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Macathiohydantoin L, a Novel Thiohydantoin Bearing a Thioxohexahydroimidazo [1,5-a] Pyridine Moiety from Maca (Lepidium meyenii Walp.)

Ranran Zhang, Junhong Liu, Hui Yan, Xing‐Rong Peng, Ling Zhang, Ming‐Hua Qiu

2021Molecules10 citationsDOIOpen Access PDF

Abstract

Five new thiohydantoin derivatives (1–5) were isolated from the rhizomes of Lepidium meyenii Walp. NMR (1H and 13C NMR, 1H−1H COSY, HSQC, and HMBC), HRESIMS, and ECD were employed for the structure elucidation of new compounds. Significantly, the structure of compound 1 was the first example of thiohydantoins with thioxohexahydroimidazo [1,5-a] pyridine moiety. Additionally, compounds 2 and 3 possess rare disulfide bonds. Except for compound 4, all isolates were assessed for neuroprotective activities in corticosterone (CORT)-stimulated PC12 cell damage. Among them, compound (−)-3 exhibited moderate neuroprotective activity (cell viability: 68.63%, 20 μM) compared to the positive control desipramine (DIM) (cell viability: 88.49%, 10 μM).

Topics & Concepts

MoietyNeuroprotectionChemistryStereochemistryViability assayTwo-dimensional nuclear magnetic resonance spectroscopyPyridineRhizomeHeteronuclear single quantum coherence spectroscopyCellBiochemistryBiologyMedicinal chemistryPharmacologyBotanyTraditional and Medicinal Uses of AnnonaceaeGinger and Zingiberaceae researchPhytochemistry and Biological Activities
Macathiohydantoin L, a Novel Thiohydantoin Bearing a Thioxohexahydroimidazo [1,5-a] Pyridine Moiety from Maca (Lepidium meyenii Walp.) | Litcius