Structure-Analgesic Activity Relationship Studies on the C18- and C19-Diterpenoid Alkaloids
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- Wang Jian-Li
- Department of Chemistry of Medicinal Natural Products, West China of Pharmacy, Sichuan University
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- Shen Xiang-Li
- West China Second Hospital, Sichuan University
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- Chen Qiao-Hong
- Department of Chemistry of Medicinal Natural Products, West China of Pharmacy, Sichuan University
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- Qi Gong
- State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institute for Biological Sciences
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- Wang Wei
- State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institute for Biological Sciences
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- Wang Feng-Peng
- Department of Chemistry of Medicinal Natural Products, West China of Pharmacy, Sichuan University
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説明
For evaluation of C18- and C19-diterpenoid alkaloids as analgesics, three C19-diterpenoid alkaloids were isolated from the roots of Aconitum hemsleyanum var. circinatum and A. transsecutum; and twenty-five semisynthetic C18- or C19-diterpenoid alkaloids were prepared from lappaconitine, crassicauline A or yunaconitine. In a mice acetic acid-induced abdominal constriction assay, four crassicauline A analogs and three yunaconitine analogs exhibited good analgesic activities with 77.8—94.1% inhibition range in 0.1—10 mg/kg subcutaneous (s.c.) dose range at the point of 20 min after drug administration. Among them, 8-O-deacetyl-8-O-ethylcrassicauline A (ED50=0.0972 mg/kg) and 8-O-ethylyunaconitine (ED50=0.0591 mg/kg) were the most potent analgesics relative to the reference drugs lappaconitine (ED50=3.50 mg/kg) and crassicauline A (ED50=0.0480 mg/kg). Analgesic activity data of these C18- and C19-diterpenoid alkaloids indicate that a tertiary amine in ring A, an acetoxyl or an ethoxyl group at C-8, an aromatic ester at C-14, and the saturation state of the ring D are important structural features necessary to the analgesic activity of the C19-diterpenoid alkaloids.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 57 (8), 801-807, 2009
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204171435520
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- NII論文ID
- 130000124163
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 10290458
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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- 使用不可