Thesinine

CAS# 488-02-8

Thesinine

2D Structure

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3D structure

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Thesinine

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Chemical Properties of Thesinine

Cas No. 488-02-8 SDF Download SDF
PubChem ID 6452120 Appearance Powder
Formula C17H21NO3 M.Wt 287.36
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1R,8R)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES C1CC2C(CCN2C1)COC(=O)C=CC3=CC=C(C=C3)O
Standard InChIKey FQVNMXZPGWLUFZ-BNVCYRGBSA-N
Standard InChI InChI=1S/C17H21NO3/c19-15-6-3-13(4-7-15)5-8-17(20)21-12-14-9-11-18-10-1-2-16(14)18/h3-8,14,16,19H,1-2,9-12H2/b8-5+/t14-,16+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Thesinine

The herbs of Lithospermum erythrorhizon

Protocol of Thesinine

Structure Identification
Frontiers in Plant Science, 2017, 8:2046.

Variability of Pyrrolizidine Alkaloid Occurrence in Species of the Grass Subfamily Pooideae (Poaceae).[Reference: WebLink]

Pyrrolizidine alkaloids (PAs) are a class of secondary metabolites found in various unrelated angiosperm lineages including cool-season grasses (Poaceae, subfamily Pooideae).
METHODS AND RESULTS:
Thesinine conjugates, saturated forms of PA that are regarded as non-toxic, have been described to occur in the two grass speciesLolium perenneandFestuca arundinacea(Poaceae, subfamily Pooideae). In a wider screen, we tested various species of the Pooideae lineage, grown under controlled conditions, for their ability to produce Thesinine conjugates or related structures. Using an LC-MS based targeted metabolomics approach we were able to show that PA biosynthesis in grasses is limited to a group of very closely related Pooideae species that produce a limited diversity of PA structures. High variability in PA levels was observed even between individuals of the same species.
CONCLUSIONS:
These individual accumulation patterns are discussed with respect to a possible function and evolution of this type of alkaloid.

Thesinine Dilution Calculator

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Thesinine Molarity Calculator

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Preparing Stock Solutions of Thesinine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.48 mL 17.3998 mL 34.7996 mL 69.5991 mL 86.9989 mL
5 mM 0.696 mL 3.48 mL 6.9599 mL 13.9198 mL 17.3998 mL
10 mM 0.348 mL 1.74 mL 3.48 mL 6.9599 mL 8.6999 mL
50 mM 0.0696 mL 0.348 mL 0.696 mL 1.392 mL 1.74 mL
100 mM 0.0348 mL 0.174 mL 0.348 mL 0.696 mL 0.87 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Thesinine

E/Z-Thesinine-O-4'-alpha-rhamnoside, pyrrolizidine conjugates produced by grasses (Poaceae).[Pubmed:18466931]

Phytochemistry. 2008 Jun;69(9):1927-32.

Based on direct infusion mass spectrometry we identified a novel alkaloid as a major component of perennial ryegrass (Lolium perenne). Initial mass spectral data suggested it to be a pyrrolizidine conjugate. As this class of alkaloids has not been described before from grasses, we isolated it to elucidate its structure. The isolated alkaloid proved to be a mixture of two stereoisomers. The structures of the two compounds as determined by 1D and 2D NMR spectroscopy, were E-Thesinine-O-4'-alpha-rhamnoside (1) and Z-Thesinine-O-4'-alpha-rhamnoside (2). These identifications were supported by the characterisation by GC-MS and optical rotation of (+)-isoretronecanol as the necine base released on alkaline hydrolysis of these alkaloids. 1 and 2 together with the aglycone and a hexoside were also detected in tall fescue (Festuca arundinacea). This is the first report of pyrrolizidine alkaloids produced by grasses (Poaceae).

Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.[Pubmed:12031432]

Phytochemistry. 2002 Jun;60(4):399-402.

The glycosylated pyrrolizidine alkaloid, Thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis.

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