Table 1.
Conditions required for extraction, isolation, and characterization of delphinidin and its glycosides.
| S. No. | Plant products containing Dp as the major anthocyanin | Method for extraction of anthocyanin | Analysis and characterization of anthocyanins | Concentration of Dp glycosides | References |
|---|---|---|---|---|---|
| 1 | Highbush blueberry (Vaccinium corymbosum L.) | Solvent aided extraction using acetone and acetic acid (99:1 v/v) and further ultrasound assisted sonification for 15 min |
HPLC conditions column: Zorbax SB-C18 column (50 × 4.6 mm, 5 μm) Flow rate: 0.4 mL/min Mobile phase A: 5% formic acid solution Mobile phase B: methanol Injection volume: 10 μL DAD wavelength: 190–600 nm ESI-MS |
Toro species Dp-3-Ga: 7.68 ± 1.42 mg/100 g Dp-3-A: 1.63 ± 0.09 mg/100 g Legacy species Dp-3-Ga: 11.44 ± 3.70 mg/100 g Dp-3-A: 4.07 ± 1.15 mg/100 g Duke species Dp-3-Ga: 14.99 ± 3.97 mg/100 g Dp-3-A: 5.10 ± 1.22 mg/100 g Bluecrop species Dp-3-Ga: 2.29 ± 0.21 mg/100 g Dp-3-G: 1.21 ± 0.10 mg/100 g Dp-3-A: 1.66 ± 0.10 mg/100 g |
(59) |
| 2 | Highbush blueberry (Vaccinium corymbosum L.) | Solvent assisted extraction with 87% v/v acetonitrile, 3% v/v water, 10% v/v formic acid from blueberry and its juice |
HPLC conditions column: Phenomenex Luna C-18, 100A (250 × 4.60 mm, 3μ) Column temperature: 25°C Flow rate: 0.5 mL/min Mobile phase A: 87% v/v acetonitrile, 3% v/v water, 10% v/v formic acid Mobile phase B: 50% v/v acetonitrile, 40% v/v water, 10% v/v formic acid DAD wavelength: 520 nm |
Blueberry from Uruguay Anthocyanins: 1,570 mg/100 g dry weight Dp-3-Ga: 298 mg/100 g Dp-3-G: 128 mg/100 g Dp-3-A: 142 mg/100 g Blueberry from Poland Anthocyanins: 2,242 mg/100 g Dp-3-Ga: 541 mg/100 g Dp-3-G: 11 mg/100 g Dp-3-A: 244 mg/100 g Blueberry from Germany Anthocyanins: 2,762 mg/100 g Dp-3-Ga: 543 mg/100 g Dp-3-G: 12 mg/100 g Dp-3-A: 250 mg/100 g |
(60) |
| 3 | Lowbush blueberry (Vaccinium angustifolium) | Solvent assisted extraction carried using acidified ethanol and then further extracted by solid phase extraction carried out using Circa, C-18 adsorbent (modified silica gel distribution of particles 40–63 um, organic load 0.38 mmol g−1, carbon load 9.16%) dispersed in 95% ethanol |
Preparative HPLC conditions column: XTerra Prep MS C-18 OBDTM (5 mm, 19 × 100 mm i.d., 5 μm) Column temperature: 25°C Flow rate: 2.0 mL/min Mobile phase A: 5% formic acid solution Mobile phase B: Methanol DAD wavelength: 520 nm |
Anthocyanin: 485 mg of cyanin equivalent Dp-3-Ga: 16 mg of cyanin equivalent Dp-3-G: 31 mg of cyanin equivalent Dp-3-Ar: 19 mg of cyanin equivalent Dp-3-(p-coumaroyl)-G: 5 mg of cyanin equivalent Dp-3-(6″-acetyl)-G: 20 mg of cyanin equivalent |
(61) |
| 4 | Lowbush blueberry (Vaccinium angustifolium) | Solid phase extraction using (SPE)-cartridge (Strata-X 300 mg/3 mL, Phenomenex) and elution was carried out using 0.01 N HCl (5 mL), ethyl acetate (10 mL), and acidified methanol (5 mL) with 0.1% HCl |
HPLC conditions column: C-18 Kinetex column (150 × 4.6 mm, 2.6 μm) Column temperature: 45°C Flow rate: 1.7 mL/min Mobile phase A: 1 % H3PO4 Mobile phase B: acetonitrile/water (35:65 v/v) DAD wavelength: 200–700 nm, Anthocyanin (520 nm) |
Anthocyanin: 29.9 ± 5.17 mg/mL Dp-3-G: 2.18 ± 0.7 mg/mL Dp-3-GA: 1.55 ± 0.15 mg/mL Dp-3-A: 0.75 ± 0.02 mg/mL |
(62) |
| 5 | Bilberry (Vaccinium myrtillus L.) | Solvent aided extraction using ethyl acetate and maceration with acidified methanol (0.6 M HCl) to extract anthocyanin |
