Isolation, Identification and Antioxidant Activity of Lignans in Jasminum lanceolarium†

doi:10.7503/cjcu20180159

Abstract

Abstract:

Using silica and Sephadex LH-20 column chromatographies, seven lignans, Jasminlanoside A(1),(+)-cycloolivil(2), syringaresinol-4-O-β-D-glucopyranoside(3), (+)-cycloolivil-6-O-β-D-glucopyranoside(4), (+)-cycloolivil-4'-O-β-D-glucopyranoside(5), (-)-olivil-4″-O-β-D-glucopyranoside(6) and syringare-sinol-4,4'-O-bis-β-D-glucopyranoside(7) were isolated from the extracts of Jasminum lanceolarium. Compound 1 was first found and compounds 3—6 were isolated from the Jasminum genus for the first time. The structure of compound 1 was determined by various spectral techniques. Compounds 1, 2, 4 and 5 exhibited antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl(DPPH) assay, with the highest activity in compound 5[(0.148±0.005) μmol/L].

Key words: Jasminum lanceolarium, Lignan, Antioxidant activity

CLC Number:

O629.9

TrendMD:

WANG Yanbing,ZHANG Hui,YANG Junshan,CHEN Bingpeng,SUN Jiaming. Isolation, Identification and Antioxidant Activity of Lignans in Jasminum lanceolarium^†[J]. Chem. J. Chinese Universities, 2018, 39(9): 1942.

Figures/Tables 5

References 21

[1]	Jiangsu New Medical College, Dictionary of Chinese Materia Medica, Shanghai Scientific and Technical Publisher, Shanghai, 1977, 1825—1826
	(江苏新医学院. 中药大辞典, 上海: 上海科学技术出版社, 1977, 1825—1826)
[2]	Sun J. M., Yang J. S., Zang H., Chem. Pharm. Bull., 2007, 55(3), 474—476
[3]	Shen Y. C., Lin S. L., Planta Med., 1996, 62, 515—518
[4]	Shen Y. C., Lin S. L., Phytochemistry, 1997, 44(52), 891—895
[5]	Zhang Y., Liang X., Zhang Z. F., Meng D. L., Li X., Journal of Shenyang Pharmaceutical University, 2014, 31(8), 610—612, 668
	(张毅, 梁旭, 张正锋, 孟大利, 李铣. 沈阳药科大学学报, 2014, 31(8), 610—612, 668)
[6]	Zhang Y. C., Lou L. L., Meng D. L., Li N., Li X., Journal of Shenyang Pharmaceutical University, 2010, 27(11), 880—882, 892
	(张予川, 楼丽丽, 孟大利, 李宁, 李铣. 沈阳药科大学学报, 2010, 27(11), 880—882, 892)
[7]	Sun J. M., Yang J. S., Chinese Pharmaceutical Journal, 2007, 42(7), 489—491
	(孙佳明, 杨峻山. 中国药学杂志, 2007, 42(7), 489—491)
[8]	Sun J. M., Yang J. S., Zang H., China Journal of Chinese Materia Medica, 2008, 33(17), 2128—2130
	(孙佳明, 杨峻山, 张辉. 中国中药杂志, 2008, 33(17), 2128—2130)
[9]	Sun J. M., Zang H., Yang J. S., Chinese Journal of Natural Medicines, 2009, 7(6), 436—439
	(孙佳明, 张辉, 杨峻山. 中国天然药物, 2009, 7(6), 436—439)
[10]	Li N., Xie Y., Hou Y. M., Hunan Journal of Traditional Chinese Medicine, 2013, 29(5), 123—124
	(李娜, 谢谊, 侯雅明. 湖南中医杂志, 2013, 29(5), 123—124)
[11]	Feng H., Zhou H. H., Ouyang D. S., Chinese Journal of Clinical Pharmacology and Therapeutics, 2015, 20(6), 713—720
	(冯晗, 周宏灏, 欧阳冬生. 中国临床药理学与治疗学, 2015, 20(6), 713—720)
[12]	Jiang C. Y., Xu J. Y., Bian X. H., Shen J. D., Kan J., Xu Y., Chinese Journal of Experimental Traditional Medical Formulae, 2010, 16(6), 218—220
	(江春艳, 许激扬, 卞筱泓, 沈继朵, 阚静, 徐逸. 中国实验方剂学杂志, 2010, 16(6), 218—220)
[13]	Zang H., Shen P., Wang E. P., Xu Q., Xu H., Zhang L. Y., Xia G. Q., Zhu J. Y., Zhang H., Yang X. H., Chem. J. Chinese Universities, 2018, 39(1), 64—70
	(臧皓, 沈鹏, 王恩鹏, 徐倩, 张露云, 夏广清, 朱俊义, 张辉, 杨晓虹. 高等学校化学学报, 2018, 39(1), 64—70)
[14]	Zhao Y. X., Luo X. D., Zhou J., Acta Botanica Yunnanica, 2004, 26(2), 229—233
	(赵友兴, 罗晓东, 周俊. 云南植物研究, 2004, 26(2), 229—233)
[15]	Chen D.C., C NMR and Its Application in Chinese Herbal Medicine, People’s Medical Publishing House, Beijing, 1971, 283—284
	(陈德昌. 碳谱及其在中草药化学中的应用. 北京: 人民卫生出版社, 1971, 283—284)
[16]	Zhen X. H., Kong L. Y., Chinese Herbal Medicine Journal, 2002, 33(11), 964—967
	(郑训海, 孔令义. 中草药, 2002, 33(11), 964—967)
[17]	Gu H . F., Chen R. Y., Sun Y. H., China Journal of Chinese Materia Medica, 2005, 30(9), 677—679
	(古海锋, 陈若芸, 孙玉华. 中国中药杂志, 2005, 30(9), 677—679)
[18]	Henry W., Kirche R., Phytochemistry, 1980, 19, 2707—2712
[19]	Kanchanapoom T., Noiarsa P., Otsuka H., Yaoita Y., Phytochemistry, 2006, 67, 516—520
[20]	Machida K., Takano M., Kakuda R., Chem. Pharm. Bull., 2002, 50(5), 669—671
[21]	Qiao L., Wang S. L., Guan H. Y., Liao S. G., Liu L. N., Li Y. J., Chinese Traditional Patent Medicine, 2015, 37(11), 2448—2451
	(乔里, 汪石丽, 关焕玉, 廖尚高, 刘丽娜, 李勇军. 中成药, 2015, 37(11), 2448—2451)

