CAS 133-04-0 (-)-Asarinin

(-)-Asarinin - CAS 133-04-0

Catalog number: 133-04-0

Not Intended for Therapeutic Use. For research use only.

Molecular Formula:
Molecular Formula	C20H18O6
Molecular Weight:
Molecular Weight	354.35
COA:
COA	Inquire
Chemical Family:
Chemical Family	Lignans
Description:
Description	(-)-Asarinin can be isolated from the herbs of Asarum sieboldii Miq. It possesses the anti- acute cardiac allograft rejection and immunosuppressive activities.

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Purity:
Purity	>98%
Appearance:
Appearance	Cryst.
Synonyms:
Synonyms	(-)-SESAMINE; ASARININ; EPI-SESAMIN; (-)-5,5'-[(1R,3aα,4S,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[1,3-benzodioxole]; 5,5'-[(1R,3aα,4S,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(1,3-benzodioxole); L-Asarinin
MSDS:
MSDS	Inquire
Application:
Application	Immunosuppressive
Quality Standard:
Quality Standard	CP2010

Quantity:
Quantity	Milligrams-Grams

1.Simultaneous quantification and identification of flavonoids, lignans, coumarin and amides in leaves of Zanthoxylum armatum using UPLC-DAD-ESI-QTOF-MS/MS.

Bhatt V;Sharma S;Kumar N;Sharma U;Singh B J Pharm Biomed Anal. 2017 Jan 5;132:46-55. doi: 10.1016/j.jpba.2016.09.035. Epub 2016 Sep 26.

The current study presents isolation and characterization of twelve compounds including catechin (1), isovitexin (2), hesperidin (3), psoralin (4), eudesmin (5), kobusin (6), fargesin (7), sesamin (8), asarinin (9), planispine-A (10), α-sanshool (11) and vitexin (12), from the leaves of Zanthoxylum armatum. Further, two rapid and simple ultra performance liquid chromatography-diode array detection (UPLC-DAD) methods were developed for the simultaneous quantitative determination of isolated compounds from Z. armatum leaves. These analytical methods were validated for linearity, precision, accuracy, limit of detection (LOD) and limit of quantification (LOQ). The LOD and LOQ were in the range of 0.06-0.21μg/mL and 0.19-0.69μg/mL, respectively. The validated method was linear (R;2;≥0.9906), precise in terms of peak area (intra-day RSDs <3.8% and inter-day RSDs <2.7%), and accurate (109.6-92.5%). This is the first report on the isolation and quantification of 1, 2, 4 and 12 in Z. armatum and 3 in Zanthoxylum genus. The methods: were successfully applied to assess the quality of samples collected from different locations of Himachal Pradesh during summer and winter season. The results demonstrated that flavonoids and furofuran lignans were the major constituents in Z.

2.The dihydrofuran template approach to furofuran synthesis.

Aldous DJ;Batsanov AS;Yufit DS;Dalençon AJ;Dutton WM;Steel PG Org Biomol Chem. 2006 Aug 7;4(15):2912-27. Epub 2006 Jun 30.

Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (+/-)-epiasarinin and (+/-)-asarinin.

3.[Study on chemical constituents of Zanthoxyli cortex's ethyl acetate extract].

Liu YQ;Yang SH;Liu Q;Pei G;Pan WW;Liu M;Peng CY Zhong Yao Cai. 2013 Nov;36(11):1792-5.

OBJECTIVE: ;To study the chemical constituents of Zanthoxyli Cortex.;METHODS: ;The chemical constituents were isolated and purified by silica gel and HP-20, MCI gel, Sephadex LH -20 column chromatography, RP-18 and PTLC. Their structures were elucidated by the analysis of spectral data and chemical properties.;RESULTS: ;Ten compounds were isolated from EtOAc extract and their structures were identified as: asarinin (I), fargesin (II), eudesmin (III), (1R, 2R, 5R, 6S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]-octane(IV), dimethoxysamin(V), rel-(1R,5R,6S)-6-(3,4-dimethoxyphen-yl)-3,7-dioxabicyclo-[3.3.0]-octan-2-one(VI), Magnone A(VII), beta-sitoste-rol( VIII), beta-armyrin(IX), beta-amyrone(X).;CONCLUSION: ;These compounds isolated from Zanthoxyli Cortex's Ethyl acetate extract are all known compounds. Fargesin(II) and beta-amyrone(X) are isolated from Zanthoxyli Cortex for the first time.

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