Delphinidin Chloride
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MedKoo CAT#: 563782

CAS#: 528-53-0 (Cl)

Description: Delphinidin Chloride is an inhibitor of BDNF-induced migration and invasion in SKOV3 ovarian cancer cells.

Chemical Structure

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Delphinidin Chloride
CAS# 528-53-0 (Cl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 563782
Name: Delphinidin Chloride
CAS#: 528-53-0 (Cl)
Chemical Formula: C15H11ClO7
Exact Mass: 338.02
Molecular Weight: 338.700
Elemental Analysis: C, 53.19; H, 3.27; Cl, 10.47; O, 33.07

Price and Availability

Size Price Availability Quantity
1mg USD 210
5mg USD 405
10mg USD 660
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Related CAS #: 528-53-0 (free base)   528-53-0 (Cl)  

Synonym: Delphinidin Chloride; Delphinidine; Delphinidol; Ephdine

IUPAC/Chemical Name: 2-(3,4,5-Trihydroxyphenyl)chromenylium-3,5,7-triol chloride

InChi Key: FFNDMZIBVDSQFI-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H

SMILES Code: OC1=C(C2=CC(O)=C(O)C(O)=C2)[O+]=C3C=C(O)C=C(O)C3=C1.[Cl-]

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info: Delphinidin Chloride is a natural anthocyanin plant pigment.

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Delphinidin chloride, an anthocyanidin, shows endothelium-dependent vasorelaxation as well as modulates JAK/STAT3 and MAPKinase signaling to induce apoptosis in HCT116 cells.
In vitro activity: Neonatal rat cardiomyocytes (NRCMs) were treated with angiotensin II (Ang II) and delphinidin in vitro. The cardiac hypertrophyrelated increase in cell size after Ang II stimulation was blocked by delphinidin (50 μM) (Figure 4B). Furthermore, delphinidin (50 μM) significantly prevented Ang II-induced increases in Anp, Bnp and β-MHC mRNA expression levels (Figure 4C). In addition, DHE and DCF-DA fluorescence images showed that the marked increase in ROS production in cardiomyocytes in response to Ang II stimulation was attenuated by delphinidin (50 μM) (Figure 4D and 4E). Consistent with these findings, delphinidin (50 μM) reduced the increased myocardial NOX activity after Ang II stimulation (Figure 4F). Delphinidin significantly blocked the increase in cell proliferation induced by Ang II, judging by the results of cell counting and CCK-8 assays (Supplementary Figure 2A, 2B). Moreover, the results of scratch wound and Transwell migration assays suggested that delphinidin administration abrogated the increased cell migration induced by Ang II stimulation (Supplementary Figure 2C, 2D). Furthermore, the administration of delphinidin dramatically suppressed Ang II-induced increases in the mRNA levels of the fibrotic markers collagen I, collagen III, and CTGF (Supplementary Figure 2E). In summary, all the above results showed that delphinidin protected against pathological cell growth, oxidative stress and activation in cardiomyocytes and cardiac fibroblasts induced by Ang II in vitro. Reference: Aging (Albany NY). 2020 Mar 31; 12(6): 5362–5383. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7138591/
In vivo activity: To determine the effect of delphinidin on cardiac hypertrophy in vivo, wild-type (WT) mice underwent TAC or sham operation; after 3 days, the mice were assigned to receive delphinidin or DMSO for 8 weeks. Delphinidin at the highest dosage used (15 mg/kg/day) significantly reversed TAC-induced cardiac hypertrophy, which manifested as decreased heart weight/body weight (HW/BW) and heart weight/tibia length (HW/TL) ratios (Figure 2A). In addition, the decreased left ventricular end-systolic dimension (LVESd) and left ventricular end-diastolic dimension (LVEDd) and increased left ventricular ejection fraction (LVEF) and left ventricular shortening rate (LVFS) compared with those of the sham surgery group further confirmed the effect of delphinidin at the high dosage on cardiac function (Figure 2B). Moreover, marked myocyte hypertrophy was observed at 8 weeks after surgery. Consistently, TAC increased myocardial mRNA expression of hypertrophic markers atrial natriuretic factor (Anp), brain natriuretic peptide (Bnp), and βmyosin heavy chain (β-MHC) in WT mice, but these changes were ameliorated by delphinidin treatment at the high dosage, but not by delphinidin at the low dosage (Figure 2F). These results suggested that treatment with delphinidin at the high dosage could inhibit pathological hypertrophy, oxidative stress, and cardiac dysfunction caused by pressure overload. Reference: Aging (Albany NY). 2020 Mar 31; 12(6): 5362–5383. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7138591/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 46.0 135.81

