Bioorg Chem
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, China; Laboratory of Xinjiang Native Medicinal and Edible Plant Resource Chemistry, College of Chemistry and Environmental Science, Kashi University, Kashi 844006, China. Electronic address:
Published: December 2024
To search for structurally novel analgesics from Ericaceae plants, the leaves of Pieris formosa collected at Yichang, Hubei, China, were phytochemically investigated for the first time. A total of fifteen ent-kaurane diterpene glucosides (1-15) including twelve new ones, named forminosides A-L (1-12), were isolated. Their structures were elucidated by comprehensive spectroscopic data analyses, quantum chemical calculations (C NMR and ECD calculations and DP4+ analysis), and chemical methods. The absolute configures of 1-3, 5-8, 11, and 13 were further determined by single-crystal X-ray diffraction analysis. Forminoside A (1) represents the first 3α-(β-d-glucopyranosyloxy)-11,16-epoxy-ent-kaurane diterpenoid bearing a unique 12-oxa-pentacyclo[9.3.3.0.0.0]heptadecane core. Forminoside J (10) is the first 17-nor-ent-kaurane type diterpenoid from Ericaceae family, while forminoside L (12) represents the first example of 4,5-seco-ent-kaurane diterpenoid glycoside bearing an unusual α-hydroxyl-α,β-unsaturated ketone block. Notably, the structure of mollisside A was revised to 3β-(β-d-glucopyranosyloxy)-16β,17-dihydroxy-ent-kaurane based on the NMR and single-crystal X-ray diffraction data analysis of forminoside C (3). All the isolates 1-15 showed potent analgesic activity in the HOAc-induced writhing test in mice. Among them, compounds 1-3, 5-12, and 15 exhibited significant analgesic effects at a dose of 5.0 mg/kg with the inhibition rates over 50%. Compounds 1, 5, 7, and 9-12 still displayed significant analgesic effects with the inhibition rates exceeding 50% at a lower dose of 1.0 mg/kg. Forminosides J (10) and L (12) still showed significant analgesic potency even at a lower dose of 0.2 mg/kg, comparable to that of the positive control, morphine. This is first report of the analgesic activity of 11,16-epoxy-ent-kaurane diterpenoid. A preliminary structure-activity relationship was explored, providing new clues to design novel analgesics based on the ent-kaurane and related diterpenoids.
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http://dx.doi.org/10.1016/j.bioorg.2024.107923 | DOI Listing |
Bioorg Chem
December 2024
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, China; Laboratory of Xinjiang Native Medicinal and Edible Plant Resource Chemistry, College of Chemistry and Environmental Science, Kashi University, Kashi 844006, China. Electronic address:
To search for structurally novel analgesics from Ericaceae plants, the leaves of Pieris formosa collected at Yichang, Hubei, China, were phytochemically investigated for the first time. A total of fifteen ent-kaurane diterpene glucosides (1-15) including twelve new ones, named forminosides A-L (1-12), were isolated. Their structures were elucidated by comprehensive spectroscopic data analyses, quantum chemical calculations (C NMR and ECD calculations and DP4+ analysis), and chemical methods.
View Article and Find Full Text PDFMost herbivorous insects are host-plant specialists that evolved detoxification mechanisms to overcome their host plant's toxins. In the evolutionary arms-races between Pieridae butterflies and Brassicaceae plants, some plant species have evolved another defence against the pierids: egg-killing. Underneath the eggs, leaves develop a so-called hypersensitive response (HR)-like cell death.
View Article and Find Full Text PDFJ Exp Bot
September 2024
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Tokyo 113-8657, Japan.
Bioassay with an insect herbivore is a common approach to studying plant defense. While measuring insect growth rate as a negative indicator of plant defense levels is simple and straightforward, analysing more detailed feeding behavior parameters of insects, such as feeding rates, leaf area consumed per feeding event, intervals between feeding events, and spatio-temporal patterns of feeding sites on leaves, is more informative. However, such observations are generally time consuming and labor-intensive.
View Article and Find Full Text PDFBMC Plant Biol
February 2024
Centro de Biotecnología y Genómica de Plantas, Universidad Politécnica de Madrid (UPM) - Instituto Nacional de Investigación y Tecnología Agraria y Alimentaria (INIA/CSIC) Campus de Montegancedo, Pozuelo de Alarcón, 28223, Madrid, Spain.
Background: Plants have acquired a repertoire of mechanisms to combat biotic stressors, which may vary depending on the feeding strategies of herbivores and the plant species. Hormonal regulation crucially modulates this malleable defense response. Jasmonic acid (JA) and salicylic acid (SA) stand out as pivotal regulators of defense, while other hormones like abscisic acid (ABA), ethylene (ET), gibberellic acid (GA) or auxin also play a role in modulating plant-pest interactions.
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