Bursehernin (Methylpluviatolide) is an antineoplastic/anticancer agent. Bursehernin causes apoptosis and cell cycle arrest in the G2/M phase. Bursehernin has antiproliferation activity.

Physicochemical Properties

Molecular Formula	C21H22O6
Molecular Weight	370.395786762238
Exact Mass	370.142
CAS #	40456-51-7
PubChem CID	94504
Appearance	Typically exists as solid at room temperature
Density	1.268g/cm3
Boiling Point	543.575°C at 760 mmHg
Flash Point	238.539 °C
LogP	3.006
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Heavy Atom Count	27
Complexity	511
Defined Atom Stereocenter Count	2
SMILES	COC1=C(C=C(C=C1)C[C@@H]2[C@@H](CC3=CC4=C(C=C3)OCO4)COC2=O)OC
InChi Key	IYBDDRJHJMFFBB-JKSUJKDBSA-N
InChi Code	InChI=1S/C21H22O6/c1-23-17-5-3-14(9-19(17)24-2)8-16-15(11-25-21(16)22)7-13-4-6-18-20(10-13)27-12-26-18/h3-6,9-10,15-16H,7-8,11-12H2,1-2H3/t15-,16+/m0/s1
Chemical Name	(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-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 the G2/M phase, bursehernin (4.3 µM for MCF-7 cells, 3.7 µM for KKU-M213 cells; 4, 48, 72 h) time-dependently promotes apoptosis and cell cycle arrest [1].
Cell Assay	Cell Proliferation Assay [1] Cell Types: MCF-7, MDA-MB-468, MDA-MB-231, HT-29, KKU-M213, KKU-K100, KKU-M055, L-929, MMNK-1 cells Tested Concentrations: 0-100 µM Incubation Duration: 72 h Experimental Results: demonstrated anti-proliferative activity with IC50s of 11.96, 8.24, 14.26, 47.53, 3.70, 12.38, 17.38, 26.36, 7.45 µM for MCF-7, MDA-MB-468, MDA-MB-231, HT-29, KKU-M213, KKU-K100, KKU-M055, L-929, MMNK-1 cells, respectively. Cell Cycle Analysis [1] Cell Types: MCF-7, KKU-M213 cells Tested Concentrations: 4.3 µM for MCF-7 cells, 3.7 µM for KKU-M213 cells Incubation Duration: 24, 48, 72 h Experimental Results: Induced cell cycle arrest at G2/M phase. Western Blot Analysis [1] Cell Types: MCF-7, KKU-M213 cells Tested Concentrations: 4.3 µM for MCF-7 cells, 3.7 µM for KKU-M213 cells Incubation Duration: 24, 48, 72 h Experimental Results: diminished the expression of topoisomerase II, STAT 3, cyclin D1, and p21. Apoptosis Analysis [1] Cell Types: MCF-7 cells Tested Concentrations: 0, 2.15, 4.30, 8.60 µM Incubation Duration: 24, 48, 72, 96 h Experimental Results: Induced apoptosis in a time- and dose
References	[1]. Anticancer activity of synthetic (±)-kusunokinin and its derivative (±)-bursehernin on human cancer cell lines. Biomed Pharmacother. 2019 Sep;117:109115. [2]. Antitumor activity of Bursera schlechtendalii (burseraceae): isolation and structure determination of two new lignans. J Pharm Sci. 1972 Dec;61(12):1992-4.
Additional Infomation	(-)-bursehernin is a butan-4-olide that is (-)-pluviatolide in which the phenolic hydroxy group has been converted to the corresponding methyl ether. It has a role as a plant metabolite. It is an aromatic ether, a member of benzodioxoles, a butan-4-olide and a lignan. It is functionally related to a (-)-pluviatolide. Bursehernin has been reported in Stellera chamaejasme, Hernandia sonora, and other organisms 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	2.6998 mL	13.4989 mL	26.9978 mL
	5 mM	0.5400 mL	2.6998 mL	5.3996 mL
	10 mM	0.2700 mL	1.3499 mL	2.6998 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.