I= STUDIES ON BIOACTIVE CONSTITUENTS FROM SPHAERANTHUS INDICUS AND BERBERIS PARKERIANA
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Title of Thesis
STUDIES ON BIOACTIVE CONSTITUENTS FROM SPHAERANTHUS INDICUS AND BERBERIS PARKERIANA

Author(s)
Pir Muazzam Shah
Institute/University/Department Details
University of Karachi, Pakistan./Department of Education.
Session
1991
Subject
Education
Number of Pages
285.
Keywords (Extracted from title, table of contents and abstract of thesis)
sphaeranthus indicus, berberis parkeriana, terpenes, terpenoids, biosynthesis, sesquiterpenes, triterpenes, steroids, antimicrobial activity, immunestimulating activity

Abstract
The isolation and structure determination of those compounds are described here which are either new or which have been isolated for the first time from the plants (See below).

The thesis is divided into two parts. In the fist part is described investigation of the chemical constituents of the flowers of Sphaeranthus indicus (Compositae), which afforded four new sesquiterpenes one new sesquiterpene glycoside, one known sesquiterpese, and one known steroid.

The new compounds were identified as 11a, 13-dihydro-3a-(B-glucopyransoyl),7a-hydroxyfrullanolide (76) 11a, 13-dihydro-7a-hydroxy-13-methoxyfrullanolide (78), 7a-hydroxyeudesm-4-ene-6, 12-B-olide(79), 11a, 13-dihydro-7a-13-dihydroxyfrullnolide (80), 11a-13-dihydro-3a-7a-dihydroxyfrullanolide (81) while the known are caryophyllene-a-oxide (82) and 24S-stigmasta-5, 22E-diene-3B-ol (83).

The second part of the thesis described studies on these chemical constituents of the roots of Berberis paarkeriana (Berberidancae). These studies have led to the isolation and identification of twonew protoberberine bases i.e parkerine (159) and 8-formylprotoberine (162). In addition five more bases have been detected. They are oxyberberine (164). 8-trichloromethyldihydroprotoberberine (165 artifact), berbamine (166), 24R-stigmast-5-ene-3B-ol (167), berberin cation (168). In addition another (supposedly new) parotoberberine base of molecular weight 366.1391, molecular formula (c2H2cNO5) has been isolated. Its structure however remain to be elucidated the proposed structure is (163). For elucidation of structures modern spectroscopic techniques, including one and two-dimensional NMR studies such as COSY, long-rang hetero-COSY, HOHAHA, 2DJ-resolved, COLOC, INADEQUATE and GASPE experiments were carrid out. X-ray crystallographic studies were performed in the case of caryophyllene-a-oxide (82). Some of the newly isolated compounds have shown some interesting biological activity (see results and discussion). In addition to this we have also investigated the chemical constituent of ficus bangolansus, which resulted in epifriendinyl-3-ol (169).

