Two novel 4,5-secoeudesmane sesquiterpenoids, oxyphyllones A （1） and B （2） were isolated from the fruits of Alpinia oxyphylla. Their structures were established by spectroscopic methods including 1D and 21） NMR spectra. These two compounds are the first example of naturally occurring sesquiterpenoids with a 4,5-secoeudesmane skeleton in the family of Zingiberaceae and oxyphyllone A （1） is the first 4,5-secoeudesmane type of 13-norsesquiterpenoid. Compounds 1 and 2 exhibited no cytotoxicities against three cancer cell lines at 10 μg/mL. ？ 2009 Ning Hua Tan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
Jun Ju XuNing Hua TanJiang XiongAbiodun Humphrey AdebayoHong Jin HanGuang Zhi ZengChang Jiu JiYu Mei ZhangMei Ju Zhu
Phytochemical investigation of the aerial parts of the monotypic plant,Musella lasiocarpa,led to the isolation of four rare bicyclic diarylheptanoids,musellarins B-E(2-5),two new phenylphenalenones,2-methoxy-9-(3′,4′-dihydroxyphenyl)-1H-phenalen-1-one(9),2-methoxy-9-(3′-methoxy-4′-hydroxyphenyl)-1H-phenalen-1-one(10),a new acenaphtylene derivative,trans-(1S,2S)-3-(4′-methoxyphenyl)-acenaphthene-1,2-diol(13),and two new sucrose esters,1,2′,3′,4′,6′-O-pentaacetyl-3-O-trans-p-coumaroylsucrose(16),1,2′,3′,4′,6′-O-pentaacetyl-3-O-cis-p-coumaroylsucrose(17),together with nine known compounds.In addition,(4E,6E)-1-(3′,4′-dihydroxyphenyl)-7-(4′′-hydroxyphenyl)-hepta-4,6-dien-3-one(15)was isolated for the first time from a natural source.The structures of new compounds were elucidated by analysis of their spectroscopic data.Compounds 2,6,8-10,12,and 14 were cytotoxic toward several of the human tumor cell lines(HL-60,SMMC-7721,A-549,MCF-7,and SW480).Of these,the new compound 9 was the most potent one,with IC50 values of 5.8,10.3,6.3,3.3,and 2.3μM,respectively.
Four new labdane-type diterpenoid glycosides,laevissiosides A-D(1-4)were isolated from the 95%ethanol extract of Diplopterygium laevissimum(Christ)Nakai,along with two known analogues,18-b-D-glucopyranosyl ester-sclareol(5)and 18-hydroxy-sclareol(6).The structures of compounds 1-4 were elucidated by extensive 1D and 2D NMR spectroscopy as well as high-resolution MS analyses.All isolated compounds were evaluated for their cytotoxic effects.
Three new Lycopodium alkaloids,obscurumines C-E(1-3),along with nine known compounds,were isolated from the club moss Lycopodium obscurum L.Structures of the new compounds were determined on the basis of their spectroscopic analysis and the relative configurations of 1 were established by X-ray crystallographic analysis.All the new isolates were tested for the acetylcholinesterase(AChE)inhibitory activity.
Two new daphnicyclidin-type Daphniphyllum alkaloids,daphmacrodins A and B(1 and 2)were isolated from the leaves and stems of Daphniphyllum macropodum.Their structures were elucidated by extensive spectroscopic techniques,including 2D NMR spectroscopy and mass spectrometry.The relative configuration of 1 was further confirmed by a single-crystal X-ray diffraction analysis.Their cytotoxic activities against five human cancer cell lines,pesticidal activities against brine shrimp(Artemia salina),and antibacterial activities against five standard bacterial and fungal strains were evaluated.The structure of 1 was successfully transformed to 2 by a chemical method.
