Delphinidin

Manufactured by Merck Group

Sourced in United States, Germany, France

Delphinidin is a type of flavonoid compound that is commonly found in various plant species. It is a naturally occurring pigment that contributes to the blue, purple, and red colors of many flowers, fruits, and vegetables. Delphinidin serves as a core functional component in various laboratory applications, such as research and analysis, without any intended use interpretation provided.

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Lab products found in correlation

Malvidin, by Merck Group (17 mentions) Pelargonidin, by Merck Group (12 mentions) Caffeic acid, by Merck Group (8 mentions) Peonidin, by Merck Group (7 mentions) Quercetin, by Merck Group (6 mentions) Epicatechin, by Merck Group (6 mentions) Gallic acid, by Merck Group (6 mentions) Catechin, by Merck Group (5 mentions) P coumaric acid, by Merck Group (5 mentions) Petunidin, by Merck Group (5 mentions) Chlorogenic acid, by Merck Group (5 mentions) Folin ciocalteu reagent, by Merck Group (4 mentions) Hydrochloric acid (hcl), by Merck Group (3 mentions) Myricetin, by Merck Group (3 mentions) Fetal bovine serum (fbs), by Thermo Fisher Scientific (3 mentions) Dimethyl sulfoxide (dmso), by Merck Group (3 mentions) Kaempferol, by Merck Group (3 mentions) Ferulic acid, by Merck Group (3 mentions) 2 4 6 tripyridyl s triazine, by Merck Group (2 mentions) Epigallocatechin gallato, by Merck Group (2 mentions)

Spelling variants of this product

Delphinidin chloride (13 citations) Delphinidin 3-O-glucoside (11 citations) Delphinidin 3-glucoside (4 citations) Delphinidin-3-O-galactoside (3 citations) Delphinidin-3-O-rutinoside (3 citations) Delphinidin-3-O-glucoside chloride (3 citations)

30 protocols using delphinidin

Characterization of Fruit Bioactive Compounds

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Raw material and chemical reagents.
The raw material, apple (cv. Fuji), and grape (cv. País) were collected from the local market (Chillán, Chile 2019). The chemical reagents were used for the different analyses: NaHCO₃, NaCl, KCl CaCl₂·2 H₂ O, K₂ HPO₄, HCl, Folin-Ciocalteu, gallic acid, 1,1-diphenyl-2-picrylhydrazyl (DPPH); 2,4,6-tripyridyl-s-triazine, chloroform, anhydrous citric acid were acquired from Merck, Germany. Also, mucin, α-amylase, pepsin, pancreatin, bile salts, delphinidin, caffeic acid, myricetin, quercetin, (-)-epicatechin, (+)-catechin, (-)-epigallocatechin gallato, malvidin, p-coumaric acid, cyaniding, Tween-20 were purchased from Sigma-Aldrich, USA. Syringe tip 45 filters µm PTFE from Merck Millipore, Ireland, were used. Ultrapure water was obtained using a Thermo, Scientific filter.

Pavez-Guajardo C., Ferreira S.R., Mazzutti S., Guerra-Valle M.E., Sáez-Trautmann G, & Moreno J. (2020). Influence of In Vitro Digestion on Antioxidant Activity of Enriched Apple Snacks with Grape Juice. Foods, 9(11), 1681.

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Delphinidin Chloride: Molecular Insights and Therapeutic Potential

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Delphinidin chloride was purchased from Extrasynthèse (Genay, France) and was used at 10⁻² g/L. This concentration has been described to induce the maximal relaxing effect on ex vivo rat aorta^{13 (link)}, to prevent angiogenesis through an inhibition of migration and proliferation^{16 (link), 17 (link)} and to inhibit endothelial apoptosis^{51 (link)}. Delphinidin was diluted in dimethylsulfoxide (DMSO) from Sigma Aldrich (St Louis, MO). The final concentration of DMSO in experiments never exceeded 0.1%. Anti-CD3 (clone OKT3) and anti-CD28 (clone CD28.2) human antibodies were purchased from BioLegend® (San Diego, CA). Histopaque®1077, Histopaque®1083, thapsigargin, Phytohemagglutinin (PHA), phorbol-12-myristate-13-acetate (PMA), ionomycin, fulvestrant, and SKF96365 were purchased from Sigma-Aldrich. Mibefradil hydrochloride was purchased from Abcam (Cambridge, UK) and trichostatin A (TSA) from Santa Cruz Biotechnology (Santa Cruz, CA). U0126 was obtained from Calbiochem (San Diego, CA). RPMI-1640, Na-pyruvate, non-essential amino-acid (NEAA) and penicillin/streptomycin were purchased from Lonza (Basel, Switzerland). Fetal bovine serum (FBS) and Fluo-4 acetoxymethyl ester (AM) were purchased from Life Technologies (Carlsbad, CA).

