MedKoo Cat#: 534794 | Name: Sydowinin B
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sydowinin B is a xanthone polyketide that has been found in A. sydowii and has immunosuppressant activity. It inhibits LPS- or concanavalin A-induced proliferation of isolated mouse splenic lymphocytes (IC50s = 19.2 and 20.8 µg/ml, respectively). Sydowinin B inhibits superoxide generation in, and elastase release from, isolated human neutrophils induced by cytochalasin B and fMLP with IC50 values of 21.2 and 12.62 µM, respectively.

Chemical Structure

Sydowinin B
Sydowinin B
CAS#58450-00-3

Theoretical Analysis

MedKoo Cat#: 534794

Name: Sydowinin B

CAS#: 58450-00-3

Chemical Formula: C16H12O7

Exact Mass: 316.0583

Molecular Weight: 316.27

Elemental Analysis: C, 60.76; H, 3.82; O, 35.41

Price and Availability

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1mg USD 800.00 2 Weeks
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Synonym
Sydowinin B; Sydowinin-B; MS-347b; MS347b; MS 347b;
IUPAC/Chemical Name
9H-Xanthene-1-carboxylic acid, 2,8-dihydroxy-6-(hydroxymethyl)-9-oxo-, methyl ester
InChi Key
SSBSKLSIZKVBFF-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O7/c1-22-16(21)13-8(18)2-3-10-14(13)15(20)12-9(19)4-7(6-17)5-11(12)23-10/h2-5,17-19H,6H2,1H3
SMILES Code
O=C(C1=C(O)C=CC(OC2=C3C(O)=CC(CO)=C2)=C1C3=O)OC
Appearance
Solid powder
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
More Info
Product Data
Biological target:
Sydowinin B's biological target primarily involves its inhibitory activity against protein tyrosine phosphatase 1B (PTP-1B). This enzyme is a critical regulator of insulin signaling and glucose metabolism, making PTP-1B inhibition a promising therapeutic approach for managing conditions like diabetes and obesity.
In vitro activity:
Sydowinin B was evaluated in an in vitro study assessing cytotoxicity alongside okadaic acid and other mycotoxins on human intestinal (HT-29) and neuroblastoma (SH-SY5Y) cell lines. Results showed sydowinin B to have lower cytotoxicity compared to okadaic acid and other mycotoxins against both cell lines. Combinations of okadaic acid with sydowinin A, alamethicin, patulin, and gliotoxin exhibited variable synergistic or antagonistic effects depending on concentration levels, highlighting potential health risks from synergistic interactions between marine algal toxins and mycotoxins in seafood consumption. Reference: Hayashi A, José Dorantes-Aranda J, Bowman JP, Hallegraeff G. Combined Cytotoxicity of the Phycotoxin Okadaic Acid and Mycotoxins on Intestinal and Neuroblastoma Human Cell Models. Toxins (Basel). 2018 Dec 8;10(12):526.
In vivo activity:
1. In this in vivo study, sydowinin B (3), isolated from Malbranchea dendritica, was evaluated for its biological activities. Although the main focus was on gymnoascolide A (1) and its α-glucosidase inhibitory properties, sydowinin B (3) and other xanthones (2 and 4) were identified from the extract. The study highlighted compound 1's ability to significantly reduce postprandial glucose peaks in mice during a sucrose tolerance test, demonstrating its potential as an anti-diabetic agent. Reference: Rebollar-Ramos D, Ovalle-Magallanes B, Palacios-Espinosa JF, Macías-Rubalcava ML, Raja HA, González-Andrade M, Mata R. α-Glucosidase and PTP-1B Inhibitors from Malbranchea dendritica. ACS Omega. 2021 Aug 25;6(35):22969-22981.

Preparing Stock Solutions

The following data is based on the product molecular weight 316.27 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.

Recalculate based on batch purity %
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:
Hayashi A, José Dorantes-Aranda J, Bowman JP, Hallegraeff G. Combined Cytotoxicity of the Phycotoxin Okadaic Acid and Mycotoxins on Intestinal and Neuroblastoma Human Cell Models. Toxins (Basel). 2018 Dec 8;10(12):526. doi: 10.3390/toxins10120526. PMID: 30544794; PMCID: PMC6315785. Cocks S, Wrigley SK, Chicarelli-Robinson MI, Smith RM. High-performance liquid chromatography comparison of supercritical-fluid extraction and solvent extraction of microbial fermentation products. J Chromatogr A. 1995 Apr 21;697(1-2):115-22. doi: 10.1016/0021-9673(94)00817-s. PMID: 7780576. Rebollar-Ramos D, Ovalle-Magallanes B, Palacios-Espinosa JF, Macías-Rubalcava ML, Raja HA, González-Andrade M, Mata R. α-Glucosidase and PTP-1B Inhibitors from Malbranchea dendritica. ACS Omega. 2021 Aug 25;6(35):22969-22981. doi: 10.1021/acsomega.1c03708. PMID: 34514267; PMCID: PMC8427789.
In vitro protocol:
Hayashi A, José Dorantes-Aranda J, Bowman JP, Hallegraeff G. Combined Cytotoxicity of the Phycotoxin Okadaic Acid and Mycotoxins on Intestinal and Neuroblastoma Human Cell Models. Toxins (Basel). 2018 Dec 8;10(12):526. doi: 10.3390/toxins10120526. PMID: 30544794; PMCID: PMC6315785. Cocks S, Wrigley SK, Chicarelli-Robinson MI, Smith RM. High-performance liquid chromatography comparison of supercritical-fluid extraction and solvent extraction of microbial fermentation products. J Chromatogr A. 1995 Apr 21;697(1-2):115-22. doi: 10.1016/0021-9673(94)00817-s. PMID: 7780576.
In vivo protocol:
Rebollar-Ramos D, Ovalle-Magallanes B, Palacios-Espinosa JF, Macías-Rubalcava ML, Raja HA, González-Andrade M, Mata R. α-Glucosidase and PTP-1B Inhibitors from Malbranchea dendritica. ACS Omega. 2021 Aug 25;6(35):22969-22981. doi: 10.1021/acsomega.1c03708. PMID: 34514267; PMCID: PMC8427789.
1: Little A, Porco JA Jr. Total syntheses of graphisin A and sydowinin B. Org Lett. 2012 Jun 1;14(11):2862-5. doi: 10.1021/ol301107m. Epub 2012 May 23. PMID: 22621405; PMCID: PMC3367002. 2: Hayashi A, José Dorantes-Aranda J, Bowman JP, Hallegraeff G. Combined Cytotoxicity of the Phycotoxin Okadaic Acid and Mycotoxins on Intestinal and Neuroblastoma Human Cell Models. Toxins (Basel). 2018 Dec 8;10(12):526. doi: 10.3390/toxins10120526. PMID: 30544794; PMCID: PMC6315785. 3: Cocks S, Wrigley SK, Chicarelli-Robinson MI, Smith RM. High-performance liquid chromatography comparison of supercritical-fluid extraction and solvent extraction of microbial fermentation products. J Chromatogr A. 1995 Apr 21;697(1-2):115-22. doi: 10.1016/0021-9673(94)00817-s. PMID: 7780576. 4: Rebollar-Ramos D, Ovalle-Magallanes B, Palacios-Espinosa JF, Macías-Rubalcava ML, Raja HA, González-Andrade M, Mata R. α-Glucosidase and PTP-1B Inhibitors from Malbranchea dendritica. ACS Omega. 2021 Aug 25;6(35):22969-22981. doi: 10.1021/acsomega.1c03708. PMID: 34514267; PMCID: PMC8427789.