Abstract
The structure of premixisterone (I) — a new ecdysteroid fromS. praemixta M. Pop. (Caryophyllaceae) — has been established. Compound (I) has the composition C27H44O5, mp 110–112°C (from C2H5OH + H2O), [α] 24D 0 ± 4° (c 0.85; MeOH),\(\lambda _{\max }^{{\text{C}}_{\text{2}} {\text{H}}_{\text{5}} {\text{OH}}}\) 202 nm (log ɛ 3.35), ν KBrmax 3415 cm−1 (OH), 1710 cm−1 (C=0), and does not contain the δ7-6-keto grouping that is characteristic of natural ecdysteroids. The acetylation of (I) with (CH3CO)2 in Py gave the amorphous 3,22-diacetylpremixisterone (II), C21H48O7. Compound (I) has the structure of 3β,14α,22R,25-tetrahydroxy-5β-cholest-8-en-6-one. The IR, PMR, and mass spectra of (I) and (II) are given.
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Literature cited
Z. Saatov, B. Z. Usmanov, and N. K. Abubakirov, Khim. Prir. Soedin., No. 6, 793 (1979).
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M. N. Galbraith, D. H. S. Horn, and E. J. Middleton, Chem. Commun., 402 (1969).
Additional information
Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 797–799, November–December, 1979.
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Saatov, Z., Usmanov, B.Z. & Abubakirov, N.K. Phytoecdysones ofSilene praemixta. II. Premixisterone. Chem Nat Compd 15, 703–705 (1979). https://doi.org/10.1007/BF00565566
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DOI: https://doi.org/10.1007/BF00565566