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Saponins from the Compositae Plants: Structures of the Saponins from Aster scaber Thunb

  • Tsuneatsu Nagao
  • Ryuichiro Tanaka
  • Hikaru Okabe
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 404)

Abstract

Many triterpene saponins have been isolated from plants belonging to a variety of families such as Leguminosae, Campanulaceae, Cucurbitaceae, and Araliaceae. Compositae, one of the largest families of the flowering plants, comprises more than 13,000 species, which make up more than 10% of all such plants. Nevertheless, very few plants of this family have been investigated as far as saponins are concerned.

Keywords

Methyl Ester Anomeric Proton Triterpene Saponin Methyl Glycoside Anomeric Proton Signal 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References and Notes

  1. 1. a)
    T. Nagao, S. Hachiyama, H. Okabe, and T. Yamauchi, Studies on the constituents of Aster tataricus L. f. H. structures of aster saponins isolated from the root, Chem. Pharm. Bull. 37, 1977 (1989);CrossRefGoogle Scholar
  2. b).
    T. Nagao, H. Okabe, and T. Yamauchi, Studies on the constituents of Aster tataricus L. f. III. structures of aster saponins E and F isolated from the root, Chem. Pharm. Bull. 38, 783 (1990);CrossRefGoogle Scholar
  3. c).
    R. Tanaka, T. Nagao, H. Okabe, and T. Yamauchi, Studies on the constituents of Aster tataricus L. f. IV. structures of aster saponins isolated from the herb, Chem. Pharm. Bull. 38, 1153 (1990).CrossRefGoogle Scholar
  4. 2. a)
    T. Nagao, R. Tanaka, and H. Okabe, Studies on the constituents of Aster scaber Thum. I. structures of scaberosides, oleanolic acid glycosides isolated from the root, Chem. Pharm. Bull. 39, 1699 (1991);CrossRefGoogle Scholar
  5. b).
    T. Nagao, R. Tanaka, H. Shimokawa, and H. Okabe, Studies on the constituents of Aster scaber T uNB. II. structures of echinocystic acid glycosides isolated from the root, Chem. Pharm. Bull. 39, 1719 (1991).CrossRefGoogle Scholar
  6. c).
    T. Nagao and H. Okabe, Studies on the constituents of Aster scaber T[-turr8. III. structures of scaberosides B7, B8 and B9, minor oleanolic acid glycosides isolated from the root, Chem. Pharm. Bull. 40, 886 (1992).PubMedCrossRefGoogle Scholar
  7. d).
    T. Nagao, R. Tanaka, Y. Iwase, and H. Okabe, Studies on the constituents of Aster scaber THuNB. IV. structures of four new echinocystic acid glycosides isolated from the herb, Chem. Pharm. Bull. 41, 659 (1993).PubMedCrossRefGoogle Scholar
  8. 3.
    The sugar species were determined by GC of the methanolysis product after trimethylsilylation. The absolute configurations of the component sugars were determined according to the method reported by Hara et al. 8 Thus, L-cysteine methyl ester and the hydrolysate of scaberoside Hcl methyl ester were heated in pyridine at 60° C for 1 hr, and the resulting mixture of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates was analyzed by GLC after trimethylsilylation. The absolute configuration of glucuronic acid was determined as D in the same way after conversion of scaberoside Hcl methyl ester to the corresponding glucoside by NaBH4 reduction of the carbomethoxyl group of the methyl glucuronopyranosyl group.Google Scholar
  9. 4.
    K. Ohtani, K. Mizutani, R. Kasai, and O.Tanaka, Selective cleavage of ester type glycoside-linkages and its application to structure determination of natural oligoglycosides, Tetrahedron Lett. 25, 4537 (1984).Google Scholar
  10. 5.
    M.-A. Dubois, R. Bauer, M. R. Cagiotti, and H. Wagner, Foetidissimoside A, a new 3,28bisdesmosidic triterpenoid saponin, and cucurbitacins from Cucurbita foe tidissima, Phytochemistry 27, 881 (1989).CrossRefGoogle Scholar
  11. 6.
    Identification of the methylated sugars were performed using the method established by Prof. K.Mihashi, Faculty of Pharmaceutical Sciences, Fukuoka University (unpublished), using standard samples prepared by his group. All standard samples were prepared according to the authorized method and identity was established by checking 1HNMR and 13C NMR spectra, and comparison of the physical data with those reported. The GC retention times and CI-MS spectra of the standard samples were measured in advance. Those of the samples were measured in the same conditions and compared with those of the standard samples. GC: glass column (3 mm i.d. x 1 m) packed with 2% OV17 on Uniport HP (80–100 mesh, GC-MS grade), carrier gas, He (20 ml/min); oven t emperature, 130–190° C (elevation rate 3° C/min). CI-MS: reactant gas, isobutane (1.0–1.5 x 10-5 Torr. in the ion source), ion source temperature, 270° C, ionization voltage, 150 eV, scan range, m/z 100400, scan interval, 4 sec.(instrument. Shimadzu Auto GC-MS 6020 equipped with GC-MS PAC 500 data analyzer).Google Scholar
  12. 7.
    K. Bock and C. Pedersen, A study of 13CH coupling constants in hexopyranoses, J. Chem. Soc., Perkin Trans. 2, 293 (1974).CrossRefGoogle Scholar
  13. 8.
    S. Hara, H. Okabe, and K. Mihashi, Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)carboxylates, Chem. Pharm. Bull. 35, 501 (1987).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1996

Authors and Affiliations

  • Tsuneatsu Nagao
    • 1
  • Ryuichiro Tanaka
    • 1
  • Hikaru Okabe
    • 1
  1. 1.Faculty of Pharmaceutical SciencesFukuoka UniversityJonan-ku Fukuoka 814-01Japan

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