Abstract
Two new phenanthroquinolizidine alkaloids, boehmeriasins A and B, were isolated from the aqueous ethanolic extract of Boehmeria siamensis Craib (Urticaceae) by bioassay-guided fractionation. Their structures were elucidated on the basis of spectral evidence. Boehmeriasin A possesses cytotoxic activity against 12 cell lines from 6 panels of cancer including lung cancer, colon cancer, breast cancer, prostate cancer, kidney cancer and leukemia with GI50 between 0.2 and 100 ng/mL, whereas boehmeriasin B showed lower activity.
Key words
Boehmeria siamensis
- Urticaceae - boehmeriasin A - boehmeriasin B - cytotoxic activity
References
-
1 Institute of B otany, the Chinese Academy of S ciences. Iconographia Cormophytorum Sinicorum, Supplementum I. 1995: p. 203
-
2 Working Group of Collects of Chinese Medicines and H erbs. Collects of Chinese Medicines and Herbs, Section B. 1988: p. 781
-
3 Yunnan Medicines and Herbs C ompany. Contents of Chinese Medicines in Yunnan. 1993: p. 82
-
4
Takemoto T, Miyase T, Kusano G.
Boehmenan, A new lignan from the roots of Boehmeria tricuspis
.
Phytochemistry.
1975;
14
1890-91
-
5
Takemoto T, Miyase T, Kusano G.
Flavones and other compounds of Boehmeria tricuspis and B. holosericea
.
Phytochemistry.
1975;
14
2534
-
6
Hart N K, Johns S R, Lamberton J A.
3,4-Dimethoxy-ω-(2′-piperidyl)acetophenone, a new alkaloid from Boehmeria platyphylla Don. (Family Urticaceae).
Australian Journal of Chemistry.
1968;
21
1397-8
-
7
Hart N K, Johns S R, Lamberton J A.
Minor alkaloids of Boehmeria platyphylla Don. (Family Urticaceae) II. Isolation of cryptopleurine and a new seco-phenanthroquinolizidine alkaloid.
Australian Journal of Chemistry.
1968;
21
2579-81
-
8
Farnsworth N R, Hart N K, Johns S R, Lamberton J A, Messmer W.
Alkaloids of Boehmeria cylindrical (Family Urticaceae): Identification of a cytotoxic agent, highly active against Eagle’s 9KB carcinoma of the nasopharynx in cell culture, as cryptopleurine.
Australian Journal of Chemistry.
1969;
22
1805-7
-
9
Al-Shamma A, Drake S D, Guagliardi L E, Mitscher L A, Swayze J K.
Antimicrobial alkaloids from Boehmeria cylindrical
.
Phytochemistry.
1982;
21
485-7
-
10
Talapatra B, Mallik A K, Talapatra S K.
Terpenoid constituents of Boehmeria platyphlla Don.: Sodium borohydride reduction of 5α-stigmastan-3,6-dione.
Journal of Indian Chemical Society.
1981;
58
815-7
-
11
Matsuura S, Lee L T.
Studies on the components of Boehmeria sp. II. Studies on the components of the roots of Boehmeria frutescens Thunb. Var. frutescens
.
Yakugaku Zasshi.
1974;
94
150-2
-
12
Takemoto T, Miyase T.
Studies on the constituents of Boehmeria tricuspis Makino. I.
Yakugaku Zasshi.
1974;
94
1597-602
-
13
Luo Y G, Li B G, Zhang G L.
A new quinolizidine alkaloid from Boehmeria siamensis
.
Chinese Chemical Letters.
2001;
12
337-8
-
14
Skehan P, Storeng R, Scudiero D, Monk A, McMahon J, Vistica D. et al .
New colorimetric cytotoxicity assay for anticancer-drug-screening.
Journal of National Cancer Institute.
1990;
82
1107-12
-
15
Rubinstein L V, Shoemaker R H, Paull K D, Simon R M, Tosini S, Skehan P. et al .
Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines.
Journal of National Cancer Institute.
1990;
82
1113-8
-
16 Li Z G, Jin Z, Huang R Q. Isolation, total synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids. Synthesis 2001: 2365-78
-
17
Gupta R S, Krepinsky J J, Siminovitch L.
Structural determinants responsible for the biological activity of (-)-emetine, (-)-cryptopleurine, and (-)-tylocrebrine: Structure-activity relationship among related compounds.
Molecular Pharmacology.
1980;
18
136-43
-
18
Stærk D, Lykkeberg A K, Christensen J, Budnik B A, Abe F, Jaroszewski J W.
In vitro cytotoxic activity of phenanthroindolizidine alkaloids from Cynanchum vincetoxicum and Tylophora tanakae against drug-sensitive and multidrug-resistant cancer cells.
Journal of Natural Products.
2002;
65
1299-302
-
19
Abe F, Hirokawa M, Yamauchi T, Honda K, Hayashi N, Ishii M. et al .
Further investigation of phenanthroindolizidine alkaloids from Tylophora tanakae
.
Chemical and Pharmaceutical Bulletin.
1998;
46
767-9
-
20
Stærk D, Christensen J, Lemmich E, Duus J Ø, Olsen C E, Jaroszewski J W.
Cytotoxic activity of some phenanthroindolizidine N-oxide alkaloids from Cynanchum vincetoxicum
.
Journal of Natural Products.
2000;
63
1584-6
Prof. Dr. Guolin Zhang
Chengdu Institute of Biology
The Chinese Academy of Sciences
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