Skip to main content
Log in

Preparation and characterization of antioxidant flavonoid-enriched extract from saffron by-product: a combination of ultrasound-assisted extraction and macroporous resin purification

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

The stigma of saffron, a precious spice widely used in the world, takes only 7.4% (w/w) of the total weight of the flower, resulting in wasting the rest 92.6% of the flower. The utilization of the waste saffron floral bio-residues (SFB) has hence attracted people’s attention. In this paper, ultrasound-assisted extraction (UAE) associated with macroporous resin (MPR) purification step was successfully applied to enrich antioxidant flavonoid in SFB extract for the first time, resulting in significant increase in flavonoid content compared with other extraction method reported in literatures. The yield of the extract was up to 10%, and the content of kaempferol-3-O-sophoroside (KS) in the obtained extract was more than 50%, which was much higher than the total flavonoid content (2.05–19.2%) reported in other literatures. UAE procedure was optimized by studying the influence of parameters, e.g., extracting solvent, time, temperature and sample–solvent ratio, based on contents of KS and delphinidin-3,5-di-O-glucoside (DG) and the antioxidant activity of the extract. Further enrichment of flavonoid was achieved by D-101 MPR with optimum purification conditions. Furthermore, 52 flavonoids, 8 alkaloids and 10 polyols were identified or putatively characterized from the SFB extract using UPLC-MS, and the contents of KS and DG were determined to be 501.90 and 22.01 mg/g, respectively. Besides, the SFB flavonoid extract showed good antioxidant activities with IC50 33.79 μg/mL for DPPH scavenging effect and 39.65 μmol/mg trolox for ORAC values

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Ahmadian-Kouchaksaraie Z, Niazmand R, Najafi MN (2016) Optimization of the subcritical water extraction of phenolic antioxidants from Crocus sativus petals of saffron industry residues: Box-Behnken design and principal component analysis. Innov Food Sci Emerg Technol 36:234–244

    Article  CAS  Google Scholar 

  • Ardalan T, Ardalan P, Heravi MM (2012) Kinetic study of free radicals scavenging by saffron petal extract. J Chem Health Risks 2(4):29–36

    Google Scholar 

  • Bajbouj K, Schulze-Luehrmann J, Diermeier S, Amin A, Schneider-Stock R (2012) The anticancer effect of saffron in two p53 isogenic colorectal cancer celllines. BMC Complement Altern Med 12:69

    Article  Google Scholar 

  • Chen N, Yang B (2018) Research progress on chemical constituents and pharmacological effects of non-medicinal parts of saffron. Chin J Chin Materia Medica 14:2884–2891

    Google Scholar 

  • Cuyckens F, Claeys M (2005) Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of electrospray-generated deprotonated and sodiated molecules. J Mass Spectrom 40(3):364–372

    Article  CAS  Google Scholar 

  • Da Porto C, Natolino A (2018) Extraction kinetic modeling of total polyphenols and total anthocyanins from saffron floral bio-residues: comparison of extraction methods. Food Chem 258:137–143

    Article  Google Scholar 

  • Dai HQ, Chen CY, Yang B (2010) AAPH scavenging activities of 22 flavonoids and phenolic acids and 9 extract of Chinese materia medica. China J Chin Mater Med 35(17):2296–2302

    CAS  Google Scholar 

  • Esmaeili N, Ebrahimzadeh H, Abdi K, Safarian S (2011) Determination of some phenolic compounds in Crocus sativus L. corms and its antioxidant activities study. Pharmacogn Mag 7(25):74–80

    Article  CAS  Google Scholar 

  • Gao ZP, Yu ZF, Yue TL, Quek SY (2016) Optimization of polyphenols removal from kiwifruit juice using a macroporous resin. J Sci Food Agric 97(8):2498

    Article  Google Scholar 

  • Georgiadou G, Grivas V, Tarantilis PA, Pitsikas N (2014) Crocins, the active constituents of Crocus sativus L. counteracted ketamine-induced behavioural deficits in rats. Psychopharmacology 231(4):717–726 (Berl)

    Article  CAS  Google Scholar 

  • Guo D, Tong YP, Yang J, Wang P (2016) Optimization of mechanical chemical-assisted extraction of total flavonoids from saffron petals by response surface methodology. Chin Tradit Pat Med 38(8):1841–1844

    Google Scholar 

  • Hosseinzadeh H, Younesi HM (2002) Antinociceptive and anti-inflammatory effects of Crocus sativus L. stigma and petal extract in mice. Bmc Pharmacol 2:7

    Article  Google Scholar 

  • Huang YH (2013) Screening of antioxidant effective fraction from petals of Crocus sativus and its preventive effect on hyperlipidemia. In: Master degree thesis of East China Normal University.

