11beta,13-Dihydrolactucin | CAS:83117-63-9

11beta,13-Dihydrolactucin

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Description:

11beta,13-Dihydrolactucin has analgesic effect and anti-inflammatory potential .

In vitro:

Nutrients . 2020 Nov 19;12(11):3547.

Assessing the Intestinal Permeability and Anti-Inflammatory Potential of Sesquiterpene Lactones from Chicory[Pubmed: 33228214]

Cichorium intybus L. has recently gained major attention due to large quantities of health-promoting compounds in its roots, such as inulin and sesquiterpene lactones (SLs). Chicory is the main dietary source of SLs, which have underexplored bioactive potential. In this study, we assessed the capacity of SLs to permeate the intestinal barrier to become physiologically available, using in silico predictions and in vitro studies with the well-established cell model of the human intestinal mucosa (differentiated Caco-2 cells). The potential of SLs to modulate inflammatory responses through modulation of the nuclear factor of activated T-cells (NFAT) pathway was also evaluated, using a yeast reporter system. Lactucopicrin was revealed as the most permeable chicory SL in the intestinal barrier model, but it had low anti-inflammatory potential. The SL with the highest anti-inflammatory potential was 11β,13-dihydrolactucin, which inhibited up to 54% of Calcineurin-responsive zinc finger (Crz1) activation, concomitantly with the impairment of the nuclear accumulation of Crz1, the yeast orthologue of human NFAT.

In vivo:

J Ethnopharmacol . 2006 Sep 19;107(2):254-258.

Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice[Pubmed: 16621374]

Lactucin (1) and its derivatives lactucopicrin (2) and 11beta,13-Dihydrolactucin (3), which are characteristic bitter sesquiterpene lactones of Lactuca virosa and Cichorium intybus, were evaluated for analgesic and sedative properties in mice. The compounds showed analgesic effects at doses of 15 and 30 mg/kg in the hot plate test similar to that of ibuprofen, used as a standard drug, at a dose of 30 mg/kg. The analgesic activities of the compounds at a dose of 30 mg/kg in the tail-flick test were comparable to that of ibuprofen given at a dose of 60 mg/kg. Lactucopicrin appeared to be the most potent analgetic of the three tested compounds. Lactucin and lactucopicrin, but not 11beta,13-Dihydrolactucin, also showed sedative properties in the spontaneous locomotor activity test.

Nutrients . 2020 Nov 28;12(12):3675.

Low Oral Bioavailability and Partial Gut Microbiotic and Phase II Metabolism of Brussels/Witloof Chicory Sesquiterpene Lactones in Healthy Humans[Pubmed: 33260567]

Free and glycosylated sesquiterpene lactones (SLs), which are abundant in leafy vegetables including Brussels/witloof chicory, possess health-promoting effects in vivo. However, the pharmacokinetics of dietary source of SLs remain largely unknown. In this open-label and single-dose trial, sixteen healthy volunteers consumed 150 g of Brussels/witloof chicory juice containing 48.77 μmol SLs in 5 min. Blood, urine, and fecal samples were collected before and after chicory consumption in 24 h. No SLs were detected in the serum, urine, and fecal samples before chicory consumption in all of the participants. Chicory consumption increased lactucin, 11β,13-dihydrolactucin, and their glucuronide/sulfate conjugates, rather than lactucopicrin and 11β,13-dihydrolactucopicrin, as well as glycosylated SLs in biological samples. The peak concentration of total SLs in serum reached 284.46 nmol/L at 1 h, while, in urine, this peak was 220.3 nmol between 2 and 6 h. The recovery of total SLs in blood, urine, and feces was 7.03%, 1.13%, and 43.76% of the ingested dose, respectively. Human fecal suspensions with intestinal microbiota degraded glycosylated SLs in chicory, and converted lactucopicrin and 11β,13-dihydrolactucopicrin to lactucin and 11β,13-dihydrolactucin, respectively. Collectively, Brussels/witloof chicory SLs are poorly bioavailable and they undergo partial gut microbial and phase II metabolism in humans.

