High-performance liquid chromatography-diode array detector-mass selective detector analysis of major natural dyes with the application of H 2 O 2 /ultraviolet treatment as a way to simulate burial degradation of textiles

Abstract

H₂O₂/ultraviolet (UV) radiation treatment was proposed to simulate burial-induced degradation of natural dyes. The method was applied to the major pigments of Phellodendron bark, madder, and indigo plant, and their silk dyeings, and the degraded samples were analyzed using high-performance liquid chromatography-diode array detector-mass selective detector (HPLC-DAD-MS). Retention times of the HPLC chromatogram, UV-visible λ_max obtained from DAD analysis, and major ion detected by the MS analysis were used to identify berberine, palmatine, alizarin, purpurin, indigotin, and indirubin included in dye solution and the extraction from silk dyeing. Alizarin, purpurin, and indirubin were more susceptible to degradation by H₂O₂/UV than berberine and palmatine. Indigotin was completely degraded with 5 minutes of treatment, producing isatin as the degradation product. Alizarin, purpurin, and indigotin were more resistant to degradation when they were affixed to the fibers.

Keywords

madder indigo degradation high-performance liquid chromatography-diode array detector-mass selective detector

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References

Crews

. The fading rates of some natural dyes. Stud Conserv 1987; 32: 65–72.

Padfield

Landi

. The light fastness of the natural dyes. Stud Conserv 1966; 11: 181–196.

Ahn

Zeng

Obendorf

. Analysis of dye extracted from Phellodendron bark and its identification in archaeological textiles. Textil Res J 2012; 82: 1645–1658.

Janaway

Degradation of clothing and other dress materials associated with buried bodies of archaeological and forensic interest. In: Haglund

Sorg

(eds). Advances in forensic taphonomy: Method, theory, and archaeological perspective, Boca Raton, FL: CRC Press LLC, 2001, pp. 379–402.

Park

. Hwasung Kupori chultoboksik sogo. Hankookboksik 1996; 14: 49–98.

Needles

Cassman

Collins

Mordanted, natural-dyed wool and silk fabrics: light and burial-induced changes in the color and tensile properties. In: Needles

Zeronian

(eds). Historic textile and paper materials: Conservation and characterization. Advances in Chemistry Series 212, Washington, DC: American Chemical Society, 1986, pp. 199–210.

Peacock

. Biodegradation and characterization of water-degraded archaeological textiles created for conservation research. Int Biodeteriorat Biodegrad 1996; 38: 49–59.

Lee

Hong

Kim

. Effect of storage conditions on the color and the mechanical properties of fabrics dyed with natural dyes. J Korean Soc Cloth Textil 2001; 25: 617–628.

Turner

Important factors in the soil burial test applied to rotproofed textiles. In: Walters

Hueck-Van Der Plas

(eds). Biodeterioration of materials 1972; Vol 2, London: Applied Science Publications, pp. 218–226.

10.

Viraraghavan

. Fungal decolorization of dye wastewaters: a review. Bioresour Technol 2001; 79: 251–262.

11.

Swamy

Ramsay

. Effects of Mn²⁺ and NH₄⁺ concentrations on laccase and manganese peroxide production and Amaranth decolorization by Trametes versicolor. Appl Microbiol Biotechnol 1999; 51: 391–396.

12.

Martinez

Speranza

Ruiz-Duenas

. Biodegradation of linocellulosics: microbial, chemical, and enzymatic aspects of the fungal attack of lignin. Int Microbiol 2005; 8: 195–204.

13.

Estrada

AER

Royse

. Pleurotus eryngii and P. nebrodensis: from the wild to commercial production. (Specialty mushrooms). Mushroom News, Washington, DC: American Mushroom Institute, 1 February 2008.

14.

Sinsabaugh

Saiya-Cork

Long

. Soil microbial activity in a Liquidambar plantation unresponsive to CO₂-driven increases in primary production. Appl Soil Ecol 2003; 24: 263–271.

15.

Petigara

Blough

Mignerey

. Mechanism of hydrogen peroxide decomposition in soil. Environ Sci Technol 2002; 36: 639–645.

16.

Colonna

Caronna

Marcandalli

. Oxidative degradation of dyes by ultraviolet radiation in the presence of hydrogen peroxide. Dyes Pigments 1999; 41: 211–220.

17.

Ahn

Obendorf

. Dyes on archaeological textiles: analyzing alizarin and its degradation products. Textil Res J 2004; 74: 949–954.

18.

Ahn

Obendorf

. GC-MS analysis of curcumin dye after selective degradation treatment. Fibers Polym 2007; 8: 278–283.

19.

Szostek

Orska-Gawrys

Surowiec

. Investigation of natural dyes occurring in historical Coptic textiles by high-performance liquid chromatography with UV-vis and mass spectrometric detection. J Chromatogr A 2003; 1012: 179–192.

20.

Puchalska

Połec-Pawlak

Zadrozna

. Identification of indigoid dyes in natural organic pigments used in historical art objects by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry. J Mass Spectrom 2004; 39: 1441–1449.

21.