Dayoub O., Le Lay S., Soleti R., Clere N., Hilairet G., Dubois S., Gagnadoux F., Boursier J., Martínez M.C, & Andriantsitohaina R. (2017). Estrogen receptor α/HDAC/NFAT axis for delphinidin effects on proliferation and differentiation of T lymphocytes from patients with cardiovascular risks. Scientific Reports, 7, 9378.

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Quantitative HPLC Analysis of Flower Anthocyanins

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HPLC analysis was carried out by Scistd Testing Co., LTD. (Qingdao, China). Anthocyanins were extracted using 50 mg of powdered petal (flower development stage 2–3) suspended in 5 ml of 0.5% (v/v) HCl‐methanol and incubated for 2 hr at 4°C in the dark. The extracts were then centrifuged for 15 min at 14,000 rpm, and the supernatants were collected and stored at −20°C. The supernatant was diluted with methanol to 5 ml and filtered through a cellulose acetate membrane (Sartorius, Göttingen, Germany). HPLC was performed with Agilent 1260 Infinity LC (Agilent Technologies, USA). Anthocyanidin profile analysis was quantified at the 530 nm wavelength by using a calibration curve from commercial standards of anthocyanidins (pelargonidin, cyanidin, delphinidin, petunidin, peonidin, and malvidin, Sigma, USA).

Zhang H., Koes R., Shang H., Fu Z., Wang L., Dong X., Zhang J., Passeri V., Li Y., Jiang H., Gao J., Li Y., Wang H, & Quattrocchio F.M. (2019). Identification and functional analysis of three new anthocyanin R2R3‐MYB genes in Petunia. Plant Direct, 3(1), e00114.

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Prostate Cancer Cell Apoptosis Pathway

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Human prostate LNCaP and Du145 cells were obtained from the American Type Culture Collection (Manassas, VA) and cultured in RPMI supplemented with 10% fetal bovine serum (FBS; Gibco-BRL, MD) and 1% antibiotic-antimycotic solution in a humidified 5% CO₂ atmosphere at 37°C. Antibodies against cleaved caspase-3, caspase-7, caspase-8, caspase-9, PARP, Survivin, XIAP, cIAP-2, BID, BAX, DR5, BCL-2 and acetylated p53 (Ac-p53) antibodies were purchased from Cell Signaling Technology (Beverly, MA). Anti-HDAC1, HDAC2, HDAC3, HDAC8, FLAG, p53, and actin antibodies were purchased from Santa Cruz Biotechnology (Dallas, TX). Anti-FLAG and β-actin antibodies were purchased from Sigma-Aldrich (St. Louis, MO). The anti-mouse or anti-rabbit secondary antibodies were purchased from Pierce (Rockford, IL). Delphinidin and TRAIL were obtained from Sigma-Aldrich (Fig. 1A).

Ko H., Jeong M.H., Jeon H., Sung G.J., So Y., Kim I., Son J., Lee S.W., Yoon H.G, & Choi K.C. (2015). Delphinidin sensitizes prostate cancer cells to TRAIL-induced apoptosis, by inducing DR5 and causing caspase-mediated HDAC3 cleavage. Oncotarget, 6(12), 9970-9984.