HPLC conditions column: Zorbax SB-C-18 column (150 × 4.6 mm i.d., 5 um) Column temperature: 25°C Flow rate: 1.0 ml/min Injection volume: 5 ul |
Anthocyanins: 568.8 ± 8.8 mg/100 g fresh weight Dp-3-Ga: 92.1 ± 4.7 mg/100 g Dp-3-G: 86.6 ± 10.5 mg/100 g Dp-3-A: 59.1 ± 4.8 mg/100 g |
(63) |
|
Mobile phase A: water–formic acid (9:1 v/v) Mobile phase B: methanol-water-formic acid(5:4:1 v/v/v) DAD wavelength: 190–650 nm ESI+/MS & MS2 conditions |
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| 6 | Bilberry (Vaccinium myrtillus L.) | Solvent assisted extraction with 87% v/v acetonitrile, 3% v/v water, 10% v/v formic acid from blueberry and its juice |
HPLC conditions column: Phenomenex Luna C-18, 100A (250 × 4.60 mm, 3 μm) Column temperature: 25°C Flow rate: 0.5 mL/min Mobile phase A: 87% v/v acetonitrile, 3% v/v water, 10% v/v formic acid Mobile phase B: 50% v/v acetonitrile, 40% v/v water, 10% v/v formic acid DAD wavelength: 520 nm |
Bilberry from Poland (sample I) Anthocyanin: 6,102 mg/100g dry weight Dp-3-Ga: 847 mg/100 g Dp-3-G: 1,047 mg/100 g Dp-3-A: 603 mg/100 g Bilberry from Poland (sample II) Anthocyanin: 7,465 mg/100 g Dp-3-Ga: 1,060 mg/100 g Dp-3-G: 1,247 mg/100 g Dp-3-A: 741 mg/100 g |
(60) |
| 7 | Bilberry (Vaccinium myrtillus L.) | Extraction carried out using 60% ethanol acidified with HCl Purification by macroporous adsorbent (Amberlite XAD-7, XAD-4, AB-8, ADS-17, and DE- 5-40) |
HPLC conditions column: Venusil ASB C18 (250 × 4.6 mm, 5 μm) Column temperature: 30°C Flow rate: 1 mL/min Mobile phase A: anhydrous formic acid/water (8.5:91.5 v/v) Mobile phase B: anhydrous formic acid/acetonitrile/methanol/water (8.5:22.5:22.5:41.5 v/v/v/v) DAD wavelength: 535 nm |
ND | (64) |
| 8 | Blackcurrant (Ribes nigrum L.) | Solvent aided extraction using acetone and acetic acid (99:1 v/v) and further ultrasound assisted sonification for 15 min |
HPLC conditions column: Zorbax SB-C18 column (50 × 4.6 mm, 5 μm) Flow rate: 0.4 mL/min Mobile phase A: 5% formic acid solution Mobile phase B: methanol Injection volume: 10 μL Gradient conditions: 5% B (5 min), 5–50% B (45 min), 50–75% B (55 min), 75–100% B (65 min) DAD wavelength: 190–600 nm ESI+/-/MS3 conditions capillary voltage: 3,100 V Capillary temperature: 325°C Nebulizing gas (N2) pressure: 50 psi Nebulizing gas (N2) flow rate: 12 L/min Collision gas (He) voltage ramping cycle: 0.3–2 V |
Rosenthal species Anthocyanin: 180.44 ± 3.59 mg/100g Dp-3-G: 16.86 ± 4.07 mg/100g Dp-3-R: 89.66 ± 8.33 mg/100g Rovada species Anthocyanin: 162.83 ± 2.46 Dp-3-G: 13.92 ± 7.33 mg/100 g Dp-3-R: 65.27 ± 25.39 mg/100 g |
(59) |
| 9 | Blackcurrant (Ribes nigrum L.) pomace | Extraction with methanol:water:formic acid (50:48:2 v/v/v) |
HPLC conditions column: Gemini 5u C-18 110A column (150 × 4.6 mm i.d., 5 μm) Column temperature: 40°C Flow rate: 1 mL/min Injection volume: 20 μl Mobile phase A: 10% v/v formic acid solution Mobile phase B: acetonitrile:water:formic acid (50:40:10 v/v/v) DAD wavelength: 520 nm |
Anthocyanin content from two harvest seasons (2006–2007) fraction 0.8 Anthocyanin-344.6 ± 0.5–729.7 ± 4.4 mg/100 g Dp-3-G: 85.3 ± 1.2–190.9 ± 0.3 mg/100 g Dp-3-R: 122.2 ± 1.7–254.2 ± 3.4 mg/100 g Fraction 2–5 Anthocyanin: 577.1 ± 32.2–1,046.1 ± 10.4 mg/100 g Dp-3-G: 150.7 ± 8.6–288.5 ± 8.1 mg/100 g |
(65) |
