Antiviral and antifungal activities of some naphthoquinones isolated from the roots of Lithospermum erythrorhizon
The roots of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) contain shikonin and its esters as purple pigments. From ancient times, these pigments have been well known to have anti-inflammatory, super(1)) antibacterial super(2,3)) and anti-tumor promoting activities. super(4)) During the s...
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| Published in | Journal of Pesticide Science Vol. 23; no. 1; pp. 54 - 57 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
Pesticide Science Society of Japan
01.01.1998
Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0385-1559 1348-589X 1349-0923 |
| DOI | 10.1584/jpestics.23.54 |
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| Abstract | The roots of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) contain shikonin and its esters as purple pigments. From ancient times, these pigments have been well known to have anti-inflammatory, super(1)) antibacterial super(2,3)) and anti-tumor promoting activities. super(4)) During the screening tests checking antiviral and antifungal activities of natural products from medicinal plants, we have found these pigments with antiviral and antifungal activities. Nine kinds of compounds, (1) deoxyshikonin, (2) isovalerylshikonin, (3) alpha -methylbutyrylshikonin, (4) beta , beta -dimethylacrylylshikonin, (5) isobutyrylshikonin, (6) propionylshikonin, (7) acetylshikonin, (8) shikonin, and (9) beta -hydroxyisovalerylshikonin were isolated and identified. All isolated compounds were tested for antiviral and antifungal activities. |
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| AbstractList | The roots of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) contain shikonin and its esters as purple pigments. From ancient times, these pigments have been well known to have anti-inflammatory, super(1)) antibacterial super(2,3)) and anti-tumor promoting activities. super(4)) During the screening tests checking antiviral and antifungal activities of natural products from medicinal plants, we have found these pigments with antiviral and antifungal activities. Nine kinds of compounds, (1) deoxyshikonin, (2) isovalerylshikonin, (3) alpha -methylbutyrylshikonin, (4) beta , beta -dimethylacrylylshikonin, (5) isobutyrylshikonin, (6) propionylshikonin, (7) acetylshikonin, (8) shikonin, and (9) beta -hydroxyisovalerylshikonin were isolated and identified. All isolated compounds were tested for antiviral and antifungal activities. |
| Author | Mizutani, J Uyeda, I Fukushi, Y Kawabata, J Li, C. (Hokkaido Univ., Sapporo (Japan)) Tahara, S |
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| Keywords | Plant pathogen Tobamovirus Lithospermum erythrorhizon Biochemistry Pesticide crop Nicotiana tabacum Screening test Medicinal plant Fungi Antifungal agent Cladosporium herbarum Tobacco mosaic virus Dicotyledones Angiospermae Botany Antiviral Aromatic compound Fungi Imperfecti Solanaceae Phytopharmacology Thallophyta Biochemical analysis Bioassay Root Mycology Naphthoquinone derivatives Boraginaceae Biological activity Virology Virus Biological compound Test plant Plant origin Spermatophyta |
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| References | 14) B. -Z. Ahn, K. -U. Baik, G. -R. Kweon, K. Lim & B. -D. Hwang: J. Med. Chem. 38, 1044 (1995 7) E. Shikata, T. Senboku, M. Kojima & T. Yoshizaki: Memoirs Fac. Agric. Hokkaido Univ. 10 (1), 76 (1976) (in Japanese 12) S. A. Fedoreyev, V. A. Denisenko, N. I. Kulesh, N. P. Krasovskaya, M. M. Kozyrenko, V. P. Bulgakov & Yu. N. Zhuravlev: Khim. -Farm. Zh. 27 (6), 33 (1993); Chem. Abstr. 120, 240061k 16) H. Terada: “Structure-Activity Relationship and Drug Design,” ed. by T. Fujita, Kagaku Supplement 107, Kagaku Dojin, Kyoto, pp. 65-78, 1986 (in Japanese 8) A. L. Homans & A. Fuchs: J. Chromatogr. 51, 327 (1970 6) R. E. F. Matthews: “Plant Virology,” 3rd ed., Academic Press, Inc., San Diego, pp. 12-17, 1991 9) Y. Uesugi: “Methods in Pesticide Science,” ed. by J. Fukami, Y. Uesugi, K. Ishizuka & C. Tomizawa, Vol. 2 Fungicides, Soft Science, Inc., Tokyo, pp. 37-61, 1981 (in Japanese 15) T. Ishitoku, S. Isayama & H. Ono (Mitsui Petrochemical Industries): Jpn. Kokai Tokkyo Koho JP 61, 143, 334 (1986); Chem. Abstr. 