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HPLC-DAD Analysis of Phenolic Compounds

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An aliquot of 3 mL was taken and filtered using 45 µm PTFE syringe tip filters (Merck Millipore, Ireland) into 2 mL vials. The following standards were used, according to availability in the laboratory depending on the investigations carried out: delphinidin, caffeic acid, myricetin, quercetin, (-)-epicatechin, (+)-catechin, (-)-epigallocatechin gallato, malvidin, p-coumaric acid, and cyanidin (Sigma-Aldrich, USA). Only the identified standards were reported. The HPLC-DAD instrument (Perkin Elmer, series 200, Massachusetts, USA) consisted of a binary pump, an autosampler, a diode array detector, a column compartment, and a Purospher STAR^® 100 RP-18 e columns (125 × 4 mm, 5 μm particle size) as described. Working conditions were established according to Ruiz et al. [22 (link)] using the following mobile phases: A= acetonitrile/formic acid/water (3:10:87); B = formic acid/water/acetonitrile (10:40:50), modifying the gradient of mobile phases. The DAD wavelengths were 280 and 520 nm for flavan-3-ols and anthocyanins, respectively.

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Procurement of Glycosylated Anthocyanins

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UDP-glucose, UDP-galactose, UDP-rhamnose, UDP-arabinose, cyanidin, delphinidin, and malvidin were purchased from Sigma-Aldrich (USA), and pelargonidin, petunidin, peonidin, cyanidin 3-O-glucoside, delphinidin 3-O-glucoside, pelargonidin 3-O-glucoside, malvidin 3-O-glucoside, petunidin 3-O-glucoside, and peonidin 3-O-glucoside were obtained from Phytolab (Germany).

Sun W., Sun S., Xu H., Wang Y., Chen Y., Xu X., Yi Y, & Ju Z. (2022). Characterization of Two Key Flavonoid 3-O-Glycosyltransferases Involved in the Formation of Flower Color in Rhododendron Delavayi. Frontiers in Plant Science, 13, 863482.

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Polyphenol Extraction and Analysis

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Methanol (employed as an extraction solvent and as mobile phase), and ultrapure water (for mobile phase preparation), both LC-MS grade, were supplied by Scharlau (Chemie S.A., Barcelona, Spain). Deionised water was produced in the laboratory with a MilliQ gradient system (Millipore, Bedford, MA, USA), while formic acid was supplied by Merck (Darmstadt, Germany). All other chemicals, such as ethanol, Folin–Ciocalteu reagent or hydrochloric acid (HCl), were purchased from Sigma-Aldrich (Chemie GmbH, Steinheim, Germany). Catechin (CAS: 154-23-4, ≥99.0%) pro cyanidin B1 (CAS: 20315-25-7, ≥90%), caffeic acid (CAS 331-39-5, ≥98.0%), pro cyanidin B2 (CAS: -49-8, ≥90%), chlorogenic acid (CAS: 327-97-9, ≥95%), epiCatechin (CAS: 490-46-0; ≥98%), 4-hydroxycinnamic acid (CAS: 7400-08-0, ≥98.0%), myricetin (CAS: 529-44-2, ≥96.0%), quercetin (CAS: 117-39-5, ≥95%), kaempferol (CAS: 520-18-3, ≥97.0%), delphinidin (CAS: 528-53-0, ≥95%), petunidin (CAS: 1429-30-7, ≥90%), cyanidin (CAS: 528-58-5, ≥98%), peonidin (CAS: 134-01-0, ≥95%), and malvidin (CAS: 643-84-5, ≥95%) were purchased from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany).

Lončarić A., Celeiro M., Jozinović A., Jelinić J., Kovač T., Jokić S., Babić J., Moslavac T., Zavadlav S, & Lores M. (2020). Green Extraction Methods for Extraction of Polyphenolic Compounds from Blueberry Pomace. Foods, 9(11), 1521.

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Phytochemical Profiling and Antioxidant Activity of Purple Corn

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Prior to use, purple corn was kept in a refrigerator (4 °C) after being purchased from Woodland Foods (Waukegan, Illinois, United States). All the standards for anthocyanins (cyanidin-3-glucoside, cyanidin chloride, delphinidin, malvidin and peonidin), flavonoids (epicatechin, kaempferol, morin, naringin and quercetin) and phenolic acids (caffeic acid, chlorogenic acid, ferulic acid, gallic acid, and hesperidin) were purchased from Sigma Aldrich (St. Louis, USA). The 1,2-Diphenylpicrylhydrazyl (DPPH), 2,2-Azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), acetonitrile, ethanol, HPLC-grade water, and methanol (HPLC-grade) were bought from Sigma Aldrich (St. Louis, USA). Other solvents and reagents were analytical grades with no other purification before usage. The deionized water for other experiments was sourced from the Milli-Q H₂O purification system (Millipore®, MA, USA).