Preparing Stock Solutions

The following data is based on the product molecular weight 338.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Chen Y, Ge Z, Huang S, Zhou L, Zhai C, Chen Y, Hu Q, Cao W, Weng Y, Li Y. Delphinidin attenuates pathological cardiac hypertrophy via the AMPK/NOX/MAPK signaling pathway. Aging (Albany NY). 2020 Mar 25;12(6):5362-5383. doi: 10.18632/aging.102956. Epub 2020 Mar 25. PMID: 32209725; PMCID: PMC7138591. 2. Kang SH, Bak DH, Chung BY, Bai HW, Kang BS. Delphinidin enhances radio-therapeutic effects via autophagy induction and JNK/MAPK pathway activation in non-small cell lung cancer. Korean J Physiol Pharmacol. 2020 Sep 1;24(5):413-422. doi: 10.4196/kjpp.2020.24.5.413. PMID: 32830148; PMCID: PMC7445475. 3. Han B, Peng X, Cheng D, Zhu Y, Du J, Li J, Yu X. Delphinidin suppresses breast carcinogenesis through the HOTAIR/microRNA34a axis. Cancer Sci. 2019 Oct;110(10):3089-3097. doi: 10.1111/cas.14133. Epub 2019 Sep 16. PMID: 31325197; PMCID: PMC6778627
In vitro protocol: 1. Chen Y, Ge Z, Huang S, Zhou L, Zhai C, Chen Y, Hu Q, Cao W, Weng Y, Li Y. Delphinidin attenuates pathological cardiac hypertrophy via the AMPK/NOX/MAPK signaling pathway. Aging (Albany NY). 2020 Mar 25;12(6):5362-5383. doi: 10.18632/aging.102956. Epub 2020 Mar 25. PMID: 32209725; PMCID: PMC7138591. 2. Kang SH, Bak DH, Chung BY, Bai HW, Kang BS. Delphinidin enhances radio-therapeutic effects via autophagy induction and JNK/MAPK pathway activation in non-small cell lung cancer. Korean J Physiol Pharmacol. 2020 Sep 1;24(5):413-422. doi: 10.4196/kjpp.2020.24.5.413. PMID: 32830148; PMCID: PMC7445475.
In vivo protocol: 1. Chen Y, Ge Z, Huang S, Zhou L, Zhai C, Chen Y, Hu Q, Cao W, Weng Y, Li Y. Delphinidin attenuates pathological cardiac hypertrophy via the AMPK/NOX/MAPK signaling pathway. Aging (Albany NY). 2020 Mar 25;12(6):5362-5383. doi: 10.18632/aging.102956. Epub 2020 Mar 25. PMID: 32209725; PMCID: PMC7138591. 2. Han B, Peng X, Cheng D, Zhu Y, Du J, Li J, Yu X. Delphinidin suppresses breast carcinogenesis through the HOTAIR/microRNA34a axis. Cancer Sci. 2019 Oct;110(10):3089-3097. doi: 10.1111/cas.14133. Epub 2019 Sep 16. PMID: 31325197; PMCID: PMC6778627.

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1: Yoshino Y, Yuan B, Okusumi S, Aoyama R, Murota R, Kikuchi H, Takagi N, Toyoda
H. Enhanced cytotoxic effects of arsenite in combination with anthocyanidin
compound, delphinidin, against a human leukemia cell line, HL-60. Chem Biol
Interact. 2018 Aug 17;294:9-17. doi: 10.1016/j.cbi.2018.08.008. [Epub ahead of
print] PubMed PMID: 30125548.