105, 226090c 2) Y. Tanaka & T. Odani: Yakugaku Zasshi 92, 525 (1972) (in Japanese 11) S. Hisamichi & F. Yoshizaki: Shoyakugaku Zasshi 36, 154 (1982) (in Japanese 13) M. Afzal & G. Al-Oriquat: Agric. Biol. Chem. 50, 1651 (1986 1) H. Mitsuhashi (ed.): “Illustrated Medicinal Plants of the World in Colour,” Hokuryukan Co., Ltd., Tokyo, p. 435, 1988 (in Japanese 3) K. Kyogoku, H. Terayama, Y. Tachi, T. Suzuki & M. Komatsu: Shoyakugaku Zasshi 27, 31 (1973) (in Japanese 4) T. Konoshima, M. Kozuka, H. Tokuda & H. Tanabe: Yakugaku Zasshi 109, 843 (1989) (in Japanese 10) K. Kyogoku, H. Terayama, Y. Tachi, T. Suzuki & M. Komatsu: Shoyakugaku Zasshi 27, 24 (1973) (in Japanese 5) K. Tomaru: “Methods in Pesticide Science,” ed. by J. Fukami, Y. Uesugi, K. Ishizuka & C. Tomizawa, Vol. 2 Fungicides, Soft Science, Inc., Tokyo, pp. 83-117, 1981 (in Japanese |
| References_xml | – reference: 2) Y. Tanaka & T. Odani: Yakugaku Zasshi 92, 525 (1972) (in Japanese) – reference: 6) R. E. F. Matthews: “Plant Virology,” 3rd ed., Academic Press, Inc., San Diego, pp. 12-17, 1991 – reference: 4) T. Konoshima, M. Kozuka, H. Tokuda & H. Tanabe: Yakugaku Zasshi 109, 843 (1989) (in Japanese) – reference: 1) H. Mitsuhashi (ed.): “Illustrated Medicinal Plants of the World in Colour,” Hokuryukan Co., Ltd., Tokyo, p. 435, 1988 (in Japanese) – reference: 8) A. L. Homans & A. Fuchs: J. Chromatogr. 51, 327 (1970) – reference: 12) S. A. Fedoreyev, V. A. Denisenko, N. I. Kulesh, N. P. Krasovskaya, M. M. Kozyrenko, V. P. Bulgakov & Yu. N. Zhuravlev: Khim. -Farm. Zh. 27 (6), 33 (1993); Chem. Abstr. 120, 240061k – reference: 3) K. Kyogoku, H. Terayama, Y. Tachi, T. Suzuki & M. Komatsu: Shoyakugaku Zasshi 27, 31 (1973) (in Japanese) – reference: 16) H. Terada: “Structure-Activity Relationship and Drug Design,” ed. by T. Fujita, Kagaku Supplement 107, Kagaku Dojin, Kyoto, pp. 65-78, 1986 (in Japanese) – reference: 15) T. Ishitoku, S. Isayama & H. Ono (Mitsui Petrochemical Industries): Jpn. Kokai Tokkyo Koho JP 61, 143, 334 (1986); Chem. Abstr. 105, 226090c – reference: 5) K. Tomaru: “Methods in Pesticide Science,” ed. by J. Fukami, Y. Uesugi, K. Ishizuka & C. Tomizawa, Vol. 2 Fungicides, Soft Science, Inc., Tokyo, pp. 83-117, 1981 (in Japanese) – reference: 10) K. Kyogoku, H. Terayama, Y. Tachi, T. Suzuki & M. Komatsu: Shoyakugaku Zasshi 27, 24 (1973) (in Japanese) – reference: 9) Y. Uesugi: “Methods in Pesticide Science,” ed. by J. Fukami, Y. Uesugi, K. Ishizuka & C. Tomizawa, Vol. 2 Fungicides, Soft Science, Inc., Tokyo, pp. 37-61, 1981 (in Japanese) – reference: 7) E. Shikata, T. Senboku, M. Kojima & T. Yoshizaki: Memoirs Fac. Agric. Hokkaido Univ. 10 (1), 76 (1976) (in Japanese) – reference: 14) B. -Z. Ahn, K. -U. Baik, G. -R. Kweon, K. Lim & B. -D. Hwang: J. Med. Chem. 38, 1044 (1995) – reference: 13) M. Afzal & G. Al-Oriquat: Agric. Biol. Chem. 50, 1651 (1986) – reference: 11) S. Hisamichi & F. Yoshizaki: Shoyakugaku Zasshi 36, 154 (1982) (in Japanese) |
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| Snippet | The roots of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) contain shikonin and its esters as purple pigments. From ancient times, these pigments... |
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| SubjectTerms | ANTIFUNGAL PROPERTIES ANTIVIRAL ANTIVIRAL AGENTS AROMATIC COMPOUNDS Biological and medical sciences Chemical control CLADOSPORIUM COMPOSE AROMATIQUE COMPUESTOS AROMATICOS Control Fundamental and applied biological sciences. Psychology Fungal plant pathogens Generalities. Techniques. Transmission, epidemiology, ecology. Antiviral substances, control LITHOSPERMUM ERYTHRORHIZON Phytopathology. Animal pests. Plant and forest protection PIGMENT PIGMENTOS PIGMENTS Plant viruses and viroids PROPIEDADES ANTIMICOSICAS PROPRIETE ANTIFONGIQUE QUINONAS QUINONE QUINONES RACINE RAICES ROOTS TOBACCO MOSAIC TOBAMOVIRUS TOBAMOVIRUS DEL MOSAICO DEL TABACO TOBAMOVIRUS MOSAIQUE DU TABAC VIRICIDAS |
| Title | Antiviral and antifungal activities of some naphthoquinones isolated from the roots of Lithospermum erythrorhizon |
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