Isolation and Structure of Woodorien, a New Glucoside Having Antiviral Activity, from Woodwardia orientalis
Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ab...
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| Published in | Chemical & pharmaceutical bulletin Vol. 41; no. 10; pp. 1803 - 1806 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
01.10.1993
公益社団法人日本薬学会 Maruzen Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2363 1347-5223 |
| DOI | 10.1248/cpb.41.1803 |
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| Abstract | Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtO Ac-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds. |
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| AbstractList | Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtOAc-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds. Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtOAc-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds.Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtOAc-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds. Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtO Ac-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds. Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1,and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtO Ac-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (^1H-^1H correlation spectroscopy (COSY), ^1H-^ C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds. |
| Author | KUROKAWA, Masahiko SHIRAKI, Kimiyasu NAMBA, Tsuneo MATSUMOTO, Takao XU, Hong-Xi KADOTA, Shigetoshi |
| Author_FL | KADOTA Shigetoshi MATSUMOTO Takao KUROKAWA Masahiko NAMBA Tsuneo SHIRAKI Kimiyasu XU Hong-Xi |
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| References | 1) Chiangsu New Medical College, "Dictionary of Chinese Crude Drugs," Shanghai Scientific and Technological Publishers, Shanghai, 1977, p. 1484. H. Hikino, T. Okuyama, C. Konno, T. Takemoto, Chem. Pharm. Bull., 23, 125 (1975). 9) Y. Kumano, M. Yamamoto, R. Mori, Antiviral Res., 7, 289 (1987). S. Ogawa, N. Nishimoto, N. Okamoto, T. Takemoto, Yakugaku Zasshi, 91, 916 (1971) 6) M. Hasegawa, J. Org. Chem., 24, 408 (1959 5) T. Takemoto, S. Ogawa, N. Nishimoto, Yakugaku Zasshi, 87, 1469 (1967 V.C. Shah, N.J. De Souza, Phytochemistry, 10, 1398 (1971) 7) Y. Yazaki, W.E. Hillis, Phytochemistry, 15, 1180 (1976 K. Fukuchi, H. Sakagami, T. Okuda, T. Hatano, S. Tanuma, K. Kitajima, Y. Inoue, S. Inoue, S. Ichikawa, M. Nonoyama, K. Konno, Antiviral Res., 11, 285 (1989) M. Baba, S. Shigeta, Antiviral Res., 7, 99 (1987) G.I. Nonaka, M. Minami, I. Nishioka, Chem. Pharm. Bull., 25, 2300 (1977). M. Ito, H. Nakashima, M. Baba, R. Pauwels, E. De Clercq, S. Shigeta, N. Yamamoto, Antiviral Res., 7, 127 (1987) 4) T. Takemoto, S. Arihara, Y. Hikino, H. Hikino, Tetrahedron Lett., 1968, 375 2) D.A. Van Den Berghe, M. leven, F. Mertens, A.J. Vlietinck, E. Lammens, Lloydia, 41, 463 (1978 R. Pompei, O. Flore, M.A. Marccialis, A. Pani, B. Loddo, Nature (London), 281, 689 (1979) 11) A. Bax, M.F. Summers, J. Am. Chem. Soc., 108, 2093 (1986 8) K. Shiraki, M. Ishibashi, T. Okuno, J. Namazue, K. Yamanishi, T. Sonoda, M. Takahashi, Arch. Virol., 117, 165 (1991). 3) K. Nakanishi, M. Koreeda, S. Sasaki, M.L. Chang, H.Y. Hsu, Chem. Comm., 1966, 915 10) K. Shiraki, F. Rapp, Intervirology, 29, 235 (1988). A. Bax, A. Aszalos, Z. Pinya, K. Sudo, J. Am. Chem. Soc., 108, 8056 (1986). H. Hikino, K. Mohri, Y. Hikino, S. Arihara, T. Takemoto, H. Mori, K. Shibata, Tetrahedron, 32, 3015 (1976). K. Weinges, Chem. Ber., 94, 3032 (1961) K.R. Markham, B. Ternal, Tetrahedron, 32, 2607 (1976). R. Aquino, F. De Simone, C. Pizza, C. Conti, M.L. Stein, J. Nat. Prod., 52, 679 (1989). W.B. John, A.L. Geoffrey, H.G.M. Murray, B.R. Graeme, Aust. J. Chem., 32, 779 (1979). |