C atom	δ_H(J/Hz)	Key NOESY	δ_C	Key HMBC
1	—		126.3(C)
2	6.70 brs		106.7(CH)	C7
3	—		147.1(C)
4	—		147.6(C)
5	—		147.1(C)
6	6.70 brs		106.7(CH)	C7
7	4.63 brs		87.6(CH)	C1, C2, C6, C9, C8',C9'
8	3.56 m	7'-H, 9'-H	60.9(CH)	C1, C7'
9	4.36d(7.6)	8'-H	97.2(CH)	C7, C7', C8'
1'	—		131.6(C)
2'	6.81 dd(8.0,1.2)		118.5(CH)	C7'
3'	—		135.0(C)
4'	—		146.0(C)
5'	6.76 d(8.0)		115.2(CH)	C1', C3'
6'	6.97 d(1.2)		110.0(CH)	C2', C4', C7'
7'	4.69d(6.0)	8-H	85.1(CH)	C8, C9, C2', C6',C9'
8'	3.28 m	9-H, 9'-H	58.7(CH)	C7, C9, C1'
9'	4.36d(7.6)	8-H, 8'-H	98.5(CH)	C7, C8, C7'
1″	4.30 d(7.6)		98.5(CH)	C9
2″	3.86 m		72.3(CH)
3″	2.94 m		77.1(CH)
4″	2.82 m		73.3(CH)
5″	2.94 m		69.8(CH)
6″	1.22 d(6.4)		15.6(CH₃)
3,5-ArOCH₃	3.74 s		56.0(CH₃)	C3, C5
4'-ArOCH₃	3.79 s		55.6(CH₃)	C4'
4-ArOH	8.94 brs			C4
3'-ArOH	8.20 brs			C3'