2: Parra-Vargas M, Sandoval-Rodriguez A, Rodriguez-Echevarria R,
Dominguez-Rosales JA, Santos-Garcia A, Armendariz-Borunda J. Delphinidin
Ameliorates Hepatic Triglyceride Accumulation in Human HepG2 Cells, but Not in
Diet-Induced Obese Mice. Nutrients. 2018 Aug 10;10(8). pii: E1060. doi:
10.3390/nu10081060. PubMed PMID: 30103390.


3: Márquez-Rodríguez AS, Grajeda-Iglesias C, Sánchez-Bojorge NA,
Figueroa-Espinoza MC, Rodríguez-Valdez LM, Fuentes-Montero ME, Salas E.
Theoretical Characterization by Density Functional Theory (DFT) of Delphinidin
3-O-Sambubioside and Its Esters Obtained by Chemical Lipophilization. Molecules.
2018 Jun 29;23(7). pii: E1587. doi: 10.3390/molecules23071587. PubMed PMID:
29966272.


4: Daveri E, Cremonini E, Mastaloudis A, Hester SN, Wood SM, Waterhouse AL,
Anderson M, Fraga CG, Oteiza PI. Cyanidin and delphinidin modulate inflammation
and altered redox signaling improving insulin resistance in high fat-fed mice.
Redox Biol. 2018 Sep;18:16-24. doi: 10.1016/j.redox.2018.05.012. Epub 2018 May
30. PubMed PMID: 29890336; PubMed Central PMCID: PMC6035912.


5: Chen J, Zhu Y, Zhang W, Peng X, Zhou J, Li F, Han B, Liu X, Ou Y, Yu X.
Delphinidin induced protective autophagy via mTOR pathway suppression and AMPK
pathway activation in HER-2 positive breast cancer cells. BMC Cancer. 2018 Mar
27;18(1):342. doi: 10.1186/s12885-018-4231-y. PubMed PMID: 29587684; PubMed
Central PMCID: PMC5870693.


6: Kang HM, Park BS, Kang HK, Park HR, Yu SB, Kim IR. Delphinidin induces
apoptosis and inhibits epithelial-to-mesenchymal transition via the ERK/p38
MAPK-signaling pathway in human osteosarcoma cell lines. Environ Toxicol. 2018
Jun;33(6):640-649. doi: 10.1002/tox.22548. Epub 2018 Feb 16. PubMed PMID:
29451351; PubMed Central PMCID: PMC5969316.


7: Kim HM, Kim SH, Kang BS. Radioprotective effects of delphinidin on normal
human lung cells against proton beam exposure. Nutr Res Pract. 2018
Feb;12(1):41-46. doi: 10.4162/nrp.2018.12.1.41. Epub 2018 Jan 18. PubMed PMID:
29399295; PubMed Central PMCID: PMC5792255.


8: Casati L, Pagani F, Fibiani M, Lo Scalzo R, Sibilia V. Potential of
delphinidin-3-rutinoside extracted from Solanum melongena L. as promoter of
osteoblastic MC3T3-E1 function and antagonist of oxidative damage. Eur J Nutr.
2018 Jan 25. doi: 10.1007/s00394-018-1618-0. [Epub ahead of print] PubMed PMID:
29372310.


9: Lee DY, Park YJ, Hwang SC, Kim KD, Moon DK, Kim DH. Cytotoxic effects of
delphinidin in human osteosarcoma cells. Acta Orthop Traumatol Turc. 2018
Jan;52(1):58-64. doi: 10.1016/j.aott.2017.11.011. Epub 2017 Dec 28. PubMed PMID:
29290536.


10: Wang CH, Zhu LL, Ju KF, Liu JL, Li KP. Anti-inflammatory effect of
delphinidin on intramedullary spinal pressure in a spinal cord injury rat model.
Exp Ther Med. 2017 Dec;14(6):5583-5588. doi: 10.3892/etm.2017.5206. Epub 2017 Sep
27. PubMed PMID: 29285096; PubMed Central PMCID: PMC5740566.


11: Aichinger G, Puntscher H, Beisl J, Kütt ML, Warth B, Marko D. Delphinidin
protects colon carcinoma cells against the genotoxic effects of the mycotoxin
altertoxin II. Toxicol Lett. 2018 Mar 1;284:136-142. doi:
10.1016/j.toxlet.2017.12.002. Epub 2017 Dec 5. PubMed PMID: 29217480.


