(±)-Evodiakine,A Pair of Rearranged Rutaecarpine-Type Alkaloids From Evodia rutaecarpa

(±)-Evodiakine(1a and 1b),a pair of rearranged rutaecarpine-type alkaloids with an unprecedented 6/5/5/7/6 ring system,were isolated from the nearly ripe fruits of Evodia rutaecarpa.Separation of the enantiomers have been achieved by chiral HPLC column.The structures of(±)-evodiakine were unambiguously elucidated by 1D and 2D NMR spectra,mass spectrometry,and single-crystal X-ray diffraction.Their absolute configurations were determined by comparison of experimental and calculated electronic circular dichroism spectra.A hypothetical biogenetic pathway for(±)-evodiakine was also proposed.Compounds 1a,1b,and the racemate(1)were tested for their cytotoxic and anti-inflammatory activities.

Gas Chromatography–Mass Spectrometry for Quantitative and Qualitative Analysis of Essential Oil from Curcuma wenyujin Rhizomes

Objectives:A rapid and sensitive gas chromatography–mass spectrometry(GC–MS)method for quantitative and qualitative analysis of essential oil from Curcuma wenyujin rhizomes was established.Methods:The essential oil of C.wenyujin rhizomes was extracted by supercritical CO2 extraction(SFE).Six main bioactive compounds(eucalyptol,β-elemene,curzerene,germacrone,curdione,and curcumol)were analyzed in selected ion monitoring mode(SIM).Results:Curzerene is not originally present in C.wenyujin rhizomes,but is a product of the transformation of furanodiene at high temperature.The six target components demonstrated good linearity(R2>0.9979)over a relatively wide concentration range.The interday and intraday variations had relative standard deviation values less than 5%and the average recovery ranged from 96.95%to 100.04%.The limit of quantitation ranged from 0.032 to 0.235μg/mL.The developed method was successfully used to analyze the six compounds in 17 samples collected from different origins.Significant variation was observed for the concentrations of the six compounds.In addition,51 constituents were identified in C.wenyujin rhizome essential oil,consisting of 87.66%of the total essential oil,including curdione,curzerene,dehydrocurdione,germacrone,1,4-bis(2-benzimidazoyl)benzene,neocurdione,curcumenone,andβ-elemene.Conclusions:The proposed method will be useful in the quality control of C.wenyujin rhizome essential oil production.

Fimbrialtols K–M, highly functionalized ent-kaurane diterpenoids from traditional Chinese plant Flickingeria fimbriata(B1.) Hawkes

Three new ent-kaurane diterpenoids fimbrialtols K–M（3–5） with highly substituted functionalities were isolated from the extract of Flickingeria fimbriata（B1.） Hawkes. The structures of these new compounds were determined by NMR and HR-ESIMS. The relative configurations of these compounds were determined by analysis of NOESY correlations. The absolute configurations of these new compounds were established by CD methods together with considering the biosynthetic pathway. Compounds 3 and4 contain a cinnamic carboxyl group, whereas compound 5 possesses a benzoic carboxyl group representing the first report in more than known 600 ent-kaurane diterpenoids.

Minor Compounds from Fungus Ganoderma cochlear

Objective To study the chemical constituents of the fungus Ganoderma cochlear. Methods The compounds were isolated by using MCI gel CHP 20P, Sephadex LH-20, RP-18 column chromatography, and preparative TLC. The structures were identified by means of spectroscopic methods. Results Two phenolic normeroterpenoid and meroterpenoid, cochlearols C and D （1 and 2）, together with six benzene derivatives, 3- methoxy-4-hydroxy-phenylethanol （3）, 4-hydroxyacetophenone （4）, p-hydroxycinnamic methyl ester （5）, 2-methoxy-4-hydroxybenzaldehyde （6）, 4-hydroxy-3-methoxy benzoic acid （7）, and 2-hydroxy-5-ethoxybenzoic acid （8）, were isolated from the fruiting bodies of Ganoderma cochlear. Conclusion Compounds 1 and 2 are new phenolic normeroterpenoid and meroterpenoid, respectively.

A New Furan Flavonol Glycoside from Epimedium koreanum

Objective To study the chemical constituents of Epimedium koreanum.Methods Separation was carried out through silica gel and Sephadex LH-20 column chromatography and HPLC method.The chemical structures were elucidated by spectroscopic method including 1D-NMR and 2D-NMR.Results A new furanflavonol glycoside（1）was isolated and identified.Conclusion Compound 1 is a new furanflavonol glycoside,and its structure is corroborated as 5,4′-dihydroxyfurano[2″,3″：7,8]flavonol 3-O-α-L-rhamnoside.