C atom	δ_H(J/Hz)	Key NOESY	δ_C	Key HMBC
1	—		126.3(C)
2	6.70 brs		106.7(CH)	C7
3	—		147.1(C)
4	—		147.6(C)
5	—		147.1(C)
6	6.70 brs		106.7(CH)	C7
7	4.63 brs		87.6(CH)	C1, C2, C6, C9, C8',C9'
8	3.56 m	7'-H, 9'-H	60.9(CH)	C1, C7'
9	4.36d(7.6)	8'-H	97.2(CH)	C7, C7', C8'
1'	—		131.6(C)
2'	6.81 dd(8.0,1.2)		118.5(CH)	C7'
3'	—		135.0(C)
4'	—		146.0(C)
5'	6.76 d(8.0)		115.2(CH)	C1', C3'
6'	6.97 d(1.2)		110.0(CH)	C2', C4', C7'
7'	4.69d(6.0)	8-H	85.1(CH)	C8, C9, C2', C6',C9'
8'	3.28 m	9-H, 9'-H	58.7(CH)	C7, C9, C1'
9'	4.36d(7.6)	8-H, 8'-H	98.5(CH)	C7, C8, C7'
1″	4.30 d(7.6)		98.5(CH)	C9
2″	3.86 m		72.3(CH)
3″	2.94 m		77.1(CH)
4″	2.82 m		73.3(CH)
5″	2.94 m		69.8(CH)
6″	1.22 d(6.4)		15.6(CH₃)
3,5-ArOCH₃	3.74 s		56.0(CH₃)	C3, C5
4'-ArOCH₃	3.79 s		55.6(CH₃)	C4'
4-ArOH	8.94 brs			C4
3'-ArOH	8.20 brs			C3'

Compd.	Appearance	m. p. /℃	MS, m/z
2	White solid	170—172	399[M+Na]⁺, 377[M+H]⁺
3	White solid	268—270	603[M+Na]⁺
4	White solid	193—195	561[M+Na]⁺, 539[M+H]⁺
5	White solid	190—192	561[M+Na]⁺, 539[M+H]⁺
6	White solid	175—177	561[M+Na]⁺, 539[M+H]⁺
7	White solid	270—272	765[M+Na]⁺

Compd.	Appearance	m. p. /℃	MS, m/z
2	White solid	170—172	399[M+Na]⁺, 377[M+H]⁺
3	White solid	268—270	603[M+Na]⁺
4	White solid	193—195	561[M+Na]⁺, 539[M+H]⁺
5	White solid	190—192	561[M+Na]⁺, 539[M+H]⁺
6	White solid	175—177	561[M+Na]⁺, 539[M+H]⁺
7	White solid	270—272	765[M+Na]⁺

