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Petunidin (chloride)

(Synonyms: 矮牵牛素PT,Petunidol) 目录号 : GC44605

An O-methylated anthocyanidin

Petunidin (chloride) Chemical Structure

Cas No.:1429-30-7

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1mg
¥668.00
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5mg
¥3,015.00
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10mg
¥5,345.00
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25mg
¥11,701.00
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产品描述

Petunidin is an O-methylated anthocyanidin derived from delphinidin that imparts blue-red pigments to flowers, fruits, and red wine. It has been shown to bind with and suppress the activity of focal adhesion kinase and to inhibit platelet-derived growth factor-induced aortic smooth muscle cell migration, which may confer a protective effect against atherosclerosis.[1] Extracts from E. jambolana fruit, which is rich in anthocyanins including petunidin, have been used to suppress the proliferation of an HCT116 colon cancer cell line, as well as colon cancer stem cells. [2]

Reference:
[1]. Son, J.E., SLee, E., Jung, S.K., et al. Anthocyanidins, novel FAK inhibitors, attenuate PDGF-BB-induced aortic smooth muscle cell migration and neointima formation. Cardiovasc.Res. 101(3), 503-512 (2014).
[2]. Charepalli, V., Reddivari, L., Vadde, R., et al. Eugenia jambolana (Java Plum) fruit extract exhibits anti-cancer activity against early stage human HCT-116 colon cancer cells and colon cancer stem cells. Cancers (Basel) 8(3), (2016).

Chemical Properties

Cas No. 1429-30-7 SDF
别名 矮牵牛素PT,Petunidol
化学名 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium, monochlorid
Canonical SMILES OC1=CC(O)=C(C=C(O)C(C2=CC(OC)=C(O)C(O)=C2)=[O+]3)C3=C1.[Cl-]
分子式 C16H13O7•Cl 分子量 352.7
溶解度 15mg/mL in DMSO,25mg/mL in DMF, 15mg/mL in Ethannol 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.8353 mL 14.1764 mL 28.3527 mL
5 mM 0.5671 mL 2.8353 mL 5.6705 mL
10 mM 0.2835 mL 1.4176 mL 2.8353 mL
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Research Update

A defined anthocyanin mixture sourced from bilberry and black currant inhibits Measles virus and various herpesviruses

BMC Complement Med Ther 2022 Jul 8;22(1):181.PMID:35804339DOI:10.1186/s12906-022-03661-7.

Background: Anthocyanin-containing plant extracts and carotenoids, such as astaxanthin, have been well-known for their antiviral and anti-inflammatory activity, respectively. We hypothesised that a mixture of Ribes nigrum L. (Grossulariaceae) (common name black currant (BC)) and Vaccinium myrtillus L. (Ericaceae) (common name bilberry (BL)) extracts (BC/BL) with standardised anthocyanin content as well as single plant extracts interfered with the replication of Measles virus and Herpesviruses in vitro. Methods: We treated cell cultures with BC/BL or defined single plant extracts, purified anthocyanins and astaxanthin in different concentrations and subsequently infected the cultures with the Measles virus (wild-type or vaccine strain Edmonston), Herpesvirus 1 or 8, or murine Cytomegalovirus. Then, we analysed the number of infected cells and viral infectivity and compared the data to non-treated controls. Results: The BC/BL extract inhibited wild-type Measles virus replication, syncytia formation and cell-to-cell spread. This suppression was dependent on the wild-type virus-receptor-interaction since the Measles vaccine strain was unaffected by BC/BL treatment. Furthermore, the evidence was provided that the delphinidin-3-rutinoside chloride, a component of BC/BL, and purified astaxanthin, were effective anti-Measles virus compounds. Human Herpesvirus 1 and murine Cytomegalovirus replication was inhibited by BC/BL, single bilberry or black currant extracts, and the BC/BL component delphinidin-3-glucoside chloride. Additionally, we observed that BC/BL seemed to act synergistically with aciclovir. Moreover, BC/BL, the single bilberry and black currant extracts, and the BC/BL components delphinidin-3-glucoside chloride, cyanidin-3-glucoside, delphinidin-3-rutinoside chloride, and petunidin-3-galactoside inhibited human Herpesvirus 8 replication. Conclusions: Our data indicate that Measles viruses and Herpesviruses are differentially susceptible to a specific BC/BL mixture, single plant extracts, purified anthocyanins and astaxanthin. These compounds might be used in the prevention of viral diseases and in addition to direct-acting antivirals, such as aciclovir.

Different color regulation mechanism in willow barks determined using integrated metabolomics and transcriptomics analyses

BMC Plant Biol 2022 Nov 15;22(1):530.PMID:36380271DOI:10.1186/s12870-022-03909-x.

