IUPAC/Chemical Name
3-(4-Hydroxyphenyl)-1-[2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]propan-1-one
InChi Key
VZBPTZZTCBNBOZ-VJXVFPJBSA-N
InChi Code
InChI=1S/C21H24O10/c22-8-14-17(27)19(29)20(30)21(31-14)16-13(26)7-12(25)15(18(16)28)11(24)6-3-9-1-4-10(23)5-2-9/h1-2,4-5,7,14,17,19-23,25-30H,3,6,8H2/t14-,17-,19+,20-,21+/m1/s1
SMILES Code
O=C(C1=C(O)C=C(O)C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1O)CCC3=CC=C(O)C=C3
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:
Nothofagin downregulates NF-κB translocation through blocking calcium.
In vitro activity:
This study assessed the inhibitory effect of nothofagin on allergic inflammation using cultured/isolated mast cells and an anaphylaxis mouse model. Nothofagin treatment prevented histamine and β-hexosaminidase release by reducing the influx of calcium into the cytosol in a concentration-dependent manner. Nothofagin also inhibited the gene expression and secretion of pro-inflammatory cytokines such as tumor necrosis factor-α and interleukin-4 by downregulating the phosphorylation of Lyn, Syk, Akt and nuclear translocation of nuclear factor-κB.
Reference: Chem Biol Interact. 2019 Jan 25;298:1-7. https://pubmed.ncbi.nlm.nih.gov/30392763/
In vivo activity:
Hypotensive effects of nothofagin (0.3, 1, and 3 mg/kg) were evaluated after acute intraduodenal administration and after 7 days of oral treatment. Acute and prolonged nothofagin administration significantly decreased systolic blood pressure and mean arterial pressure in Wistar rats. Pretreatment with N(G)-nitro-L-arginine methyl ester, methylene blue, and tetraethylammonium prevented the hypotensive effect of nothofagin.
Reference: Minerva Cardioangiol. 2020 Dec;68(6):602-608. https://pubmed.ncbi.nlm.nih.gov/32657557/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
436.41
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. Kang BC, Kim MJ, Lee S, Choi YA, Park PH, Shin TY, Kwon TK, Khang D, Kim SH. Nothofagin suppresses mast cell-mediated allergic inflammation. Chem Biol Interact. 2019 Jan 25;298:1-7. doi: 10.1016/j.cbi.2018.10.025. Epub 2018 Oct 28. PMID: 30392763.
2. Lee W, Bae JS. Anti-inflammatory Effects of Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) In Vitro and In Vivo. Inflammation. 2015 Aug;38(4):1502-16. doi: 10.1007/s10753-015-0125-1. PMID: 25655391.
3. da Silva CH, Palozi RA, de Souza P, de Almeida CL, Cechinel-Filho V, Lourenço EL, Gasparotto A Jr. Nitric oxide/cGMP signaling pathway and potassium channels contribute to hypotensive effects of nothofagin. Minerva Cardioangiol. 2020 Dec;68(6):602-608. doi: 10.23736/S0026-4725.20.05243-3. Epub 2020 Jul 10. PMID: 32657557.
In vitro protocol:
1. Kang BC, Kim MJ, Lee S, Choi YA, Park PH, Shin TY, Kwon TK, Khang D, Kim SH. Nothofagin suppresses mast cell-mediated allergic inflammation. Chem Biol Interact. 2019 Jan 25;298:1-7. doi: 10.1016/j.cbi.2018.10.025. Epub 2018 Oct 28. PMID: 30392763.
2. Lee W, Bae JS. Anti-inflammatory Effects of Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) In Vitro and In Vivo. Inflammation. 2015 Aug;38(4):1502-16. doi: 10.1007/s10753-015-0125-1. PMID: 25655391.
In vivo protocol:
1. da Silva CH, Palozi RA, de Souza P, de Almeida CL, Cechinel-Filho V, Lourenço EL, Gasparotto A Jr. Nitric oxide/cGMP signaling pathway and potassium channels contribute to hypotensive effects of nothofagin. Minerva Cardioangiol. 2020 Dec;68(6):602-608. doi: 10.23736/S0026-4725.20.05243-3. Epub 2020 Jul 10. PMID: 32657557.
