(±)-Emodin bianthrone (compound 10), is a naturally occurring compound with antimalarial, antituberculous and antifungal activities.

Physicochemical Properties

Molecular Formula	C30H22O8
Molecular Weight	510.49
CAS #	61281-20-7
PubChem CID	12096290
Appearance	Typically exists as solid at room temperature
Density	1.585±0.06 g/cm3(Predicted)
Boiling Point	773.7±60.0 °C(Predicted)
LogP	5.8
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	1
Heavy Atom Count	38
Complexity	865
Defined Atom Stereocenter Count	2
SMILES	C1(C2(c3c([H])c(O[H])c([H])c(O[H])c3C(=O)c3c(c(c(c([H])c23)C([H])([H])[H])[H])O[H])[H])(c2c([H])c(O[H])c([H])c(O[H])c2C(=O)c2c(c(c(c([H])c12)C([H])([H])[H])[H])O[H])[H]
InChi Key	UUXPVUHOWQPCSC-ZEQRLZLVSA-N
InChi Code	InChI=1S/C30H22O8/c1-11-3-15-23(17-7-13(31)9-21(35)27(17)29(37)25(15)19(33)5-11)24-16-4-12(2)6-20(34)26(16)30(38)28-18(24)8-14(32)10-22(28)36/h3-10,23-24,31-36H,1-2H3/t23-,24-/m0/s1
Chemical Name	(10S)-1,3,8-trihydroxy-6-methyl-10-[(9S)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one
Synonyms	Trans-Emodin bianthrone; ( inverted exclamation markA)-Emodin bianthrone; CHEMBL464711;
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

Targets	Natural product
ln Vitro	Two novel cyclopropyl diketones, hamavellone A (1) and B (2), and two new 14-membered nonaketide macrolactones, hamigeromycin A (3) and B (4), together with six known compounds, 89-250904-F1 (radicicol analogue A, 5), pseurotin A (6), emodin (7), ω-hydroxyemodin (8), and emodin bianthrones (9 and 10) were isolated from the soil fungus Hamigera avellanea BCC 17816. The structures of the new compounds were defined by analysis of NMR and MS data. The absolute stereochemistry of 3 was addressed by chemical correlation to 5. Hamavellone B (2) exhibited antimalarial activity with an IC50 of 5.2 μg/mL, whereas it also showed comparable cytotoxicity [1].
Cell Assay	Assay for activity against P. falciparum (K1, multi-drug resistant strain) was performed using the microculture radioisotope technique.17 Growth inhibitory activity against M. tuberculosis H37Ra and cytotoxicity to Vero cells (African green monkey kidney fibroblasts) were performed using the green fluorescent protein microplate assay (GFPMA).18 Antifungal activity against C. albicans and anticancer activities against KB cells (oral human epidermoid carcinoma), MCF7 cells (human breast cancer), and NCI-H187 cells (human small-cell lung cancer) were evaluated using the resazurin microplate assay [1].
References	[1]. Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816. Tetrahedron. 2008; 64(49): 11028-11033.
Additional Infomation	(10S)-1,3,8-trihydroxy-6-methyl-10-[(9S)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one has been reported in Rhamnus prinoides with data available. Pseurotin A (6) was first described from Pseudeurotium ovalis S2269/F,3a and it has been isolated from various fungi such as Aspergillus species4, 12 and Pochonia chlamydosporia var. catenulata.13 Emodin (7) and its hydroxy analogue 8 are commonly occurring as constituents of plants and fungi. Emodin bianthrones (9 and 10) and structurally related bianthrones have been known as constituents of plants.5, 6, 6(a), 6(b), 6(c) To the best of our knowledge, this is the first report of the isolation of 9 and 10 as fungal secondary metabolites. There have been only a few other reports on the new metabolites of Hamigera species, such as the cyclopentapeptides, avellanins A and B from H. avellanea14 and their analogues PF1171A–PF1171E from H. avellanea PF1171,15 and polyketide metabolites, hamigerone and dihydrohamigerone from H. avellanea NN005492.16, 16(a), 16(b) In the present study four different chemical classes of polyketide metabolites, comprising 10 compounds, have been isolated from H. avellanea BCC 17816, demonstrating that fungi in this genus are potent sources of bioactive compounds. All isolated compounds were subjected to our in vitro biological protocols, inclusive of antimalarial (Plasmodium falciparum K1), antitubercular (Mycobacterium tuberculosis H37Ra), and antifungal (Candida albicans) activities, and cytotoxicity against three human cancer cell-lines (KB, MCF7, and NCI-H187 cells) and noncancerous Vero cells (Table 3). Hamavellone B (2) exhibited moderate antimalarial activity, while it also showed cytotoxic activities. Among 14-membered macrolides, only compound 5 exhibited moderate cytotoxicity, and no other biological activities were shown in this class of compounds. It should be noted that emodin bianthrones (9 and 10) strongly inhibited the proliferation of the malarial parasite, although they showed comparable cytotoxicity to Vero cells.[1]

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	1.9589 mL	9.7945 mL	19.5890 mL
	5 mM	0.3918 mL	1.9589 mL	3.9178 mL
	10 mM	0.1959 mL	0.9795 mL	1.9589 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.