期刊
CHINESE JOURNAL OF CHEMISTRY
卷 40, 期 9, 页码 1019-1027出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202100764
关键词
Biological activity; Kalmane diterpenoids; Natural products; Rhododendron dauricum L; (Ericaceae); Structure elucidation
资金
- Scientific Research Project of Traditional Chinese Medicine of Hubei Provincial Health Commission [ZY2021M056]
- Open Project of State Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources [CMEMR-2021-B03]
This study investigated the phytochemical constituents of Rhododendron dauricum L. flowers, leading to the identification of eight kalmane diterpenoids, including four new ones. All isolated compounds showed significant analgesic effects, with rhodokalmanol C and kalmanol exhibiting even stronger analgesic activity than morphine.
Comprehensive Summary Kalmane diterpenoids, featuring a 5/8/5/5 tetracyclic carbon skeleton, are very rare in nature. The flowers of Rhododendron dauricum L. (Ericaceae) were phytochemically investigated for the first time, leading to the isolation of eight kalmane diterpenoids (1-8) including four new ones, named rhodokalmanols A-D (1-4). The structures of 1-8 were elucidated by comprehensive spectroscopic methods and C-13 NMR-DP4+ analysis, and the absolute configurations of 1, 2, 4, and 5 were defined by single-crystal X-ray diffraction analysis with Cu K alpha radiation. Rhodokalmanol A (1) represents the first 5,8-epoxykalmane diterpenoid and also the first kalm-15(16)-ene diterpenoid. Rhodokalmanols B-D (2-4) are the first examples of kalm-7(8)-ene, kalm-16(17)-ene, and 8 alpha-methoxykalmane diterpenoids, respectively. All the isolated kalmane diterpenoids 1-8 exhibited significant analgesic effects, and rhodokalmanol C (3) and kalmanol (8) expressed more potent analgesic activity than morphine at doses of 0.2 and 0.04 mg/kg. The preliminary structure-activity relationships of kalmane diterpenoids as potent analgesics are discussed.
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