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Dactylorhin A

Cat No.:V19126 Purity: ≥98%
Dactylorhin A is a succinic acid analogue ester extracted from the rhizome of Gymnadenia conopsea.
Dactylorhin A
Dactylorhin A Chemical Structure CAS No.: 256459-34-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Dactylorhin A is a succinic acid analogue ester extracted from the rhizome of Gymnadenia conopsea. Dactylorhin A has a moderate inhibitory activity against NO production by RAW 264.7 macrophages.
Dactylorhin A (CAS#: 256459-34-4) is a succinic acid analogue ester isolated from the rhizomes of plants such as Gymnadenia conopsea and Bletilla striata. It is a natural product with reported moderate inhibitory activity against nitric oxide (NO) production in RAW 264.7 macrophage cells. It also exhibits moderate antibacterial activity against several Gram-positive bacteria. It is used as a reference compound in phytochemical studies.
Biological Activity I Assay Protocols (From Reference)
Targets
Dactylorhin A targets the production of nitric oxide (NO) in macrophages, likely by inhibiting inducible nitric oxide synthase (iNOS) expression or activity. It suppresses NO production in LPS-stimulated RAW 264.7 cells, indicating an anti-inflammatory mechanism. Additionally, it has antibacterial activity against Gram-positive bacteria such as Staphylococcus aureus and Bacillus subtilis, suggesting a possible membrane-disrupting or enzyme-inhibiting effect.
ln Vitro
In vitro, Dactylorhin A moderately inhibits NO production in RAW 264.7 macrophages with an IC50 value reported in the micromolar range (e.g., ~20 µM). It also shows moderate antibacterial activity with minimum inhibitory concentrations (MICs) against S. aureus and B. subtilis typically in the range of 50-100 µg/mL. The compound is not cytotoxic to mammalian cells at active concentrations, as assessed by MTT assays.
ln Vivo
No specific in vivo animal data is publicly available for Dactylorhin A. Its effects have been primarily characterized in vitro. The compound is a natural product and its bioavailability and systemic activity have not been studied. Any potential in vivo anti-inflammatory or antibacterial effects remain speculative.
Enzyme Assay
As a natural product with anti-inflammatory activity, Dactylorhin A is not typically evaluated in cell-free enzyme binding assays. Its mechanism is assessed in cell-based systems measuring NO production. No specific cell-free assay protocols are published. However, if needed, one could measure direct iNOS enzyme inhibition using purified iNOS and a fluorometric assay, but this has not been reported for this compound.
Cell Assay
In vitro assays for Dactylorhin A involve culturing RAW 264.7 macrophage cells in 96-well plates. Cells are pretreated with various concentrations of the compound for 1 hour, then stimulated with lipopolysaccharide (LPS, 1 µg/mL) for 24 hours. The culture supernatant is collected, and nitrite (a stable NO metabolite) is measured using Griess reagent. Antibacterial activity is assessed by broth microdilution in Mueller-Hinton broth against overnight cultures of Gram-positive bacteria.
Animal Protocol
No in vivo animal protocols are available for Dactylorhin A. Since it is a natural product with limited systemic characterization, no standard animal models have been reported. If future studies were conducted, typical anti-inflammatory models (e.g., carrageenan-induced paw edema in rats) or infection models (e.g., mouse peritonitis) could be employed, but these are not documented.
ADME/Pharmacokinetics
No pharmacokinetic data is publicly available for Dactylorhin A. Being a natural glycosidic ester, it is likely poorly absorbed orally, with potential hydrolysis in the gut. Its plasma half-life, protein binding, and metabolism are unknown. For research use, it is typically applied in vitro or as a phytochemical standard.
Toxicity/Toxicokinetics
No toxicity data is publicly available for Dactylorhin A. In cell-based assays, it did not show cytotoxicity at concentrations up to 100 µM, but systemic toxicity has not been evaluated. As a natural product, it may have a favorable safety profile, but no formal toxicological studies exist. It is for research use only and not for human consumption.
References

[1]. Chemical fingerprint analysis of rhizomes of Gymnadenia conopsea by HPLC-DAD-MSn. J Chromatogr B Analyt Technol Biomed Life Sci. 2006;844(2):301-307.

[2]. Chemical constituents from Bletilla striata and their NO production suppression in RAW 264.7 macrophage cells. J Asian Nat Prod Res. 2018;20(4):385-390.

Additional Infomation
According to reports, Dactylorhin A has been found in Gymnadenia conopsea, Bletilla striata, and Dactylorhiza hatagirea, and relevant data are available for reference.
Dactylorhin A is a natural product, a succinic acid analogue ester, with molecular formula C40H56O22 and molecular weight 888.86. It is isolated from orchids and used as a reference compound for phytochemical analysis. It is categorized as an anti-inflammatory and antibacterial agent in research. The compound is available from chemical suppliers for laboratory use only. No clinical development has been reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C40H56O22
Molecular Weight
888.859455108643
Exact Mass
888.326
CAS #
256459-34-4
PubChem CID
10819499
Appearance
White to off-white solid powder
LogP
-2.1
Hydrogen Bond Donor Count
12
Hydrogen Bond Acceptor Count
22
Rotatable Bond Count
20
Heavy Atom Count
62
Complexity
1380
Defined Atom Stereocenter Count
16
SMILES
O([C@@](C(=O)OCC1C=CC(=CC=1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)(CC(=O)OCC1C=CC(=CC=1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)CC(C)C)[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
InChi Key
QUCKZYFUROTIBC-HDQVGPIMSA-N
InChi Code
InChI=1S/C40H56O22/c1-18(2)11-40(62-38-35(53)32(50)29(47)25(15-43)61-38,39(54)56-17-20-5-9-22(10-6-20)58-37-34(52)31(49)28(46)24(14-42)60-37)12-26(44)55-16-19-3-7-21(8-4-19)57-36-33(51)30(48)27(45)23(13-41)59-36/h3-10,18,23-25,27-38,41-43,45-53H,11-17H2,1-2H3/t23-,24-,25-,27-,28-,29-,30+,31+,32+,33-,34-,35-,36-,37-,38+,40-/m1/s1
Chemical Name
bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R)-2-(2-methylpropyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanedioate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~112.50 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (2.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (2.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.1250 mL 5.6252 mL 11.2504 mL
5 mM 0.2250 mL 1.1250 mL 2.2501 mL
10 mM 0.1125 mL 0.5625 mL 1.1250 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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