Planta Med 2008; 74 - PB124
DOI: 10.1055/s-0028-1084469

Cyclopeptides from Gypsophila arabica (Caryophyllaceae)

M Bruzual De Abreu 1, F Dal Piaz 2, A Temraz 3, A Bader 4, N De Tommasi 2, A Braca 1
  • 1Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy
  • 2Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy
  • 3Faculty of Pharmacy, Al Azhar University, Nasr-City, 11371 Cairo, Egypt
  • 4Faculty of Pharmacy, Al-Zaytoonah Private University of Jordan, P.O. Box 130, 11733 Amman, Jordan

The family Caryophyllaceae is well known to contain saponins of industrial interest [1], flavonoids [2], and cyclopeptides [3]: these last compounds showed interesting biological activities including cytotoxic, antiplatelet, antimalarial, immunomodulating, immunosuppressive, Ca2+ antagonistic, cyclooxigenase and tyrosinase inhibiting, and estrogen-like activity [4]. As a part of a continuing investigation of the Caryophyllaceae of Jordan [5], we carried out the phytochemical study of Gypsophila arabica Barkoudah, a glabrous perennial herb, 30–80cm high, occurring mainly in West Irano-Turanian and Saharo-Arabian territories [6]. A previous pharmacological study on the aqueous extract of the aerial parts showed strong activity in a cytotoxic assay [7] but no phytochemical study of the plant has been reported to date. Five new cyclopeptides, named gypsins A-E (1-5), together with one known oleanane saponin, vaccaroside C, were isolated and characterized from the plant roots extract. The structures of cyclo(-Leu1-Pro2-Leu3-Trp4-Pro5-Gly6-) (1), cyclo(-Leu1-Pro2-Tyr3-Phe4-Pro5-Gly6-) (2), cyclo(-Ala1-Pro2-Tyr3-Leu4-Leu5-Pro6-Pro7-Ala8-) (3), cyclo(-Leu1-Trp2-Pro3-Gly4-Gly5-Ser6-Ser7-) (4), and cyclo(-Leu1-Ser2-Ser3-Gly4-Pro5-Gly6-Trp7-) (5) were elucidated by 1D and 2D NMR spectroscopy, as well as ESI tandem mass spectrometric fragmentation analysis and chemical evidence.

References: 1. Liu, Z et al. (1995)J. Nat. Prod. 58: 1632. 2. Ding, Z. et al. (1999) Planta Med. 65: 578. 3. Zhao, Y-R. et al. (1997) Phytochemistry 46: 709. 4. Tan, N-H., Zhou, J. (2006) Chem. Rev. 106: 840. 5. Braca, A. et al. (2008) Magn. Reson. Chem. 46: 88. 6. Zohary, M. (1966) Flora Palaestina Part I. The Israel Academy of Sciences and Humanities. Jerusalem, p.100. 7. Sathiyamoorthy, P. et al. (1999) Pharm. Biol. 37, 188.