Identification of shikonin and its ester derivatives from the roots of Echium italicum L.

Albreht, Alen; Vovk, Irena; Simonovska, Breda; Srbinoska, Marija

doi:10.1016/j.chroma.2009.01.098

Cited by 45 publications

(40 citation statements)

References 36 publications

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“…10). The 13 C NMR spectral data obtained in this study is provided in Table 4 and coincided with previous reports (Albreht et al, 2009;Ito et al, 2011). The purity of the naphthoquinones (shikonin derivatives 1-5) was determined by the percentage of total peak area in HPLC and found to be of 98% purity (Fig.…”

Section: Groupsupporting

confidence: 88%

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In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma

Seetharaman

Park

et al. 2012

Journal of Ethnopharmacology

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Section: Groupsupporting

confidence: 88%

“…and 13 C-NMR results were in agreement with data provided in the literature(Albreht et al, 2009;Ito et al, 2011).Deoxyshikonin (2) Red purple solid. GC-MS (m/z): 272 [M þ -NMR and 13 C-NMR results were in agreement with data provided in the literature(Papageorgiou, 1979).b-Hydroxyisovalerylshikonin(3)Red purple solid.…”

supporting

confidence: 88%

In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma

Seetharaman

Park

et al. 2012

Journal of Ethnopharmacology

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“…20) However, there are no reports on the isolation and structural elucidation of 9 from any Boraginaceae plants, although HPLC analysis recently suggested the presence of 9 in addition to 10 in the roots of Echium italicum collected in Macedonia. 21) The root extract of L. erythrorhizon has been traditionally used as dye and crude drag in Japan, and the pigment constitution in it has been eagerly studied ever since Japanese scientists first purified shikonin (1) as its acetate (3) from the roots of L. erythrorhizon. 22) Therefore, the discovery of a new shikonin derivative was surprising and suggested the presence of unidentified minor pigments in the roots of this species.…”

Section: Resultsmentioning

confidence: 99%

Tigloylshikonin, a New Minor Shikonin Derivative, from the Roots and the Commercial Root Extract of Lithospermum erythrorhizon

Itô¹,

Onobori²,

Yamazaki³

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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NoteThe red pigments from the roots of Lithospermum erythrorhizon SIEBOLD et ZUCCARINI (Boraginaceae) have been used in Asia since ancient times as dyestuffs for fabrics, cosmetics, and food and as crude drugs for anti-inflammatory ointment.1) The pigments were naphthoquinone natural products, shikonin (1) 2) and its ester derivatives. In many previous studies, various shikonin derivatives, such as those of b-hy-6) isovalerylshikonin (7), 7) and a-methylbutyrylshikonin (8), 7) were reported from the roots of L. erythrorhizon (Fig. 1). Shikonin derivatives have several biological activities such as anti-inflammatory, 8) antiviral, 9) antibacterial, 7,10) antifungal, 9) and antitumor activities, 11) and recent studies showed that the level of these activities were affected by the structures of the derivatives.12) Therefore, the evaluation of various natural and synthetic shikonin analogues as new drug candidates has been eagerly reported. 1,8,[13][14][15] In our continuous study to secure safe for the natural food additives, the commercial root extract of L. erythrorhizon used as food colorant (Shikon color) was analyzed using liquid chromatography-electrospray ionization mass spectrometry (LC/ESI-MS). In addition to shikonin (1) and its ester derivatives (2-8), we found a new shikonin derivative, tigloylshikonin (9), as a minor pigment. Here we report for the first time the isolation and structural elucidation of 9 with mass spectrometry and NMR techniques. Results and DiscussionThe commercial root extract of L. erythrorhizon, "Shikon color," was diluted with MeOH and subjected to reversedphase LC/ESI-MS analysis. The chromatogram detected at 515 nm indicated some pigment peaks (Fig. 2), and the positive-mode ESI-MS analysis of each peak showed ion peaks at m/z 311, 411, 353, 367, 381, 393, and 395 as [MϩNa] ϩ , corresponding to shikonin (1), b-hydroxyisovalerylshikonin (2), acetylshikonin (3), propionylshikonin (4), isobutyrylshikonin (5), b,b-dimethylacryloylshikonin (6), and isovalerylshikonin (7) with a-methylbutyrylshikonin (8), respectively. Except for 7 and 8, each compound was purified with preparative HPLC and its structure was identified with NMR experiments. Because 7 and 8 could not be clearly separated on HPLC, both compounds were purified and their structures elucidated as a mixture.A minor shikonin derivative (9) was found between the peaks of isobutyrylshikonin (5) and b,b-dimethylacryloylshikonin (6) on the chromatogram (Fig. 2). The positive ESI-MS spectrum of 9 showed the ion peak at m/z 393 as [MϩNa] ϩ , which was the same as that of 6. Therefore, it was presumed that 9 was a structural isomer of 6 and a derivative esterified with tiglic acid ((E)-2-methylbut-2-enoic acid; cis form) or angelic acid ((Z)-2-methylbut-2-enoic acid; trans form) as a substitution of b,b-dimethylacrylic acid of 6. The 1 H-NMR spectrum of 9 recorded in CDCl 3 showed the set of resonances about shikonin (1) Additives, National Institute of Health Sciences; 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan. ...

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“…Alkannin is an isohexenylnaphthazarin derivative of hydroxynaphthoquinones and mostly present as ester derivatives in the outer surface of the roots of the Alkanna species and have been proven a broad spectrum of significant biological activities. The other applications were reported as dye for oleomargarine, sausage casings, as ink to mark food products [1], also in printing, industrial cosmetic and fabric fields [2].…”

Section: Introductionmentioning

confidence: 99%

Supercritical CO2 extraction of Alkanna species and investigating functional characteristics of alkannin-enriched yoghurt during storage

Pilavtepe

Erkucuk

Akgün

et al. 2012

Eur Food Res Technol

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Alkannin is a potent pharmaceutical substance with a wide spectrum of biological activities. In the scope of this study, supercritical CO 2 extraction and sonication with hexane were applied to various Alkanna species, which were then subjected to hydrolysis. Total alkannins were quantified by HPLC/DAD and incorporated into yoghurt. Viscosities, pH values and microbial analyses were reported at 7 days of intervals for 21 days of storage. A. tinctoria possessed the highest amounts of alkannins and total phenols (686.3 mg GAE/g extract). The results revealed no significant changes in pH values (4.1-4.0), viable counts of Streptococcus salivarius ssp. thermophilus (80-150 9 10 6 cfu g -1 ) and slightly lower viscosities of enriched yoghurts (8,250-6,750 cPs) compared with the control (4.15-4.0; 110-105 9 10 6 cfu g -1 ; 12,600-11,310 cPs) during storage. However, viable counts of Lactobacillus delbrueckii ssp. bulgaricus of enriched yoghurts (87 9 10 3 cfu g -1 ) were much better than the control (191 9 10 3 cfu g -1 ), indicating a significant decrease in post acidification and generation of bitter peptides. Among the species investigated, A. tinctoria is the most promising source, obtained at higher yields via supercritical fluid extraction technology as a green alternative to solvent extraction and thus can be utilized at industrial scale in order to develop yoghurt products with improved health benefits.

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Identification of shikonin and its ester derivatives from the roots of Echium italicum L.

Cited by 45 publications

References 36 publications

In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma

In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma

Tigloylshikonin, a New Minor Shikonin Derivative, from the Roots and the Commercial Root Extract of Lithospermum erythrorhizon

Supercritical CO2 extraction of Alkanna species and investigating functional characteristics of alkannin-enriched yoghurt during storage

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