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Diterpenoids with an unusual tricyclo[10.3.0.02,9]pentadecane skeleton from Pedilanthus tithymaloides as multidrug resistance modulators.
Zhang, Lan-Jun; Huang, Pei-Zhi; Li, Ke-Jing; Cao, Yue-Yang; Sun, Yue; Feng, Wei-Jiao; Wang, Yu-Xian; He, Yi-Lin; Mi, Le-Yuan; Wei, Yan-Li; Lai, Qi-Zhong; Chen, Jian-Jun; Gao, Kun.
Affiliation
  • Zhang LJ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Huang PZ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Li KJ; The First Hospital of Lanzhou University, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China.
  • Cao YY; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Sun Y; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Feng WJ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Wang YX; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • He YL; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China; Research Institute, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China.
  • Mi LY; The First Hospital of Lanzhou University, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China.
  • Wei YL; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Lai QZ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Chen JJ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
  • Gao K; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China. Electronic address: npchem@lzu.edu.cn.
Bioorg Chem ; 138: 106619, 2023 09.
Article in En | MEDLINE | ID: mdl-37253310
ABSTRACT
Three new diterpenoids with an unusual carbon skeleton, pedilanins A-C (1-3), and nine new jatrophane diterpenoids, pedilanins D-L (4-12), along with five known ones (13-17), were isolated from Pedilanthus tithymaloides. Compounds 1-3 characterize an unprecedented tricyclo[10.3.0.02,9]pentadecane skeleton. Compounds 4-8 are rare examples of the jatrophanes bearing a cyclic hemiketal substructure. Their structures were determined by an extensive analysis of HRESIMS, NMR, quantum-chemical calculation, DP4+ probability, and X-ray crystallographic data. In the bioassay, compounds 1-12 dramatically reversed multidrug resistance in cancer cells with the fold-reversals ranging from 17.9 to 396.8 at the noncytotoxic concentration of 10 µM. The mechanism results indicated that compounds 2 and 3 inhibited the P-glycoprotein (Pgp) transporter function, thus reversing the drug resistance.
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Full text: 1 Database: MEDLINE Main subject: Euphorbia / Diterpenes Language: En Year: 2023 Type: Article
Fulltext
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Full text: 1 Database: MEDLINE Main subject: Euphorbia / Diterpenes Language: En Year: 2023 Type: Article