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Coniferin Sale

(Synonyms: 松柏苷; Laricin) 目录号 : GC35725

A phenylpropanoid glycoside with diverse biological activities

Coniferin Chemical Structure

Cas No.:531-29-3

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产品描述

Coniferin is a phenylpropanoid glycoside and a lignan precursor that has been found in V. album and has diverse biological activities.1,2,3 It inhibits ADP-induced platelet aggregation in isolated human platelet-rich plasma when used at concentrations ranging from 0.01 to 1 ?M.1 Coniferin has antioxidant activity in an oxygen radical absorbance capacity (ORAC) assay.2 It induces contractions in isolated rat aortic rings when used at concentrations ranging from 0.001 to 1 mM.3 In vivo, coniferin (1 mg/kg) increases blood pressure in spontaneously hypertensive rats.4

1.Panossian, A., Kocharian, A., Matinian, K., et al.Pharmacological activity of phenylpropanoids of the mistletoe, Viscum album L., host: Pyrus caucasica Fed.Phytomedicine5(1)11-17(1998) 2.Kayano, S., Kikuzaki, H., Ikami, T., et al.A new bipyrrole and some phenolic constituents in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC)Biosci. Biotechnol. Biochem.68(4)942-944(2004) 3.Deliorman, D., ?ali?, ?., Ergun, F., et al.Studies on the vascular effects of the fractions and phenolic compounds isolated from Viscum album ssp. albumJ. Ethnopharmacol.72(1-2)323-329(2000) 4.Sawabe, A., Kumamoto, H., and Matsubara, Y.Bioactive glycosides in citrus fruit peelsBull. Inst. Compr. Agr. Sci. Kinki Univ.657-67(1998)

Chemical Properties

Cas No. 531-29-3 SDF
别名 松柏苷; Laricin
Canonical SMILES COC(C=C(/C=C/CO)C=C1)=C1O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO.[E]
分子式 C16H22O8 分子量 342.34
溶解度 DMSO: 10 mM 储存条件 Store at -20°C
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1 mM 2.9211 mL 14.6054 mL 29.2107 mL
5 mM 0.5842 mL 2.9211 mL 5.8421 mL
10 mM 0.2921 mL 1.4605 mL 2.9211 mL
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Research Update

Distribution of Coniferin in freeze-fixed stem of Ginkgo biloba L. by cryo-TOF-SIMS/SEM

Sci Rep 2016 Aug 11;6:31525.PMID:27510918DOI:10.1038/srep31525.

To clarify the role of Coniferin in planta, semi-quantitative cellular distribution of Coniferin in quick-frozen Ginkgo biloba L. (ginkgo) was visualized by cryo time-of-flight secondary ion mass spectrometry and scanning electron microscopy (cryo-TOF-SIMS/SEM) analysis. The amount and rough distribution of Coniferin were confirmed through quantitative chromatography measurement using serial tangential sections of the freeze-fixed ginkgo stem. The lignification stage of the sample was estimated using microscopic observations. Coniferin distribution visualized at the transverse and radial surfaces of freeze-fixed ginkgo stem suggested that Coniferin is stored in the vacuoles, and showed good agreement with the assimilation timing of Coniferin to lignin in differentiating xylem. Consequently, it is suggested that Coniferin is stored in the tracheid cells of differentiating xylem and is a lignin precursor.

NaCl dependent production of Coniferin in Alluaudiopsis marnieriana suspension cultured cells

Plant Biotechnol (Tokyo) 2021 Mar 25;38(1):183-186.PMID:34177341DOI:10.5511/plantbiotechnology.21.0102a.

A stable salt-tolerant cell-suspension culture of Alluaudiopsis marnieriana was established, and intracellular compounds that accumulated under salt-stress conditions were investigated. HPLC/MS, and NMR analyses indicated that enhanced accumulation of Coniferin was found during the growth phase in medium containing 150 mM NaCl. Coniferin or its derivatives may play an important role in salt-tolerance mechanisms in this plant.

