Isolation of dammarane saponins from Panax notoginseng by high-speed counter-current chromatography

The Chinese phytomedicinal formulation Sanqi Zongdai Pian, traditionally prepared from crude extracts from roots of Panax notoginseng (Araliaceae), contains highly polar dammarane saponins which were separated at a preparative scale using high-speed counter-current chromatography (HSCCC). In each operation, 283 mg methanolic extract of five tablets was separated and yielded pure 157, 17, 13 and 56 mg of ginsenoside-Rb1, notoginsenoside-R1, ginsenoside-Re and ginsenoside-Rg1, respectively, n-hexane-n-butanol-water (3:4:7, v/v/v) was used for the two-phase solvent system of the HSCCC separation. The chemical structures of three ginsenosides and one notoginsenoside were elaborated by means of electrospray ionization MS-MS and NMR analysis.     

Development of a systematic approach to rapid classification and identification of notoginsenosides and metabolites in rat feces based on liquid chromatography coupled triple time-of-flight mass spectrometry

The present work contributes to the development of a powerful technical platform to rapidly identify and classify complicated components and metabolites for traditional Chinese medicines. In this process, notoginsenosides, the main active ingredients in Panaxnotoginseng, were chosen as model compounds. Firstly, the fragmental patterns, diagnostic product ions and neutral loss of each subfamily of notoginsenosides were summarized by collision-induced dissociation analysis of representative authentic standards. Next, in order to maximally cover low-concentration components which could otherwise be omitted from previous diagnostic fragment-ion method using only single product ion of notoginsenosides, a multiple product ions filtering strategy was proposed and utilized to identify and classify both non-target and target notoginsenosides of P.notoginseng extract (in vitro). With this strategy, 13 protopanaxadiol-type notoginsenosides and 30 protopanaxatriol-type notoginsenosides were efficiently extracted. Then, a neutral loss filtering technique was employed to trace prototype components and metabolites in rats (in vivo) since diagnostic product ions might shift therefore become unpredictable when metabolic reactions occurred on the mother skeleton of notoginsenosides. After comparing the constitute profiles in vitro with in vivo, 62 drug-related components were identified from rat feces, and these components were classified into 27 prototype compounds and 35 metabolites. Lastly, all the metabolites were successfully correlated to their parent compounds based on chemicalome–metabolome matching approach which was previously built by our group. This study provided a generally applicable approach to global metabolite identification for the complicated components in complex matrices.     

Two New Dammarane‐Type Bisdesmosides from the Fruit Pedicels of Panax notoginseng

Two new dammarane‐type triterpenoidal saponins, notoginsenosides FP₁ ( 1 ) and FP₂ ( 2 ), were isolated from the fruit pedicels of Panax notoginseng, along with 22 known compounds. Their structures were elucidated on the basis of spectroscopic evidences and chemical methods. The known compounds were identified as ginsenosides Rg₁ ( 3 ), Re ( 4 ), Rb₃ ( 5 ), Rc ( 6 ), Rd ( 7 ), Rb₂ ( 8 ), Rb₁ ( 9 ), F₂ ( 10 ), and F₁ ( 11 ); as notoginsenosides R₁ ( 12 ), Fa ( 13 ), and Fc ( 14 ); as vina‐ginsenoside R₇ ( 15 ); as gypenosides IX ( 16 ), XVII ( 17 ), and XIII ( 18 ), and as chikusetsusaponin‐L₅ ( 19 ), quercetin 3‐O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐galactopyranoside ( 20 ), kaempferol 3‐O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐galactopyranoside ( 21 ), benzyl‐β‐primeveroside ( 22 ), (S)‐tryptophan ( 23 ), and icariside B₆ ( 24 ). Compounds 15, 19 and 22 – 24 are reported for the first time from the title plant.