Synonym
Segetalin B; Vaccarin A, Segetalin B, Segetaline B; Cyclo(L-alanylglycyl-L-valyl-L-alanyl-L-tryptophyl)
IUPAC/Chemical Name
(3S,6S,9S,12S)-6-(1H-indol-3-ylmethyl)-12-isopropyl-3,9-dimethyl-1,4,7,10,13pentaaza-cyclopentadecane-2,5,8,11,14-pentaone
InChi Key
VBQDUSUKSGAFMN-OACKDKIBSA-N
InChi Code
InChI=1S/C24H32N6O5/c1-12(2)20-24(35)28-14(4)22(33)29-18(9-15-10-25-17-8-6-5-7-16(15)17)23(34)27-13(3)21(32)26-11-19(31)30-20/h5-8,10,12-14,18,20,25H,9,11H2,1-4H3,(H,26,32)(H,27,34)(H,28,35)(H,29,33)(H,30,31)/t13-,14-,18-,20-/m0/s1
SMILES Code
O=C([C@H](C)NC([C@H](CC1=CNC2=C1C=CC=C2)NC([C@H](C)NC([C@H](C(C)C)N3)=O)=O)=O)NCC3=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Segetalin B, a cyclopentapeptide from Vaccaria segetalis, possesses estrogen-like activity.
In vitro activity:
To be determined
In vivo activity:
SB is a potential therapeutic option for postmenopausal osteoporosis (PMOP). In ovariectomized (OVX) rats, SB treatment significantly decreased bone loss, inhibited calcium and phosphorus loss, elevated ALP activity, upregulated Runx2, Osterix, and SIRT1, and downregulated NICD and Hes1.
Reference: Drug Dev Res. 2022 Dec;83(8):1845-1857. https://pubmed.ncbi.nlm.nih.gov/36207817/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
250.0 |
515.94 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
484.56
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Lan X, Ma H, Cheng Q, Xiao Y, Zou L, Yuan Z, Luo J. 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. Epub 2022 Oct 7. PMID: 36207817.
In vivo protocol:
1. Lan X, Ma H, Cheng Q, Xiao Y, Zou L, Yuan Z, Luo J. 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. Epub 2022 Oct 7. PMID: 36207817.
1: Lan X, Ma H, Cheng Q, Xiao Y, Zou L, Yuan Z, Luo J. 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. Epub 2022 Oct 7. PMID: 36207817.
2: Morita H, Yun YS, Takeya K, Itokawa H, Shirota O. Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis. Bioorg Med Chem. 1997 Mar;5(3):631-6. doi: 10.1016/s0968-0896(97)00001-1. PMID: 9113340.
3: Wang X, Dong H, Liu Y, Yang B, Wang X, Huang L. Application of high-speed counter-current chromatography for preparative separation of cyclic peptides from Vaccaria segetalis. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Apr 1;879(11-12):811-4. doi: 10.1016/j.jchromb.2011.02.001. PMID: 21396894.
4: Itokawa H, Yun Y, Morita H, Takeya K, Yamada K. Estrogen-like activity of cyclic peptides from Vaccaria segetalis extracts. Planta Med. 1995 Dec;61(6):561-2. doi: 10.1055/s-2006-959373. PMID: 8824953.
