Synonym
Scirpusin B; Scirpusin-B;
IUPAC/Chemical Name
(E)-4-(2-(2-(3,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2,3-dihydrobenzofuran-4-yl)vinyl)benzene-1,2-diol
InChi Key
MTYSFTYBAMMIGE-HNQUOIGGSA-N
InChi Code
InChI=1S/C28H22O8/c29-18-9-17(10-19(30)12-18)27-26-15(3-1-14-2-5-21(32)23(34)7-14)8-20(31)13-25(26)36-28(27)16-4-6-22(33)24(35)11-16/h1-13,27-35H/b3-1+
SMILES Code
OC1=CC=C(/C=C/C2=C3C(C4=CC(O)=CC(O)=C4)C(C5=CC=C(O)C(O)=C5)OC3=CC(O)=C2)C=C1O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
486.47
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 |
1: Sano S, Sugiyama K, Ito T, Katano Y, Ishihata A. Identification of the strong vasorelaxing substance scirpusin B, a dimer of piceatannol, from passion fruit (Passiflora edulis) seeds. J Agric Food Chem. 2011 Jun 8;59(11):6209-13. doi: 10.1021/jf104959t. Epub 2011 May 13. PubMed PMID: 21526844.
2: Maruki-Uchida H, Kurita I, Sugiyama K, Sai M, Maeda K, Ito T. The protective effects of piceatannol from passion fruit (Passiflora edulis) seeds in UVB-irradiated keratinocytes. Biol Pharm Bull. 2013;36(5):845-9. PubMed PMID: 23649341.
3: Viganó J, Aguiar AC, Moraes DR, Jara JLP, Eberlin MN, Cazarin CBB, Maróstica MR Junior, Martínez J. Sequential high pressure extractions applied to recover piceatannol and scirpusin B from passion fruit bagasse. Food Res Int. 2016 Jul;85:51-58. doi: 10.1016/j.foodres.2016.04.015. Epub 2016 Apr 16. PubMed PMID: 29544852.
4: Kobayashi K, Ishihara T, Khono E, Miyase T, Yoshizaki F. Constituents of stem bark of Callistemon rigidus showing inhibitory effects on mouse alpha-amylase activity. Biol Pharm Bull. 2006 Jun;29(6):1275-7. PubMed PMID: 16755033.
5: Sim Y, Choi JG, Gu PS, Ryu B, Kim JH, Kang I, Jang DS, Oh MS. Identification of Neuroactive Constituents of the Ethyl Acetate Fraction from Cyperi Rhizoma Using Bioactivity-Guided Fractionation. Biomol Ther (Seoul). 2016 Jul 1;24(4):438-45. doi: 10.4062/biomolther.2016.091. PubMed PMID: 27350341; PubMed Central PMCID: PMC4930289.
6: Yang GX, Zhou JT, Li YZ, Hu CQ. Anti-HIV bioactive stilbene dimers of Caragana rosea. Planta Med. 2005 Jun;71(6):569-71. PubMed PMID: 15971132.
7: Arraki K, Totoson P, Decendit A, Badoc A, Zedet A, Jolibois J, Pudlo M, Demougeot C, Girard-Thernier C. Cyperaceae Species Are Potential Sources of Natural Mammalian Arginase Inhibitors with Positive Effects on Vascular Function. J Nat Prod. 2017 Sep 22;80(9):2432-2438. doi: 10.1021/acs.jnatprod.7b00197. Epub 2017 Aug 24. PubMed PMID: 28837342.
