I= STUDIES ON THE CHEMICAL CONSTITUENTS OF THE FRUIT OF GUAIACUM OFFICINALE LINN. AND SOME MARINE ORGANISMS
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Title of Thesis
STUDIES ON THE CHEMICAL CONSTITUENTS OF THE FRUIT OF GUAIACUM OFFICINALE LINN. AND SOME MARINE ORGANISMS
Author(s)
Shafi Uddin
Institute/University/Department Details
University of Karachi
Session
1990
Subject
Chemistry
Number of Pages
177
Keywords (Extracted from title, table of contents and abstract of thesis)
saponins, guaiacum officinale linn, triterpenoid saponins, guaianin f(1), guaianin g(2), guaianin h(3), guaianin i(4), guaianin j(5), guaianin k(6), guaianin l(7), star fishes, halymenia porphyroides, endarachne binghamiae, astropecten indicus

Abstract
The present research work is carried out in two parts.

Part-I deals with the isolation and characterization of triterpenoid saponins from the fruit of Guaiacum efficinale Linn. (Zygophyllaceae). The column chromatography of biologically active n-butanolic extract of the fruit of G.officinale Linn. Yielded seven new triterpenoid saponins, guaianin F,G.H,I,J,K and L. All of these saponins were purified on HPLC and their structures were elucidated by the help of spectroscopic methods and chemical reactions as 3-0(aL-rhamnophyranosyl (1-3) a L-rhamnophyranosyl (1-2)a-L-arabinopyranosyl (3-1) B-D-glucopyranosyl)-30 norolean-12,20(29)-dien-28-oic acid 28-0 (B-D-glucopyranosyl (1-6) B-D-glucopyranosyl)ester (I), 3-0(a-L-rhamnopyranosyl(1-3) rhamnophranosyl (1-2) a-L arabinopyranosyl (3-1) B-D-glucopyranosly) oleanolic acid 28-0 (a-D-glucopyranosyl (1-6) B-D-glucopyranosly) easter (2) 3-0(a-L-rhamnopyranosyl (1-3) a-L-arabinopyranosyl) oleanolic acid (3) 3-0 (a-L-rhamnopyranosyl(1-2) a-L-rhamnopytranosyl(1-2) a-L-arabinopyranosyl(1-3)B-D-glucuronopyransosyl)oleanolic acid-28-0 (B-D-glucopyranosyl(1-6) B-D-glucopyranosyl) ester (4), 3-0 –(a-L-arabinopyranosyl (1-3) B-D-glucuronopyranosyl) oleanolic acid 28-0-(a-L-rhamnopyranosyl (1-2) a-L-rhamnopyranosyl (1-4)B-D-glucopyranosyl (1-6) B-D-glucopyranosyl) easter (5), 3-0 (B-D-glucuronopyranosyl) oleanolic acid 28-0 (a-L-rhamnopyranosyl (1-2) a-L-rhamnopyranosyl (1-2) a-L-arabinopyranosyl (3-1) B-D-glucopyranoslyl) (1-3) B-D-glucopyranosyl) ester (6) and 3-0 (B-D-glucopyranosyl (1-4) B-D-glucuronopyranosyl(3-1) a-L-arabinopyranosyl) oleanolic acid 28-0(a-L-rhamnopyranosyl (1-6) B-D-glucopyranosyl (1-6) B-D-glucopyranosyl)ester (7), respectively.

Part II deals with the isolation and characterization of the chemical constituents of following marine organisms.

a).Halymenia porphyroides (red alga) b).Endarachne binghamiae (brown alga) c).Astropecten indicus (star fish)

The column chromatography of ethyl acetate extract of H.porphyroides yielded a new N-acyl sphingosine, Halyminine (8) which was purified, after acetylation, on a silica gel column and the structure of 8 was determined by spectroscopic methods. The same column also afforded sterols and fatty acids, identified by spectral data as cholesterol (9), 7-oxo-cholesterol (10) methyl ester of hexadecanoic acid (11). Bexadecanoic acid (12) and hexadec 5-enic acid (13). The compounds 9 and 10 were purified on preparative TLC while the compounds 11-13 were obtained in pure form. All of these compounds have been isolated for the first time from the same source.

