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Thermopsine Sale

(Synonyms: 黄华碱) 目录号 : GC39034

An alkaloid with anti-inflammatory activity

Thermopsine Chemical Structure

Cas No.:486-90-8

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5mg
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10mg
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产品描述

Thermopsine is an alkaloid that has been found in Sophora tonkinensis and has anti-inflammatory activity.1 It reduces LPS-induced production of TNF-α in RAW 264.7 cells when used at a concentration of 50 ?M.

1.He, L.-J., Liu, J.-S., Luo, D., et al.Quinolizidine alkaloids from Sophora tonkinensis and their anti-inflammatory activitiesFitoterapia139104391(2019)

Chemical Properties

Cas No. 486-90-8 SDF
别名 黄华碱
Canonical SMILES O=C1C=CC=C2N1C[C@]3([H])[C@@](CCCC4)([H])N4C[C@@]2([H])C3
分子式 C15H20N2O 分子量 244.33
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 4.0928 mL 20.4641 mL 40.9283 mL
5 mM 0.8186 mL 4.0928 mL 8.1857 mL
10 mM 0.4093 mL 2.0464 mL 4.0928 mL
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Research Update

Thionation of quinolizidine alkaloids and their derivatives via Lawesson's reagent

Nat Prod Res 2022 Jul;36(14):3538-3543.PMID:33397149DOI:10.1080/14786419.2020.1868460.

Direct thionation of quinolizidine alkaloids (-)-cytisine, methylcytisine, Thermopsine and some of their carbonyl derivatives was realized. It was established that carrying out of the reaction in the boiling toluene with 0.5 eq. of Lawesson's reagent (LR) is most effective for synthesis of thio analogues of methyl-, allyl-, benzylcytisine and Thermopsine. It was found, that formation of thioamides is preferable in the case with starting 3-carboxamides of (-)-cytisine or 2-oxo and 4-oxo derivatives of methylcytisine; and an excess of LR is needed for their exhaustive thionation. It was shown, that thionation of 'cytisine substituted' urea and thiourea, as well as Diels-Alder adducts of methylcitisine with phenylmaleimide on basis of this approach was not quite successful: only thionation of the 2-pyridone core has occurred. It should be noted that transformation of urea and thiourea is complicated by side reactions leading to low yields of thio products, and the result of LR interaction with mentioned above diastereomeric Diels-Alder adducts depends on their stereochemistry and thermodynamic stability under reaction conditions.

Alkaloids from Lupinus argenteus var. stenophyllus

J Pharm Sci 1978 Mar;67(3):430-1.PMID:641742DOI:10.1002/jps.2600670348.

TLC and GLC of an alkaloid extract of the aboveground portions of Lupinus argenteus Pursh. var. stenophyllus (Rydb.) Davis (Leguminosae) suggested the presence of sparteine, beta-isosparteine, delta5-dehydrolupanine, alpha-isolupanine, lupanine, Thermopsine, and anagyrine. GLC-mass spectrometry confirmed these preliminary findings. Preparative TLC was used to isolate sparteine, and this alkaloid was further characterized by IR spectral analysis and derivatization.

A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry

Phytochem Anal 2005 Jul-Aug;16(4):264-6.PMID:16042152DOI:10.1002/pca.832.

Gas chromatography coupled with mass spectrometry has been used to analyse the alkaloids present in the aerial parts of Genista tenera. Anagyrine, cytisine, N-formylcytisine, N-methylcytisine and lupanine were the major compounds, the last two alkaloids being known for their hypoglycaemic activity. Dehydrocytisine, 5,6-dehydrolupanine, rhombifoline, aphylline and Thermopsine were the minor alkaloids. The characterisation of the constituents was based on comparison of their Kovats retention indexes and electron impact-mass spectrometric data recorded on-line with those of reference compounds and literature data.

[Toxic principles of Oxytropis glabra DC]

Zhongguo Zhong Yao Za Zhi 1991 Mar;16(3):160-3, 191.PMID:1883498doi

Eight alkaloids were isolated from Oxytropis glabra and identified as anagirine, Thermopsine, N-methylcytisine, sparteine, baptifoline, adenine, dictamnine and ethyl allophanate respectively by spectral analysis and physicochemical methods. All these alkaloids were isolated from this genus for the first time and ethyl allophanate was found in nature for the first time.

Myopathy in cattle induced by alkaloid extracts from Thermopsis montanta, Laburnum anagyroides and a Lupinus sp

J Comp Pathol 1990 Aug;103(2):169-82.PMID:2246392DOI:10.1016/s0021-9975(08)80173-9.

A purified alkaloid preparation containing N-methylcytisine, cytisine, 5,6-dehydrolupanine, Thermopsine and anagyrine from Thermopsis montana induced prolonged recumbency and microscopic acute hyaline skeletal myodegeneration with myofibre regeneration in cattle similar in type and severity to that induced by Thermopsis montanta plant material. This indicates that the alkaloid(s) of Thermopsis montana are responsible for the myopathy caused by the plant. An alkaloid preparation containing mostly anagyrine from a Lupinus sp. and an alkaloid preparation containing only cytisine from Laburnum anagyroides each caused microscopic skeletal muscle degeneration and necrosis similar to, but less severe than, the alkaloid extract from T. montana, but without clinical recumbency. Dosage and severity of response suggest that neither of those two alkaloids alone can account for the effects induced by Thermopsis. The data suggest that quinolizidine alkaloids with a alpha-pyridone A-ring may be responsible for the lesions and that individual alpha-pyridones may have additive effects.