Two New Halimanes with a γ-Lactone from Croton argyratus

Kanami Watanabe; Yohei Saito; Shuichi Fukuyoshi; Katsunori Miyake; David J. Newman; Barry R. O’Keefe; Kuo-Hsiung Lee; Kyoko Nakagawa-Goto

doi:10.1248/cpb.c24-00734

Current Topics: Regular Article

Two New Halimanes with a γ-Lactone from Croton argyratus

Kanami Watanabe, Yohei Saito , Shuichi Fukuyoshi, Katsunori Miyake, David J. Newman, Barry R. O’Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto

Author information

Kanami Watanabe
School of Pharmacy, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Ishikawa 920–1192, Japan
Yohei Saito Corresponding author
School of Pharmacy, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Ishikawa 920–1192, Japan
Shuichi Fukuyoshi
School of Pharmacy, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Ishikawa 920–1192, Japan
Katsunori Miyake
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo 192–0392, Japan
David J. Newman
NIH Special Volunteer, Wayne, PA 19087, U.S.A.
Barry R. O’Keefe
Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, NCI at Frederick, Frederick, MD 21702–1201, U.S.A.
Molecular Targets Program, Center for Cancer Research, National Cancer Institute, NCI at Frederick, Frederick, MD 21702–1201, U.S.A.
Kuo-Hsiung Lee
Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599–7568, U.S.A.
Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40447, Taiwan
Kyoko Nakagawa-Goto Corresponding author
School of Pharmacy, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, Ishikawa 920–1192, Japan
Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40447, Taiwan
WPI Nano Life Science Institute, Kanazawa University, Kanazawa, Ishikawa 920–1192, Japan

Keywords: Croton argyratus, halimane, 5,6-γ-lactone, crotargyolide

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Supplementary material

2025 Volume 73 Issue 3 Pages 162-167

DOI https://doi.org/10.1248/cpb.c24-00734

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Abstract

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.

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