Eleganoside A (1) and odoratanone A (15), a triterpenoid trisaccharide glycoside and a nortriterpenoid, together with twelve known compounds (2–13) and a mixture of cerebrosides (14) were isolated from Gelsemium elegans and Aglaia odorata. Their structures were elucidated by extensive spectroscopic and spectrometric analysis. Eleganoside A (1) features a 3-O-α-L-rhamnopyranosyl (1→4)-β-D-glucopyranosyl (1→4)-β-D-glucopyranoside of a peculiar 3,16-dihydroxyl-lanosta-8,24-dien-26-oic acid triterpenoid skeleton, and odoratanone A (15) is a 29-norcycloartane-type triterpenoid bearing an unusual five-membered methyl acetal ring. Anti-acetylcholinesterase/butyrylcholinesterase (AChE/BChE) assay indicated that at 50 μM, ethyl caffeate (5) was promising as a dual inhibitor of AChE and BChE, and paeonol (3) and 24-hydroperoxy-24-vinylcholesterol (9) exhibited BChE-selective inhibition.
ZhangQ.P., ZhangB.F., ChouG.X., WangZ.T. (2011) Two new megastigmane glycosides and a new iridoid glycoside from Gelsemium elegans. Helvetica Chimica Acta, 94, 1130–1138.
2.
DuttV., ThakurS., DharV.J., SharmaA. (2010) The genus Gelsemium: An update. Pharmacognosy Review, 4, 185–194; (b) Kitajima M. (2007) Chemical studies on monoterpenoid indole alkaloids from medicinal plant resources Gelsemium and Ophiorrhiza. Journal of Natural Medicines, 61, 14–23; (c) Zhang Z, Zhang Y, Wang YH, Zhang Q, Yan XH, Di YT, He HP, Hao XJ. (2012) Three novel D-carboline alkaloids from Gelsemium elegans. Fitoterapia, 83, 704–708; (d) Yin S, He XF, Wu Y, Yue JM. (2008) Monoterpenoid indole alkaloids bearing an N4-iridoid from Gelsemium elegans. Chemistry-An Asian Journal, 3, 1824–1829.
3.
TakayamaH., MorohoshiY., KitajimaM. (1994) Two new iridoids from the leaves of Gelsemium elegans Benth. in Thailand. Natural Product Letters, 5, 15–20; (b) Zhang BF, Zhang QP, Liu H, Chou GX, Wang ZT. (2011) Iridoids from leaves of Gelsemium elegans. Phytochemistry, 72, 916–922.
4.
XuY.K., YangS.P., LiaoS.G., ZhangH., LinL.P., DingJ., YueJ.M. (2006) Alkaloids from Gelsemium elegans. Journal of Natural Products, 69, 1347–1350; (b) Xu YK, Liao SG, Na Z, Hu HB, Li Y, Luo HR. (2012) Gelsemium alkaloids, immunosuppressive agents from Gelsemium elegans. Fitoterapia, 83, 1120–1124.
5.
KurimotoS., OkasakaM., KashiwadaY., KodzhimatovO.K., TakaishiY. (2011) Four new glucosides from the aerial parts of Mediasia macrophylla. Journal of Natural Medicines, 65, 180–185.
6.
YasudaT., KonR., NakazawaT., OhsawaK. (1999) Metabolism of paeonol in rats. Journal of Natural Products, 62, 1142–1144.
7.
MuQ.Z., ZhouQ.L. (1983) Studies on constituents of Cynanchum otophyllum Schneid. Acta Botanica Yunnanica, 5, 99–103.
8.
EtzenhouserB., HanschC., KapurS., SelassieC.D. (2001) Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids. Bioorganic & Medicinal Chemistry, 9, 199–209.
9.
WeiK., LiW., KoikeK., PeiY.P., ChenY.J., NikaidoT. (2004) Complete 1H and 13C NMR assignments of two phytosterols from roots of Piper nigrum. Magnetic Resonance in Chemistry, 42, 355–359.
10.
SheuJ.H., WangG.H., SungP.J., ChiuY.H., DuhC.Y. (1997) Cytotoxic sterols from the Formosan brown alga Turbinaria ornata. Planta Medica, 63, 571–572.
11.
Menezes-de-OliveiraD., AguilarM-I, King-DíazB., Vieira-FilhoS.A., Pains-DuarteL., SilvaG-D, Lotina-HennsenB. (2011) The triterpenes 3β-lup-20(29)-en-3-ol and 3β-lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors. Molecules, 16, 9939–9956.
12.
PieroniL.G., RezendeF.M., XimenesV.F., DokkedalA.L. (2011) Antioxidant activity and total phenols from the methanolic extract of Miconia albicans (Sw.) Triana leaves. Molecules, 16, 9439–9450.
13.
ShenY.C., PrakashC.V.S., WangL.T., ChienC.T., HungM.C. (2003) New triterpenoid fatty acid esters from the small twigs of Viburnum odoratissimum. Journal of the Chinese Chemical Society, 50, 297–302.
14.
KangS.S., KimJ.S., SonK.H., KimH.P., ChangH.W. (2001) Cyclooxygenase-2 inhibitory cerebrosides from Phytolaccae Radix. Chemical & Pharmaceutical Bulletin, 49, 321–323.
15.
CaiX.H., LuoX.D., ZhouJ., HaoX.J. (2005) Compound representatives of a new type of triterpenoid from Aglaia odorata. Organic Letters, 7, 2877–2879; (b) Yodsaoue O, Sonprasit J, Karalai C, Ponglimanont C, Tewtrakul S, Chantrapromma S. (2012) Diterpenoids and triterpenoids with potential anti-inflammatory activity from the leaves of Aglaia odorata. Phytochemistry, 76, 83–91.
16.
XuY.J., BaiL., LiuY.H., LiuY., XuT.H., XieS.X., SiY.S., ZhouH.O., LiuT.H., XuD.M. (2010) A new triterpenoid saponin from Pulsatilla cernua. Molecules, 15, 1891–1897; (b) Shao B, Guo HZ, Cui YJ, Ye M, Han J, Guo DA. (2007) Steroidal saponins from Smilax china and their anti-inflammatory activities. Phytochemistry, 68, 623–630.
17.
IsaevM.I., GorovitsM.B., AbubakirovN.K. (1985) Triterpenoids of the cycloartane series. Chemistry of Natural Compounds, 21, 399–447.
18.
GorinP.A.J., MazurekM. (1976) Carbon-13 and proton nuclear magnetic resonance studies on methyl aldofuranosides and their O-alkyl derivatives. Carbohydrate Research, 48, 171–186; (b) Shashkov AS, Chizhov OS. (1976) C-13-NMR spectroscopy in chemistry of carbohydrates and related compounds. Bioorganicheskaya Khimiya, 2, 437–497.
19.
KolakU., HacibekirogluI., OzturkM., OzgokceF., TopcuG., UlubelenA. (2009) Antioxidant and anticholinesterase constituents of Salvia poculata. Turkish Journal of Chemistry, 33, 813–823.
20.
EllmanG.L., CourtneyK.D., AndresV., FeatherstoneR.M. (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88–95.