Three new acylated flavonol diglycosides that were characterized as quercetin 3-O-(6′”-O-E-isoferuloyl)-sophoroside (1), quercetin 3-O-(6′”-O-Z-isoferuloyl)-sophoroside (2) and quercetin 3-O-[2″-O-(E-6″′-O-isoferuloyl)-β-D-glucopyranosyl]-β-D-galactopyranoside (3), along with twelve known metabolites, have been isolated from the leaves of Cynanchum acutum L. The latter were identified as quercetin 3-O-β-D-neohesperidoside (4), rutin (5), quercetin 3-O-sophoroside (6), kaempferol 3-O-β-D-rutinoside (7), quercitrin (8), isoquercitrin (9), hyperin (10), guaijaverin (11), quercetin 7-O-β-D-glucopyranoside (12), quercetin (13), scopoletin (14) and (E)-3-(3,4-dihydroxyphenyl)-propenoic acid (15). All metabolites have been isolated for the first time from the genus Cynanchum, except for 9 and 14. The structures were determined on the basis of chromatographic behavior, acid hydrolysis, chemical and physicochemical evidence (UV, HRESI-MS/MSn, 1H, 13C NMR, 1H-1H COSY, HSQC and HMBC). The chloroform extract and compounds 8 and 10 exhibited lethal effects towards brine shrimp, Artemia salina.
KimJG. (1984) Illustrated Natural Drugs Encyclopedia (color Edition). 1, Nam san dang, Seoul, 201.
5.
ZhangZX, ZhouJ, HayashiK, KanekoK. (1988) Atratosides A, B, C and D, steroid glycosides from the root of Cynanchum atratum. Phytochemistry, 27, 2935–2941.
6.
LeeMK, YeoH, KimJ, KimYC. (2000) Protection of rat hepatocytes exposed to CCl4 in vitro by Cynanchum walfordii. Journal of Pharmacy and Pharmacology, 52, 341–345.
7.
SugamaK and HayashiK. (1988) A glycoside from dried roots of Cynanchum paniculatum. Phytochemistry, 27, 3984–3996.
8.
StaerkD, ChristensenJ, LemmichE, DuusJØ, OlsenCE and JaroszewskiJW. (2000) Cytotoxic activity of some phenanthroindolizidine N-oxide alkaloids from Cynanchum vincetoxicum. Journal of Natural Products, 63, 1584–1586.
9.
DaySH, WangJP, WonSJ and LinCN. (2001) Bioactive constituents of the roots of Cynanchum atratum. Journal of Natural Products, 64, 608–611.
10.
AwaadA (2000) Phytochemical investigation and biological activities of Cynanchum acutum growing in Egypt. Bulletin Faculty of Pharmacy Cairo University, 38, 153–162.
11.
Abou ZeidAH, IbrahimNA, SammourEA. (2001) Phytochemical, Insecticidal and molluscicidal investigation of the aerial parts of Cynanchum acutum. Bulletin Faculty of Pharmacy Cairo University, 39, 235–245.
12.
YeoH, ChoiYH, KimJ (2002) New Pregnane Glycosides from Cynanchum ascyrifolium. Chemical and Pharmaceutical Bulletin, 50, 847–849.
13.
KanchanapoomT, KasaiR, OhtaniK, AndriantsiferanaM, YamasakiK. (2002) Pregnane and pregnane glycosides from the Malagasy plant. Chemical and Pharmaceutical Bulletin, 50, 1031–1034.
14.
LiSL, TanH, ShenYM, KawazoeK, HaoXJ (2004) A pair of new C-21 steroidal glycoside epimers from the roots of Cynanchum paniculatum. Journal of Natural Products, 67, 82–84.
15.
WangP, QinHL, ZhangL, LiZH, WangYH, ZhuHB. (2004) Steroids from the roots of Cynanchum stauntonii. Planta Medica, 70, 1074–1079.
16.
YeoH, WookKW, KimJ, ChortYH (1998) Steroidal glycosides of the 14,15-Seco-18 nor-pregnane series fromCynanchum ascyrifolium, Phytochemistry, 49, 1129–1133.
WarashingT, NoroT. (1998) Steroidal glycosides from roots of Cynanchum caudatum. Phytochemistry, 49, 2103–2108.
19.
AbeF, YamauchiT, HondaK and HayashiN. (2000) Conduritol F glucosides and terpenoid glucosides from Cynanchu liukiuense and distribution of conduritol F glucosides in several Asclepiadaceous plants. Chemical and Pharmaceutical Bulletin, 48, 1090–1092.
AgrawalPK, BansalMC. (1989) Flavonoid glycosides, in Studies in Organic Chemistry, 39, Carbon-13 NMR of Flavonoids, AgrawalPK. (Eds) Elsevier, New York USA. 283.
22.
MarkhamKR, MohanchariV (1982) Carbon-13 NMR spectroscopy of flavonoids, In: The Flavonoids: Advances in Research, HarborneJB, MabryTJ. (Eds), Chapman & Hall, London, UK, 119–132.
23.
LuY, FooLY. (2002) Polyphenolics of Salvia—a review. Phytochemistry, 59, 117–140.
24.
MohamedMA, MarzoukMSA, MoharramFA, El-SayedMM, BaiuomyAR. (2005) Phytochemical constituents and hepatoprotective activity of Viburnum tinus. Phytochemistry, 66, 2780–2786.
25.
KamelMS (2003) Flavone C-glycosides from Lupinus hartwegii. Phytochemistry, 63, 449–452.
26.
WangAX, ZhongQ and JiaZJ. (2004) A new furobenzopyranone and other constituents from Anaphalis lacteal. Pharmazie, 59, 807–811
27.
NakanishiK. (1990) One-Dimensional and Two-Dimensional NMR spectra by Modern pulse Techniques. Part 1. Kodansha Ltd, Mill Valley, Japan, 62–83.
