Abstract
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, Ca
2+
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
(-Leu
1
-Pro
2
-Leu
3
-Trp
4
-Pro
5
-Gly
6
-) (
1
),
cyclo
(-Leu
1
-Pro
2
-Tyr
3
-Phe
4
-Pro
5
-Gly
6
-) (
2
),
cyclo
(-Ala
1
-Pro
2
-Tyr
3
-Leu
4
-Leu
5
-Pro
6
-Pro
7
-Ala
8
-) (
3
),
cyclo
(-Leu
1
-Trp
2
-Pro
3
-Gly
4
-Gly
5
-Ser
6
-Ser
7
-) (
4
), and
cyclo
(-Leu
1
-Ser
2
-Ser
3
-Gly
4
-Pro
5
-Gly
6
-Trp
7
-) (
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.