白花洋紫荆中的二苯并[b,f]氧杂䓬类成分和黄酮类成分

doi:10.6023/cjoc202412010

摘要/Abstract

对白花洋紫荆(Bauhinia variegata var. candida)枝叶进行化学成分研究, 通过现代多种色谱技术和波谱技术, 从中分离并鉴定14个化合物, 分别是二苯并[b,f]氧杂䓬类成分bauhinine A (1)、parachrin (2)、bauhiniastatin 3 (3)和bauhiniastatin 1 (4), 黄酮类成分异甘草素-4-甲醚(5)、表阿夫儿茶精(6)、表儿茶素(7)、圣草酚(8)、7,8-(2"-甲基-2"-羟甲基吡喃)-5,3',4'-三羟基-3-甲氧基黄酮(9)、bauhinine B (10)、表阿夫儿茶精-(4β→8)-表阿夫儿茶精(11)、原花青素B2 (12)、原花青素A2 (13)、表阿夫儿茶精-(4β→6)-表阿夫儿茶精(14), 其中化合物1和10为新化合物. 除化合物2、6和7外, 其余化合物为首次从该植物中得到. 利用3-(4,5-二甲基噻唑-2-基)-5-(3-羧甲氧基)-2-(4-磺苯基)-2H-四唑(MTS)法对二苯并[b,f]氧杂䓬类成分1~4的体外肿瘤细胞抑制活性进行了评价, 化合物2对肝癌HepG2细胞体现出一定抑制活性 [IC₅₀=(21.22±2.02) μmol/L], 化合物4对乳腺癌MDA-MB-231细胞体现出一定抑制活性[(20.14±1.69) μmol/L].

关键词: 白花洋紫荆, 二苯并[b,f]氧杂䓬类, 原花青素

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

引用此文

黄丹, 段成宝, 司福, 谢会平, 朱虹星, 王利勤. 白花洋紫荆中的二苯并[b,f]氧杂䓬类成分和黄酮类成分[J]. 有机化学, 2025, 45(7): 2600-2604.

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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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