Antiviral and Antifungal Activities of Some Naphthoquinones Isolated from the Roots of &lt;i&gt;Lithospermum erythrorhizon&lt;/i&gt;

重九, 李; 幸治, 福士; 潤, 川端; 哲士, 田原; 純也, 水谷; 一郎, 上田

doi:10.1584/jpestics.23.54

Cited by 9 publications

(8 citation statements)

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“…A minor shikonin derivative (9) was found between the peaks of isobutyrylshikonin (5) and b,b-dimethylacryloylshikonin (6) on the chromatogram (Fig. 2).…”

Section: Resultsmentioning

confidence: 97%

“…In the past, angeloylshikonin (10), a geometrical isomer of tigloylshikonin (9), was reported as a major pigment from the roots of Alkanna hirsutissima collected in northern Iraq. 19) As the optical isomer of 10, angeloylalkannin was also reported from the roots of Alkanna tinctoria, a common source of alkannin derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…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.…”

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confidence: 89%

“…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.…”

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confidence: 99%

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

Itô¹,

Onobori²,

Yamazaki³

et al. 2011

Chem. Pharm. Bull.

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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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“…A minor shikonin derivative (9) was found between the peaks of isobutyrylshikonin (5) and b,b-dimethylacryloylshikonin (6) on the chromatogram (Fig. 2).…”

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 89%

mentioning

confidence: 99%

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

Itô¹,

Onobori²,

Yamazaki³

et al. 2011

Chem. Pharm. Bull.

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“…Thus, shikonin exhibited a stable fungistatic effect to various cultures of Candida genus and one culture of Trichosporon genus [60]. Propionylshikonin and β-hydroxyisovalerylshikonin, isolated from the roots of Lithospermum erythrorhizon, showed both antifungal (Cladosporium herbarum) and antiviral (tobacco mosaic virus) activities [64]. Acetylshikonin and β-hydroxyisovalerylshikonin were biologically active against soil-born bacteria and fungi [65].…”

Section: Antimicrobial Effectsmentioning

confidence: 99%

Recent Advances in Chemistry, Biology and Biotechnology of Alkannins and Shikonins

Papageorgiou¹,

Assimopoulou²,

Samanidou³

et al. 2006

COC

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Isohexenylnaphthazarins (IHN), commonly known as Alkannins and Shikonins (A/S), are lipophilic red pigments. They are found in the outer surface of the roots of at least a hundred and fifty species that belong to the genera Alkanna, Lithospermum, Echium, Onosma, Anchusa and Cynoglossum of the Boraginaceae family. The chiral pairs A/S are potent pharmaceutical substances with a well-established and wide spectrum of wound healing, antimicrobial, antiinflammatory, antioxidant, anticancer and antithrombotic biological activity.For organic chemists uninitiated in the chemistry of quinones, the structures of alkannin (1) and shikonin (2) may look misleading simple. However, in spite of great efforts over many years by several research groups worldwide, a much needed viable synthetic route to these enantiomers has remained elusive until very recently.The value of A/S motivated biotechnologists to develop the world's first manufacturing process utilizing plant cell cultures. The research in this area has provided a wealth of knowledge to the field of biotechnology. In addition, great insights into the biosynthesis of these natural products and to our understanding of plant secondary metabolism in general, has been gained from this work.The last years there has been extensive scientific research in many areas throughout the disciplines of chemistry and biology and more specifically in cancer chemotherapy and a number of papers have appeared in the literature. Significant research has been conducted on A/S effectiveness on several tumors and on their mechanism of anticancer action. The aim of this paper was to review the recent advances in chemistry, biology, biotechnology and biosynthesis of alkannins and shikonins.

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Euchronin A–F isolated from the Arnebia euchroma (Royle) Johnst. and their anti-proliferative activities in vitro

Zhang,

Liu,

Zou

et al. 2023

J Nat Med

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Antiviral and Antifungal Activities of Some Naphthoquinones Isolated from the Roots of <i>Lithospermum erythrorhizon</i>

Cited by 9 publications

References 1 publication

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

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

Recent Advances in Chemistry, Biology and Biotechnology of Alkannins and Shikonins

Euchronin A–F isolated from the Arnebia euchroma (Royle) Johnst. and their anti-proliferative activities in vitro

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