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1.
Org Biomol Chem ; 20(20): 4176-4182, 2022 05 26.
Article in English | MEDLINE | ID: mdl-35535577

ABSTRACT

Zanthoxylum avicennae fruits were traditionally used to treat many inflammatory-related diseases, such as icterohepatitis, nephritis and colitis, which inspired us to explore the active chemicals and pharmacological activity. As a result, ten quinoline alkaloids, including six new ones, avicenines A-F (1-6), were isolated and structurally characterized by solid data. Compounds 1, 7 and 8 were identified as three pairs of enantiomers by chiral HPLC separation, of which 1 was an unusual 6/6/5/5-fused quinoline alkaloid bearing a unique cis-hexahydrofuro[3,2-b]furan moiety. The putative biosynthetic pathway for enantiomeric compounds was also proposed. In addition, compound 6 significantly suppressed the gene expression and secretion of pro-inflammatory cytokines IL-1ß and IL-6 in macrophages.


Subject(s)
Alkaloids , Quinolines , Zanthoxylum , Alkaloids/chemistry , Alkaloids/pharmacology , Anti-Inflammatory Agents/pharmacology , Chromatography, High Pressure Liquid , Quinolines/pharmacology , Zanthoxylum/chemistry
2.
Phytochemistry ; 198: 113142, 2022 Jun.
Article in English | MEDLINE | ID: mdl-35231502

ABSTRACT

A chemical investigation on the aerial parts of Euphorbia neriifolia led to the identification of thirteen undescribed diterpenoids, phorneroids A-M, including ent-abietane (A-D), ent-kaurane (E-G), ent-atisane (H-K), and ent-isopimarane (L and M) types, together with three known compounds. Phorneroid A represents the first example of 8-spiro-fused 9,10-seco-ent-abietane diterpenoid lactone featuring a unique 6/5/6/5 spirocyclic framework. Biological assays showed that some of the compounds displayed moderate cytotoxicity against two human tumor cell lines, A549 and HL-60.


Subject(s)
Diterpenes, Kaurane , Diterpenes , Euphorbia , Cell Line, Tumor , Diterpenes/chemistry , Diterpenes/pharmacology , Diterpenes, Kaurane/chemistry , Euphorbia/chemistry , Molecular Structure
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