beilstein J. Org. Chem.

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Adamantyloxyamine reacts with formaldehyde to give N-(adamantyloxy)formaldimine as a room-temperature-stable compound that exists in solution in monomeric form. This product was used for reactions with α-hydroxyiminoketones leading to a new class of 2-unsubstituted imidazole 3-oxides bearing the adamantyloxy substituent at N(1). Their reactions with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or with acetic acid anhydride occurred analogously to those of 1-alkylimidazole 3-oxides to give imidazol-2-thiones and imidazol-2-ones, respectively. Treatment of 1-(adamantyloxy)imidazole 3-oxides with Raney-Ni afforded the corresponding imidazole derivatives without cleavage of the N(1)–O bond. Finally, the O-alkylation reactions of the new imidazole N-oxides with 1-bromopentane or 1-bromododecane open access to diversely substituted, non-symmetric 1,3-dialkoxyimidazolium salts. Adamantyloxyamine reacts with glyoxal and formaldehyde in the presence of hydrobromic acid yielding symmetric 1,3-di(adamantyloxy)-1H-imidazolium bromide in good yield. Deprotonation of the latter with triethylamine in the presence of elemental sulfur allows the in situ generation of the corresponding imidazol-2-ylidene, which traps elemental sulfur yielding a 1,3-dihydro-2H-imidazole-2-thione as the final product.

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“…Lepidiline A (LA) and lepidiline B were first isolated from maca root in 2003, [ 15 ] and in 2016, lepidiline C and lepidiline D were also identified from alcoholic extracts. [ 16 ] However, there is no additional information available as to their biologic properties. Maca has a range of biologic activities, including promotion of reproduction; and it exhibits anticancer, antioxidative, immunomodulatory, and hepato‐protecting activities.…”

Section: Introductionmentioning

confidence: 99%

Lepidiline A Improves the Balance of Endogenous Sex Hormones and Increases Fecundity by Targeting HSD17B1

Cheng

Shen

Ding

et al. 2020

Molecular Nutrition Food Res

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Scope: Maca (Lepidium meyenii), a well-known plant from the Andean highlands of Peru, has been used widely as a nutritional supplement to increase sexual function and fecundity. However, the identity of its active ingredients and how they function remain unknown. Methods and results: Chemical substances in maca are identified by UPLC-Q-TOF, and the active ingredients are screened through HotMap coupled with an artificial neural network. Lepidiline A (LA), an imidazole alkaloid, is identified as the key active compound. LA affects the balance of endogenous sex hormones in mice and improves fecundity in Drosophila. Using a molecular LA probe, 17ß-hydroxysteroid dehydrogenase type 1 (HSD17B1) is revealed to be the potential target of LA using a fishing-rod strategy. It is demonstrated with experimental data that LA targets HSD17B1 to enhance the enzyme's activity and increases its bioconversion efficiency of actively formed sex hormones including estrogen to 17 -estradiol and 4-androsten-3,7-dione to testosterone, which ultimately improves reproductive activity. Conclusion: LA improves the balance of endogenous sex hormones and increases fecundity by targeting HSD17B1. This underlying mechanism of action provides a useful insight into the application of maca in the regulation of dietary nutrition and healthy fertility.

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Lepidiline C and D: Two new imidazole alkaloids from Lepidium meyenii Walpers (Brassicaceae) roots

Cited by 32 publications

References 18 publications

Is the hype around the reproductive health claims of maca (Lepidium meyenii Walp.) justified?

Is the hype around the reproductive health claims of maca (Lepidium meyenii Walp.) justified?

Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

Lepidiline A Improves the Balance of Endogenous Sex Hormones and Increases Fecundity by Targeting HSD17B1

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