Abstract
A phytochemical study on the chemical constituents of the roots of Actaea rubra led to the isolation and characterization of eleven xylosides of 9,19-cyclolanostane type triterpenes including the new rubraside A (1) and a β-sitosterol glucoside. The structures of the isolates were determined with the help of spectroscopic data including 2-dimensional NMR as well as comparison with reported data. The compounds were tested for cytotoxic, estrogenic, antioxidant, and anticomplement activities. They were found inactive in the tested assays, except for 4, which showed moderate anticomplement activity.
References
-
1
Shao Y, Harris A, Wang M, Zhang H, Cordell G, Bowman M. et al .
Triterpene glycosides from Cimicifuga racemosa
.
J Nat Prod.
2000;
63
905-10
-
2
Wende K, Mugge C, Thurow K, Schopke T, Lindequist U.
Actaeaepoxide 3-O-beta-D-xylopyranoside, a new cycloartane glycoside from the rhizomes of Actaea racemosa (Cimicifuga racemosa).
J Nat Prod.
2001;
64
986-9
-
3
Watanabe K, Mimaki Y, Sakagami H, Sashida Y.
Cycloartane glycosides from the rhizomes of Cimicifuga racemosa and their cytotoxic activities.
Chem Pharm Bull.
2002;
50
121-5
-
4
Zerega N JC, Mori S, Lindqvist C, Zheng Q, Motley T J.
Using amplified fragment length polemorphisms (AFLPs) to identify black cohosh, (Actaea racemosa).
Econ Bot.
2002;
56
154-64
-
5
Takemoto T, Kusano G, Kawahara M.
Studies on the constituents of Cimicifuga spp. VI. Structures of 25-O-acetylcimigenoside and 25-O-methylcimigenoside.
Yakugaku Zasshi.
1970;
90
64-7
-
6
Li C J, Chen D H, Xiao P G.
Chemical constituents of traditional Chinese drug ”sheng-ma” (Cimicifuga dahurica).
Yaoxue Xuebao.
1993;
28
777-81
-
7
Kadota S, Li J X, Tanaka K, Namba T.
Constituents of Cimicifuga Rhizoma II. Isolation and structures of new cycloartanenol triterpenoids and related compounds from Cimicifuga foetida L.
Tetrahedron.
1995;
51
1143-66
-
8
Kimura O, Sakurai N, Inoue T.
Studies on the Chinese crude drug ”Shoma.” VII. Isolation and determination of genuine natural products, acetyl shengmanol xyloside, 24-O-acetylhydroshengmanol xyloside, and shengmanol xyloside, in Cimicifuga dahurica and the other Cimicifuga plants.
Yakugaku Zasshi.
1983;
103
293-9
-
9
Chen S, Fabricant D S, Santarsiero B D, Mesecar A, Fitzloff J F, Fong H S. et al .
Isolation, structure elucidation, and absolute configuration of 26-deoxyactein from Cimicifuga racemosa and clarification of nomenclature associated with 27-deoxyactein.
J Nat Prod.
2002;
65
601-5
-
10
Koeda M, Aoki Y, Sakurai N, Nagai M.
Studies on the Chinese crude drug ”shoma.” IX. Three novel cyclolanostanol xylosides, cimicifugosides H-1, H-2 and H-5, from Cimicifuga rhizome.
Chem Pharm Bull.
1995;
43
771-6
-
11
Mustafa J, Khan S I, Ma G, Walker L A, Khan I A.
Synthesis, spectroscopic, and biological studies of novel estolides derived from anticancer active 4-O-podophyllotoxinyl 12-hydroxyl-octadec-Z-9-enoate.
Lipids.
2004;
39
659-66
-
12
Tabanca N, Khan S I, Bedir E, Annavarapu S, Willett K, Khan I A. et al .
Planta Med.
2004;
70
728-35
-
13
Takamatsu S, Galal A M, Ross S A, Ferreira D, Elsohly M A, Ibrahim A R. et al .
Antioxidant effect of flavonoids on DCF production in HL-60 cells.
Phytother Res.
2003;
17
963-6
-
14
Lee S, Park J, Lee Y, Lee C, Min B, Kim J. et al .
Anti-complementary activity of triterpenoides from fruits of Zizyphus jujuba
.
Biol Pharm Bull.
2004;
27
1883-6
-
15
Master H E, Khan S I, Poojari K A.
Design and synthesis of low molecular weight compounds with complement inhibition activity.
Bioorg Med Chem.
2005;
13
4891-9
Ikhlas A. Khan
National Center for Natural Products Research
University of Mississippi
Oxford
MS 38677
USA
Phone: +1-662-915-7821
Fax: +1-662-915-7989
Email: ikhan@olemiss.edu
