Studies On The Chemical Constituents Of Two Plants From Yunnan Province

This thesis consists of three chapters.The first chapter is the research on the chemical constituents from the aerial part of Dendrobium officinale Kimura et Migo planted in a large scale.The second chapter discusses the chemical constituents from the leaves of Juglans regia L.The third chapter reviews the research progress of the natural bibenzyl compounds.In chapter 1 studies the chemical compositions of D.officinale planted in a large scale.To date,with over-harvestigation,wild D.officinale is on the edge of extinction.Large-scale planting of D.officinale was urged to meet the needs.Domestic and foreign scholars had mostly done phytochemical work on wild D.officinale.However,the research on cultivated D.officinale was poor.In order to study the chemical compositions of cultivated resource,chemical constituents of D.officinale planted in Dehong of Yunnan Province was explored.The aerial part（50 kg）of D.officinale was extracted with 70% aqueous acetone and then with 100% methanol at room temperature and filtered.These compounds were elucidated as:（±）-officinalol A（1）,（±）-officinalol B（2）,（±）-4-acetonyl-3,α-dihydroxy-4’,5-dimethoxy bibenzyl（3）,officinalol C（4）,officinalol D（5）,densiflorol A（6）,3-hydroxy-4’,5-dimethoxybibenzyl（7）,amoenylin（8）,gigantol（9）,3,4-dihydroxy-4’,5-dimethoxy bibenzyl（10）,3,4’-dihydroxy-5-methoxybibenzyl（11）,batatasin Ⅲ（12）,4,4’-dihydroxy-3,5-dimethoxy bibenzyl,（13）,3,4’-dihydroxy-4,5-dimethoxybibenzyl（14）,（S）-3,4,α-trihydroxy-5,4’-dimethoxybibenzyl（15）,dendrocandin A（16）,3,4,4’-trihydroxy-5-methoxybibenzyl（17）,chrysotoxine（18）,3-O-methylgigantol（19）,tristin（20）,dihydroresveratrol（21）,3’,4,4’-trihydroxy-3,5-dimethoxybibenzyl（22）,moscatilin（23）,9,10-dihydro-2,4-dihydroxy-7-methoxyphenanthrene（24）,cannabidihydrophenanthrene（25）,2,5-dihydroxy-4,6-dimethoxy-9,10-dihydrophenanthrene（26）,dendrocandin I（27）,dendrofalconerols A（28）,fimbriadimerbibenzyl E（29）,fimbriadimerbibenzyl F（30）,dendrocandin U（31）,dendrocandin B（32）,2-acetonyl-3-methoxy-5-[4-methoxyphenethyl]-o-benzoquinol（33）,ficusal（34）,naringenin（35）,5,7,4’-trihydroxy-3’,5’-dimethoxy-flavanone（36）,eriodictyol（37）,3’-bis（3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran）（38）,medioresinol（39）,4-ketopinoresinol（40）,p-hydroxybenzaldehyde（41）,isovanillin（42）,pyrocatechol（43）,4-hydroxyaceophenone（44）,evofolin-A（45）,E-1-（4’-hydroxyphenyl）-but-1-ene-3-one（46）,methoyeugenol（47）,methyl p-hydroxycinnamate（48）,hydroquinone（49）,3,4,5-trimethoxyphenol（50）,p-hydroxybenzoic acid（51）,3,5-dimethoxy-4-hydroxypropiophe-none（52）,syringaldehyde（53）,dihydroconiferyl alcohol（54）,1-（6-hydroxy-[3]pyridyl）-propan-1-one（55）,indole acid（56）,（4S）-4-（2-methylbutyl）-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldeh yde（57）,N-transcinnamoyltyramine（58）,paprazine（59）,5-hydroxymethyl-1-[2-（4-hydroxyphenyl）-ethyl]-1H-pyrrole-2-carbaldehyde（60）,N-（3’-maleimidy1）-5-hydroxymethyl-2-pyrrole formaldehyde（61）,loliolide（62）,（3R,6S）-3-hydroxyl-a-ionone（63）,5-hydroxymethyl-furaldehyde（64）,dihydroconiferyl dihydro-p-coumarate（65）,sinapyl p-coumarate（66）,2’-acetyl-4,4’-dimethoxybiphenyl-2-carbaldehyde（67）,grasshopper ketone（68）,4-acetonyl-3,5-dimerhoxy-p-quinol（69）.Compounds 1-5 were new compounds,and compounds 7,30,36,48,62 and 67 were found from this species for the first time.Furthermore,compounds 26,34,40,46,47,50,51,52,54,60,63,68,69 were obtained from Dendrobium genus for the first time.From the completed experiments,it was found that compared with wild D.officinale,there were more bibenzyl compounds and less phenanthrene compounds on cultivated D.officinale.In chapter 2 studies the chemical compositions from Juglans regia L.Most of the research on Juglans by domestic and foreign scholars were about the unmatured pericarps,and there were less research on its branches and leaves.In order to discover the chemical compositions in J.regia leaves,phytochemical survey on the leaves of J.regia from Yangbi County,Yunnan Province were carried out.17 compounds were obtained,and elucidated as: myricatomentogenin（1’）,3’,4’’-epoxy-2-hydroxy-1-（4-hydroxyphenyl）-7-（3-methoxyphenyl）heptan-3-one（2’）,pterocarine（3’）,galeon（4’）,juglanin C（5’）,juglanin A（6’）,engelheptanoxide A（7’）,juglanin C（8’）,sakuranetin（9’）,5,4’-dihydroxy-3’,7-dimethoxyflavanone（10’）,（4S）-4-hydroxy-1-tetralone（11’）,ferulyl aldehyde（12’）,isosclerone（13’）,frambinone（14’）,loliolide（15’）,dehydrovomifoliol（16’）,2α,3β-dihydroxy-lup-20（29）-ene（17’）.compounds 10’,15’ were found from this genus for the first time.In chapter 3 reviews the research progress of the natural bibenzyl compounds.