Studies on Non-sesquiterpenoid Constituents of Gaillardia pulchella. II. Less Lipophilic Substances, Methyl Caffeate as an Antitumor Catecholic
A less lipophilic non-sesquiterpenoid antitumor constituent, methyl caffeate, along with D-fructose, was isolated from the aqueous methanol extract of the dried whole plant of Gaillardia pulchella. Among forty-three synthetic catechol analogues related to methyl caffeate tested for antitumor activit...
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| Published in | Chem. Pharm. Bull Vol. 32; no. 3; pp. 1135 - 1141 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
1984
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.32.1135 |
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| Abstract | A less lipophilic non-sesquiterpenoid antitumor constituent, methyl caffeate, along with D-fructose, was isolated from the aqueous methanol extract of the dried whole plant of Gaillardia pulchella. Among forty-three synthetic catechol analogues related to methyl caffeate tested for antitumor activity against Sarcoma 180 in mice, acetates of methyl catecholylpropionoid type showed stronger activity than the corresponding catechuic acid and catechualdehyde derivatives as well as simple benzaldehyde (so-called vidrol). None of the catecholic and related compounds tested showed significant antimicrobial activity in vitro. |
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| AbstractList | A less lipophilic non-sesquiterpenoid antitumor constituent, methyl caffeate, along with D-fructose, was isolated from the aqueous methanol extract of the dried whole plant of Gaillardia pulchella. Among forty-three synthetic catechol analogues related to methyl caffeate tested for antitumor activity against Sarcoma 180 in mice, acetates of methyl catecholylpropionoid type showed stronger activity than the corresponding catechuic acid and catechualdehyde derivatives as well as simple benzaldehyde (so-called vidrol). None of the catecholic and related compounds tested showed significant antimicrobial activity in vitro. |
| Author | HARIMAYA, KENZO YOKOKURA, TERUO OHKURA, TAMIKO HORI, HITOSHI INAYAMA, SEIICHI KAWAMATA, TAKESHI HIKICHI, MANABU |
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| References | 5) a) W. Herz, K. Ueda and S. Inayama, Tetrahedron, 19, 483 (1963 b) S. Takeuchi, M. Kochi, K. Sakaguchi, K. Nakagawa and T. Mizutani, Agric. Biol. Chem., 42, 1449 (1978). b) S. Inayama, K. Harimaya, H. Hori, T. Kawamata, T. Ohkura, H. Nakamura and Y. litaka, Heterocycles, 19, 1801 (1982). 2) S. Inayama, T. Kawamata and M. Yanagita, Phytochemistry, 112, 1743 (1973). f) K. Aota, C. N. Caughlan, M. T. Emerson, W. Herz, S. Inayama and Mazhar-ul-Haque, J. Org. Chem., 35, 1448 (1970). 11) a) F. Bohlmann and K. H. Knal, Phytochemistry, 17, 319 (1978 b) F. Bohlmann and Le van Ngu, Phytochemistry., 17, 1173 (1978 3) W. Herz and S. Inayama, Tetrahedron, 20, 341 (1964 c) M. Yanagita, S. Inayama and T. Kawamata, Tetrahedron Lett., 1970, 131 T. Sekita., Acta Crystallogr., B27, 877 (1971) 1) S. Inayama, Chemical Studies on Constituents of Gaillardia pulchella, series 38. b) M. Yanagita, S. Inayama, T. Kawamata, T. Ohkura and W. Herz, Tetrahedron Lett., 1969, 2037, 4170 7) S. Inayama, T. Kawamata and T. Ohkura, Chem. Pharm. Bull., 23, 2998 (1975 8) S. Inayama, K. Harimaya, H. Hori, T. Kawamata, T. Ohkura, I. Miura and Y. litaka, Heterocycles, 20, 1501 (1983). 12) a) J. L. Hartwell, Lloydia, 33, 184 (1970 9) S. Inayama, K. Harimaya, T. Ohkura and T. Kawamata, Heterocycles, 17, 219 (1982). 6) a) M. Yanagita, S. Inayama and T. Kawamata, Tetrahedron Lett., 1970, 3007 10) S. Inayama, T. Ohkura, K. Harimaya and T. Kawamata, Shoyakugaku Zasshi, 36, 362 (1982). e) F. Bohlmann, C. Zdero, R. M. King and H. Robinson, Phytochemistry, 19, 2669 (1980). 4) T. A. Dullforce, G. A. Sim, D. N. White, J. E. Kelsey and S. M. Kupchan, Tetrahedron Lett., 1969, 973 and references loc. cit. d) H. Shimomura, Y. Sashida, Y. Ohshima, T. Azuma and M. Saito, Yakugaku Zasshi, 100, 1164 (1980 S. Inayama, Tetrahedron Lett., 1978, 1557. c) F. Bohlmann and C. Zdero, Phytochemistry., 18, 95 (1979 d) T. Kawamata and S. Inayama, Chem. Pharm. Bull., 19, 643 (1971 e) T. Sekita, S. Inayama and Y. litaka, Tetrahedron Lett., 1970, 135 H. Yoshioka, T. J. Mabry, N. Dennis and W. Herz, J. Org. Chem., 35, 627 (1970) and references cited therein. |