2. Lee W, Bae JS. Anti-inflammatory Effects of Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) In Vitro and In Vivo. Inflammation. 2015 Aug;38(4):1502-16. doi: 10.1007/s10753-015-0125-1. PMID: 25655391.
1: Kang BC, Kim MJ, Lee S, Choi YA, Park PH, Shin TY, Kwon TK, Khang D, Kim SH. Nothofagin suppresses mast cell-mediated allergic inflammation. Chem Biol Interact. 2018 Oct 28;298:1-7. doi: 10.1016/j.cbi.2018.10.025. [Epub ahead of print] PubMed PMID: 30392763.
2: Yang S, Lee C, Lee BS, Park EK, Kim KM, Bae JS. Renal protective effects of aspalathin and nothofagin from rooibos (Aspalathus linearis) in a mouse model of sepsis. Pharmacol Rep. 2018 Jul 27;70(6):1195-1201. doi: 10.1016/j.pharep.2018.07.004. [Epub ahead of print] PubMed PMID: 30340097.
3: de Almeida CLB, Cechinel-Filho V, Boeing T, Mariano LNB, Silva LMD, Andrade SF, de Souza P. Prolonged diuretic and saluretic effect of nothofagin isolated from Leandra dasytricha (A. Gray) Cogn. leaves in normotensive and hypertensive rats: Role of antioxidant system and renal protection. Chem Biol Interact. 2018 Jan 5;279:227-233. doi: 10.1016/j.cbi.2017.11.021. Epub 2017 Dec 1. PubMed PMID: 29198636.
4: Schmölzer K, Lemmerer M, Nidetzky B. Glycosyltransferase cascades made fit for chemical production: Integrated biocatalytic process for the natural polyphenol C-glucoside nothofagin. Biotechnol Bioeng. 2018 Mar;115(3):545-556. doi: 10.1002/bit.26491. Epub 2017 Nov 27. PubMed PMID: 29131308.
5: de Almeida CL, Boeing T, Somensi LB, Steimbach VM, da Silva LM, Andrade SF, Delle Monache F, Cechinel-Filho V, de Souza P. Diuretic, natriuretic and potassium-sparing effect of nothofagin isolated from Leandra dasytricha (A. Gray) Cogn. leaves in normotensive and hypertensive rats. Chem Biol Interact. 2017 Apr 25;268:103-110. doi: 10.1016/j.cbi.2017.03.004. Epub 2017 Mar 8. PubMed PMID: 28284659.
6: Lee W, Kim KM, Bae JS. Ameliorative Effect of Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) on HMGB1-Induced Septic Responses In Vitro and In Vivo. Am J Chin Med. 2015;43(5):991-1012. doi: 10.1142/S0192415X15500573. Epub 2015 Jul 30. PubMed PMID: 26224030.
7: Lee W, Bae JS. Anti-inflammatory Effects of Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) In Vitro and In Vivo. Inflammation. 2015 Aug;38(4):1502-16. doi: 10.1007/s10753-015-0125-1. PubMed PMID: 25655391.
8: de Beer D, Malherbe CJ, Beelders T, Willenburg EL, Brand DJ, Joubert E. Isolation of aspalathin and nothofagin from rooibos (Aspalathus linearis) using high-performance countercurrent chromatography: sample loading and compound stability considerations. J Chromatogr A. 2015 Feb 13;1381:29-36. doi: 10.1016/j.chroma.2014.12.078. Epub 2015 Jan 7. PubMed PMID: 25614190.
9: Kwak S, Han MS, Bae JS. Aspalathin and nothofagin from rooibos (Aspalathus linearis) inhibit endothelial protein C receptor shedding in vitro and in vivo. Fitoterapia. 2015 Jan;100:179-86. doi: 10.1016/j.fitote.2014.12.002. Epub 2014 Dec 12. PubMed PMID: 25510322.
10: Ku SK, Kwak S, Kim Y, Bae JS. Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) inhibits high glucose-induced inflammation in vitro and in vivo. Inflammation. 2015 Feb;38(1):445-55. doi: 10.1007/s10753-014-0049-1. PubMed PMID: 25338943.
