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

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 thio...

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Published inMolecules (Basel, Switzerland) Vol. 26; no. 16; p. 4934
Main Authors Zhang, Ranran, Liu, Junhong, Yan, Hui, Peng, Xingrong, Zhang, Ling, Qiu, Minghua
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 14.08.2021
MDPI
Subjects
Chemical bonds
Chromatography
Lepidium meyenii
neuroprotective activities
thiohydantoins
thioxohexahydroimidazo [1,5-a] pyridine
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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).
AbstractList 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).
Five new thiohydantoin derivatives ( 1 – 5 ) were isolated from the rhizomes of Lepidium meyenii Walp. NMR ( 1 H and 13 C NMR, 1 H− 1 H 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).
Author Peng, Xingrong
Liu, Junhong
Qiu, Minghua
Zhang, Ling
Zhang, Ranran
Yan, Hui
AuthorAffiliation 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; zhangranran@mail.kib.ac.cn (R.Z.); liujunhong@mail.kib.ac.cn (J.L.); yanhui@mail.kib.ac.cn (H.Y.); pengxingrong@mail.kib.ac.cn (X.P.); zhang-874005@163.com (L.Z.)
2 University of the Chinese Academy of Sciences, Beijing 100049, China
AuthorAffiliation_xml – name: 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; zhangranran@mail.kib.ac.cn (R.Z.); liujunhong@mail.kib.ac.cn (J.L.); yanhui@mail.kib.ac.cn (H.Y.); pengxingrong@mail.kib.ac.cn (X.P.); zhang-874005@163.com (L.Z.)
– name: 2 University of the Chinese Academy of Sciences, Beijing 100049, China
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crossref_primary_10_1016_j_phytol_2022_07_007
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Snippet 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,...
Five new thiohydantoin derivatives ( 1 – 5 ) were isolated from the rhizomes of Lepidium meyenii Walp. NMR ( 1 H and 13 C NMR, 1 H− 1 H COSY, HSQC, and HMBC),...
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SubjectTerms Chemical bonds
Chromatography
Lepidium meyenii
neuroprotective activities
thiohydantoins
thioxohexahydroimidazo [1,5-a] pyridine
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Title Macathiohydantoin L, a Novel Thiohydantoin Bearing a Thioxohexahydroimidazo [1,5-a] Pyridine Moiety from Maca (Lepidium meyenii Walp.)
URI https://www.proquest.com/docview/2565470376
https://pubmed.ncbi.nlm.nih.gov/PMC8398295
https://doaj.org/article/2fa8266f432d4161a0cfd7ba0b89c678
Volume 26
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