(+)-Viroallosecurinine is a naturally occurring cytotoxic alkaloid extracted from Securinega virosa. It exhibits antibacterial activity with MIC of 0.48 μg/mL for Ps. Aeruginosa and Staph. aureus.

Physicochemical Properties

Molecular Formula	C13H15NO2
Molecular Weight	217.26400
Exact Mass	217.11
CAS #	1857-30-3
Related CAS #	Allosecurinine;884-68-4
PubChem CID	442872
Appearance	Light yellow to yellow solid powder
Density	1.3±0.1 g/cm3
Boiling Point	459.0±45.0 °C at 760 mmHg
Melting Point	145-147 ºC (hexane acetone)
Flash Point	197.0±19.6 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.633
LogP	0.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Heavy Atom Count	16
Complexity	426
Defined Atom Stereocenter Count	3
SMILES	C1CCN2C(C1)C34CC2C=CC3=CC(=O)O4
InChi Key	SWZMSZQQJRKFBP-WZRBSPASSA-N
InChi Code	InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1
Chemical Name	(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-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	Viroallosecurinine exhibited potent in vitro antibacterial activity. The minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) were determined against five bacterial strains using the agar dilution macromethod. For Pseudomonas aeruginosa, the MIC was 0.048 mg/ml and the MBC was 0.192 mg/ml. For Staphylococcus aureus, the MIC was 0.048 mg/ml and the MBC was 0.098 mg/ml. For Escherichia coli, the MIC was 0.78 mg/ml and the MBC was 1.56 mg/ml. For Enterococcus faecium, the MIC was 0.70 mg/ml and the MBC was 1.56 mg/ml. For Mycobacterium smegmatis, the MIC was 0.096 mg/ml and the MBC was 0.192 mg/ml. The compound was determined to be bactericidal, as the MIC/MBC ratios were less than 1 for all tested bacteria.[1]
References	[1]. Antibacterial activity of the leaves of Phyllanthus discoideus. J Ethnopharmacol. 1990 Feb;28(1):129-33.
Additional Infomation	Securinine is a member of indolizines. Securinine has been reported in Flueggea suffruticosa, Phyllanthus amarus, and other organisms with data available. See also: Phyllanthus amarus top (part of). Viroallosecurinine was identified as one of the two major alkaloids isolated from the leaves of Phyllanthus discoideus. It was tested alongside the lyophilized aqueous leaf extract (LWE), the alkaloid fraction (AF), the aqueous residue (WR), and the other major alkaloid securinine. The study concludes that the antibacterial effects of these alkaloids may provide a scientific basis for the traditional use of P. discoideus in treating infectious diseases.[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	4.6028 mL	23.0139 mL	46.0278 mL
	5 mM	0.9206 mL	4.6028 mL	9.2056 mL
	10 mM	0.4603 mL	2.3014 mL	4.6028 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.