Study On The Chemical Constituents Of Iodes Cirrhosa And Machilus Yaoshansis

This dessertation investigated chemical constituents of ethanolic extracts of the rootsof Iodes cirrhosa and Machilus yaoshansis and their bioactivities on severalpharmacological models.In addition, based on a systematic analysis of NMR data ofthreo and erythro 8-4′-oxyneolignans and arylglycerols in different solvents, thevalidity, existing problems and application conditions of the coupling constant of thebenzyl proton (⁽³⁾J_(7,8)) and the chemical shift difference between C-8 and C-7 (△δ_(C8-C7))values to distinguish threo and erythro derivatives were discussed in detail, as well asthe relationship between the absolute configuration of arylglycerols and their opticalrotations were confirmed through a chiral synthesis of and arylglycerol aglycone.The chemical constituents of the plants of the genus Iodes were investigated forthe first time. By using a variety of chromatographic techniques and spectroscopicmethods, 58 (I1^(*)-I58) and 17 (M1^(*)-M17) compounds were isolated and determinedfrom the 95% ethanol extracts of the roots of I.cirrhosa and M. yaoshansis,respectively. Chemical names and structures of purified compounds are listed in Table1 and Figure 1. Among them, I1^(*)-I4^(*), I7^(*)-I10^(*), I12^(*), I14^(*) and M1^(*)-M5^(*) are newwhile I13^{(^)} was obtained from nature and the absolute configurations of I5^(#), I6^(#), andI11^(#) were determined, for the first time. I1^(*)-I3^(*) are unsual 8-4′oxyneoliganglycosides with a glycosyoxyl group at C-3′. M1^(*) and M2^(*) are two cucurbitanetritepenoids with an unusual furo[3,2-b]pyran ring consisiting of two hemiacetals, andM3^(*) is the first example of the trinorcucurbitane tritepenoid losing a three carbon unitat the side chain. I4^(*) and I56 exhibited nuroprotective activity againstglutamate-induced PC12 cell damage at 10^(-5) M while I3^(*), I11^(#), I12^(*), and I13^{(^)} wereactive against serum deprivation-induced PC12 cell apoptosis at 10^(-6) M. I16, I17, I19,I23, I24, I27, I30, I32, and I35 were active against serum deprivation-inducedSH-SY5Y-JNK3 apoptosis at a concentration of 10^(-6) M. 128 showed inhibitory effectagainst potassium channels in both non-specific and specific K⁽⁺⁾ channel-regulatorscreening models. I35 showed antioxidant activities inhibiting Fe⁽⁺²⁾-cystine-induced rat liver microsomal lipid peroxidation at a concentration of 10^(-6) M. I35 was active toTNFαsecretion of mouse peritoneal macrophages with an inhibition rate of 33.4% at aconcentration of 10^(-5) M. I35 showed selective cytotoxicity against several humancancer cell lines including colon (HCT-8), lung (A549) and ovarian (A2780) cancercells, while I37 exhibited cytotoxicity against HCT-8 and M6 against BGC-823 andA549 cells. M6 was also active against H5N1 avian influenza virus, M2, M4 and M9inhibited the protein tyrosine phosphatase 1B at a concentration of 10^(-5) M.Table 1. Compounds isolated from lodes cirrhosa (I1^(*)-I58) and Machilus yaoshansis(MI^(*)-M17) ^(*) New compounds.^(#) The absolute configuration of which was determined for the first time.^{(^)} New natural compound.