ECDYSTEROID ACETATES FROM Ajuga reptans L. I. Alekseeva, I V. V. Volodin, l V. G. Luksha, t and R. Lafont 2 UDC. 547.926The compounds 20-hydroayecdysone-22-acetate and viticosterone E (20-hydroxvecdysone-25-acetate) are obsela,ed for the fi~'st time in Ajuga reptans L. growing at the northern limit of its range in a middle taiga subzone of European northeastern Russia.The plant Ajuga reptans L. (Lamiaceae) is interesting because it is traditionally used in the folk medicine of many peoples as a tonic and stimulant owing to the presence in it of ecdysteroids [ 1 ].It has been shown that the ecogeographic conditions under which A. reptans grows can affect the ecdysteroid composition [2][3][4][5]. We found that A. reptans growing at the northern limit of its range contains polypodin B, 20hydroxyecdysone. 29-norcyasterone, 29-norsengosterone, sengosterone, and ajugalactone, which are characteristic of this species. Cyasterone is absent. Ajugasterone B is observed for the first time [5]. Minor ecdysteroids are known to be present in addition to the principal ones. The purified minor ecdysteroids of A. reptans were obtained by preparative and semipreparative normal-phase HPLC (Table 1).Mass spectral analysis of compounds I and 2 showed that the principal fragmentation patterns are cleavage of the MH + and MNH4+ ions at the Ci7-C~_o and C_~_0-C2_~ bonds and loss of one or several water molecules from the MH + and MNH4 + ions, side-chain fragments, or fragment ions. The fragment ions of I and 2 that are formed by cleavage at the Ci7-C20 and C2o-C22 bonds (Table 2) are identical to those from 20-hydroxyecdysone. The side-chain fragment ions are m/-203 (C10Hi904 +) and 159 (CIsHI503+), which differ from the side-chain ions of 20-hydroxyecdysone by 42 mass units. The unsaturation factor (UF) of these ions is 1. Furthermore, the side-chain ions that are lormed by cleavage of MH + and MNH4 + at the C_~II-C_,_~ bonds have the same UF as the side-chain fragments from cleavage at the Ci7-C20 bonds. This indicates that the side chains are unsaturated after the C20 atoms. The collection of ions with m/-271,240, 222, and 180 of I and 2 results most probably from fragmentation
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