Isochamaejasmin is a biflavonoid with anticancer, antiplasmodial, and insecticidal activities. Isochamaejasmin displays potent NF-κB (NF-κB) activating activity. Isochamaejasmin can cause DNA damage and cause apoptosis in AW1 cells through the mitochondrial pathway. Isochamaejasmin also has moderate antiplasmodial activity (IC50 against Plasmodium falciparum of 7.3 μM) and relatively low cytotoxic effect (CC50 of 29.0 μM).

Physicochemical Properties

Molecular Formula	C30H22O10
Molecular Weight	542.49
Exact Mass	542.121
CAS #	93859-63-3
PubChem CID	390361
Appearance	Typically exists as solid at room temperature
Density	1.6±0.1 g/cm3
Boiling Point	932.6±65.0 °C at 760 mmHg
Flash Point	314.2±27.8 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.750
LogP	6.61
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	3
Heavy Atom Count	40
Complexity	854
Defined Atom Stereocenter Count	4
SMILES	O=C1C2C(=CC(=CC=2O[C@@H](C2C=CC(O)=CC=2)[C@@H]1[C@H]1C(=O)C2C(=CC(=CC=2O[C@@H]1C1C=CC(O)=CC=1)O)O)O)O
InChi Key	RNQBLQALVMHBKH-SQYWJIFTSA-N
InChi Code	InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26+,29+,30-
Chemical Name	(2S,3R)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
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
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In AW1 cells, isochamaejasmin (6.25-100μM; 24-72 h) demonstrated possible toxicity in a dose- and time-dependent way. Time-varying potential against H is exhibited by isochamaejasmin (1000 mg/L, 500 mg/L, 250 mg/L, 125 mg/L, 62.5 mg/L; 24 h, 48 h, 72 h, and 96 h). The toxicity and dose-dependent behavior of zea larvae [1]. In AW1 cells, isochamaejasmin (40-80μM; 24 h) damages DNA and raises γH2AX and OGG1 levels. In the G2/M phase, stop the cell cycle [1]. A dose-dependent mechanism of apoptosis induction in AW1 cells is induced by isochamaejasmin (20-80μM; 24 h)[1]. Isochamaejasmin (20-80μM; 24 h) exhibits a dose-dependent increase in reactive oxygen species (ROS) levels, accumulation of lipid peroxidation products, and inactivation of antioxidant enzymes in AW1 cells. It also shows a decrease in MMP and an upregulation of Bax/Bcl-2 expression, which causes the release of cytochrome c into the cytosol, activation of caspase-3/9, and PARP cleavage [1]. With an EC50 of 3.23 μM, isochamaejasmin stimulates the expression of a reporter gene controlled by NF-κB in transfected HeLa cells. A dominant-negative construct of IκBα blocks isochamaejasmin-stimulated NF-κB reporter activity, which is followed by nuclear translocation of NF-κB protein. Together with PKCδ, isochamaejasmin also phosphorylates ERK1/2, p38, and other mitogen-activated protein kinases in a time-dependent manner [2].
Cell Assay	Cell Viability Assay[1] Cell Types: Larvae and neuronal cells (AW1) Tested Concentrations: 6.25 μM, 12.5 μM, 25 μM, 50 μM and 100 μM Incubation Duration: 24 h, 48 h and 72 h Experimental Results: Had potential toxicity against H. zea both in vivo and in vitro via time- and dose-dependent manners. Cell Cycle Analysis[1] Cell Types: Neuronal cells ( AW1) Tested Concentrations: 40 μM and 80 μM Incubation Duration: 24 h Experimental Results: The cell cycle was arrested at the G2/M phase. Apoptosis Analysis[1] Cell Types: Neuronal cells (AW1) Tested Concentrations: 20 μM, 40 μM, and 80 μM Incubation Duration: 24 h Experimental Results: Induced apoptosis via the mitochondrial pathway in AW1 cells. Western Blot Analysis[1] Cell Types: Neuronal cells (AW1) Tested Concentrations: 20 μM, 40 μM, and 80 μM Incubation Duration: 24 h Experimental Results: demonstrated upregulation of Bax/Bcl-2 expression resulting in the release of cytochrome c into the cytosol, activation of caspase-3/9, and cleavage of PARP.
References	[1]. Isochamaejasmin induces toxic effects on Helicoverpa zea via DNA damage and mitochondria-associated apoptosis. Pest Manag Sci. 2021 Jan;77(1):557-567. [2]. Stereospecific induction of nuclear factor-kappaB activation by isochamaejasmin. Mol Pharmacol. 2005 Dec;68(6):1534-42. [3]. Antiplasmodial activity of (I-3,II-3)-biflavonoids and other constituents from Ormocarpum kirkii. Phytochemistry. 2010 May;71(7):785-91.
Additional Infomation	Isochamaejasmin is a biflavonoid that consists of two units of 5,7,4'-trihydroxyflavanone joined together at position 3 and 3''. It has a role as a plant metabolite. It is a biflavonoid and a hydroxyflavone. Isochamaejasmin has been reported in Stellera chamaejasme, Brackenridgea zanguebarica, and Ormocarpum kirkii with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8434 mL	9.2168 mL	18.4335 mL
	5 mM	0.3687 mL	1.8434 mL	3.6867 mL
	10 mM	0.1843 mL	0.9217 mL	1.8434 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.