  • Jafari SM, Khazaei KM, Assadpour E (2019) Production of a natural color through microwave-assisted extraction of saffron tepal’s anthocyanins. Food Sci Nutr 7:1438–1445

    Article  CAS  Google Scholar 

  • Keyume A, Zeper A, Shang XY, He JM, Zhang RP, Shi; J. G. (2006) Structural characterization of flavonol 3,7-di-O-glycosides and determination of the glycosylation position by using negative ion electrospray ionization tandem mass spectrometry. J Mass Spectrom 41(3):352–360

    Article  Google Scholar 

  • Khazaei KM, Jafari SM, Ghorbani M, Kakhki H, Sarfarazi M (2016) Optimization of anthocyanin extraction from saffron petals with response surface methodology. Food Anal Methods 9(7):1993–2001

    Article  Google Scholar 

  • Kim TH, Ku SK, Bae JS (2012) Inhibitory effects of kaempferol-3-O-sophoroside on HMGB1-mediated proinflammatory responses. Food Chem Toxicol 50:1118–1123

    Article  CAS  Google Scholar 

  • Lahmass I, Ouahhoud S, Elmansuri M, Sabouni A, Elyoubi M, Benabbas R (2018) Determination of antioxidant properties of six by-products of Crocus sativus L. (saffron) plant products. Waste Biomass Valor 9:1349–1357

    Article  CAS  Google Scholar 

  • Lakka A, Grigorakis S, Karageorgou I, Batra G, Kaltsa O, Bozinou E, Lalas S, Makris PD (2019) Saffron processing wastes as a bioresource of high-value added compounds: development of a green extraction process for polyphenol recovery using a natural deep eutectic solvent. Antioxidants 8:586

    Article  CAS  Google Scholar 

  • Li CY, Wu TS (2002) Constituents of the pollen of Crocus sativus L. and their tyrosinase inhibitory activity. Chem Pharm Bull 50(10):1305–1309

    Article  CAS  Google Scholar 

  • Liu JD, Chen N, Yang J, Yang B, Ouyang Z, Wu CX, Yuan Y, Wang WH, Chen M (2018) An integrated approach combining HPLC, GC/MS, NIRS, and chemometrics for the geographical discrimination and commercial categorization of saffron. Food Chem 253:284–292

    Article  CAS  Google Scholar 

  • Lotfi L, Kalbasiashtari A, Hamedi M, Ghorbani F (2015) Effects of enzymatic extraction on anthocyanins yield of saffron tepals (Crocus sativus) along with its color properties and structural stability. J Food Drug Anal 23(2):210

    Article  CAS  Google Scholar 

  • Morikawa T, Imura K, Miyake S, Ninomiya K, Matsuda H, Yamashita C, Muraoka O, Hayakawa T, Yoshikawa M (2012) Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells. J Nat Med 66:39–48

    Article  CAS  Google Scholar 

  • Nakamura S, Tanaka J, Imada T, Shimoda H, Tsubota K (2014) Delphinidin 3,5-O-diglucoside, a constituent of the maqui berry (Aristotelia chilensis) anthocyanin, restores tear secretion in a rat dry eye model. J Funct Foods 10:346–354

    Article  CAS  Google Scholar 

  • Omidi A, Totrabi Z (2016) The protective role of saffron petal extract on gentamicin-induced nephrotoxicity in rats. Vet Sci Dev 6:9–12

    CAS  Google Scholar 

  • Omidi A, Rahdari S, Fard MH (2014) A preliminary study on antioxidant activities of saffron petal extracts in lambs. Vet Sci Dev 4:5161–5164

