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Crotonianoids A-C, Three Unusual Tigliane Diterpenoids from the Seeds of Croton tiglium and Their Anti-Prostate Cancer Activity.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2022 Jul 15; Vol. 87 (14), pp. 9301-9306. Date of Electronic Publication: 2022 Jun 25. - Publication Year :
- 2022
-
Abstract
- Crotonianoids A-C ( 1 - 3 ), three unusual tigliane diterpenoids, were isolated from the seeds of Croton tiglium . Compound 1 is a 13,14:13,15- diseco -tigliane featuring a unique spiro[bicyclo[5.3.0]decane-2,5'-2'(3' H ,4' H )-furanone] core; 2 is a 13,15- seco -tigliane incorporating a rare peroxide bridge between C-13 and C-15; and 3 is the first example of a phorbol ester with a 10 R -configuration. Their structures were determined by spectroscopic, computational, and X-ray diffraction methods. Compounds 1 and 2 markedly inhibited the growth and survival of prostate cancer cell C4-2B at micromolar concentrations and induced cell apoptosis. Mechanistic study revealed that 1 and 2 could suppress androgen receptor (AR) signaling pathway by promoting the degradation of AR protein.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 87
- Issue :
- 14
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 35758034
- Full Text :
- https://doi.org/10.1021/acs.joc.2c01024