Abstract
A sesquiterpene lactone of the germacrane series, mucrochin, has been isolated from the epigeal part ofTanacetopsis mucronata, and its structure has been studied by IR and mass spectral methods and PMR spectroscopy. It structure has been determined unambiguously by x-ray structural analysis as 5,6-dihydroxy-5α,6β,7α,8β(H)-germacra-1(10),4(15) 1(13)-trien-8,12-olide. A boat-chair conformation with a configuration of the1D14 15D5 type has been established.
Similar content being viewed by others
References
B. Kh. Abduazimov, A. I. Yunusov, S. A. Khamidkhodzhaev, and G. P. Sidyakin, Khim. Prir. Soedin., 398 (1981).
B. Kh. Abduazimov, A. I. Yunusov, and G. P. Sidyakin, Khim. Prir. Soedin., 797 (1983).
B. Kh. Abduazimov, A. I. Yunusov, M. R. Yagudaev, and G. P. Sidyakin, Khim. Prir. Soedin., 314 (1984).
M. K. Makhmudov, B. Kh. Abduazimov, B. Tashkodzhaev, B. T. Ibragimov, and M. R. Yagudaev, Khim. Prir. Soedin., 58 (1978).
B. Kh. Abduazimov, B. Tashkodzhaev, S. Nasirov, I. D. Sham'yanov, M. R. Yagudaev, V. M. Malikov, and S. N. Aminov, Khim. Prir. Soedin., 19 (1991).
Z. Samek, Tetrahedron Lett., 671 (1970).
Z. Samek and G. Harmatha, Coll. Czech. Chem. Commun.,43, 2779 (1978).
Z. Samek, Coll. Czech. Chem. Commun.,43, 3210 (1978).
H. Yoshioka, T. J. Mabry, M. A. Irwin, T. A. Geissman, and Z. Samek, Tetrahedron,27, 3317 (1971).
J. De Pascual-T, M. S. Gonzalez, M. A. Moreno Valle, and I. S. Bellido, Phytochemistry,22, 1985 (1983).
F. Bohlmann, A. Adler, R. M. King, and H. Robinson, Phytochemistry,22, 1985 (1983).
W. Herz, W. Kumar, and J. F. Blount, J. Org. Chem.,45, 489 (1980).
W. Herz, S. V. Govindan, and J. F. Blount, J. Org. Chem.,45, 1113 (1980).
M. Holub and Z. Samek, Coll. Czech. Chem. Commun.,42, 1053 (1977).
H. Tada and K. Takeda, Chem. Pharm. Bull.,24, 667 (1976).
B. A. Nagasampagi, U. G. Bhat, F. Bohlmann, and C. Zdero, Phytochemistry,20, 2031 (1981).
F. Bohlmann, C. Zdero, R. M. King, and H. Robinson, Phytochemistry,19, 115 (1980).
F. Shafizadeh and N. R. Bhadane, Phytochemistry,12, 857 (1973).
F. Bohlmann, A. Adler, J. Jakupovic, R. M. King, and H. Robinson, Phytochemistry,21, 1349 (1982).
M. K. Makhmudov, B. Kh. Abduazimov, B. Tashkodzhaev, and B. T. Ibragimov, Khim. Prir. Soedin., 198 (1989).
F. N. Allen, O. Kennard, and D. G. Watson, J. Chem. Soc., Perkin Trans. II, No. 12, S1-S19 (1987).
J. Jakupovic, R. N. Barunh, F. Bohlmann, R. M. King, and H. Robinson, Planta Med., 214 (1986).
L. Quijano, J. S. Calderon, G. F. Gomez, J. Lopez, T. Rios, and F. R. Fronzcek, Phytochemistry,23, 1971 (1984).
A. Quick and D. Rogers, J. Chem. Soc., Perkin Trans.,2, 465 (1976).
G. Appendino, G. M. Nano, M. Calleri, and G. Chiari, Gazz. Chem. Ital.,116, 57 (1986).
G. M. Sheldrick, Acta Crystallogr.,46, 467 (1990).
G. M. Sheldrick, SHELXS-76: Program for Crystal Structure Determination, Cambridge University, England (n.d.).
A. T. McPhail and K. D. Onan, J. Chem. Soc., Perkin Trans.2, 578 (1976).
M. G. B. Drew, S. P. Hitchman, J. Mann, and J. L. C. Lopes, J. Chem. Soc., Chem. Commun., 802 (1980).
H. Ueda, C. Katayama, and J. Tanaka, Bull. Chem. Soc. Jpn.,53, 1263 (1980).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 492–498, July–August, 1998.
Rights and permissions
About this article
Cite this article
Izbosarov, M.B., Abduazimov, B.K., Yusupova, I.M. et al. Germacranolide fromTanacetopsis mucronata . Chem Nat Compd 34, 456–461 (1998). https://doi.org/10.1007/BF02329594
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02329594