Planta Med 2001; 67(8): 774-776
DOI: 10.1055/s-2001-18362
Letter

© Georg Thieme Verlag Stuttgart · New York

Two New Sesquiterpene Lactones from Montanoa tomentosa ssp. microcephala

Alessandra Braca1,*, Giuseppina Cioffi2 , Ivano Morelli1 , Fabio Venturella3 , Cosimo Pizza2 , Nunziatina De Tommasi2
  • 1 Dipartimento di Chimica Bioorganica e Biofarmacia, Pisa, Italy
  • 2 Dipartimento di Scienze Farmaceutiche, Fisciano, Salerno, Italy
  • 3 Dipartimento di Scienze Farmacologiche, Palermo, Italy
Further Information

Publication History

October 25, 2000

March 24, 2001

Publication Date:
09 November 2001 (online)

Abstract

Two new sesquiterpene lactones: 8α-(4′-acetoxymethacryloyloxy)-3α,9β-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6α-olide (1) and 8α-(2′E)-(2′-acetoxymethyl-2′-butenoyloxy)-3α,9β-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6αolide (2), together with the known zoapatanolide A were isolated from the aerial parts of Montanoa tomentosa Cerv. in La Llave et Lex ssp. microcephala (Sch. Bip. In K. Koch) V.A. Funk (Asteraceae). The structures of all compounds were established on the basis of 1D, 2D NMR, and EIMS analysis.

References

  • 1 Levine S D, Adams R E, Chen R, Cotter M L, Hirsch A F, Kane V V, Kanojia R M, Shaw C, Watcher M P. Zoapatanol and montanol, novel oxepane diterpenoids, from the Mexican plant zoapatle (Montanoa tomentosa).  J. Am. Chem. Soc.. 1979;  101 3404-5
  • 2 Quijano L, Calderon J S, Gomez-Garibay F, Rosario V, Rios T. Acyclic precursors of the uterotonic oxepane diterpenoids of ”zoapatle” (Montanoa tomentosa).  Phytochemistry. 1985;  24 2741-3
  • 3 Enriques R G, Escobar L I, Romero M L, Chavez M A, Lozoya X. Determination of grandiflorenic acid in organic and aqueous extracts of Montanoa tomentosa (zoapatle) by reversed-phase high-performance liquid chromatography.  J. Chromatogr.. 1983;  258 297-301
  • 4 Lozoya X, Enriques R G, Bejar E, Estrada A V, Giron H, Ponce-Monter H, Gallegos A J. The zoapatle. The effect of kauradienoic acid upon uterine contractility.  Contraception. 1983;  27 267-79
  • 5 Quijano L, Calderon J S, Gomez F, Rios T. Zoapatanolide A and B, two new heliangolides from Montanoa tomentosa .  Phytochemistry. 1982;  21 2041-4
  • 6 Quijano L, Gomez G F, Calderon J S, Lopez P J, Rios T. Zoapatanolides C and D, two guaianolides from Montanoa tomentosa .  Phytochemistry. 1984;  23 125-7
  • 7 Seaman F C, Malcolm A J, Fronczek F R, Lee I Y, Fischer N H. Montanoa terpenes. Part 4. Guaianolide-type sesquiterpene lactones of Montanoa tomentosa subsp. xanthifolia and M. tomentosa subsp. rosei and the molecular structures of two pumilin analogs.  Phytochemistry. 1984;  23 817-22
  • 8 Castro V, Jakupovic J. Two further 6,12-cis-germacranolides from Montanoa tomentosa subsp. xanthifolia .  Phytochemistry. 1985;  24 2449-50
  • 9 Topcu G, Cordell G A, Farnsworth N R, Fong H HS. Studies on zoapatle. VIII: Novel cytotoxic sesquiterpenes lactones from Montanoa tomentosa ssp. microcephala .  J. Pharm. Sci.. 1988;  77 553-6
  • 10 Oshima Y, Gordell G A, Fong H HS. Studies on zoapatle. III. Flavonoid glycosides from Montanoa tomentosa ssp. tomentosa .  J. Nat. Prod.. 1986;  49 551-2

Dr. A. Braca

Dipartimento di Chimica Bioorganica e Biofarmacia

Università di Pisa

Via Bonanno, 33

56126 Pisa

Italy

Email: braca@farm.unipi.it

Fax: +39 050 43321

    >