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Chemistry of Natural Products

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Chemistry of Natural Products CHEMISTRY OF NATURAL PRODUCTS THESIS SUBMITTED FOR THE DEGREE OF Boctor of ^hilo^ophp IN CHEMISTRY NAZNEEN PARVEEN DEPARTVENT OF CHEMISTRY ALICARH MUSLIM UNIVERSITY ALIO ARM (INDIA) JUNE 1987 M T3445 CKED-2002 ^Q "% ^. ^-<?» Dedicated to my Loving Parents PHO\E-Oflfice 551-^ DEPARTMENT OF CHEMISTRY ALIGARH MUSLIM UNIVERSITY A L I G A R H, U. P.. INDIA mf No. Date 29.6.1987 This is to certify that the work discussed in this thesis is an original contribution of the can­ didate and is suitable for submission for the partial fulfilment for the award of Ph.D. degree. •fNizam Ud-din Khan) Supervisor ACKNOWLEDGEMENT I place on record my deep sense of gratitude to Dr. 'lizam- ':: Khan who not only guided me but inspired me at all st^i^es. With­ out his keen interest affectionate supervision and constant help thro\ighout, it would have been impossible for rae to complete this work. I express my sincere thanlcs to Prof. M.S. Ahmad, Ghaiman, Department of Chemistry'-, Aligarh Muslim University, Aligarh for providing necessary facilities. The continuous help and cooperation of Ms. Fe)imeeda Khatoon is gratefully acknowledged. Thanks are also due to other labo­ ratory collegues for their help throughout the work. ( NA^EEN PARVEEN ) GO II TENTS Pa^ e^JAi o, CHAPTjiR - 1 INTKODUCTION 1 1. Gneraistry of Biflavonoids 1 (i) Natural Siflavonoids 1 (A) Biaryl type of Biflavonoid 4 The Amentoflavone group 4 The Agathisflavone grout) 10 The Gupressuflavone group 11 The Robustaflavone group 13 The SuGcedaneaflavonoid group 14 The Strychnobiflavone group 15 (J3) Garcinia and Taiwania Biflavonoids 15 Garcinia biflavonoid 15 Taiwania biflavonoid 17 (G) Biaryl ether type of biflavonoid 18 The Hinokiflavone group 18 The Ochnaflavone group 20 (ii) Extraction and Purification 21 (iii) Identification and Structure Elucida­ tion 21 Ultraviolet spectroscopy 22 Infrared Spectscopy 24 Huclear Magnetic Resonance Spectro­ scopy 25 "^^G iniR 34 ilass Spectroscopy 5e Pa^e Mo, Constituent of the gen.is Araucaria 52 Terpenoids 5? Lignins 66 Biflavonoids 68 I'liQcellaneous compounds 69 Dis emission 70 Experimental 77 References 84 CHAPTJII - 2 Constituents of genus Taxus 95 Alkaloids a^id other Taxane derivatives 93 Jicdysones and Triterpenoids 103 [jignins 104 Glycosides 106 Flavonoids 108 Kiscellaneous compounds 109 Discussion 110 Bxnerimental 116 References 122 CHAPTER - 3 The glycoside 128 Constituents of the genus G-elonium 138 Discussion 138 Experimental 145 Referecnes 150 CHAPTER - 4 Constituents of genus Acer 152 Flavones 152 Pa^e No. Terpenoids and steroids 153 Glycosides 154 Tannins 158 Acids 159 Miscellaneous compounds 162 Discussion 165 Experimental 175 References 182 CHAPTER - 5 Constituents of genus Rhus 188 Flavonoids 188 (a) Plavones 183 (b) Biflavanones 191 (c) Biflavones 193 (d) Flavonoidic glycosides 195 Miscellaneous comnounds 198 (a) Aromatic acid 198 b) Aliphatic acid 200 c) Tannins 201 Discussion 204 Experimental 211 References 218 CHAPTER - 6 Constituents of Homonoia 223 Discussion 224 Experimental 230 References 234 GHAPTJiR - 7 Antileukemic activity of a biflavonoid isolated from the leaves of Thu.j a oriontalis 255 Introduction 235 Discussion 236 Experimental 237 References 241 List of