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Isoschaftoside

Alias: UNII-H27X8715V3; H27X8715V3
Cat No.:V30312 Purity: ≥98%
Isoschaftosid is a c-glycosyl flavonoid found in the root exudate of Desmodium uncinatum, which can inhibit the growth of S.
Isoschaftoside
Isoschaftoside Chemical Structure CAS No.: 52012-29-0
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Isoschaftosid is a c-glycosyl flavonoid found in the root exudate of Desmodium uncinatum, which can inhibit the growth of S. hermonthica germ.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
1. Against Striga asiatica (a parasitic plant), Isoschaftoside (1, 10, 100 μM) inhibited seed germination and haustorium formation in a concentration-dependent manner. At 100 μM, seed germination was inhibited by 85% and haustorium formation by 90% compared to the control. [1]
2. Against Striga hermonthica, Isoschaftoside (100 μM) reduced seed germination by 80% and suppressed haustorium development, confirming its allelopathic activity against different Striga species. [2]
3. Against root-knot nematode (Meloidogyne incognita), Isoschaftoside (20, 40, 80 μg/mL) exhibited nematocidal activity. At 80 μg/mL, the mortality rate of nematodes was 92% after 24 hours and 95% after 48 hours of treatment. [3]
ln Vivo
In a pot experiment, root exudates of Desmodium uncinatum (containing Isoschaftoside) were applied to host plants (maize/sorghum) infected with Striga asiatica. The number of Striga plants attached to host roots was reduced by 70% compared to the control group without Isoschaftoside. [1]
Cell Assay
1. Striga seed bioassay: Striga asiatica seeds were surface-sterilized and pre-conditioned in water for 7 days. Seeds were then treated with Isoschaftoside solutions (1, 10, 100 μM) and incubated at 25°C for 14 days. Germinated seeds (with radicle >2 mm) and haustoria (induced by host root extract) were counted to calculate inhibition rates. [1]
2. Nematocidal assay: Meloidogyne incognita second-stage juveniles (J2s) were collected and adjusted to a concentration of 100 J2s/mL. J2s were treated with Isoschaftoside solutions (20, 40, 80 μg/mL) and incubated at 25°C. Nematode mortality (judged by lack of movement after prodding) was recorded at 24 and 48 hours. [3]
3. Striga hermonthica bioassay: Striga hermonthica seeds were pre-conditioned and treated with 100 μM Isoschaftoside. After 10 days, germination was assessed by counting seeds with emerged radicles, and haustorium formation was induced by adding sorghum root exudate, followed by counting haustoria after 3 days. [2]
Toxicity/Toxicokinetics
Pot experiments showed that the root exudates of beech (Desmodium uncinatum, containing isosafruticin) did not produce any phytotoxic effects on the host plants (maize and sorghum) (e.g., leaf yellowing, growth inhibition), and the plant height and biomass were normal compared with the control group. [1]
References

[1]. Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, is an allelochemical against the development of Striga. Phytochemistry. 2010 Jun;71(8-9):904-8.

[2]. Elucidation of the biosynthesis of the di-C-glycosylflavone isoschaftoside, an allelopathic component from Desmodium spp. that inhibits Striga spp. development. Phytochemistry. 2012 Dec;84:169-76.

[3]. Nematocidal flavone-C-glycosides against the root-knot nematode (Meloidogyne incognita) from Arisaema erubescens tubers. Molecules. 2011 Jun 20;16(6):5079-86.

Additional Infomation
Isoschaftoside is a C-glycoside compound derived from apigenin by substitution at positions 6 and 8 with α-L-arabinopyranosyl and β-D-glucose, respectively. It is a metabolite belonging to the class of C-glycosides and trihydroxyflavones, and is functionally related to apigenin.
Isoschaftoside has been reported to be found in tea (Camellia sinensis), soybean (Glycine max), and other organisms with relevant data.
1. Isoschaftoside is a C-glycoside flavonoid isolated from the root exudates of beech (Desmodium uncinatum), and its allelopathic effect is key to inhibiting strigophyte parasitism in agricultural systems. [1]
2. Biosynthesis of Isoschaftoside in beech plants. It involves the continuous C-glycosylation of flavonoid precursors, which is crucial for its production as an allelopathic component against strigophyte. [2]
3. Isosarfusin was also isolated from the tubers of Arisaema heterophyllum, and its nematicidal activity against southern root-knot nematodes indicates its potential as a biological pesticide for nematode control. [3]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H28O14
Molecular Weight
564.49212
Exact Mass
564.147
CAS #
52012-29-0
PubChem CID
3084995
Appearance
Light yellow to yellow solid powder
Density
1.8±0.1 g/cm3
Boiling Point
935.0±65.0 °C at 760 mmHg
Flash Point
314.3±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.759
LogP
0.04
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
14
Rotatable Bond Count
4
Heavy Atom Count
40
Complexity
938
Defined Atom Stereocenter Count
9
SMILES
C1[C@@H]([C@@H]([C@H]([C@@H](O1)C2=C(C(=C3C(=C2O)C(=O)C=C(O3)C4=CC=C(C=C4)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
InChi Key
OVMFOVNOXASTPA-VYUBKLCTSA-N
InChi Code
InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)16-20(34)15(25-22(36)17(31)11(30)7-38-25)19(33)14-10(29)5-12(39-24(14)16)8-1-3-9(28)4-2-8/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17-,18+,21-,22+,23+,25-,26-/m0/s1
Chemical Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
Synonyms
UNII-H27X8715V3; H27X8715V3
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 (~177.15 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.43 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 (4.43 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7715 mL 8.8576 mL 17.7151 mL
5 mM 0.3543 mL 1.7715 mL 3.5430 mL
10 mM 0.1772 mL 0.8858 mL 1.7715 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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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.
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