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Characterization of a New Insecticide, Clavamine, from the Venom of a Spider, Nephila clavata by Use of a Synthetic Compound.

1992; Pharmaceutical Society of Japan; Volume: 40; Issue: 11 Linguagem: Inglês

10.1248/cpb.40.3005

1347-5223

Masanori Yoshioka, Noriko Narai, Tadashi Teshima, Takahiro Matsumoto, Tateaki Wakamiya, Tetsuo Shiba, Naomi TOKORO, Tetsuo Okauchi, Yoshiaki Kono,

Venomous Animal Envenomation and Studies

In this paper, we compared the chemical and biological activities of natural and synthetic clavamines, N-[2, 4-dihydroxyphenylacetyl-4-L-asparaginyl)-N'-[N-(L-arginyl-glycyl-L-alanyl)-8-amino-4-azaoctanoyl]-1, 5-pentane-diamine (DPA→Asn→Cad←Ptr←Ala←Gly←Arg)[DPA, 2, 4-dihydroxyphenylacetic acid; Cad, 1.5-pentanediamine (cadaverine); Ptr, 8-amino-4-azaoctanoic acid (putreanine, or carboxyethylputrescine)], and found that both were identical. Both compounds showed the same Rf value in thin-layer chromatography and the same retention time in high performance liquid chromatography (HPLC). Both hydrolyzates consisted of the same components, such as Gly, DPA, Ala, Asp, Arg and Ptr in gas chromatography. The Edman degradation of both compounds also gave exactly the same sequence. The 1H-NMR spectrum and fast atom bombardment (FAB) mass spectrum of the synthetic compound coincided with those of the natural one. Both were active on the insects used. Clavamine was the main component of the insecticidal activity in the crude venom. By this synthetic study, the structure of a new venom insecticide was thus established. The synthetic compound in abundant quantity will be advantageous for practical use as an insecticide over natural ones, because the latter is available only in small amounts. Also, it will be useful for the exploitation of a new field of biochemistry for polyamines.