164991-89-3

Segetalin B, a cyclopentapeptide from Vaccaria segetalis, possesses estrogen-like activity.

Cyclic pentapeptide. Constit. of the seeds of Vaccaria segetalis (Caryophyllaceae).Needles.Mp 153-155°C.

Segetalin B, an orally active cyclopentapeptide found in Vaccaria segetalis, possesses estrogen-like activity. Segetalin B promotes mineralization of ovariectomized rat-derived bone marrow mesenchymal stem cells (BMSCs) in vitro and increases the level of osteocalcin, BMP-2, ALP, and SIRT1 activity. Segetalin B is promising for research of post-menopausal osteoporosis (PMOP)[1][2][3][4].

Examples of naturally occurring bioactive cyclopeptides are Segetalins A and B，which were isolated from Vaccaria segetalis (Caryophyllacea) and were shown to have estrogen-like activity. The seeds of Vaccaria segetalis are used in Chinese folk medicine to activate blood flow, to promote milk secretion, and to treat amenorrhea and breast infections. That Segetalin A and Segetalin B have the Try-Ala-Gly-Val (WAGV) sequence in common indicates this is the biologically active part of the molecules. NMR studies indicate,however,that the orientation of the Val residue is different in the molecules.The effect of this amino acid on the activity of the compounds might not be very important.

SIRT1; RUNX2

[1] HiroshiMorita, et al. Segetalins B, C and D, three new cyclic peptides from Vaccaria segetalis. Tetrahedron Volume 51, Issue 21, 22 May 1995, Pages 6003-6014.
[2] PascalSonnet, et al. First synthesis of segetalins B and G: two cyclopentapeptides with estrogen-like activity. Tetrahedron Letters. Volume 44, Issue 16, 14 April 2003, Pages 3293-3296
[3] DONG H, et al. HPLC simultaneous determination of segetalin A and segetalin B in Vaccariae Semen[J]. Chinese Journal of Pharmaceutical Analysis, 2012, 32(5): 793-796.
[4] Lan X, et al. SIRT1/Notch1 signal axis involves in the promoting effect of Segetalin B on bone formation. Drug Dev Res. 2022 Dec;83(8):1845-1857. DOI:10.1002/ddr.22001