Zhang

Laursen

. Application of LC-MS to the analysis of dyes in objects of historical interest. Int J Mass Spectrom 2009; 284: 108–114.

22.

Petroviciu

Medvedovici

Albu

. LC-MS as analytical technique for the identification of natural dyes in historic textiles. Rom Rep Phys 2012; 64: 507–515.

23.

Kim

Wooriui saek jaihyunul wiehan jeontong yeomsaek. In: Korea Cultural Heritage Foundation (ed). The Korean traditional natural dyeing and crafts, Seoul: Korea Cultural heritage Foundation, 2005, pp. 85–120.

24.

Bingheogakissi. In: Chung YW (trans) Kyuhopchongseo. Seoul: Bojinjae, 1975, p.151.

25.

Schmeller

Latz-Bruning

Wink

. Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defense against microorganisms and herbivores. Phytochemistry 1997; 44: 257–266.

26.

Grycová

Dostál

Marek

. Quaternary protoberberine alkaloids. Phytochemistry 2007; 68: 150–175.

27.

Kumar

Chandel

Kumar

. Amelioration of oxidative stress by anthraquinones in various in vitro assays. Asian Pacific J Tropical Dis 2012; 2012: S692–S698.

28.

Samanta

Konar

Dyeing of textiles with natural dyes. In: Kumbasar

(ed). Natural dyes (2011). InTech, http://www.intechopen.com/books/natural-dyes/dyeing-of-textiles-with-natural-dyes.

29.

Kokubun

Edmonds

John

. Indoxyl derivatives in woad in relation to medieval indigo production. Phytochemistry 1998; 49: 79–87.

30.

Cooksey

. Indigo: an annotated bibliography. Biotech Histochem 2007; 82: 105–125.

31.

Lee

Eom

. Narrowbore high performance liquid chromatography of berberine and palmatine in crude drugs and pharmaceuticals with ion-pair extraction using cobalt thiocyanate reagent. J Pharm Biomed Anal 1999; 21: 59–63.

32.

Sze

SCW

. Quality assessment of Cortex Phellodendri by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry. Biomed Chromatogr 2010; 24: 438–453.

33.

Liu

Chen

. Effects of ultrahigh pressure extraction conditions on yields of berberine and palmatine from cortex Phellodendri amurensis. Anal Methods. Epub ahead of print 2013. DOI: 10.1039/c3ay40784e.

34.

Bányai

Kuzovkina

Kursinszki

. HPLC analysis of alizarin and purpurin produced by Rubia tinctorum L. hairy root cultures. Chromatographia 2006; 63(Supplement): S111–S114.

35.

Boldizsár

Szűcs

Füzfai

. Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography. J Chromatogr A 2006; 1133: 259–274.

36.

Derken

GCH

Lelyweld

van Beek

. Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars. Phytochem Anal 2004; 15: 397–406.

37.

Maugard

Enaud

Choisy

. Identification of an indigo precursor from leaves of Isatis tinctoria (Woad). Phytochemistry 2001; 58: 897–904.

38.

Zou

Koh

. Determination of indican, isatin, indirubin and indigotin in Isatis indigotica by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 2007; 21: 1239–1246.

39.

Ahn

Zeng

Obendorf

. Simultaneous analysis of the coloring compounds in indigo, Phellodendron bark, and madder dye using HPLC-DAD-MS. J Korean Soc Clothing Textil 2013; 37: 827–836.

40.

Ren

Xue

Zhang

. High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs. J Separ Sci 2007; 30: 833–842.

41.

Wyplosz

. Laser desorption mass spectrometric studies of artist's organic pigments. PhD Thesis , FOM Institute for Atomic and Molecular Physics: Amsterdam, the Netherlands, 2003.

42.

Sousa

Miguel

Rorigues

. A photochemical study on the blue dye indigo from solution to ancient Andean textiles. Photochem Photobiol Sci 2008; 7: 1353–1359.

43.

Sadek

. The HPLC solvent guide, 2nd ed. New York: Wiley-Interscience, 2002.

44.

Zucca

Vinci

Sollai

. Degradation of Alizarin Red S under mild experimental conditions by immobilized 5,10,15,20-tetrakis(4-sulfonatophenyl) porphine–Mn(III) as a biomimetic peroxidase-like catalyst. J Mol Catal A Chem 2008; 288: 97–102.

45.

Novotná

Boon

van der Horst

. Photodegradation of indigo in dichloromethane solution. Color Technol 2003; 119: 12–127.

46.

Iuga

Ortíz

Alvarez-Idaboy

. Molecular description of indigo oxidation mechanisms initiated by OH and OOH radicals. J Phys Chem A 2012; 116: 3643–3651.

47.

Khan

Ahmad

Khan

. Antimicrobial activity of wool yarn dyed with Rheum emodi L. (Indian Rhubarb). Dyes Pigments 2012; 95: 206–214.

48.

Giles

Mckay

. The lightfastness of dyes: a review. Textil Res J 1963; 33: 528–577.

49.

Poulin

. Identification of indigo and its degradation products on a silk textile fragment using gas chromatography-mass spectrometry. J Can Assoc Conserv 2007; 32: 48–56.