| References_xml | – reference: 7) S. Inayama, T. Kawamata and T. Ohkura, Chem. Pharm. Bull., 23, 2998 (1975); – reference: c) M. Yanagita, S. Inayama and T. Kawamata, Tetrahedron Lett., 1970, 131; – reference: 3) W. Herz and S. Inayama, Tetrahedron, 20, 341 (1964); – reference: b) F. Bohlmann and Le van Ngu, Phytochemistry., 17, 1173 (1978); – reference: S. Inayama, Tetrahedron Lett., 1978, 1557. – reference: 5) a) W. Herz, K. Ueda and S. Inayama, Tetrahedron, 19, 483 (1963); – reference: b) S. Inayama, K. Harimaya, H. Hori, T. Kawamata, T. Ohkura, H. Nakamura and Y. litaka, Heterocycles, 19, 1801 (1982). – reference: f) K. Aota, C. N. Caughlan, M. T. Emerson, W. Herz, S. Inayama and Mazhar-ul-Haque, J. Org. Chem., 35, 1448 (1970). – reference: 8) S. Inayama, K. Harimaya, H. Hori, T. Kawamata, T. Ohkura, I. Miura and Y. litaka, Heterocycles, 20, 1501 (1983). – reference: c) F. Bohlmann and C. Zdero, Phytochemistry., 18, 95 (1979); – reference: d) T. Kawamata and S. Inayama, Chem. Pharm. Bull., 19, 643 (1971); – reference: 11) a) F. Bohlmann and K. H. Knal, Phytochemistry, 17, 319 (1978); – reference: e) F. Bohlmann, C. Zdero, R. M. King and H. Robinson, Phytochemistry, 19, 2669 (1980). – reference: 2) S. Inayama, T. Kawamata and M. Yanagita, Phytochemistry, 112, 1743 (1973). – reference: d) H. Shimomura, Y. Sashida, Y. Ohshima, T. Azuma and M. Saito, Yakugaku Zasshi, 100, 1164 (1980); – reference: 9) S. Inayama, K. Harimaya, T. Ohkura and T. Kawamata, Heterocycles, 17, 219 (1982). – reference: 12) a) J. L. Hartwell, Lloydia, 33, 184 (1970); – reference: b) M. Yanagita, S. Inayama, T. Kawamata, T. Ohkura and W. Herz, Tetrahedron Lett., 1969, 2037, 4170; – reference: e) T. Sekita, S. Inayama and Y. litaka, Tetrahedron Lett., 1970, 135; – reference: 6) a) M. Yanagita, S. Inayama and T. Kawamata, Tetrahedron Lett., 1970, 3007; – reference: 4) T. A. Dullforce, G. A. Sim, D. N. White, J. E. Kelsey and S. M. Kupchan, Tetrahedron Lett., 1969, 973 and references loc. cit. – reference: 10) S. Inayama, T. Ohkura, K. Harimaya and T. Kawamata, Shoyakugaku Zasshi, 36, 362 (1982). – reference: T. Sekita., Acta Crystallogr., B27, 877 (1971); – reference: H. Yoshioka, T. J. Mabry, N. Dennis and W. Herz, J. Org. Chem., 35, 627 (1970) and references cited therein. – reference: 1) S. Inayama, Chemical Studies on Constituents of Gaillardia pulchella, series 38. – reference: b) S. Takeuchi, M. Kochi, K. Sakaguchi, K. Nakagawa and T. Mizutani, Agric. Biol. Chem., 42, 1449 (1978). |
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| SubjectTerms | Animals antimicrobial activity Antineoplastic Agents, Phytogenic - isolation & purification antitumor activity benzaldehyde Biological and medical sciences Caffeic Acids - isolation & purification Caffeic Acids - pharmacology catecholylpropionoid Chemical Phenomena Chemistry Cinnamates - isolation & purification Compositae Gaillardia pulchella General pharmacology Male Medical sciences methanol extraction methyl caffeate Mice Mice, Inbred ICR non-sesquiterpenoid Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - analysis synthetic catecholic |
| Title | Studies on Non-sesquiterpenoid Constituents of Gaillardia pulchella. II. Less Lipophilic Substances, Methyl Caffeate as an Antitumor Catecholic |
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