| Dp-3-R: 213.9 ± 12.9–369.3 ± 2.6 mg/100 g Fraction 5 Anthocyanin: 513.7 ± 26.4–911.7 ± 13.1 mg/100g Dp-3-G: 133.1 ± 5.9–249.9 ± 7.6 Dp-3-R: 191.4 ± 13.2–320.2 ± 1.3 |
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| 10 | Blackcurrant (Ribes nigrum L.) pomace | Extraction with acidified water (0.01% v/v concentrated HCl) and purification with Amberlite XAD-7HP resin and elution with acidified ethanol (0.01% v/v conc. HCl). Further extraction with acidified water, isopropylacetate and ethyl acetate |
HPLC conditions column: Zorbax Eclipse XDB C18 (150 × 4.6 mm, 5 μm) Flow rate: 1 mL/min Injection volume: 10 μL Mobile phase A: water (0.5% TFA) Mobile phase B: acetonitrile (0.5% TFA) DAD wavelength: 190–600 nm and for anthocyanin-520 nm Preparative HPLC conditions column: XBridge Prep C18 (10 × 50, 5 μm) Flow rate: 5 mL/min Injection volume: 300 μL Rest conditions were similar to analytical HPLC |
Concentration of Dp-3-R (22.6%) was highest followed by Cy-3-R (20.4%), Dp-3-G (7.7%), Cy-3-G (4%) | (66) |
| 11 | Eggplant (Solanum melongena L) | Sadilova et al. reported the extraction from eggplant peel with aqueous acetone maintained at pH 1 i.e., water acidified with trifluoroacetic acid/acetone, 30:70, v/v Solvent assisted extraction employing methanol with 3% trifluoroacetic acid Dranca et al. reported the ultrasound assisted extraction from eggplant peel with frequency of 12.5, 25, and 37.5 KHz at temperature of 50, 60 and 70°C with extraction time of 15, 30, and 45 min and employing solvents methanol and 2-propanol |
HPLC conditions column: C18 sunfire column, Waters (250 × 4.6 mm, 5 μm) and a C18 pre-column, Phenomenex (4 × 3.0 mm i.d.) Column temperature: 25°C Flow rate: 1 mL/min Mobile phase A: 5% formic acid solution Mobile phase B: 100% acetonitrile DAD wavelength: 520 nm |
Dp-3-R: 378 ± 9.9 mg/kg Dp-3-G: 16.5 ± 1.0 mg/kg Dp-3-R-5G: 36.5 ± 0.8 mg/kg Dp-3-R-G: 19.1 ± 0.1 mg/kg. |
(67, 68) |
| 12 | Violet pepper (Capsicum annuum L.) peel | Extraction from voilet pepper peel with aqueous acetone maintained at pH 1 i.e., water acidified with trifluoroacetic acid/acetone, 30: 70, v/v Solvent assisted extraction employing methanol with 3% trifluoroacetic acid |
HPLC conditions column: C18 sunfire column, Waters (250 × 4.6 mm, 5 μm) and a C18 pre-column, Phenomenex (4 × 3.0 mm i.d.) Column temperature: 25°C Flow rate: 1 mL/min Mobile phase A: 5% formic acid solution Mobile phase B: 100% acetonitrile DAD wavelength: 520 nm Characterization was further done by ESI-MS |
Dp-3-R-5-G: 36.5 ± 0.8 mg/kg Dp-3-G: 2.2 ± 0.0 mg/kg Dp-3-R: 2.9 ± 0.2 mg/kg Dp-3-rhamnoside: 2.4 ± 0.5 mg/kg Dp-3-caffeoyl-rutinoside-5-G: 7.8 ± 0.4 mg/kg Dp-3-cis-coumaroyl-rutinoside-5-G: 14.7 ± 0.8 mg/kg Dp-3-trans-coumaroyl-rutinoside-5-G: 286.2 ± 1.7 mg/kg Dp-3-feruloyl-rutinoside-5-hexose: 3.8 ± 0.1 mg/kg |
(67) |
| 13 | Hibiscus sabdariffa (Roselle) | Solvent-aided extraction from Hibiscus sabdariffa dried calyces using distilled water as a solvent |
HPLC conditions column: Phenomenex Gemini C18 column (250 × 4.6 mm, 5 μm) Column temperature: 35°C Flow rate: 1 mL/min Injection volume: 10 μl Mobile phase A: 0.1% (v/v) trifluoroacetic acid Mobile phase B: trifluoroacetic acid/acetonitrile/water (50:49.9:0.1) DAD wavelength: 265–520 nm |
Dark red variety Anthocyanin: 2,732 ± 260 mg/100 g Dp-3-S: 2,116 ± 216 mg/100 g Dp-3-G: 76 ± 8 mg/100 g Light red variety Anthocyanin: 727 ± 55 mg/100 g Dp-3-S: 535 ± 37 mg/100 g Dp-3-G: 38 ± 1 mg/100 g |
(18) |