Lobetyolin is a biologically active compound extracted from Codonopsis pilosula. Lobetyolin has anti~inflammatory, antioxidant and xanthine oxidase inhibitory activities. Lobetyolin also causes apoptosis by inhibiting ASCT2-mediated glutamine metabolism. Lobetyolin is a click chemical agent. It has Alkyne groups and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing Azide groups.

Physicochemical Properties

Molecular Formula	C20H28O8
Molecular Weight	396.43152
Exact Mass	396.178
CAS #	129277-38-9
PubChem CID	6369123
Appearance	White to yellow solid powder
Density	1.4±0.1 g/cm3
Boiling Point	698.5±55.0 °C at 760 mmHg
Flash Point	376.2±31.5 °C
Vapour Pressure	0.0±5.0 mmHg at 25°C
Index of Refraction	1.607
LogP	2.02
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Heavy Atom Count	28
Complexity	646
Defined Atom Stereocenter Count	0
SMILES	C/C=C/C#CC#CC(C(/C=C/CCCO)OC1C(C(C(C(O1)CO)O)O)O)O
InChi Key	MMMUDYVKKPDZHS-FWTOVJONSA-N
InChi Code	InChI=1S/C20H28O8/c1-2-3-4-5-7-10-14(23)15(11-8-6-9-12-21)27-20-19(26)18(25)17(24)16(13-22)28-20/h2-3,8,11,14-26H,6,9,12-13H2,1H3/b3-2+,11-8+
Chemical Name	2-[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
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 Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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	Lobetyolin is produced from Codonopsis pilosula and possesses antioxidant effects. Pretreatment with Lobetyolin, lobetyol, or methyl linoleate reduced phorbol 12-myristate 13-acetate (PMA)-induced MUC5AC gene expression from NCI-H292 cells. Lobetyolin does not influence PMA-induced MUC5AC synthesis in NCI-H292 cells. The amount of mucin in cells from cultures treated with lobetolin was 100±25%, 487±33%, 524±38%, 411±24% and 402±45% (control, 10 ng/mL PMA alone, PMA) plus Lobetyolin 1 μM, PMA plus Lobetyolin 10 μM and PMA plus Lobetyolin 100 μM accordingly [1].
References	[1]. Effects of Lobetyolin, Lobetyol and Methyl linoleate on Secretion, Production and Gene Expression of MUC5AC Mucin from Airway Epithelial Cells. Tuberc Respir Dis (Seoul). 2014 Nov;77(5):203-8. [2]. Lobetyolin induces apoptosis of colon cancer cells by inhibiting glutamine metabolism. J Cell Mol Med. 2020 Mar;24(6):3359-3369.
Additional Infomation	See also: Lobetyolin (annotation moved to).

Solubility Data

Solubility (In Vitro)

H2O : ~50 mg/mL (~126.13 mM) DMSO : ~50 mg/mL (~126.13 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.31 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.31 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 33.33 mg/mL (84.08 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5225 mL	12.6126 mL	25.2251 mL
	5 mM	0.5045 mL	2.5225 mL	5.0450 mL
	10 mM	0.2523 mL	1.2613 mL	2.5225 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.