49(P07) 王不留行Vaccaria segetalisに含有される新規環状ペプチドSegetalin類について(ポスター発表の部)
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概要
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Recently, a number of naturally occurring cyclic peptides with unique structures and biological activities have been isolated. However, despite their importance, surprisingly few studies of higher plants occurring cyclic peptides exist in the literature. In our investigation of bioactive cyclic peptides from higher plants, new cyclic peptide, called segetalins A-H (1-8), were isolated from the seeds of Vaccaria segetalis (Caryophyllaceae), which are used to activate blood flow and promote milk secretion, and also to treat amenorrhea and breast infections in China. The structures of segetalins A-H were elucidated by 2D NMR, ESI-MS/MS, and chemical degradations. Conformational analysis of segetalins A, B, G, and H, which showed estrogen-like activity, was made by using X-ray, high field NMR and computational methods. To propose the 3D requirements to exhibit the estrogen-like activity, superposition using DISCO was undertaken and each cyclic peptide was suggested to possess a partial conformation similar to that of segetalin A in the region of Trp-Ala-Gly-Val. The sequence and coformation may play an important role to show the activity. To elucidate the relation between their conformation and estrogen-like activity, backbone transformation with Lawesson's reagent was examined. Thionation of segetalins A and B with Lawesson's reagent in dioxane gave each two dithionated products; dithiosegetalins Al (9) and A2 (10), and dithiosegetalins B1 (11) and B2 (12). The only dithiosegetalin A2 showed estrogen-like activity. Conformational preference of dithiosegetalins analyzing by NMR and computational methods suggested that dithiosegetalins A2, dithiosegetalins B1 and B2 took different solution conformations from their parent compounds.
- 天然有機化合物討論会の論文
- 1996-09-02
著者
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森田 博史
Department Of Pharmacognosy School Of Pharmacy Tokyo University Of Pharmacy And Life Sciences
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竹谷 孝一
東京都立衛生研究所
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竹谷 孝一
東京薬大薬
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森田 肇
Research Laboratories Toyama Chemical Co. Ltd.
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糸川 秀治
東京薬科大学 薬学部
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森田 博史
東京薬科大学
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尹 永淑
東京薬大、薬
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森田 博史
東京薬大、薬
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竹谷 孝一
東京薬大、薬
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糸川 秀治
東京薬大、薬
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糸川 秀治
東京薬科大学
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