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Hortor of ^Uumpbf M Cmmmim CHEMISTRY OF NATURAL PRODUCTS THESIS SUBMITTED FOR THE DEGHEE OF Hortor of ^UUmpbf m cmmmim BY BmjkHk ABYA DEPARTMENT OF CHEMISTRY ALIGARH MUSUM UNIVERSITY ALIGARH 1987 *•.•» AhJ'^^''-!-!m Iff «CC W« 3 M"- »0 T3441 CHEMISTRY SECTION Z. H. COLLEGE OF ENGG. & TECHNOLOGY ALIGARH MUSLIM UNIVERSITY ALIGARH-202001 (INDIA) ^/^€/. No.... Dated. This if t© certify that «i« worlt ^ttixibcd in th* thtftis ontititd *CHEMISTRY OF NATURAL PRODUOTS* it tht original work of the candidate and it tuitablo for tubnittion for the award of Ph*D, dtgrot in ChtiBittry* (Prof* K«T»Natia) SUPERVISOR I DEDICATED TO Y LOVING FAMILY >^y^s«<B*!>aiaMaesmisissi>^Ji!>iiiBsiaias^s^!^^, '•. >_.^.,.'.x':,.-c^m.^„-'-i--ir!fls.-.:.f ','.'.. ^.=5;gr,>::^a<^f.tf^.iwV,..J.;...i!., y ,^i.i-\7, ^ -.-«=^J»«.v.f.':«?A.wrj- CONTENTS Page 1. Theoretical 1- 54 2. Discussion Plant ' I : Anacardium occidentale Linn 55- 77 (Anacardiaceae) Plant II : Buchanania lanzan Sprend 78- 93 (Anacardiaceae) Plant III : Rhus mysurensis Heyne 94-106 (Anacardiaceae) Plant IV : Calophyllum tomentosum 107-115 T. Anders. (Guttiferae) 3. Experimental 116-157 4. Bibliography 158-169 •it********** ACKNOWLEDGEMENT It gives me an immense pleasure in recording my indebt- ness to Prof. K,T. Nasim for his able and inspiring guidance. I have all the regards and admiration for his helpful attitude in bringing up this thesis. I wish to express my sincere thanks to Dr.M.Ilyas, Reader, Department of Chemistry, Aligarh Muslim University, Aligarh for his keen interest, encouragement and valuable suggestions throughout this research work. My sincere thanks are due to Prof. W. Rahman, Prof. M. S. Ahmad, Ex-Chairman, Prof. S.M. Osman, Chairman, Department of Chemistry and Prof. A.U. Malik, Chairman, Chemistry Section, Z. H. College of Engineering & Technology, Aligarh Muslim University, Aligarh for providing me the necessary facilities in the Department for the execution of the work embodied in this thesis. The continuous co-operation and valuable discussion of Dr. S.K. Roy, tfcc. M.Sarv/ar Alam and other laboratory collea­ gues is greatly acknowledged. Finally but certainly not the least, I take this oppor­ tunity to express my heartfelt gratitude to my parents and other family members who have been instrumental in the execution of this work. (RARJANA mrk) THEORETICAL Vegetation is responsible for the sustainment of various forms of life on the earth. Isolation and examination of natural products have drawn considerable attention of chemists from early days. Many valuable products were obtained from the natural wealth and used for innumerable purposes in the past for human welfare and various other activities. Although the natural products have been obtained mostly from plant sources, still only a meagre percentage of the plant world has been explored for its chemical constituents, particularly in India where there is abundance of wide variety of vegetation since this country possess different types of climatic conditi­ ons and soil etc. The classes of organic compounds generally associated with the term 'Natural Products' include mainly alkaloids, carbohydrates, fats, fatty acids, proteins, steroids, terpen­ oids, essential oils, carotenoids, vitamins, glycosides and numerous derivatives of heterocycle (e.g. flavonoids and coumarines). The flavonoids, one of the most numerous and wide spread group of the natural products are important to man not only because they contributes to plant colour but also because many members (e.g. coumestrol, phloridzin, rotenone) are physiolo­ gically active. They are universally distributed among vascular plants and found practically in all parts of plants. Gabor has reviewed trends in research on the pharmacodynamic effects of flavonoids, mostly rutin and its derivatives. With the extensive screening programmes of plants products for anti- 2-6 cancer drugs, it is not surprising that claims have been made that flavonoids may contribute to or be effective in combating certain type of cancer. Numerous other physiolo- gical activities have been attributed to them.7-1 ' 6 In addition to their medicinal activity, natural products have attracted attention of taxonomists for phytogenetic studies also. Flavonoics and terpenoids have been used as taxonomic l6c markers in several cases. Since 1962, most plant surveyor in taxonomically groups have included flayonoid studies and indeed these pigments now occupy a pre-eminent position as the 17 most favoured of all plant constituent as taxonomic markers. In recent years a number of natural products have been isolated, which are dimers of simpler compounds known as bifla- vonoids. Biflavonoids