Studies On The Constituents Of Hedychium Sinoaureum And Metasequoia Glyptostroboides

In this thesis,the chemical constituents of Hedychium sinoaureum and Metasequoia glyptostyoboides were studied.Sixty-eight compounds were obtained,and two of them are new labdane-type diterpenoids.Meanwhile,summarized the labdane-type diterpenoids isolated from plants since 2018 and their biological activity.H.sinoaureum is a member of the Hedychium in Zingiberaceae,which is distributed in Yunnan,Tibet and India.Through investigation,domestic and foreign scholars have found that the roots of Hedychium are rich in labdane-type diterpenoids with good biological activities such as anti-inflammatory,antibacterial,cytotoxicity and enzyme inhibition.Only Chen Jianhua et al.reported on the chemical constituents of rhizome of H.sinoaureum,from which 11 labdane-type diterpenes,3 flavonoids and 3 simple aromatic compounds were isolated and identified.To further understand the constituents of H.sinoaureum,this paper studied the chemical constituents of rhizome of H.sinoaureum from Lincang,Yunnan.In this thesis,various separation technologies were used and total 30 compounds were obtained.Their structural types involves 21 labdane-type diterpenes,1 nor-labdane diterpene,2 sesquiterpenes,3 flavonoids,1 diaryl heptane,and 2 simple aromatic compounds.Among them,compounds 1,2 are new labdane-type diterpenes and named hedysinorin A（1）,hedysinorin B（2）;other compounds whose structures were identified as:forrestin A（3）,yunnancoronarin B（4）,hedylongnoid B（5）,galanolactone（6）,hedyforrestin B（7）,labda-8（17）,13（14）-dien-15,16-olide（8）,16-hydroxylabda-8（17）,11,13-trien-15（16）-olide（9）、hedyforrestin C（10）,hedycoronarin D（11）,hedychenoid B（12）,6-oxo-labda-7,11,13-triene-16-oic lactone（13）,hedycoronarin A（14）,hedychenone（15）,7-hydroxyl-hedychenone（16）,hedychin D（17）,hedylongnoid A（18）,coronarin E（19）,（+）-coronarin A（20）,yunnancoronarin A（21）,15,16-bisnorlabda-7,11-diene-6,13-dione（22）,3,7,11-trimethyldodeca-1,6,10-triene-3,9-diol（23）,3,7,1l-trimethyldodeca-l,6,9-triene-3,ll-diol（24）,letestuianin B（25）,5,6-dehydrokawain（26）,pinocembrin（27）,3,5,7,4’-tetramethoxyflavone（28）,5-hydroxy-3,7,4’-trimethoxyflavone（29）,vanillin（30）respectively.Among them,compounds 5-9、11-14、17-20 and 22-27 were identified from H.sinoaureumt for the first time.M.glyptostyoboides is the only existing plant of the Metasequoia in Taxodiaceae.M.glyptostroboides is distributed in Sichuan,Hubei and northwestern Hunan at altitudes of 750-1500 meters,and is also cultivated in Yunnan.Studies have shown that M.glyptostroboides contains flavonoids,diterpenoids,lignans and other constituents,of which total flavone have a good effect on the treatment of cardiovascular diseases,but also has anti-tumor and anti-fungal activities.In order to further understand its chemical constituents,the bark of M.glyptostroboides collected from Kunming,Yunnan Province was studied.In this paper,a variety of modern separation methods were used and total 38 compounds were obtained.The structure types of these compounds covers 1 abietane-type diterpene,3 labdane-type diterpenes,4 diarylpropanes,11 flavonoids,2 lignans,15 other aromatic compounds and 2 steroids.The structure is respectively:（+）-ferruginol（1’）,3β-acetoxy-8（17）,13E-labdadien-15-oic acid（2’）,3β-hydroxyanticopalic acid（3’）,8-hydroxy-labda-13（16）,14-dien-19-yl trans-coumarate（4’）,trans-hinokiresinol（5’）,agatharesinol（6’）,sequosempervirin D（7’）,agatharesinol acetonide（8’）,（+）-catechin（9’）,gallocatechin（10’）,naringenin（11’）,isoginkgetin（12’）,podocarpusflavone A（13’）,bilobetin（14’）,amentoflavone（15’）,2,3-dihydro-4’,4’’’-di-O-methylamentoflavone（16’）,（2S）-2,3-dihydroamentoflavone（17’）,（2’’S）-2’,3’’-dihydroamentoflavone（18’）,tetrahydrohinokiflavone（19’）,meridinol（20’）,（-）-hinokinin（21’）,hexadecyl ferulate（22’）,dodecyl ferulate（23’）,hexadecyl caffeate（24’）,ɑ-tocopherol（25’）,ɑ-tocopherolquinone（26’）,egonol（27’）,4,4’-dihydroxy-chalcone（28’）,4,4’-dihydroxydiphenylmethane（29’）,7-hydroxycoumarin（30’）,vanillic acid（31’）,p-hydroxy benzaldehyde（32’）,p-hydroxybenzyl alcohol（33’）,4-hydroxybenzyl methyl ether（34’）,p-hydroxybenzoic acid（35’）,p-hydroxyacetophenone（36’）,β-sitosterol（37’）,sitosterol-β-D-glucoside（38’）.Among them,compounds 11’,18’-19’,22’-25’,27’-30’,33’-34’,36’were isolated from M.glyptostyoboides for the first time.The activity of compound 10 was tested on human breast cancer cell line（MDA-MB-231）and human colon cancer cell line（HCT-116）.The results showed that the IC₅₀value of compound 10 against human breast cancer cell line was 25.85μM,and the IC₅₀value against human colon cancer cell line was 23.11μM,showing moderate activity.