Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii)

Abstract

Maca (Lepidium meyenii Walp.), a famous food supplement, has drawn an unprecedented international interest over the last two decades. It was assumed that glucosinolates, macamides, macaenes, and alkaloids are the main bioactive components of Maca before. Recently, a series of novel thiohydantoins which generally exhibit a variety of activities have been isolated from Maca. This review focuses on the progress on the main bioactive components of Maca and their biosynthetic pathway, which indicates that macamides, thiohydantoins, and some alkaloids may originate from glucosinolates. Interestingly, thiohydantoins from Maca are the first type of thiohydantoin derivatives to be found from a natural source and may contribute to some significant effects of Maca.Graphical Abstract

Anti-inflammatory Potential of Macamides Isolated from Yellow Tubers of Mashua (Tropaeolum Tuberosum)

“…[13]. The presence of eighteen macamides have been reported in Maca, among which N-benzylpalmitamide is the most abundant compound in the Maca of Peruvian origin, while N-benzyllinoleamide is the richest compound in the Maca of Chinese origin (Yunnan) and is the second most abundant compound in the Peruvian Maca [34]. However, the presence of N-oleoyldopamine was recently reported in purple tubers from Mashua (T. tuberosum) of Bolivian origin [24].…”

“…We can conclude that these types of compounds may be markers of plant species that grow exposed to extreme climatic conditions (poor soils with a slightly acidic pH between 5-6 and exposure to ultraviolet radiation at altitudes of 3.800 meters above sea level), consequently producing this type of compounds. The importance of isolating this type of compounds is due to their chemical nature, since they can easily cross the intestinal wall and the blood-brain barrier, exerting a greater pharmacological effect [13,34].…”

N‐(3‐methoxybenzyl)‐(9Z,12Z,15Z)‐octadecatrienamide promotes bone formation via the canonical Wnt/β‐catenin signaling pathway

“…Maca, a famous food supplement, has drawn an unprecedented attention over the last two decades. It was recognized that glucosinolates, macamides, macaenes, alkaloids, and a series of novel thiohydantoins are the main bioactive components of Maca (Huang et al, ). Although Maca has been proven to increase bone mass and restore the trabecular network in the lumbar vertebrae of OVX rats (C. Gonzales et al, ; Y. Zhang et al, ), the monomer(s) responsible for this effect and the underlying mechanism remains unclear.…”

“…In our study, MBOC suppressed phosphorylation of GSK‐3β at Tyr216 in a dose‐dependent manner in C3H/10T1/2 cells, suggesting that MBOC's effect on Wnt/β‐catenin signaling pathway may be through inhibition of GSK‐3β activity. Although the most active macamide, N‐benzyl‐9Z,12Z‐octadecadienamide, showed selective binding affinities for the cannabinoid CB1 receptor and a potent inhibition of anandamide cellular uptake (Huang et al, ), further investigation is needed to unravel the membrane receptor or cytosolic receptor of MBOC in MSCs, which may help to reveal the detailed mechanism by which MBOC treatment dephosphorylates GSK‐3β and activates Wnt pathway.…”

“…However, the active ingredient and the potential signaling pathway remain unknown. Among the chemical constituents of Maca, macamides and macaenes are assumed to be the characteristic marker compounds as they have not been found in any other plants (Huang, Peng, & Qiu, ). To explore the active ingredient of macamides and their potential role in bone formation, we selected three different monomer components of the macamides to detect their effect on bone formation as follows: N‐(3‐methoxybenzyl)‐(9Z,12Z,15Z)‐octadecatrienamide (MBOC), N‐benzyl‐(9Z,12Z)‐octadecadienamide (BOD), and N‐(3‐methoxybenzyl)‐(9Z,12Z)‐octadecadienamide (MBOD).…”