Inuviscolide is an inducer of apoptosis. Inuviscolide induces G2/M arrest in human melanoma cell lines. Inuviscolide has antitumor and anti-inflammatory activities.

Physicochemical Properties

Molecular Formula	C15H20O3
Molecular Weight	248.32
Exact Mass	248.141
CAS #	63109-30-8
PubChem CID	176489
Appearance	Typically exists as solid at room temperature
LogP	2.211
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Heavy Atom Count	18
Complexity	439
Defined Atom Stereocenter Count	5
SMILES	CC1(CCC2C1CC3C(CC2=C)OC(=O)C3=C)O
InChi Key	GTYUWNQOOLJZBM-XLFUENPSSA-N
InChi Code	InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h10-13,17H,1-2,4-7H2,3H3/t10-,11-,12-,13+,15-/m1/s1
Chemical Name	(3aS,5aS,8R,8aR,9aR)-8-hydroxy-8-methyl-1,5-dimethylidene-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-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	Inuviscolide (9-72 μM; 24 h) has IC50 values of 37, 41.1, and 39 μM, respectively, which inhibit the growth of SK-28, 624, and 1363 melanoma cells [2]. Dose-dependent increase of SK-28 cells in the G2/M phase is caused by inuviscolide (36–54 μM; 4–24 h) [2]. At 72 μM for 48 hours, inuviscolide causes early apoptotic markers to appear in about 70% of SK-28 cells [2]. Human leukocyte elastase release is 51% inhibited by inuviscolide at 100 μM[1]. An IC50 value of 80.5 μM is observed for inuviscolide, which inhibits the secretion of PLA2 (sPLA2) by bee venom. As opposed to its lack of action against inducible COX-2, inuviscolide inhibits COX-1 (40%) at 50 μM [1].
ln Vivo	Mice whose dermatitis was brought on by repeated application of 12-O-tetradecanoylphorbol 13-acetate have less leukocyte infiltration in their skin when inuviscolide is applied [1].
Cell Assay	Cell Proliferation Assay[2] Cell Types: SK-28, 624 and 1363 melanoma cells Tested Concentrations: 9-72 μM Incubation Duration: 24 hrs (hours) Experimental Results: Resulted in a dose-dependent inhibition of cellular proliferation, with no significant changes between the three cell lines.
References	[1]. Inhibition of pro-inflammatory enzymes by inuviscolide, a sesquiterpene lactone from Inula viscosa. Fitoterapia. 2007 Jun;78(4):329-31. [2]. Induction of G2/M arrest and apoptosis by sesquiterpene lactones in human melanoma cell lines. Biochem Pharmacol. 2008 Jan 15;75(2):369-82. [3]. A mechanistic approach to the in vivo anti-inflammatory activity of sesquiterpenoid compounds isolated from Inula viscosa. Planta Med. 2001 Nov;67(8):726-31.
Additional Infomation	Inuviscolide is a sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. It has a role as an anti-inflammatory agent and a plant metabolite. It is a gamma-lactone, an organic heterotricyclic compound, a sesquiterpene lactone and a tertiary alcohol. Inuviscolide has been reported in Inula japonica, Inula hupehensis, 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	4.0271 mL	20.1353 mL	40.2706 mL
	5 mM	0.8054 mL	4.0271 mL	8.0541 mL
	10 mM	0.4027 mL	2.0135 mL	4.0271 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.