Two New Halimanes with a <i>γ</i>-Lactone from <i>Croton argyratus</i>
The phytochemical investigation of the rainforest plant Croton argyratus (Euphorbiaceae) led to the isolation of two halimane-type diterpenes, crotargyolides A (1) and B (2), with an uncommon γ-lactone ring at C-5 and C-9, together with a crotofolane-type diterpene, 3-hydroxylated crotofolin C (3, crokocrotogenoid A), and the known clerodane diterpenes, junceic acid (4) and epoxyjunceic acid (5). The structures of the newly isolated compounds were elucidated by various NMR techniques, high resolution (HR)MS analysis, and electronic circular dichroism (ECD) spectroscopy. The proposed biosynthetic pathway of 1 from 4 was discussed. Crotargyolide A (1) and known compounds 4 and 5 were evaluated for antiproliferative activity and displayed no growth inhibitory effect toward all tested tumor cell lines.
Authors
- Katsunori Miyake (ORCID: https://orcid.org/0000-0001-6199-8781)
- Kuo‐Hsiung Lee (ORCID: https://orcid.org/0000-0002-6562-0070)
- Kyoko Nakagawa‐Goto (ORCID: https://orcid.org/0000-0002-1642-6538)
- Shuichi Fukuyoshi (ORCID: https://orcid.org/0000-0002-9015-0920)
- Kenji Watanabe (ORCID: https://orcid.org/0000-0002-3781-4724)
- Barry R. O’Keefe (ORCID: https://orcid.org/0000-0003-0772-4856)
- David Newman (ORCID: https://orcid.org/0000-0002-4959-2428)
- Yohei Saito (ORCID: https://orcid.org/0000-0003-2313-8339)
Institutions
- Kanazawa University (JP)
- University of North Carolina at Chapel Hill (US)
- Tokyo University of Pharmacy and Life Sciences (JP)
- China Medical University (TW)
- Health Volunteers Overseas (US)
- Life Science Institute (JP)
- China Medical University Hospital (TW)
- Frederick National Laboratory for Cancer Research (US)
Publication Details
- Journal
- Chemical and Pharmaceutical Bulletin
- Published
- 2025-03-06
- DOI
- https://doi.org/10.1248/cpb.c24-00734
- Citations
- 3
- Primary Topic
- Bioactive Natural Diterpenoids Research
- Type
- article
- Field-Weighted Citation Impact
- 2.42
Funders
- University of North Carolina at Chapel Hill
- Japan Society for the Promotion of Science