Journal
PHYTOCHEMISTRY
Volume 190, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2021.112866
Keywords
Delphinium grandiflorum; Ranunculaceae; Diterpenoid alkaloids; Grandiflonines A-B; Analgesic activity
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Funding
- National Natural Science Foundation of China [82073734, 81773605]
- Science and Technology Program of Sichuan (China) [2018JY0077]
- Cultivation Program for the Excellent Doctoral Dissertation of Southwest Jiaotong University (China) [2020YBPY10]
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Seven new diterpenoid alkaloids were isolated from Delphinium grandiflorum, along with eight reaction products and thirteen known compounds. Grandiflonines A and B have a unique C-20 diterpenoid alkaloid skeleton, with the configuration of C-18 inverted. The analgesic and anti-inflammatory activities of these compounds were evaluated, with deoxylappaconitine showing superior analgesic activity compared to lappaconitine.
Seven previously undescribed diterpenoid alkaloids, eight reaction products and thirteen known compounds were isolated from the whole plant of Delphinium grandiflorum L. (Ranunculaceae). Grandiflonines A and B have an unprecedented C-20-diterpenoid alkaloid skeleton, which features inversion of the configuration of C-18. Their structures were determined by comprehensive analyses of spectroscopic data, X-ray diffraction and Mosher's method. The probable biosynthetic pathway of grandiflonine A was discussed. Additionally, the analgesic activity and anti-inflammatory activity by inhibition of NO production were evaluated. Among them, deoxylappaconitine (ED50 = 0.35 mg/kg, TI = 46.22) showed significant analgesic activity that was superior to the reference drug lappaconitine (ED50 = 3.5 mg/kg, TI = 3.34).
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