Boateng I.D., Kumar R., Daubert C.R., Flint-Garcia S., Mustapha A., Kuehnel L., Agliata J., Li Q., Wan C, & Somavat P. (2023). Sonoprocessing improves phenolics profile, antioxidant capacity, structure, and product qualities of purple corn pericarp extract. Ultrasonics Sonochemistry, 95, 106418.

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Antioxidant Compounds Characterization

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6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox; 97%); 2,2-diphenyl-2-picrylhydrazyl hydrate (DPPH); 2,4,6-tris(2-pyridyl)-1,3,5-triazine (TPTZ; ≥ 98%); 3-aminophthal-hydrazide (Luminol; 97%); 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AAPH; 97%); Folin-Ciocalteu reagent (2N); p-hydroxybenzoic acid (≥ 99%), chlorogenic acid (≥ 95%), p-coumaric acid (≥ 98%), caffeic acid ≥ 98%, ferulic acid (99%), syringic acid (≥ 95%), gallic acid (97.5–102.5%), ellagic acid (≥ 95%), and ascorbic acid (≥ 99%); beta-carotene (≥ 95%); rutin (≥ 94%); kaempferol (≥ 90%); kaempferol-3-glucoside (≥ 97%); malvidin (≥ 95%); delphinidin (≥ 95%); pelargonidin (≥ 95%); cyanidin (≥ 95%); cyanidin-3-glucoside (≥ 95%); quercetin-3-O-galactoside (hyperoside; ≥ 97%); quercetin-3-beta-D-glucoside (isoquercitrin; ≥ 90%); and quercetin-3-rhamnoside (quercitrin; ≥ 78%) were obtained from Sigma Chemical Co. (St. Louis, MO, USA). Quercetin (≥ 98%) was purchased from Jassem Chemical (Beerse, Belgium). Vanillic acid (≥ 97%) was purchased from Fluka Chemical (Bochus, Switzerland).

Denardin C.C., Hirsch G.E., da Rocha R.F., Vizzotto M., Henriques A.T., Moreira J.C., Guma F.T, & Emanuelli T. (2015). Antioxidant capacity and bioactive compounds of four Brazilian native fruits. Journal of Food and Drug Analysis, 23(3), 387-398.

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Autophagy Regulation Signaling Pathway

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Alexa Fluor 488 Phalloidin (8878), caspase-3 (9665 s), caspase-9 (9502), light chain 3 (LC3)-I/II (2775), AKT (4685), phospho-AKT (4051), mTOR (2972), phospho-mTOR (5536), eukaryotic initiation factor 4E (eIF4E, 2067), phospho-eukaryotic initiation factor 4E (p-eIF4E, 9741), ribosomal protein S6 kinase (p70s6k) (9202), phospho-ribosomal protein S6 kinase, (p-p70s6k, 9206), serine/threonine kinase LKB1/STK11 (3047), phospho-LKB1 (3482), forkhead box O3a (FOXO3a, 2497), AMPK (2532), phospho-forkhead box O 3a (p-FOXO3a, 9465), UNC-51-like kinase-1 (ULK1, 4776), phospho-UNC-51-like kinase-1 (ULK1, 12,753), anti-rabbit secondary antibody (7054), and anti-mouse secondary antibody (7056) were purchased from Cell Signaling Technology, USA. Atg5 (ab78073) and phospho-AMPK (ab195946) were purchased from Abcam, UK. β-Actin (TA-09) was purchased from ZSGB-BIO, China. Other reagents were obtained from the following sources as required: delphinidin (Sigma, USA, 43725); 3-MA (Sigma, USA, M9281); BA1 (Cayman, USA, 88899–55-2); DMSO (Sigma, USA, D2650); and cell counting kit-8 (CCK-8) (Dojindo, Japan, CK04–20).

Chen J., Zhu Y., Zhang W., Peng X., Zhou J., Li F., Han B., Liu X., Ou Y, & Yu X. (2018). Delphinidin induced protective autophagy via mTOR pathway suppression and AMPK pathway activation in HER-2 positive breast cancer cells. BMC Cancer, 18, 342.

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