Chlorajaponins A—Q, Lindenane‐Related Sesquiterpenoid Dimers from Chloranthus japonicus and Their Biological Activities

Comprehensive Summary Seventeen undescribed lindenane‐related sesquiterpenoid dimers, chlorajaponins A—Q (1—17), and 13 reported analogs (18—30) were isolated from Chloranthus japonicus Sieb. Compound 1 possesses an unprecedented 3/5/7/5/5/6/5/3 fused octacyclic scaffold, featuring a 6(5→4)‐abeo‐lin...

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Bibliographic Details
Published in:Chinese journal of chemistry 2024-06, Vol.42 (11), p.1247-1259
Main Authors: Feng, Wei‐Jiao, Gu, Yue, Huang, Pei‐Zhi, Yang, Hong‐Ying, Zhang, Rui, He, Yi‐Lin, Lv, Ting‐Hong, Li, Ya, Gao, Kun
Format: Article
Language:English
Subjects:
Alanine
Alanine transaminase
Analogs
Anti‐inflammatory activity
Aspartate aminotransferase
Chloranthus japonicus
Cholesterol
Crystallography
Dimers
Fatty acids
Fatty-acid synthase
Inflammation
Lindenane‐type sesquiterpenoid dimers
Lipids
Lipid‐lowering activity
Lipopolysaccharides
Macrophages
Natural products
NMR spectroscopy
Proteins
Scaffolds
Sterols
Transaminases
Triglycerides
X‐ray diffraction
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Summary:Comprehensive Summary Seventeen undescribed lindenane‐related sesquiterpenoid dimers, chlorajaponins A—Q (1—17), and 13 reported analogs (18—30) were isolated from Chloranthus japonicus Sieb. Compound 1 possesses an unprecedented 3/5/7/5/5/6/5/3 fused octacyclic scaffold, featuring a 6(5→4)‐abeo‐lindenane monomer, while 2 exhibits a 3/5/6/6/5/6/5/3 fused octacyclic scaffold. Their structures were determined through a combination of spectroscopic analyses and X‐ray crystallography. Compounds 1, 2, and 18 demonstrated significant inhibitory effects on lipid accumulation and effectively reduced the levels of triglycerides and total cholesterol, as well as the levels of aspartate aminotransferase and alanine aminotransferase in a HepG2 cell model. In addition, compounds 1, 2, and 18 significantly suppressed the protein expression of the fatty acid synthase (FASN) and the sterol regulatory element‐binding protein 1 (SREBP1). Moreover, the anti‐inflammatory assay showed that compounds 19—22 and 25 inhibited the NO production induced by lipopolysaccharide in RAW 264.7 macrophages with IC50 values of 7.89 ± 0.44, 6.25 ± 0.46, 2.98 ± 0.29, 10.77 ± 0.60, and 3.60 ± 0.28 μmol/L. Seventeen new lindenane sesquiterpenoid dimers (LSDs), chlorajaponins A—Q (1—17), including two rearranged skeleton meroterpenoids (1—2), and 13 reported analogs (18—30) were isolated from the Chloranthus japonicus Sieb. Compounds 1, 2, and 18 demonstrated significant inhibitory effects on lipid accumulation, dose‐dependently reduced TG and TC levels, and significantly downregulated expression of FASN and SERBP1 validated by western blot assay. Moreover, compounds 19—22 and 25 exhibited the most potent anti‐inflammatory effects with IC50 values of 7.89, 6.25, 2.98, 10.77, and 3.60 μmol/L, respectively.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202300731