Water-soluble constituents of fennel. VII. Acyclic monoterpenoid glycosides

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 11, 1998, Pages 1748-1751

  Ishikawa, Toru ^a   Tanaka, Yasuko ^a   Kitajima, Junichi ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Acyclic monoterpenoid glycoside; Fennel; Foeniculum vulgate fruit; Linalyl oxide glycoside; Umbelliferae

Indexed keywords

3,7 DIMETHYLOCT 3(10) ENE 1,2,6,7 TETROL; GLYCOSIDE; LINALOOL; METHANOL; TERPENOID; UMBELLIFERONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; EXTRACTION; FENNEL; HERBAL MEDICINE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NONHUMAN; SOLUBILITY; STRUCTURE ANALYSIS;

EID: 0031760515     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1748     Document Type: Article

References (19)

1. Part VI: Ishikawa T., Kitajima J., Tanaka Y., Ono M., Ito Y., Nohara T., Chem. Pharm. Bull., 46, 1738-1742 (1998); Ono M., Ito Y., Ishikawa T., Kitajima J., Tanaka Y., Nohara T., Niiho, Y., ibid., 44, 337-342 (1996).
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3. Ishikawa T., Kitajima J., Tanaka Y., Chem. Pharm. Bull., 46, 1599-1602 (1998).
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5. Kitajima J., Tanaka Y., Chem. Pharm. Bull., 41, 1667-1669 (1993).
6. Tschesche R., Ciper F., Breitmaie E., Chem. Ber., 110, 3111-3117 (1977); Matsubara Y., Sawabe A., Iizuka Y., Okamoto K., J. Jpn. Oil. Chem. Soc., 37, 13-18 (1988).
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8. Kasai R., Suzuo M., Asakawa J., Tanaka O., Tetrahedron Lett., 1977, 175-178; Tori K., Seo S., Yoshimura Y., Arita H., Tomita Y., ibid., 1977, 179-182; Kasai R., Okihara M., Asakawa J., Mizutani K., Tanaka O., Tetrahedron, 35, 1427-1432 (1979); Mizutani K., Kasai R., Tanaka O., Carbohydr. Res., 87, 19-23 (1980).
9. Kasai R., Suzuo M., Asakawa J., Tanaka O., Tetrahedron Lett., 1977, 175-178; Tori K., Seo S., Yoshimura Y., Arita H., Tomita Y., ibid., 1977, 179-182; Kasai R., Okihara M., Asakawa J., Mizutani K., Tanaka O., Tetrahedron, 35, 1427-1432 (1979); Mizutani K., Kasai R., Tanaka O., Carbohydr. Res., 87, 19-23 (1980).
10. Kasai R., Suzuo M., Asakawa J., Tanaka O., Tetrahedron Lett., 1977, 175-178; Tori K., Seo S., Yoshimura Y., Arita H., Tomita Y., ibid., 1977, 179-182; Kasai R., Okihara M., Asakawa J., Mizutani K., Tanaka O., Tetrahedron, 35, 1427-1432 (1979); Mizutani K., Kasai R., Tanaka O., Carbohydr. Res., 87, 19-23 (1980).
11. Kasai R., Suzuo M., Asakawa J., Tanaka O., Tetrahedron Lett., 1977, 175-178; Tori K., Seo S., Yoshimura Y., Arita H., Tomita Y., ibid., 1977, 179-182; Kasai R., Okihara M., Asakawa J., Mizutani K., Tanaka O., Tetrahedron, 35, 1427-1432 (1979); Mizutani K., Kasai R., Tanaka O., Carbohydr. Res., 87, 19-23 (1980).
12. Compound 9 was isolated from the methanol extract of fruit of Cnidium monnieri CUSSON by us; Kitajima J., Aoki Y., Tanaka Yu., Ishikawa T., Tanaka Ya., 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, Abstracts of Papers part 2, p. 161 (1997).
13. Kitajima J., Ishikawa T., Tanaka Y., Chem. Pharm. Bull., 46, 1591-1594 (1998).
14. Linalyl oxide which has a trans relationship between the vinyl and 2-hydroxy isopropyl groups [(3R*,6R*)-form] is named trans-linaly oxide, while the compound having a cis relationship [(3R*,6S*)-form] is named cis-linalyl oxide; Felix D., Melera A., Seibl J., Kovats E., Helv. Chim. Acta, 46, 1513-1536 (1963); Rychnovsky S. D., Bartlett P. A., J. Am. Chem. Soc., 103, 3963-3964 (1981).
15. Linalyl oxide which has a trans relationship between the vinyl and 2-hydroxy isopropyl groups [(3R*,6R*)-form] is named trans-linaly oxide, while the compound having a cis relationship [(3R*,6S*)-form] is named cis-linalyl oxide; Felix D., Melera A., Seibl J., Kovats E., Helv. Chim. Acta, 46, 1513-1536 (1963); Rychnovsky S. D., Bartlett P. A., J. Am. Chem. Soc., 103, 3963-3964 (1981).
16. b) a) Naves Y. R., Alves H. M., Arndt V. H., Gottlieb O. R., Magalhaes M. T., Helv. Chim. Acta, 46, 1056-1059 (1963); b) Okazaki T., Ohsuka A., Kotake M., Nippon Kagaku Kaishi, 1973, 355-358; idem, ibid., 1973, 359-362.
17. b) a) Naves Y. R., Alves H. M., Arndt V. H., Gottlieb O. R., Magalhaes M. T., Helv. Chim. Acta, 46, 1056-1059 (1963); b) Okazaki T., Ohsuka A., Kotake M., Nippon Kagaku Kaishi, 1973, 355-358; idem, ibid., 1973, 359-362.
18. b) a) Naves Y. R., Alves H. M., Arndt V. H., Gottlieb O. R., Magalhaes M. T., Helv. Chim. Acta, 46, 1056-1059 (1963); b) Okazaki T., Ohsuka A., Kotake M., Nippon Kagaku Kaishi, 1973, 355-358; idem, ibid., 1973, 359-362.
19. Ishikawa T., Kitajima J., Tanaka Y., Chem. Pharm. Bull., 46, 1643-1646 (1998).