Studies On The Chemical Constituents Of Ranunculus Sieboldii And Ligularia Macrophylla

This dissertation mainly deals with the chemical constituents of two folk medicinal plants, Ranunculus sieboldii (Ranunculaceae) and Ligularia macrophylla (Compositae). From the above two plants, 45 compounds were isolated by repeated column chromatography and were identified by various spectroscopic methods. The thesis comprises of three chapters.Chapter 1 Chemical Constituents of Ranunculus sieboldiiRanunculus sieboldii belongs to the Ranunculaceae family. It is distributed widely in China and traditionally used in the treatment of various diseases such as jaundice, hepatitis, tuberculosis and sarcoma etc in local people. Pharmacologic tests revealed that the plant has antibacterial and antihistaminic activities. So far, little is known about its chemical constituents. In a search for its biologically active compounds, our phytochemical investigation on the title plant led to the characterization of ninteen compounds including four coumarins and glycosides (I -1 ~ I -4); seven flavones and flavonoid glycosides (I -9 ~ I -15); three phenolic acids (I -6 ~ I -8); one lactone (I -5); two glucoses (I -16,1 -17); together with #-sitosterol (I -18) and daucosterol (I -19).The compounds from R. sieboldii were listed as follows, and their structures were illustrated in Figure 1.1. Esculetin (I-1);2. Scopoletin (1-2);3. Scoparone (I -3);4. Scoplin (I -4);5. Ternatolide (I -5);6. Protocatechuic acid (I -6);7. Ferulic acid (I-7);8. Oxalic acid (I-8);9. Luteolin (I-9); l.0Tricin(I-l0);11. Tricin-7-O-D-glucopyranoside (I -11);12. Apigenin-8-C-D-galactopyranoside (I -12);13. Apigenin-8-C-L-arabinopyranoside (I -13);14. Apigenin-4'-O-L-rhamnopyranoside (I -14);15. Apigenin-7-O-D-glucopyranosyl-4'-O-L-rhamnopyranoside (I -15);16. D-glucopyranose (I -16);17. D-glucopyranose (I -17); 18.Sitosterol(I-18);19. Daucosterol (I -19).Except for compounds I -5 and I -18, the other seventeen compounds were obtained from this genus for the first time. Compound I -14 is a new natural product, and the 13C NMR data of compounds I -13 and I -15 were firstly concluded.Chapter 2 Phytochemical Investigation oiLigularia macrophyllaLigularia macrophylla mainly distributes in the Asian regions. Its roots and rhizomes are used for treatment of cough, tuberculosis, inflammation, ulcer and rheumatism in traditional Chinese medicine. In order to look for the active ingredients that are responsible for its pharmacological effects, 95% ethanolic extract of the roots and rhizomes of I. macrophylla was examined. And 26 compounds purified from this species were identified as follows, while their structures were illustrated in Figure 2.20. MachilinG(E-l);21. Calopeptin(II-2);22. Veraguensin (II -3);23. Eupomateniod-8 (II-4);24. DenudatinA(II-5);25. Hancinone (II-6);26. Fargesone A (II -7);27. Denudanolide A (II -8); 28.Burchellin(II-9);29. Cis-burchellin(II-10);30. Rel-(2S,3S,5S)-5-Allyl-5-methoxy-3-methyl-2-(3',4'-methylenedioxyphenyl)-2,3,5,6-tetrahydro-6-oxobenzofuran (11-11);31. Rel-(2S,3S,5R)-5-Allyl-5-methoxy-3-methyl-2-(3 ',4'-methylenedioxyphenyl)-2,3,5,6-tetrahydro-6-oxobenzofuran (11-12);32. Rel-(2R,3S,5R)-5-Allyl-5-methoxy-3-methyl-2-(3',4'-methylenedioxyphenyl) -2,3,5,6-tetrahydro-6-oxobenzofuran (II -13);33. Rel-(2S,3S,5R)-5-Allyl-5-methoxy-3-methyl-2-(3',4',5'-trimethoxyphenyl)-2,3,5,6-tetrahydro-6-oxobenzofuran (II -14);34. Rel-(2S,3S',5S)-5-Allyl-5-methoxy-3-methyl-2-(3',4',5'-trimethoxyphenyl)-2,3,5,6-tetrahydro-6-oxobenzofuran (11-15);35. (6S)-Menthiafolic acid (H-16);36. 6-Hydroxy-2,6-dimethyl-7-octenoic acid (11-17);37. Betulalbuside A (II -18);38. 2,6-Dimethyloct-7-en-l,6-diol-1-O-D-glucopyranoside (11-19);39. Quercetin(II-20);40. Rutin(n-21);41. Rhamnetin-3-O-D-rutinoside (11-22);42. Rhamnazin-3-O-D-rutinoside (11-23); 43.Afzelin(II-24); 44.Sitosterol(II-25);45. Daucosterol (II-26).Except for compounds II-20, II-21, II-25 and II-26, the other twenty-...