11beta,13-Dihydrolactucin Description

Source:	The herbs of Picris hieracioides L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Magn Reson Chem . 2011 Nov;49(11):753-756.

Complete NMR spectral assignments of two lactucin-type sesquiterpene lactone glycosides from Picris conyzoides[Pubmed: 22002327]

Complete (1)H and (13)C NMR signal assignments of two lactucin-type sesquiterpene lactone glycosides, derivatives of 11β,13-dihydrolactucin, isolated from roots of Picris conyzoides, were achieved by one- and two-dimensional NMR experiments, allowing the correction of previously published data for cichorioside B and the structure elucidation of its new ester with 3-hydroxy-2-methylpropanoic acid. In addition, seven known sesquiterpene lactones and three phenolic compounds were isolated from the plant material.

Nat Prod Res . 2021 May 8;1-5.

Chemical constituents from Lactuca plumieri (L.) Gren. & Godr. (Asteraceae)[Pubmed: 33969755]

This is the first report concerning the natural products of the hitherto unstudied Lactuca plumieri (L.) Gren. & Godr., a member of the tribe Cichorieae (Asteraceae). From aerial parts and roots of this plant, five sesquiterpene lactones and one coumarin were isolated. The compounds were identified as sonchuside A, 11β,13-dihydrolactucin-8-O-acetate, 11β,13-dihydrolactucin, cichorioside B, 11β,13-dihydrolactucin-8-O-acetate-15-O-β-glucopyranoside and coumarin - cichoriin. Their structures were established by 1H NMR. Moreover, HPLC/PAD analysis of a hydroalcoholic extract from the aerial parts of the plant revealed the presence of caffeic acid derivatives, coumarins and flavonoids commonly found in lettuces.

CAS No.	83117-63-9	Price	$318 / 10mg
Catalog No.	CFN95433	Purity	>=98%
Molecular Weight	278.3	Type of Compound	Sesquiterpenoids
Formula	C₁₅H₁₈O₅	Physical Description	Powder
Download	COA MSDS	Similar structural	Comparison (Web) (SDF)

Product Name	11beta,13-Dihydrolactucin
CAS No.:	83117-63-9
Catalog No.:	CFN95433
Molecular Formula:	C₁₅H₁₈O₅
Molecular Weight:	278.3 g/mol
Purity:	>=98%
Type of Compound:	Sesquiterpenoids
Physical Desc.:	Powder
Source:	The herbs of Picris hieracioides L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price:	$318 / 10mg
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Sesquiterpenoids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.5932 mL	17.9662 mL	35.9324 mL	71.8649 mL	89.8311 mL
5 mM	0.7186 mL	3.5932 mL	7.1865 mL	14.373 mL	17.9662 mL
10 mM	0.3593 mL	1.7966 mL	3.5932 mL	7.1865 mL	8.9831 mL
50 mM	0.0719 mL	0.3593 mL	0.7186 mL	1.4373 mL	1.7966 mL
100 mM	0.0359 mL	0.1797 mL	0.3593 mL	0.7186 mL	0.8983 mL

CFN98720	Dehydrocostus lactone	477-43-0	230.3	C₁₅H₁₈O₂
CFN99030	Sulfocostunolide A	1016983-51-9	312.4	C₁₅H₂₀O₅S
CFN99075	Sulfocostunolide B	1059671-65-6	312.4	C₁₅H₂₀O₅S
CFN89195	1alpha,4beta,10beta-Trihydroxyguaia-2,11(13)-dien-12,6alpha-olide	221148-94-3	280.32	C₁₅H₂₀O₅
CFN90378	Eupalinilide B	757202-08-7	360.41	C₂₀H₂₄O₆
CFN90379	Eupalinilide C	757202-11-2	376.4	C₂₀H₂₄O₇
CFN90380	Eupalinilide D	757202-14-5	314.76	C₁₅H₁₉ClO₅
CFN96796	8-Epicrepiside E	93395-30-3	424.44	C₂₁H₂₈O₉
CFN93077	Cynaropicrin	35730-78-0	346.37	C₁₉H₂₂O₆
CFN96392	8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C	93395-31-4	538.6	C₂₆H₃₄O₁₂