Chemical Constituents Of Piper Wallichii (Miq.) Hand.-Mazz

Piper wallichii（Miq.）Hand.-Mazz)is a genus of pepper in the family Piperaceae and is Included in"Quality Standards for Traditional Chinese Medicines and Ethnic Medicines in Guizhou Province"（2019Edition）,the 2018"Quality Standards for Traditional Chinese Medicines of Hubei Province",and the"Guangxi Zhuang Autonomous Region Yao Medicinal Materials Quality Standards"and other local standards.It is mainly distributed in Hubei,Hunan,Guangxi and Guizhou in China.The name of Piper wallichii（Miq.）Hand.-Mazz was first published in"Ben Cao Tu Jing",and has a thousand-year history of medicinal use.It is pungent,sweet,warm,and belongs to the liver and kidney meridians,and is effective in clearing meridians,activating blood circulation,resolving blood stasis,iron injury,wind-cold and dampness,and tonifying the kidneys and strengthening yang.The reported active ingredients in Piper wallichii（Miq.）Hand.-Mazz mainly include,lignans,alkaloids,saponins and triterpenes.Its pharmacological effects are mainly anti-thrombotic,antibacterial,antioxidant and anti-inflammatory,etc.It has rich medicinal value.The group found that the petroleum ether,ethyl acetate and n-butanol extracted parts of the alcoholic extracts of Piper wallichii（Miq.）Hand.-Mazz were all active in degrading ADP-Tau protein,but the main material basis of their action was not clear.In order to further reveal the active constituents of Piper wallichii（Miq.）Hand.-Mazz and provide a material basis for the subsequent development of its medicinal value,the alcoholic,petroleum ether,ethyl acetate and n-butanol parts extracts of Piper wallichii（Miq.）Hand.-Mazz were separated in this paper.Fifty compounds were isolated from Piper wallichii（Miq.）Hand.-Mazz using silica gel,Sephadex-LH-20,ODS,C8 column chromatography and high performance preparative liquid chromatography.Thirty-five of these compounds were identified using nuclear magnetic resonance,high-resolution mass spectrometry,infrared spectroscopy and spectroscopic techniques,as well as reference literature data,as piperhancins B（1）,6-allyl-7-（3,4-dimethoxyphenyl）-2,3-dimeth oxy-8-methyl-tricyclo[4.2.0.0.^2,8]oct-3-en-5-one（2）,（-）-puberulin B（3）,isodihydrofutoquinol-B（4）,（E）-2-allyl-4-（1-（benzo[d][1,3]dioxol-5-yl）prop-1-en-2-yl）-4-hydroxy-5-methoxycyclohexa-2,5-dien-1-one（5）futoquinol（6）,isofutoquinol A（7）,machilin D（8）,liliflorin E（9）,lancifolin C（10）,lancifolin D（11）,acuminatin（12）,（+）-syringaresinol（13）,（+）-medioresinol（14）,cis-hancinone C（15）,hancinone C（16）,hancinone B（17）,（+）-denudatin B（18）,nectandrin A（19）,wallichinine（20）,piperamide-B5（21）,futoamide（22）,4,5-dihydropiperlonguminine（23）,cis-acuminatin（24）,1-[4-Hydroxy-2-methoxy-5-（2-propen-1-yl）phenyl]ethanone（25）,2-（3,4-dihydro-xyphenyl）ethanol glucoside（26）,methoxyhydroquinone-4-β-D-glucopy-ranoside（27）,hydroxytyrosol（28）,byzantionoside B（29）,（-）-crotepoxide（30）,（+）-sootepoxide chlorohydri-n C（31）,decane-1-thiol（32）,luteolin-7,4’-dimethyl Ether（33）,vicenin-2（34）,dibutylphthhalate（35）.Among them,compounds 5 and 15are new lignans,compound 25 is a new natural product,and compounds1-4,8-12,19,21,24,26-29,and 31-35 are isolated from Piper wallichii（Miq.）Hand.-Mazz for the first time.This study further elucidated the chemical composition of Piper wallichii（Miq.）Hand.-Mazz and provided more material basis for the study of its biological activity,as well as for the further development and utilization of Piper wallichii（Miq.）Hand-Mazz.