Dibenz[b,f]oxepins and Flavonids from Bauhinia variegata var. candida

doi:10.6023/cjoc202412010

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2600-2604.DOI: 10.6023/cjoc202412010 Previous Articles Next Articles

白花洋紫荆中的二苯并[b,f]氧杂䓬类成分和黄酮类成分

黄丹, 段成宝, 司福, 谢会平, 朱虹星, 王利勤^*()

云南师范大学化学化工学院昆明 650050

收稿日期:2024-12-12 修回日期:2025-01-17 发布日期:2025-03-07

Dibenz[b,f]oxepins and Flavonids from Bauhinia variegata var. candida

Dan Huang, Chengbao Duan, Fu Si, Huiping Xie, Hongxing Zhu, Liqin Wang^*()

College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650050

Received:2024-12-12 Revised:2025-01-17 Published:2025-03-07
Contact: *E-mail: lqwang@ynnu.edu.cn

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Abstract

Through a variety of chromatographic techniques and spectroscopic methods, four dibenz[b,f]oxepins and ten flavonids were isolated from the twigs and leaves of Bauhinia variegata var. candida. Their structures were identified to be bauhinine A (1), parachrin (2), bauhiniastatin 3 (3), bauhiniastatin 1 (4), isoliquiritigenin-4-methyl ether (5), epiafzelechin (6), epicatechin (7), eriodictyol (8), 7,8-(2''-hydroxymethyl-2''-methylpyrano)-5,3',4'-trihydroxy-3-metho xylflavone (9), bauhinine B (10), epiafzelechi-(4β→8)-epiafzelechi (11), procyanidin B2 (12), procyanidin A2 (13), epiafzelechi-(4β→6)-epiafzelechi (14). Compounds 1 and 10 were new. Except for compounds 2, 6 and 7, other compounds were isolated from this plant for the first time. Dibenz[b,f]oxepins 1~4 were evaluated for their inhibitory activities against a panel of cancer cell lines in vitro by 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfopheny)-2H-tetrazolium (MTS) method. Compounds 2 and 4 showed moderate inhibitory activities agains HepG2 and MDA-MB-231 cell lines with IC₅₀ values of (21.22±2.02) and (20.14±1.69) μmol/L, respectively.

Key words: Bauhinia variegata var. candida, dibenz[b,f]oxepin, procyanidin

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Dan Huang, Chengbao Duan, Fu Si, Huiping Xie, Hongxing Zhu, Liqin Wang. Dibenz[b,f]oxepins and Flavonids from Bauhinia variegata var. candida[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2600-2604.

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Fig. & Tab. 4

References 18

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1 (in CD₃COCD₃)			10 (in CD₃OD)
No.	δ_H, mult, J/Hz	δ_C	No.	δ_H (Part A), mult, J/Hz	δ_C (Part A)	δ_H (Part B), mult, J/Hz	δ_C (Part B)
1		147.8	2	3.84, brs	73.0	5.09, brs	81.0
2		114.3	3	4.46, d, 5.0	65.2	4.29, brs	66.5
3		156.1	4	2.95, brd, 17.4	29.6	2.85, brd, 17.4	25.1
4	6.35, s	101.3		2.85, brd, 17.4		2.67, dd, 4.8, 17.4
4a		128.9	4a		99.0		103.7
5	6.80, d,11.5	129.9	5		157.8		166.9
6	7.02, d, 11.5	125.1	6	5.92, d,5.3	96.8	6.17, s	91.8
6a		120.4	7		157.5		166.5
7		149.7	8	5.95, br s	95.5		104.7
8	6.67, d, 8.8	111.5	8a		155.8		156.4
9	6.99, d, 8.8	113.8	1′		91.9		130.6
10		144.5	2′		164.7	7.39, d, 8.5	129.1
10a		147.1	3′	6.51, s	113.6	6.85, d, 8.5	116.1
11a		138.5	4′		193.8		158.3
1-OH	7.66, s		5′		95.6	6.85, d, 8.5	116.1
2-CH₃	2.06, 3H, s	8.8	6′	2.97, d, 11.0	40.9	7.39, d, 8.5	129.1
3-OCH₃	3.78, 3H, s	56.1		2.23, d, 11.0
7-OH	8.52, s
10-OCH₃	3.95, 3H, s	57.1

1 (in CD₃COCD₃)			10 (in CD₃OD)
No.	δ_H, mult, J/Hz	δ_C	No.	δ_H (Part A), mult, J/Hz	δ_C (Part A)	δ_H (Part B), mult, J/Hz	δ_C (Part B)
1		147.8	2	3.84, brs	73.0	5.09, brs	81.0
2		114.3	3	4.46, d, 5.0	65.2	4.29, brs	66.5
3		156.1	4	2.95, brd, 17.4	29.6	2.85, brd, 17.4	25.1
4	6.35, s	101.3		2.85, brd, 17.4		2.67, dd, 4.8, 17.4
4a		128.9	4a		99.0		103.7
5	6.80, d,11.5	129.9	5		157.8		166.9
6	7.02, d, 11.5	125.1	6	5.92, d,5.3	96.8	6.17, s	91.8
6a		120.4	7		157.5		166.5
7		149.7	8	5.95, br s	95.5		104.7
8	6.67, d, 8.8	111.5	8a		155.8		156.4
9	6.99, d, 8.8	113.8	1′		91.9		130.6
10		144.5	2′		164.7	7.39, d, 8.5	129.1
10a		147.1	3′	6.51, s	113.6	6.85, d, 8.5	116.1
11a		138.5	4′		193.8		158.3
1-OH	7.66, s		5′		95.6	6.85, d, 8.5	116.1
2-CH₃	2.06, 3H, s	8.8	6′	2.97, d, 11.0	40.9	7.39, d, 8.5	129.1
3-OCH₃	3.78, 3H, s	56.1		2.23, d, 11.0
7-OH	8.52, s
10-OCH₃	3.95, 3H, s	57.1

Compd.	HepG2	MDA-MB-231
2	21.22±2.02	—^b
4	—^b	20.14±1.69
Doxorubicin^c	0.309±0.022	0.058±0.006
Taxol^c	<0.016	<0.016

Compd.	HepG2	MDA-MB-231
2	21.22±2.02	—^b
4	—^b	20.14±1.69
Doxorubicin^c	0.309±0.022	0.058±0.006
Taxol^c	<0.016	<0.016

白花洋紫荆中的二苯并[b,f]氧杂䓬类成分和黄酮类成分

Dibenz[b,f]oxepins and Flavonids from Bauhinia variegata var. candida

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