    Article  Google Scholar 

  • Ongkowijoyo P, Luna-Vital DA, Elvira GDM (2018) Extraction techniques and analysis of anthocyanins from food sources by mass spectrometry: an update. Food Chem 250:113–126

    Article  CAS  Google Scholar 

  • Pitsikas N (2016) Constituents of saffron (Crocus sativus L.) as potential candidates for the treatment of anxiety disorders and schizophrenia. Molecules 21(3):303

    Article  Google Scholar 

  • Serrano-Díaz J, Sánchez AM, Alvarruiz A, Alonso GL (2013) Preservation of saffron floral bio-residues by hot air convection. Food Chem 141(2):1536–1543

    Article  Google Scholar 

  • Serrano-Díaz J, Sánchez AM, Martínez-Tomé M, Winterhalter P, Alonso GL (2014) Flavonoid determination in the quality control of floral bioresidues from Crocus sativus L. J Agric Food Chem 62:3125–3133

    Article  Google Scholar 

  • Sivamaruthi BS, Kesika P, Chaiyasut C (2020) The influence of supplementation of anthocyanins on obesity-associated comorbidities: a concise review. Foods 9(6):687

    Article  CAS  Google Scholar 

  • Swer TL, Chauhan K, Paul PK, Mukhim C (2016) Evaluation of enzyme treatment conditions on extraction of anthocyanins from Prunus nepalensis L. Int J Biol Macromol 92:867–871

    Article  CAS  Google Scholar 

  • Tuberoso CI, Rosa A, Montoro P, Fenu MA, Pizza C (2016) Antioxidant activity, cytotoxic activity and metabolic profiling of juices obtained from saffron (Crocus sativus L.) floral by-products. Food Chem 199:18–27

    Article  CAS  Google Scholar 

  • Tungmunnithum D, Drouet S, Kabra A, Hano C (2020) Enrichment in antioxidant flavonoids of stamen extracts from Nymphaea lotus L. using ultrasonic-assisted extraction and macroporous resin adsorption. Antioxidants 9:576

    Article  CAS  Google Scholar 

  • Wang XH, Wang JP (2019) Effective extraction with deep eutectic solvents and enrichment by macroporous adsorption resin of flavonoids from Carthamus tinctorius L. JPBA 176:112804

    CAS  Google Scholar 

  • Zhang XL, Li YT, Wang YX, Shi XK, Li FJ, Gui JQ (2010) Extraction and content determination of safflower polysaccharide. Chin J Exp Tradit Med Formul 16(7):19–21

    CAS  Google Scholar 

  • Zhang L, Wu TT, Xiao W, Wang Z, Ding G, Zhao L (2018) Enrichment and purification of total Ginkgo flavonoid O-glycosides from Ginkgo Biloba extract with macroporous resin and evaluation of anti-inflammation activities in vitro. Molecules 23(5):1167–1178

    Article  Google Scholar 

  • Zhao CG, Zhai WJ (2013) Extraction of total flavonoids and antioxidant activities of saffron petals. Food Res Dev 34(2):29–33 (Tianjin, China)

    Google Scholar 

  • Zheng CJ, Li L, Ma WH, Han T, Qin LP (2011) Chemical constituents and bioactivities of the liposoluble fraction from different medicinal parts of Crocus sativus. Pharm Biol 49(7):756–763

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors acknowledge Ms. Xue Zhang from Shanghai Traditional Chinese Medicine Co., Ltd. (Shanghai, China) who kindly provided the plant material for this experiment.

Funding

This research was funded by National Key R&D Program of China [Grant No. 2018YFC1706103] and Key Project at Central Government Level: The ability establishment of sustainable use for valuable Chinese medicine resources [Grant No. 2060302].

Author information

Authors and Affiliations

Authors

Contributions

BY conceived and designed the experiments ; NC, JX and YL performed the experiment; NC analyzed the data and wrote the paper. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Bin Yang.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chen, N., Xiang, J., Liu, Y. et al. Preparation and characterization of antioxidant flavonoid-enriched extract from saffron by-product: a combination of ultrasound-assisted extraction and macroporous resin purification. Chem. Pap. 75, 2749–2763 (2021). https://doi.org/10.1007/s11696-021-01522-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-021-01522-0

Keywords

Navigation