The DOI matches its Crossref record.
Isolation and extraction of ruberythric acid from Rubia tinctorum L. and crystal structure elucidation
Abstract
Madder (Rubia tinctorum L.) has been exploited as a dye throughout history. The roots of the plant are very rich in the highly coloured glycosidic compounds ruberythric acid and lucidin primeveroside, alongside the corresponding aglycons which can be readily formed by deglycosylation, particularly during extraction. Supported by (1)H and (13)C NMR data, the conclusive X-ray crystal structure of the natural dye ruberythric acid is presented for the first time. The solid state structure revealed extensive intermolecular hydrogen bonding interactions between the sugar moieties in the unit cell, but only intramolecular hydrogen bonding through the hydroxyquinone groups. There is also some additional π-π stacking from the anthraquinone moiety.
Overview
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
In the citing paper
“Nevertheless, a comparison of solvents such as ethanol and water for extraction of alizarin from madder root [112], revealed that ethanol was preferable since it gave a higher yield of glycosides.”
From Natural Quinone Dyes: A Review on Structure, Extraction Techniques, Analysis and Application Potential (2021) · cites this paper as [112]
In the citing paper
“The lower amount of glycoside in water possibly reflected hydrolysis of the glycosides due to the use of high extraction temperatures [112].”
From Natural Quinone Dyes: A Review on Structure, Extraction Techniques, Analysis and Application Potential (2021) · cites this paper as [112]
In the citing paper
“However, the alizarin glycoside-to-aglycone ratio was found to be 237:1 mg/cm 3 in ethanol and 22:1 mg/cm 3 in water.”
From Natural Quinone Dyes: A Review on Structure, Extraction Techniques, Analysis and Application Potential (2021) · cites this paper as [112]
Citations
Cites
No references could be resolved yet.
Research works printed but not linked: 14
- Baghalian, 2010, Genetic diversity of Iranian madder (Rubia tinctorum) populations based on agro-morphological traits, phytochemical content and RAPD markers, Ind. Crops Prod., 31, 557, 10.1016/j.indcrop.2010.02.012 · DOI
- Balakina, 2006, HPLC and molecular spectroscopic investigations of the red dye obtained from an ancient Pazyryk textile, Dyes Pigm., 71, 54, 10.1016/j.dyepig.2005.06.014 · DOI
- Desrochers, P., 2008. Bringing interregional linkages back. In: industrial symbiosis, international trade and the emergence of the synthetic dyes industry in the late 19th century Progress in Industrial Ecology – An International Journal 5, 465–481. · DOI
- Derksen, 1998, High-performance liquid chromatographic method for the analysis of anthraquinone glycosides and aglycones in madder root (Rubia tinctorum L.), J. Chromatogr. A, 816, 227, 10.1016/S0021-9673(98)00492-0 · DOI
- Derksen, 2002, Rubia tinctorum L, Vol. 26, 629
- Derksen, 2002, Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection, J. Chromatogr. A, 978, 119, 10.1016/S0021-9673(02)01412-7 · DOI · Paper page
- Derksen, 2003, Chemical and enzymatic hydrolysis of anthraquinone glycosides from madder roots, Phytochem. Anal., 14, 137, 10.1002/pca.694 · DOI
- Derksen, 2004, Two validated hplc methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars, Phytochem. Anal., 15, 397, 10.1002/pca.800 · DOI
- Drivas, 2011, Natural anthraquinonoid colorants as platform chemicals in the synthesis of sustainable disperse dyes for polyesters, Dyes Pigm., 88, 7, 10.1016/j.dyepig.2010.04.009 · DOI
- Henderson, 2013, Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation, Phytochemistry, 95, 105, 10.1016/j.phytochem.2013.07.001 · DOI
- Karapanagiotis, 2005, Identification of red natural dyes in post-byzantine icons by HPLC, J. Liq. Chromatogr. Related Technol., 28, 739, 10.1081/JLC-200048896 · DOI
- Lech, 2011, Novel methodology for the extraction and identification of natural dyestuffs in historical textiles by HPLC–UV–Vis–ESI MS. Case study: chasubles from the Wawel Cathedral collection, Anal. Bioanal. Chem., 399, 3241, 10.1007/s00216-010-4591-x · DOI
- Novotna, 1999, High-performance liquid chromatographic determination of some anthraquinone and naphthoquinone dyes occurring in historical textiles, J. Chromatogr. A, 235, 10.1016/S0021-9673(99)00980-2 · DOI
- Zhang, 2005, Development of mild extraction methods for the analysis of natural dyes in textiles of historical interest using LC–diode array detector–MS, J. Anal. Chem., 77, 2022, 10.1021/ac048380k · DOI
Cited by
Sorted by citations
Dulo, B., Phan, K., Githaiga, J., Raes, K., & De Meester, S. (2021) · Waste and Biomass Valorization · doi:10.1007/s12649-021-01443-9 · Cited by 181
“The lower amount of glycoside in water possibly reflected hydrolysis of the glycosides due to the use of high extraction temperatures [112].”
Background
Metadata
- Authors
- Ford, L., Rayner, C. M., & Blackburn, R. S.
- Affiliations
- University of Leeds (GB)
- Corresponding author
- Blackburn, Richard S.
- Venue
- Phytochemistry
- Publisher
- Elsevier BV
- Published
- 2015-09
- Volume
- 117
- Pages
- 168-173
- ISSN
- 0031-9422 (ISSN-L)
- OpenAlex
- W593826287
- Cited by
- 25
- References
- 0
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 1 · 2023: 3 · 2021: 5 · 2020: 5 · 2019: 2 · 2018: 1 · 2017: 3
- FWCI
- 1.61
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Phytochemistry (publishedVersion)
- PubMed (publishedVersion)
- White Rose Research Online (University of Leeds, The University of Sheffield, University of York) (acceptedVersion)
- Funders
- The Clothworkers’
- Topics
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and biological activity of medicinal plants
- Health Sciences › Medicine › Pathology and Forensic Medicine › Biological Stains and Phytochemicals
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Keywords
- Rubia tinctorum, madder, natural dyes, X-ray crystal structure, aglycone, deglycosylation, intermolecular hydrogen bonding, intramolecular hydrogen bonding, π-π stacking, anthraquinones, root extract
- MeSH terms
- Anthraquinones, Chromatography, High Pressure Liquid, Disaccharides, Coloring Agents, Molecular Conformation, Molecular Structure, Crystallography, X-Ray, Plant Roots, Nuclear Magnetic Resonance, Biomolecular, Rubia
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