| References_xml | – reference: M. Ito, H. Nakashima, M. Baba, R. Pauwels, E. De Clercq, S. Shigeta, N. Yamamoto, Antiviral Res., 7, 127 (1987) – reference: 8) K. Shiraki, M. Ishibashi, T. Okuno, J. Namazue, K. Yamanishi, T. Sonoda, M. Takahashi, Arch. Virol., 117, 165 (1991). – reference: R. Pompei, O. Flore, M.A. Marccialis, A. Pani, B. Loddo, Nature (London), 281, 689 (1979) – reference: 3) K. Nakanishi, M. Koreeda, S. Sasaki, M.L. Chang, H.Y. Hsu, Chem. Comm., 1966, 915 – reference: K.R. Markham, B. Ternal, Tetrahedron, 32, 2607 (1976). – reference: H. Hikino, K. Mohri, Y. Hikino, S. Arihara, T. Takemoto, H. Mori, K. Shibata, Tetrahedron, 32, 3015 (1976). – reference: M. Baba, S. Shigeta, Antiviral Res., 7, 99 (1987) – reference: 4) T. Takemoto, S. Arihara, Y. Hikino, H. Hikino, Tetrahedron Lett., 1968, 375 – reference: A. Bax, A. Aszalos, Z. Pinya, K. Sudo, J. Am. Chem. Soc., 108, 8056 (1986). – reference: 7) Y. Yazaki, W.E. Hillis, Phytochemistry, 15, 1180 (1976) – reference: K. Fukuchi, H. Sakagami, T. Okuda, T. Hatano, S. Tanuma, K. Kitajima, Y. Inoue, S. Inoue, S. Ichikawa, M. Nonoyama, K. Konno, Antiviral Res., 11, 285 (1989) – reference: R. Aquino, F. De Simone, C. Pizza, C. Conti, M.L. Stein, J. Nat. Prod., 52, 679 (1989). – reference: K. Weinges, Chem. Ber., 94, 3032 (1961) – reference: G.I. Nonaka, M. Minami, I. Nishioka, Chem. Pharm. Bull., 25, 2300 (1977). – reference: 10) K. Shiraki, F. Rapp, Intervirology, 29, 235 (1988). – reference: V.C. Shah, N.J. De Souza, Phytochemistry, 10, 1398 (1971) – reference: 11) A. Bax, M.F. Summers, J. Am. Chem. Soc., 108, 2093 (1986) – reference: 6) M. Hasegawa, J. Org. Chem., 24, 408 (1959) – reference: 2) D.A. Van Den Berghe, M. leven, F. Mertens, A.J. Vlietinck, E. Lammens, Lloydia, 41, 463 (1978) – reference: W.B. John, A.L. Geoffrey, H.G.M. Murray, B.R. Graeme, Aust. J. Chem., 32, 779 (1979). – reference: H. Hikino, T. Okuyama, C. Konno, T. Takemoto, Chem. Pharm. Bull., 23, 125 (1975). – reference: 5) T. Takemoto, S. Ogawa, N. Nishimoto, Yakugaku Zasshi, 87, 1469 (1967) – reference: S. Ogawa, N. Nishimoto, N. Okamoto, T. Takemoto, Yakugaku Zasshi, 91, 916 (1971) – reference: 1) Chiangsu New Medical College, "Dictionary of Chinese Crude Drugs," Shanghai Scientific and Technological Publishers, Shanghai, 1977, p. 1484. – reference: 9) Y. Kumano, M. Yamamoto, R. Mori, Antiviral Res., 7, 289 (1987). |
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| SubjectTerms | Animals antiviral activity Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology Biological and medical sciences General pharmacology Glucosides - chemistry Glucosides - isolation & purification Glucosides - pharmacology herpes simplex virus type 1 Herpesvirus 1, Human - drug effects Hydroxybenzoates - chemistry Hydroxybenzoates - isolation & purification Hydroxybenzoates - pharmacology Magnetic Resonance Spectroscopy Measles virus - drug effects Medical sciences Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants - chemistry Poliovirus - drug effects Vero Cells woodorien Woodwardia orientalis |
| Title | Isolation and Structure of Woodorien, a New Glucoside Having Antiviral Activity, from Woodwardia orientalis |
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