Ursane Saponins from the Stems of <i>Firmiana simplex</i> and their Cytotoxic Activity

Woo, Kyeong Wan; Choi, Sang Un; Kim, Ki Hyun; Lee, Kang Ro

doi:10.5935/0103-5053.20150113

Acessibilidade / Reportar erro

Brasil

Journal of the Brazilian Chemical Society

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

Articles • J. Braz. Chem. Soc. 26 (7) • July 2015 • https://doi.org/10.5935/0103-5053.20150113 copy

Ursane Saponins from the Stems of Firmiana simplex and their Cytotoxic Activity

Authorship SCIMAGO INSTITUTIONS RANKINGS

Three new ursane triterpene saponins, together with twelve known ursane triterpenes were isolated from the stems of Firmiana simplex. The structures of the saponines were elucidated on the basis of spectroscopic and chemical methods. The cytotoxic activity of all compounds was evaluated in vitro against lung adenocarcinoma (A549), ovarian cancer (SK-OV-3), skin melanoma (SK-MEL-2), and colon cancer (HCT-15) human cell lines, using a sulforhodamine (SRB) assay. 23-Hydroxyursolic acid showed cytotoxicity against the tested cell lines with IC₅₀ values ranging from 11.96 to 14.11 µM.

Keywords:
Firmiana simplex ; Sterculiaceae; ursane triterpene saponin; cytotoxicity

Position	1	2	3
1	1.60 m, 1.29 m	1.63 m, 1.34 m	2.05 m, 0.93 m
2	3.95 m	3.91 m	4.09 m
3	3.38 m	3.63 d (2.0)	2.91 d (9.0)
4	–	–	–
5	1.28 m	1.58 m	1.05 m
6	1.46 m, 1.40 m	1.42 m, 1.37 m	1.79 m
7	1.59 m, 1.34 m	1.65 m, 1.31 m	1.53 m, 1.40 m
8	–	–	–
9	1.87 m	1.90 m	1.72 m
10	–	–	–
11	2.05 m, 1.99 m	2.07 m, 2.02 m	2.07 m, 2.01 m
12	5.33 t (3.5)	5.34 t (3.5)	5.33 t (3.5)
13	–	–	–
14	–	–	–
15	1.84 m, 1.04 m	1.84 m, 1.03 m	1.84 m, 1.05 m
16	2.64 td (13.0, 4.5), 1.64 m	2.64 td (13.0, 4.0), 1.66 m	2.63 td (13.0, 3.0), 1.66 m
17	–	–	–
18	2.54 brs	2.56 brs	2.54 brs
19	–	–	–
20	1.40 m	1.40 m	1.39 m
21	1.77 m, 1.28 m	1.76 m, 1.28 m	1.76 m, 1.27 m
22	1.79 m, 1.64 m	1.81 m, 1.62 m	1.80 m, 1.63 m
23	1.01 s	3.56 d (11.0), 3.41 m	1.45 s
24	0.89 s	0.81 s	-
25	1.02 s	1.05 s	0.98 s
26	0.79 s	0.80 s	0.81 s
27	1.36 s	1.37 s	1.35 s
28	–	–	–
29	1.22 s	1.23 s	1.22 s
30	0.95 d (7.0)	0.96 d (6.5)	0.95 d (7.0)
1'	5.31 d (8.0)	5.31 d (8.0)	5.32 d (8.0)
2'	3.36 m	3.35 m	3.34 m
3'	3.42 m	3.42 m	3.44 m
4'	3.44 m	3.44 m	3.44 m
5'	3.52 m	3.52 m	3.52 m
6'	4.17 dd (12.0, 2.0), 3.78 dd (12.0, 5.0)	4.13 dd (12.0, 2.0), 3.78 dd (12.0, 5.0)	4.13 m, 3.78 dd (12.0, 5.0)
1''	4.37 d (8.0)	4.37 d(8.0)	4.37 d (8.0)
2''	3.23 dd (9.0, 8.0)	3.23 dd (9.0, 8.0)	3.23 t (8.5)
3''	3.38 m	3.38 m	3.38 m
4''	3.32 m	3.31 m	3.32 m
5''	3.26 m	3.27 m	3.26 m
6''	3.87 dd (12.0, 2.0), 3.69 dd (12.0, 5.0)	3.87 dd (12.0, 2.0), 3.69 dd (12.0, 5.0)	3.87 dd (12.0, 2.0), 3.70 dd (12.0, 5.0)

Position	1	2	3
1	42.6	42.0	48.5
2	67.3	67.3	69.2
3	80.2	78.4	84.3
4	39.5	42.3	49.9
5	49.7	43.9	57.6
6	19.4	19.2	21.5
7	34.1	33.7	34.3
8	41.5	41.1	41.2
9	48.3	48.1	48.0
10	39.5	38.9	39.7
11	24.9	24.8	25.0
12	129.7	129.2	129.6
13	139.8	139.5	139.7
14	42.9	42.6	42.9
15	29.8	29.5	29.7
16	26.3	26.6	26.6
17	49.3	49.3	49.2
18	55.0	54.9	55.0
19	73.8	73.4	73.7
20	43.0	42.9	42.8
21	27.3	27.2	27.1
22	38.5	38.1	38.3
23	29.4	71.4	24.9
24	22.6	17.8	180.7
25	17.2	17.5	15.5
26	17.8	17.7	17.6
27	24.9	24.8	24.6
28	178.7	178.7	178.6
29	24.7	27.5	27.2
30	16.7	16.6	16.7
1'	95.9	95.8	95.8
2'	73.6	73.8	73.8
3'	78.3	78.2	78.2
4'	71.1	71.0	71.0
5'	77.9	77.9	77.7
6'	69.6	69.4	69.7
1''	104.8	104.7	104.7
2''	75.2	75.2	75.2
3''	78.3	78.1	78.2
4''	71.6	71.6	71.5
5''	78.1	78.0	78.0
6''	62.8	62.8	62.8

Sociedade Brasileira de Química Instituto de Química - UNICAMP, Caixa Postal 6154, 13083-970 Campinas SP - Brazil, Tel./FAX.: +55 19 3521-3151 - São Paulo - SP - Brazil
E-mail: office@jbcs.sbq.org.br

Acompanhe os números deste periódico no seu leitor de RSS

[1] *e-mail: krlee@skku.edu