Background: The rich yellow-orange to vividly deep red bark of willow (Salix spp.) branches have high ornamental and economic value. However, the mechanism underlying the regulation of willow branch color remains unknown. Therefore, we performed metabolomics and transcriptomics analyses of purple, green, and red willow barks to elucidating the mechanisms regulating color development. Results: Seven anthocyanins were isolated; pelargonidin, Petunidin 3-O-rutinoside, and cyanin chloride were the most abundant in red bark, whereas pelargonin chloride was most abundant in purple bark. The green bark contained the highest level of malvidin; however, the malvidin level was not significantly higher than in the red bark. The purple bark contained the largest amount of canthaxanthin, a carotenoid pigment. The integrated pathways of flavonoid biosynthesis, carotenoid biosynthesis, and porphyrin and chlorophyll metabolism were constructed for the willow barks. Among the three barks, the expression of the structural genes ANS, ANR, and BZ1, which are involved in anthocyanin synthesis, was the highest in red bark, likely causing anthocyanin accumulation. The expression of CrtZ, which participates in the carotenoid pathway, was the highest in purple bark, likely leading to canthaxanthin accumulation. The high expression of DVR, POR, and CRD1 may be associated with green pigment synthesis in the chlorophyll biosynthesis pathway. Conclusions: Purple bark color is co-regulated by anthocyanins and carotenoids, whereas red bark is characterized by anthocyanin accumulation and chlorophyll degradation. The green pigment is regulated by maintaining chlorophyll synthesis. BZ1 and CrtZ are candidate genes regulating anthocyanin and canthaxanthin accumulation in red and purple barks respectively. Collectively, our results may facilitate the genetic breeding and cultivation of colorful willows with improved color and luster.

The Role of Taraxacum mongolicum in a Puccinellia tenuiflora Community under Saline-Alkali Stress

Molecules 2022 Dec 9;27(24):8746.PMID:36557878DOI:10.3390/molecules27248746.

Coexisting salt and alkaline stresses seriously threaten plant survival. Most studies have focused on halophytes; however, knowledge on how plants defend against saline-alkali stress is limited. This study investigated the role of Taraxacum mongolicum in a Puccinellia tenuiflora community under environmental saline-alkali stress to analyse the response of elements and metabolites in T. mongolicum, using P. tenuiflora as a control. The results show that the macroelements Ca and Mg are significantly accumulated in the aboveground parts (particularly in the stem) of T. mongolicum. Microelements B and Mo are also accumulated in T. mongolicum. Microelement B can adjust the transformation of sugars, and Mo contributes to the improvement in nitrogen metabolism. Furthermore, the metabolomic results demonstrate that T. mongolicum leads to decreased sugar accumulation and increased amounts of amino acids and organic acids to help plants resist saline-alkali stress. The resource allocation of carbon (sugar) and nitrogen (amino acids) results in the accumulation of only a few phenolic metabolites (i.e., Petunidin, chlorogenic acid, and quercetin-3-O-rhamnoside) in T. mongolicum. These phenolic metabolites help to scavenge excess reactive oxygen species. Our study primarily helps in understanding the contribution of T. mongolicum in P. tenuiflora communities on coping with saline-alkali stress.

An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity

Food Chem 2016 Apr 15;197 Pt B:1226-34.PMID:26675861DOI:10.1016/j.foodchem.2015.11.076.

An efficient process for the purification of anthocyanin monomeric isomers from wild blueberries of Lake Saint-Jean region (Quebec, Canada) was developed and easy scalable at industrial purpose. The blueberries were soaked in acidified ethanol, filtered, and the filtrate was cleaned by solid phase extraction using silica gel C-18 and DSC-SCX cation-exchange resin. Anthocyanin-enriched elutes (87 wt.%) were successfully fractionated by preparative liquid chromatography. The major anthocyanins mono-galactoside, -glucoside and -arabinoside isomers of delphinidin, cyanidin, Petunidin, peonidin and malvidin were isolated with a purity up to 100% according to their LC-MS and (1)H NMR spectra. The oxygen radical absorbance capacity (ORAC) of the obtained pure anthocyanins was evaluated. Delphinidin-3-galactoside has the highest capacity (13.062 ± 2.729 μmol TE/μmol), and malvidin-3-glucoside the lowest (0.851 ± 0.032 μmol TE/μmol). A mechanistic pathway preview is suggested for the anthocyanins scavenging free radical activity by hydrogen transfer.

Anthocyanin composition and oxygen radical scavenging capacity (ORAC) of milled and pearled purple, black, and common barley

J Agric Food Chem 2009 Feb 11;57(3):1022-8.PMID:19159302DOI:10.1021/jf802846x.

The importance of anthocyanins to the total antioxidant capacity of various fruits and vegetables has been well established, but less attention has been focused on cereal grains. This study investigated the antioxidant capacity and anthocyanin composition of a bran-rich pearling fraction (10% outer kernel layers) and whole kernel flour of purple (CI-1248), black (PERU-35), and yellow (EX-83) barley genotypes. HPLC analysis showed that as much as 6 times more anthocyanin per unit weight (microg/g) was present in the bran-rich fractions of yellow and purple barley (1587 and 3534, respectively) than in their corresponding whole kernel flours (210 and 573, respectively). Delphinidin 3-glucoside, delphinidin 3-rutinoside, cyanidin 3-glucoside, Petunidin 3-glucoside, and cyanidin chloride were positively identified in barley, with as many as 9 and 15 anthocyanins being detected in yellow and purple barley, respectively. Antioxidant activity analysis showed that the ORAC values for the bran-rich fractions were significantly (p < 0.05) higher than for the whole kernel flour.