12: Lim WC, Kim H, Kim YJ, Park SH, Song JH, Lee KH, Lee IH, Lee YK, So KA, Choi
KC, Ko H. Delphinidin inhibits BDNF-induced migration and invasion in SKOV3
ovarian cancer cells. Bioorg Med Chem Lett. 2017 Dec 1;27(23):5337-5343. doi:
10.1016/j.bmcl.2017.09.024. Epub 2017 Sep 18. PubMed PMID: 29122484.


13: Goszcz K, Deakin SJ, Duthie GG, Stewart D, Megson IL. Bioavailable
Concentrations of Delphinidin and Its Metabolite, Gallic Acid, Induce Antioxidant
Protection Associated with Increased Intracellular Glutathione in Cultured
Endothelial Cells. Oxid Med Cell Longev. 2017;2017:9260701. doi:
10.1155/2017/9260701. Epub 2017 Sep 7. PubMed PMID: 29081896; PubMed Central
PMCID: PMC5610832.


14: Dayoub O, Le Lay S, Soleti R, Clere N, Hilairet G, Dubois S, Gagnadoux F,
Boursier J, Martínez MC, Andriantsitohaina R. Estrogen receptor α/HDAC/NFAT axis
for delphinidin effects on proliferation and differentiation of T lymphocytes
from patients with cardiovascular risks. Sci Rep. 2017 Aug 24;7(1):9378. doi:
10.1038/s41598-017-09933-4. PubMed PMID: 28839227; PubMed Central PMCID:
PMC5570903.


15: Tani T, Nishikawa S, Kato M, Tsuda T. Delphinidin 3-rutinoside-rich
blackcurrant extract ameliorates glucose tolerance by increasing the release of
glucagon-like peptide-1 secretion. Food Sci Nutr. 2017 Apr 7;5(4):929-933. doi:
10.1002/fsn3.478. eCollection 2017 Jul. PubMed PMID: 28748082; PubMed Central
PMCID: PMC5520870.


16: Vázquez-Calvo Á, Jiménez de Oya N, Martín-Acebes MA, Garcia-Moruno E, Saiz
JC. Antiviral Properties of the Natural Polyphenols Delphinidin and
Epigallocatechin Gallate against the Flaviviruses West Nile Virus, Zika Virus,
and Dengue Virus. Front Microbiol. 2017 Jul 11;8:1314. doi:
10.3389/fmicb.2017.01314. eCollection 2017. PubMed PMID: 28744282; PubMed Central
PMCID: PMC5504193.


17: Lim W, Song G. Inhibitory effects of delphinidin on the proliferation of
ovarian cancer cells via PI3K/AKT and ERK 1/2 MAPK signal transduction. Oncol
Lett. 2017 Jul;14(1):810-818. doi: 10.3892/ol.2017.6232. Epub 2017 May 23. PubMed
PMID: 28693237; PubMed Central PMCID: PMC5494655.


18: Hidalgo J, Teuber S, Morera FJ, Ojeda C, Flores CA, Hidalgo MA, Núñez L,
Villalobos C, Burgos RA. Delphinidin Reduces Glucose Uptake in Mice Jejunal
Tissue and Human Intestinal Cells Lines through FFA1/GPR40. Int J Mol Sci. 2017
Apr 5;18(4). pii: E750. doi: 10.3390/ijms18040750. PubMed PMID: 28379159; PubMed
Central PMCID: PMC5412335.


19: Chen J, Zhou J, Li F, Zhu Y, Zhang W, Yu X. [Delphinidin induces autophagy in
HER-2+ breast cancer cells via inhibition of AKT/mTOR pathway]. Zhong Nan Da Xue
Xue Bao Yi Xue Ban. 2017 Mar 28;42(3):264-270. doi:
10.11817/j.issn.1672-7347.2017.03.005. Chinese. PubMed PMID: 28364098.


20: Tatsuzawa F, Tanikawa N, Nakayama M. Red-purple flower color and
delphinidin-type pigments in the flowers of Pueraria lobata (Leguminosae).
Phytochemistry. 2017 May;137:52-56. doi: 10.1016/j.phytochem.2017.02.004. Epub
2017 Feb 9. PubMed PMID: 28189342.