oul3lic,?.tj.onc 2^^2 ABBRBVIATI0N3 1 "^ 13 G NMR G Nuclear magnetic resonance ?ig. Figure H MR n Uuclear magnetic resonance IR Infrared spectroscopy MS Mass spectrum m.p. melting point ra.m.p, mixed melting poi^^t nm nanometre PC Ppper chromatography PLC Preparative layer chromatography % TLG Jhin layer diromatography UV UltraTiolet spectroscopy Chapter 1 Phytochemistry, developed as a distinct discipline, deals with chemical structure, biosynthesis, natural distribution and biological function of org-mic substances accumulated by plants. Investigation of drag plants used in indigeneous medicine in India was started in the early part of the present century. Since 1940s onward new vegetable driags cane into prominence so much so that approximately one third of pharma­ ceuticals are of plant origin. The much greater emphasis on the exr)loitation of plants as source of chemicals can be expected in future, consequently, tnere has been a return to natural Droducts as sources of inspiration for organic chemists. Althought our country abounds in medicinal herbaceous flora, very few indigenous plants have been subjected to phytoc lemic^J. study for the characterization of active principles. This inspired us to investigate some medicinally important plaints for the presence of acti/e compounds of possible therapeutic values. The flavonoids, a comparatively neglected class of natural metabolites, have recently attracted attention due to their physiological importance. The term flavonoid covers a large group of naturally occurring com-oounds in which t\ra benzene rings are linke by a - 2 - propane bridge i.e. having (G/:-G^-G^) carbon skeleton except in isoflavone in which the arrangement is (G/--0-G-G), however, the "6 flavojaoid coranounds are now tiLon to include not only those substances having the true flavonoid structure but also such closely related classes of compounds such as chalcone, isoflavones, aurones, the stilbenes and th*^ cinnamic acids and counarins, which are demonstrably associn-ted with the true flavonoids being formed in plants by a single synthetic Pathway . The potent uses of flavonoids may be listed as contraceptive 2 3 4 drugs , heart stimulants , coronary vasodxalators , antiviral 5 6 effect , analgesic and bronchodilator activity , spasmolytic and 7 8 9 antihistamine activity , oesterogenic activity ' , anthelmintic activity , treatment of allergic diseases , antitumor effect and effective inhibitors of blood cell aggregation 13 . GertaJn flavonoids influence the metabolism of blood vessel walls and cause an increase in capillary resistance. The most important flavonoids that produce a normalization of pathologically reduced capillary resistance are rutin derivatives, Citrus flavonoids, catechins and some flavones and isofalvones, such as taxifolin, diosmetin or sar)horicogide. The chief theraDeutic areas are haemorrhagic diathesis, diabetes, hypertension and arterios- chlerosis. - 3 - The flavonoida are of commercial interest as antioxidants for fats and oils ' . The hiflavonoids which are dimer of monoflavonoids have lately been given more attention because of their physiological properties. - 4 - I, CHEMISTRY OF BIFLAV0N0ID3 (i) NATURAL BIFLAVONOIDS Siflavonoids may be classified into three catagories: (A) Biaryl type (B) G-arcinia and Taiwania "biflavonoids (C) Biaryl ether type. The formation of all tyxDe of