Download Full Thesis
2126.09 KB
S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents
90.41 KB
2 1 General Introduction 4
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  1.0 Introduction Part A 10
  1.1 Terpenes And Terpenoids 11
  1.2 Biosynthesis 17
  1.3 Sesquiterpenes 17
  1.4 Triterpenes And Steroids 24
3 2 Pharmacological Importance 31
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  2.1 Sesquiterpenes And Sesquiterpenoids 32
  2.2 Triterpenes And Triterpenoids 37
  2.3 Few Plants Of Family Compositae In Daily Life 40
  2.4 Medicinal Important Of Sphaeranthus Indicus 42
4 3 Results And Discussion 45
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  3.1 Studies On The Chemical Constituents Sphaeranthus Indicus 48
  3.2 Antimicrobial Activity Of Sphaeranthus Indicus 49
  3.3 Brine Shrimp Leathality Test 49
  3.4 New Terpenoids And Glycosides From The Flowers Of Sphaeranthus Indicus 52
  3.5 11a-13-Dihyro-3a-(B-Glycopyranosyl), 7a-Dihydroxyfrullanolide (76) And Its Aglycone(77) 52
  3.6 Immunestimulating Activity Of (76) 52
  3.7 Determinationof LD50 Value Of (76) In Mice 52
  3.8 Brine Shrimpsleathality Assay Of (76) 52
  3.9 11a-13-Dihydro-7a-Hydroxy-13-Methoxyfrullanolide (78) 76 An Anticancer, Antifgal And Antimicrobial 7a-Hydroxyenudesm-4-En-6, 12-B-Olide (79) 86
  3.10 Antifungal Activity Of (79) 93
  3.11 Antineoplastic Activity Of (79) 94
  3.12 Antimicrobial Activity Of (79) 95
  3.13 Brine Shrimp Lethality Bioassay Of (79) 96
  3.14 11a-13-Dihydro-7a-13-Dihydroxyfrullanolide (80) 102
  3.15 11a-13-Dihydro-3a-7a-Dihydroxyfrullanolide (81) 113
  3.16 Known Compound Detected For The First Time From Sphaeranthus Indicus 115
  3.17 Caryophyllene-A-Oxide (82) 115
  3.18 X-Ray Structure Of (82) 118
  3.19 24S-Stigmasta-5a,22E-Dien-3-Ol(83) 126
5 4 Introduction Part (B) 133
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  4.1 Isoquinoline Alkaloids 134
  4.2 Biogenesis And Biosynthesis 135
  4.3 Biogenesis Of Simple Isoquinoline Alkaloids 135
  4.4 Biogenesis Of Benzylisoquinoline Alkaloids 141
  4.5 Biogenesis Of Protobvercerine Alkaloids 144
  4.6 Biogenesis Of Bisbenzylisoquinoline Alkaloids 149
6 5 Pharmacological Importance 154
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  5.1 Isoquinoline Alkaloids 155
  5.2 Few Plants Of Berberidaceae Family In Daily Life 160
  5.3 Biologicla Importance Berteris Parkeriana 161
7 6 Results And Discussion 162
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  6.1 Anitmicrobial Activity Of Berberis Parkeriana 163
  6.2 Studies On The Chemical Constituents Of Berberis Parkeriana Schineid 164
  6.3 Parkerine (159)-A New Antimicrobial Protoberberine Alkaloid 164
  6.4 8-Formylprotoberberine (162)-A New Probererine Alkaloid 172
  6.5 Chatterine (163) – A New Protoberberine Alkaloid 178
  6.6 Known Compounds Detected For The First Time From Berberis Parkeriana 186
  6.7 Oxyberberine (164)-A Protoberberine Alkaloids 186
  6.8 8-Trichloromethyldihydroberberine (165)-A Protoberberine Alkaloid 191
  6.9 Berbernine (166)-A Bisbenzylisoquinoline Alkaloid 195
  6.10 Berberine Action (167)-A Protoberberine Alkaloid 201
  6.11 24R-Stigmast-5-En-3B-Ol (168) 205
  6.12 Epifriedinyl-3-Ol-(179) From Ficus Bangolansus 210
8 7 Experimental Section 215
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  7.1 General Experimental Conditions 216
  7.2 Reagents For Visualization Of Spot 218
  7.3 Plant Material Of Sphaeranthus Indicus 220
  7.4 Antimicrobial Activity On Crude Extract Of Sphearanthus Induicus 221
  7.5 Extraction And Fractionation Procedure Of Sephaeranthus Indicus 221
  7.6 Isolation And Spectral Studies Of Compounds Of Sephaeranthus Indicus 222
  7.7 11-A,13-Dihydro-3a-(B-Glucopyransoyl), 7a Dihydroxyfrullanolide (76) 222
  7.8 Enzymatic Hydrolysis Of Sphaeranthanolide (76) 225
  7.9 Immunestimulating Activity Of (76) 226
  7.10 Jern Plaque Assay Of 11a, 13-Dihydro-3-A-(B-Glucopyranosyl) 7a-Hydroxyfrullanolide (76) 226
  7.11 Determination LD50 Value Of 11a, 13-Dihydro-3a-)B-Glycopylanoyl) 7a-Hydroxyfrullanolide (76) In Mice 227
  7.12 Brine Shrimps Leathality Assay Of (76) 228
  7.13 Determination Of LD50 Value Of (76) 228
  7.14 Isolation Of 11a, 13-Dihydio-7a-Hydroxy-13-Metholxyfrullanolide (81) 228
  7.15 Isolation Of 11a, 13-Dihydio-7a-Hydroxy -13-Metholxyfrullanolide (71) 228
  7.16 7a-Hydroxy-4-En-6, 12-B-Olide (79) 230
  7.17 Antimicrobial Activity Of (79) 232
  7.18 Antifungal Activity Of (79) 233
  7.19 Antineoplastic Activity Of (79) 235
  7.20 Isolation Of 11a, 13-Dihydro-7a-13-Dihydorxyfrullanolide (79) 235
  7.21 Isolation Of 11a, 13-Dihydro-3a-7a-Dihydorxyfrullanolide (81) 236
  7.22 Isolation Of Caryophyllene-A-Oxide (82) 238
  7.23 X-Ray Data Of Compounds (82) 240
  7.24 Isolation Of 24S-Stigmasta-5, 22E-Diene-3-Ol (83) 246
  7.25 Antimicrobial Activity Of Berberis Parkeriana 247
  7.26 Plant Material Of Berberis Parkeriana 249
  7.27 Extraction And Fractionation Procedure Of Berberis Parkeriana 249
  7.28 Isolation Of Parkerine (159) 250
  7.29 Reaction Of Patkerine (159) With Sodium Borohydride 251
  7.30 Antimicrobial Activity Of (159) 252
  7.31 Isolation Of 8-Formylprotoberberine (162) 252
  7.32 Isolation Of Chattarine (163) 254
  7.33 Isolation Of Oxyberberine (164) 255
  7.34 Isolation 8-Trichlomethyldihydroprotoberbine (165) 257
  7.35 Isolation Of Berbamine (166) 258
  7.36 Isolation Of Berberine Cation (167) 260
  7.37 Isolation Of 24R-Stigmast-5-En-3-B-Ol (168) 261
  7.38 Isolation Epifriedinyl-3-Ol (169) From Ficus Bangolansus LNN 263
9 8 References 266
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10 9 List Of ublications 284
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