are the most recent addition to this class and mostly isolated from Gymnosperms. Among the angio- soerms, some plants belonging to Guttifereae ' Euphorbiaceae '^ , Caorifoliaceae , Ochanaceae , 24 25 26 Casurinaceae ,_Rhamnaceae , Anacardiaceae and some ferns 27 belonging to Selaginellaceae have been found to contain biflavonoids. A recent survey of literature shoves that the flavonoid fielo is still very pooular with the chemists ana their interest is increasing in isolating new flavbnoids. A large number of naturally occurring new and novel flavonoids are added to the literature every year. Few of them are listed as - 1. Fulvinervin C - G.Venkataratnam et al have isolated a new flavone, fulvinervin-C, (I) from the seeds of Tephrosia fulvinervis. ,Me R = -CH = CH - C—OOH ^Me (I) 2. Chromenoflavones : S. Sultana and M. Ilyas 29 have reported the presence of chromenoflavones, macaflavone 1 and 2 (II) from the leaves of Macaranaga Indica. OH 0 (II) 1. R = OH 2. R = OMe 30 3. Eight new flavonoids : Recently Mabry et al have isolated fifty one flavonoids from the whole plant material of Gutierrezia microcephala of which eight (llla-h) are new. ^2 0 (III) Ill, R2 \ ^3 ^4 ^5 ^6 ^7 ^8 R9 a. H OH OCH3 OH OCH3 OH H OH OCH. b. H OH H OH OCH3 OH H OH OCH, c. OCH3 OH OCH3 OH OCH3 H OH OH OCH d. OCH3 OH OH OCH3 OCH3 H °^3 OCH3 OH e. OCH3 OH OCH3 OCH3 OCH3 H OCH3 OCH3 OCH, f. OH OH OCH3 OCH3 OCH3 H OH OH H g- OCH3 OH OCH3 OCH3 OCH3 H OH OCH3 H h. OCH3 OH OCH3 OH OH H H OH H 0 4. Three new flavonoids : NGole-Van et al3 i have reported 3 new flavonoids IV (a-c) from the leaves of Gutierrezia qrandis. HO R 3 MeO HO 0 (IV) ^1 ^2 ^3 ^4 (a) OH OH OH H (b) OMe OH OMe OMe (c) OMe OGl c OMe OH ^32 Polyoxyge nate d Flavones : A. V. Vyas et al hav three new polyoxygenated flavones (V a-c) from the whole plant material of Ageratum. MeO (a) R^ + R^ = OCH-.0, R = H 3 (b) R-^ = OMe, R^ = OH, R^ = H (c) R-^ = R^ OMe, R = OH o 6. Candidone, A new Flavanone : Mita Roy et al have reported the presence of a new flavanone, candidone (VI) from the stems and leaves of Tephrosia Candida. MeO 7. A new Flavanone : S. Sultana and M. Ilyas 34 have reported the presence of a new flavanone (VII) from the leaves of Lannea acida. 8. 6,8-Di-C-methyldihydromyricetin : Bernard Voirin et al 35 have isolated from bark and spines of Alluaudia humbertii, a novel flavanonol the 6,8-Di-C-methyldihydromyricetin (VIII). (VIII) 9. 5,2'-Dihydroxy-6, 7-Methylene dioxyisoflevone : Recently Hideyubi Chiji et al have isolated from the seed balls of sugar beet a nev; isoflavone (IX) . (IX) 10. Flavonol Glycosides : Masakazu Aritonii et al have isolated three new flavonol glycosides (Xe-c) from the leaves of Spinacia oleracea. They have been identified 0 as patuletin 3-0-/3-D-glucopyranosyl-(l—> 6)-(^-D- apiof uranosyld—> 2 )-/3-D-glucopyranoside (a), patuletin 3-0- 3-gentibioside and spinacetin-3-0-/3- gentiobioside respectively. MeO HO 0 (X) 6-1 /3 -D-Glcpyr .1 (a) R =/3-D-Glcpyr- R2 = R2 = H 2-1 /3-D-Apifur 1 /i 1 (b) R~=/3-D-Glcpyr —=— /S-D-Glcpyr R2 •55 R^ = H (c) R-^=y3-D-Glcpyr ^"^ • /^-D-Glcpyr R = Me, R3 = H 38 11. Kaempferol Coumaroyl Glucorhamnoside_ : Chamel Nasr et al have isolated from the leaves of Ginkgo biloba a new kaemoferol coumaroyl glucorhamnoside (Xl). HO OH / (XI) 0 12. Two new Rhamnetin Glycosides : J.E.Averebt and B.A. 39 Bohm have reported the isolation of two new flavonal glycosides (Xll a-b) from the plant of Pyrola (pyrolaceae) and identified them as rhamnetin 3,3',4'-tri-0-glucoside and rhamnetin 3-0-arabinoside-3',4'-di-0-glucoside. .OR. MeO (XII) a = R, = R2 = /3 -D-glucoside b = R = arabinoside; R^ = R3 = ^-D-glucoside 40 13. A novel Flavanone Glycoside : Recently M.SoAlam et al have reported a novel flavanone glycoside from the leaves of Mesua ferra. This is the first flavanone glycoside with a C-methyl substituent in the B-ring and a sugar linkage (galactooyranosyl (1—> 4)»<-L-rhamnopyranose) unusual to flavanones. CH^OR 10 14. Three Flavone Glycosides : T.Horie, M.Tsukayama et al have isolated three new flavone glycosides from the green peel of citrus sudachi (XIV). They have identified them as sudachiin B,C and D respectively. Sudachiins B-> Sudachiin A 6" - (3-hydroxy-3-methyl) -glutarate. Sudachiins C-> 7-C)-/3-D-glucosyl sudachitin-6"- (3-hydroxy-3-methyl) glutarate. Sudachiin D-> Both sudachiin A and 7-0-/3-D-glucosyl sudachiin were esteified at their 6" position with 3-hydroxy-3-C-methyl glutaric acid. -H c >- •rH 11 10 +J o •H o x: a o r-) TO cn -o 1 3 Q 0) 1 I O t^ /VVVVV\^V>l/\/\AA. Q I C •H •H O <X5 X3 > to M 03 I •H • H o •o cn "* 2 The problem of structure determination of natural products is a complex one.
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