naturally occ"urring bifla- vonoidsmay be explained in terms of oxidative coupling of two chalkone units 15 (A) BIARYL TYPE 0? BIFLAVOITOIDS; In this category of bifla- vanoids, two raonoflavonoid units are linked thro\igh A or B ring. The amontoflavone grouT): This group is represented by (l-3",II-8) linked biflavones (I to IV), flavanone-flavone (V), biflavanones (VI to VIII). - 5 WO OM OR3 OR^O 0R3 ( I ) 1 R R' R- R' , 4 (>T 16,17 (la; Ii • H H H H IS— '^C/ do. Saqaoiaflavone GH^ H H ii H (ic: Bilobetln H H H H J 2? (Id: yotet'3uCl xvone""' H Oli^r H d H o-^ (le; Podocarpa'jilavone-A.'' H H H H ^H ,. , ,.21,24 (If 0, i.-^- H H H (ig: loOt^inkf^etin ' '^ H !I H Gli^ CH "J -^ (Ih, Podocarrjuotlavone-B CHv H II il OH 1-4',II-7-Di-O-nethyl- (ii; 1 T a^ientoflavone 2-^ H H ra. ) I-7,II-7-Dl-0-methyl- (ij amentoflavone" ^ GIL, CH., H H H 11-7,11-4'-Di-0-methy] 27 araentoflavone H CH- H H CH. HeveaflavonTT -f>T e 28a', "b (ii: CH 3 CH. H H CH- (im; Xayaflavone'^^'^'^ H GH; H GH rn. - 6 - r R' r R' (In) Sciadopitysin ' CH, H H JH. GH, do) I_4«^I_7,IT-7-'rri-0- 26a methylamentoflavone GH, GH. II GH. H 1-4',11-4 M-7,II-7-Tetra- 29 30 0-methylamentoflavone * CH. GH, H OH. OH, 31 GH. GH (Iq) Hexa-0-raethylaraentoflavone GH, 3 GH, CH, HO (II) 1-5' Methoxy bilobetin^^ (III) Biluteolin^^ OH 0 (IV) 1-4•,II-4',1-5,II-5,II-7-Pent ahydroxy,I-7-O-methyl, I_6-G-methyl[l-3',II-8]biflavone^^. F\'0 R-*- R^ R^ R^ (Va) 2,3-Dihydroamen-toflavone^'^'^^ H H H H (Vb) II-4',II-7-Di-0-methyl-2,3~ 27 dihyd ro ament of la vo ne H GH^ H CH, (Vc) 1-4',11-4',I-7-Tri-0-methyl- 27 2,3-dihydroamentoflavone GH.'T H GH-r CH-7 8 - OH 0 OH 0 (VI) Tetrahydroamentoflavone 36 HoCO OCH, R (Vila) I-7,l-4',II-4'-Tri-0-methyl-I-5,II-5,II-3'' Trihydroxy[l-3',II-8]biflavanone^ H (VIlb) 1-7,1-4',11-4',II-3•-Tetra-O-methyl-I-5, II-5-dihydroxy[l-3',II-8]biflavanone^'^ CH, - 9 - (VIII) R (Villa) Semecarpusflavanone H (Vlllb) Galluflavanone OH lu The Agathisflavone .fi:roup: Thase are (1-6,11-8) iinkea biflava- noids comprising biflavones (IXa--^), flavanonyl-flavone-rhu.^fla- vone (X) md bifiavanones-rhusLlavanone (XI). OW/ \VOR3 OH 0 (IX) R^ K^ R-^ R4 40 (IXa) AgatUisriavone H H H 50 (IXb) I-V-O-Methylagathisflavone CH^ H H (IXc) 1-7, II-7-Di-0-metlijrlajathi3- flavone CH^ GH^ H H (iXd) 11-4 ' ,I-7-Di-0-methylagathi3- flavone OiU H E JH (iXe) II-4',I-7,II-7-Tri-0-methyl- ?6a CH.^ GiL agathisflavono" ' (iXf) I-4',II-4M-7,II-7-.etra-0- metayla^athijflavon.' Gil;, :H , G^i, ^r - 11 - OH 0 (X) Rh\isflavone'^5 (XI) Hhusflavanone^^ The Gupressuflavono .f^roupsrThls jroup comprises [l-8,Il-8] linked loiflavone (Xlla-g), flavanone-flavone (XIII) and ciflavaiione (XIV). - 12 - OH 0 (XII 1 R- R^ R' R 4 45 (Xlla) Cupressuflavone H H H H 46 (Xllb) 1-4'-0-raethylcupressuflavone H n G?I^ H (XIIc) I-7-O-raethylcupressuflavone CH, H H H (Xlld) 1-7, II-7-Di-0-meth.ylcut)ressu- PT 40 flavone GH, GH- H II (Xlle) I-4'/lI-4',I-7/lI-7-Di-0- methylcupressuflavone •^b 3 J:l CH^ H (Xllf) 1-4 '/II-4 ' , 1-7, II-7-'rri-0- methylcupressuflavone" GH^ GH3 H GH.^ H Oil 47 (XII^) Tetra-O-methylcupressuflavone GH, GH, GH^ Gil - 13 - OH 0 OH HO OH 0 OH 0 (XIII) Mesuaferrone-B,4' 8 (XIV) Mesuaferrone-A^^ The RobustafIavone i^roup; This groups is represented by robusta- flavone (XV), a [l-3',II-6] linlced biflavone and its methyl ethers which are not completely characterized.
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