The column chromatography of ethyl acetate fraction of E. binghamiae (brown alga), yielded three known sterols, which were identified by means of spectroscopy as 24-methylene cholesterol (14), 24-methyl cholesta 5,25 dien 3B ol (15) and 24 hydroxy, 24,vinyl cholesterol (16). The compound 14 was purified on preparative TLC while the compounds 15 and 16 were purified on a silica gel column. The compounds 14-16 have not been reported from the same source, so far.

The column chromatography of chioroform sox-extract of A.indicus (star fish)afforded a crude sterol mixture, which was purified on HPLC. Thepurification led to the isolation of four known sterols, which were identified on the basis of spectral evidences as cholesta-7,22-dien 3B-ol (17) 24-methylene cholesta 7 en-3B-ol (18). 24-methyl cholesta 7-22-dien 3B-ol (19) and cholesta-7 en 3B-ol(20). All of these sterols have not been reported from the same source, so far
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S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents
109.23 KB
2 1 Part I Introduction 13
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  1.1 Biological Importance Of Saponins 14
  1.2 Medicinal Uses Of Saponins 18
  1.3 Structure Determination Of Triterpenoid Saponins 20
  1.4 Guaiacum Officinale Linn 43
  1.5 Biological Importance Of Guaiacum Officinale Linn. 44
  1.6 Reported Saponins From The Bark Of Guaiacum Officinate Linn 45
3 2 Present Work 56
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  2.1 Isolation And Structure Elucidation Of Guaianin F(1) 57
  2.2 Isolation And Structure Elucidation Of Guaianin G(2) 64
  2.3 Isolation And Structure Elucidation Of Guaianin H(3) 69
  2.4 Isolation And Structure Elucidation Of Guaianin I(4) 74
  2.5 Isolation And Structure Elucidation Of Guaianin J(5) 80
  2.6 Isolation And Structure Elucidation Of Guaianin K(6) 85
  2.7 Isolation And Structure Elucidation Of Guaianin L(7) 90
4 3 Experimental 95
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  3.1 General Instrumentation 95
  3.2 Extraction And Isolation Of Saponins 96
  Characterization Of Guaianin F(1) 98
  3.4 Characterization Of Guaianin G(2) 101
  3.5 Characterization Of Guaianin H(3) 103
  3.6 Characterization Of Guaianin I(4) 104
  3.7 Characterization Of Guaianin J(5) 108
  3.8 Characterization Of Guaianin K(6) 110
  3.9 Characterization Of Guaianin L(7) 112
5 4 Part II Introduction 126
103.12 KB
  4.1 Biological Importance Of Alga 126
  4.2 Biological Importance Of Star Fishes 128
  4.3 Biological Importance Of Some Pakistani Marine Organisms 129
  4.4 Halymenia Porphyroides 134
  4.5 Endarachne Binghamiae 134
  4.6 Astropecten Indicus 134
6 5 Present Work 136
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  5.1 Isolation And Structure Elucidation Of Halyminine (8) From Halymenia Porphyroides 138
  5.2 Isolation And Structure Elucidation Of Sterols From Halymenia Porphyroides 142
  5.3 Isolation And Structure Elucidation Of Fatty Acids From Halymenia Porphyroides 146
  5.4 Isolation And Structure Elucidation Of Sterols From Endarachne Birghamiae 151
  5.5 Isolation And Structure Elucidation Of Sterols From Astropecten Indicus 156
7 6 Experimental 159
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  6.1 General Instrumentation 159
  6.2 Extraction Of Isolation 160
  6.3 Characterization Of Halyminine (8) From Halymenia Porphyroides 163
  6.4 Characterization Of Sterols From Halymenia Porphyroides 165
  6.5 Characterization Of Fatty Acids From Halymenia Porphyroides 167
  6.6 Characterization Of Sterois From Endarachne Binghamiae 169
  6.7 Characterization Of Sterols From 171
8 7 Literature Cited 173
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