Distribution of Coniferin in differentiating normal and compression woods using MALDI mass spectrometric imaging coupled with osmium tetroxide vapor treatment

Tree Physiol 2016 May;36(5):643-52.PMID:26507270DOI:10.1093/treephys/tpv116.

Matrix-assisted laser desorption/ionization mass spectrometric imaging (MALDI-MSI) was employed to detect monolignol glucosides in differentiating normal and compression woods of two Japanese softwoods, Chamaecyparis obtusa and Cryptomeria japonica Comparison of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry collision-induced dissociation fragmentation analysis and structural time-of-flight (MALDI-TOF CID-FAST) spectra between Coniferin and differentiating xylem also confirmed the presence of Coniferin in differentiating xylem. However, as matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and MALDI-TOF CID-FAST spectra of sucrose were similar to those of Coniferin, it was difficult to distinguish the distribution of Coniferin and sucrose using MALDI-MSI and collision-induced dissociation measurement only. To solve this problem, osmium tetroxide vapor was applied to sections of differentiating xylem. This vapor treatment caused peak shifts corresponding to the introduction of two hydroxyl groups to the C=C double bond in Coniferin. The treatment did not cause a peak shift for sucrose, and therefore was effective in distinguishing Coniferin and sucrose. Thus, it was found that MALDI-MSI combined with osmium tetroxide vapor treatment is a useful method to detect Coniferin in differentiating xylem.

Coniferin dimerisation in lignan biosynthesis in flax cells

Phytochemistry 2007 Nov-Dec;68(22-24):2744-52.PMID:17988697DOI:10.1016/j.phytochem.2007.09.016.

[(13)C(2)]-Coniferin was provided to a flax (Linum usitatissimum L.) cell suspension to monitor subsequent dimerisation by MS and NMR. The label was mainly incorporated into a 8-8'-linked lignan, lariciresinol diglucoside, a 8-5'-linked neolignan, dehydrodiconiferyl alcohol glucoside and a diastereoisomeric mixture of a 8-O-4'-linked neolignan, guaiacylglycerol-beta-coniferyl alcohol ether glucoside. This latter compound is reported for the first time in flax. The strong and transient increase in these compounds in fed cells was concomitant with the observed peak in Coniferin content. These results suggest (i) a rapid metabolisation of Coniferin into lignans and neolignans and indicate the capacity of flax cells to operate different types of couplings, and (ii) a continuous synthesis and subsequent metabolisation of coniferin-derived dimers all over the culture period.

Unexpected behavior of Coniferin in lignin biosynthesis of Ginkgo biloba L

Planta 2005 Sep;222(1):58-69.PMID:15986215DOI:10.1007/s00425-005-1517-5.

To gain insight into the behavior of monolignol glucoside in Ginkgo biloba L., we examined glucosides potentially involved in lignin biosynthetic pathway. Coniferin (coniferyl alcohol 4O-beta-D-glucoside) is a strong candidate for the storage form of monolignol. Coniferaldehyde glucoside may also have a role in lignin biosynthesis; this was examined with tracer experiments using labeled glucosides fed to stem segments. A series of tracer experiments showed that Coniferin and coniferaldehyde glucoside were modified into coniferyl alcohol and then efficiently incorporated into lignin under the experimental conditions used. Interestingly, more than half of the administered Coniferin underwent an oxidation to the aldehyde form before its aglycone; coniferyl alcohol was polymerized into lignin. This suggests that there is an alternative pathway for Coniferin to enter the monolignol biosynthetic pathway, in addition to the direct pathway beginning with the deglucosylation of Coniferin catalyzed by beta-glucosidase. Enzymatic assays revealed that coniferaldehyde glucoside was produced enzymatically from Coniferin, and that coniferaldehyde glucoside can be deglucosylated to yield coniferaldehyde, which could be fated to become coniferyl alcohol . Albeit the findings cannot be taken as proof for the in-planta functioning, these results present a possibility for the existence of alternative pathway in which some of the stored Coniferin is oxidized to coniferaldehyde glucoside, which is deglucosylated to generate coniferaldehyde that joins the monolignol biosynthesis pathway.