New oligomeric terpenoids fused with an oxazoline ring linkage from cones of Taxodium ascendens and their biological activities
• Taxodascaloids A-C, three uncommon oligomeric terpenoids , were purified from the cones of Taxodium ascendens . • Compounds 1 and 2 represented the first identified diterpenoid-monoterpenoid adducts linked by an oxazoline ring. • All these three compounds were determined using extensive spectroscopic analysis and X-ray diffraction techniques. Taxodascaloids A-C ( 1–3 ), three uncommon oligomeric terpenoids featuring an oxazoline ring linkage, were purified from the cones of Taxodium ascendens . Compounds 1 and 2 , a unique pair of stereoisomers, represented the first identified diterpenoid-monoterpenoid adducts linked by an oxazoline ring. Compound 3 was an uncommon dimeric diterpenoid and composed of a seco-abietane unit and an abietane unit, also containing an oxazoline ring. The planar structures and absolute configurations of these compounds were determined using extensive spectroscopic analysis and X-ray diffraction techniques. Compounds 1 and 2 demonstrated potent anticancer activity against human colon cancer HCT cells, with the IC 50 values of 25.7 and 40.1 μ M, respectively. Further research indicated that compound 1 could induce both ferroptosis and apoptosis in HCT-116 cells. Additionally, compound 3 showed notable α -glucosidase inhibitory activity in a mixed-type manner with an IC 50 value of 2.9 μ M.
Authors
- Yu‐Cheng Gu (ORCID: https://orcid.org/0000-0002-6400-6167)
- Jianbo Xiao (ORCID: https://orcid.org/0000-0003-3311-770X)
- Bo‐Yi Fan (ORCID: https://orcid.org/0000-0003-1581-8422)
- Bin Lin (ORCID: https://orcid.org/0000-0003-2369-4765)
- Qi Gao (ORCID: https://orcid.org/0000-0003-4234-8761)
- Guangtong Chen (ORCID: https://orcid.org/0000-0002-3274-9281)
- Kai Chen (ORCID: https://orcid.org/0000-0002-0206-3502)
- Jianlin Li (ORCID: https://orcid.org/0000-0002-5267-3931)
- Min Yang (ORCID: https://orcid.org/0000-0002-9034-3175)
- Andong Wang (ORCID: https://orcid.org/0000-0003-2281-7946)
- Weizhong Zhu (ORCID: https://orcid.org/0000-0002-8740-3210)
- Jinjuan Wei
- Wenli Wang (ORCID: https://orcid.org/0000-0003-3831-1405)
Institutions
- Shenyang Pharmaceutical University (CN)
- Nantong University (CN)
- Syngenta (United Kingdom) (GB)
Publication Details
- Journal
- Journal of Molecular Structure
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1016/j.molstruc.2024.140206
- Citations
- 5
- Primary Topic
- Biological Activity of Diterpenoids and Biflavonoids
- Type
- article
- Field-Weighted Citation Impact
- 1.17
Funders
- Natural Science Foundation of Nantong City
- National Natural Science Foundation of China