Pergamon 0031~ 9422(94)E0291-Y zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFED Phyfahcmwy, Vol. 37. No. 3. pp 707 71 I. 1994 Copyright 0 1994 Elsevln Science Ltd Printed m Great Bruin. All nghb reserved 0031~W22D.4 S7.00+0.00 zyxwvutsrqpo ECDYSTEROIDS FROM THE ROOTS OF LEUZEA CARTHAMOIDES* JAROSLAV Pis, MILOS BUDkSiNSKY, KAREL VOKAC,VERA LAUDOVA and JURAJ HARMATHAt Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 IO Prague 6, The Czech Republic (Receiced in zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGF recked form 21 March 1994) Key Word Index-fazea carthamoides; Asteraceae; roots; ecdysteroids; phytoecdysones; makisterone A; 20-hydroxyecdysone 2,3;20,22_diacetonide; polypodine B 20,22-acetonide; isovitexirone. Abstract-Three new ecdysteroids: polypodine B 20,22-acetonide, 20-hydroxy-ecdysone 2,3;20,22_diacetonide and isovitexirone along with 20-hydroxyecdysone, 20-hydroxyecdysone 2,3-acetonide, 20-hydroxyecdysone 20,22-acet- onide, ajugasterone C, makisterone A and polypodine B were isolated from the roots of Leuzea carthamoides. INTRODUflION Leuzea carthamoides (Willd.) DC. [syn. Rhaponticum carthamoides (Willd.) Iljin] species endemic in Siberia is known to contain various ecdysteroids. In one of the earliest reports [l] it was established that the plant contains inokosterone in addition to substantial amounts of 20-hydroxyecdysone. A later paper [2] reported the presence of 20-hydroxyecdysone and several minor ec- dysteroids: 2-deoxy-20_hydroxyecdysone, 20-hydroxyec- dysone 2.3 and 20,22 monoacetonides, integristerone A, 2428)-dehydromakisterone, polypodine B and rapis- teron. Analytical and phytochemical studies [3] of the plant introduced and cultivated in Hungary revealed the presence of some previously reported ecdysteroids (20- hydroxyecdysone, polypodine B, 24(28)-dehydromakis- terone A), together with several known ecdysteroids, which occurr also in other plant species (ajugasterone C, makisterone C, 5deoxykaladasterone, identical with the dacryhainansterone [4]) and the newly described car- thamosterone. This plant has been used as a source of ecdysteroids for analytical and chemical transformation studies in our laboratory [S-9]. Several previously re- ported ecdysteroids l-6 have been identified along with three ecdysteroids 7-9, not found before in natural sources, and with makisterone A (4) not described pre- viously in Leuzea carthamoides. The isolation and identi- fication of the three new natural ecdysteroids from the roots of this plant are reported. RESULTS ANDDISCUSSION Ecdysteroids 1-9 were isolated from the butanol- soluble material from a methanol-water extract of the *Part 56 in the series ‘Plant substances’. For Part 55 see: B&hem. Syst. Ecol. (1989) 17, 55. tAuthor to whom correspondence should be addressed. 1 HHHOH 2 OHHHOH 3 H OH H H 4 H H CH, OH RI0 R2O 6 (CH&C H H H 6 H H H (CH&$ 7 (CH3)2C H (CH&C 0 H H OH (CHJ.$ plant. 20-Hydroxyecdysone (I), polypodine B (2), ajugas- terone C (3), makisterone A (4), 20-hydroxyecdysone 2,3- monoacetonide (5) and 2@hydroxyecdysone 20,22- monoacetonide (6) were identified by NMR, mass and IR zyxwvutsrqponm 707