Compd.		¹H NMR(400 MHz, DMSO-d₆ ), δ
2	8.36(1H, s, 4'-OH), 8.73(1H, s, 4-OH), 6.65(1H, d, J=1.6 Hz, 2-H), 6.70(1H, d, J=8.0 Hz, 5-H), 6.52(1H, dd, J=8.0, 1.6 Hz, 6-H),3.84(1H, d, J=11.6 Hz, 7-H), 1.88(1H, dt, J=11.6, 3.7 Hz, 8-H), 3.62(1H, m, 9-H), 3.37(1H, m, 9-H), 6.55(1H, s, 2'-H), 6.05(1H, s, 5'-H), 3.09(1H, d, J=16.5 Hz, 7'-H), 2.43(1H, d, J=16.5 Hz, 7'-H), 3.60(1H, m, 9'-H), 3.37(1H, m, 9'-H), 3.73(6H, s, 3, 3'-OCH₃)		136.9(C1), 113.4(C2), 147.3(C3), 144.7(C4), 115.3(C5), 121.8(C6) ,43.7(C7), 45.6(C8), 59.0(C9),132.0(C1'), 112.3(C2'), 145.7(C3'), 143.8(C4'), 116.1(C5'), 125.1(C6'), 39.5(C7'), 72.9(C8'), 68.0(C9'), 55.6(3-OCH₃), 55.5(3'-OCH₃)
3	6.66(2H, s, 2,6-H), 6.60(2H, s, 2',6'-H), 4.66(1H, d, J=4.2 Hz, 7-H), 4.60(1H, d, J=4.2 Hz, 7'-H), 4.18(2H, t, J=13.2, 6.6 Hz, 9_e, 9'_e-H), 3.89(2H, dd, J=13.2, 6.6 Hz, 9_a, 9'_a-H), 3.10(2H, m, 8, 8'-H), 3.75(12H, s, 4-OCH₃), 4.87(1H, d, J=5.4 Hz, 1″-H)		131.3(C1,1'), 103.7(C2, 6, 2', 6'), 152.6(C3, 5), 147.9(C3', 5'), 137.1(C4), 134.8(C4'), 85.3(C7), 85.0(C7'), 53.6(C8), 53.5(C8'), 71.2(C9), 71.1(C9'), 102.6(C1″), 74.1(C2″), 76.5(C3″), 69.9(C4″), 77.2(C5″), 60.9(C6″), 56.4(3, 5-OCH₃), 56.0(3', 5'-OCH₃)
4	8.73(1H, brs, 4'-OH), 6.65(1H, d, J=0.8 Hz, 2'-H), 6.71(1H, d, J=8.0 Hz, 5'-H), 6.53(1H, dd, J=8.0, 0.8 Hz, 6'-H), 6.63(1H, brs, 8-H), 6.32(1H, brs, 5-H), 3.90(1H, d, J=11.6 Hz, 4-H) 1.96(1H, d, J=11.6 Hz, 3-H), 2.48(1H, d, J=17.2 Hz, 1_a-H), 3.15(1H, d, J=17.2 Hz, 1_b-H), 4.26(1H, d, J=8.0 Hz, 1'-H), 3.71(6H, s, 7, 3'-OCH₃)		40.0(C1), 73.0(C 2), 69.2(C2_a), 45.3(C3), 59.0(C3_a), 43.3(C4), 116.4(C5), 144.2(C6) ,146.8(C7), 112.7(C8), 128.1(C9), 132.1(C10), 136.5(C1'), 113.4(C2'), 147.3(C3'), 146.8(C4'), 115.3(C5'), 121.7(C6'), 100.7(C1″), 73.0(C2″), 76.9(C3″), 69.2(C4″), 77.0(C5″), 60.1(C6″), 55.6(7-OCH₃), 55.7(3'-OCH₃)
5	8.77(1H, brs, 6-OH), 6.65(1H, d, J=0.8 Hz, 2'-H), 6.68(1H, d, J=8.0 Hz, 5'-H), 6.53(1H, dd, J=8.0, 0.8 Hz, 6'-H), 6.63(1H, brs, 8-H), 6.32(1H, brs, 5-H),3.89(1H, d, J=12.0 Hz, 4-H), 1.95(1H, d, J=11.2 Hz, 3-H), 2.48(1H, d, J=14.0 Hz, 1_a-H), 3.17(1H, d, J=14.0 Hz, 1_b-H), 4.85(1H, d, J=7.2 Hz, 1'-H), 3.74(6H, s, 7, 3'-OCH₃)		39.5(C1), 72.9(C2), 69.2(C2_a), 45.2(C3), 58.9(C3_a), 43.2(C4), 116.4(C5), 145.6(C6),147.3(C7), 113.4(C8), 132.1(C9), 128.1(C10), 134.4(C1'), 114.7(C2'),148.1(C3'), 146.8(C4'), 116.4(C5'), 122.2(C6'),100.2(C1″), 73.0(C2″), 76.8(C3″), 69.7(C4″), 76.9(C5″), 60.6(C6″), 55.6(7-OCH₃), 55.7(3'-OCH₃)
6	8.78(1H, brs, 4'-OH), 7.03(1H, d, J=1.6 Hz, 2'-H), 6.70(1H, d, J=8.4 Hz, 5'-H), 6.80(1H, dd, J=8.4, 1.6 Hz, 6'-H), 6,91(1H, d, J=1.6 Hz, 2″-H), 6.96(1H, d, J=8.4 Hz, 5″-H), 6.75(1H, dd, J=8.4, 1.6 Hz, 6″-H), 3.63(1H, d, J=9.2 Hz, 5_a-H), 2.75(1H, d, J=14.0 Hz, 4_a-H), 2.88(1H, d, J=14.0 Hz, 4_b-H), 4.59(1H, d, J=7.2 Hz, 2-H), 2.14(1H, dd, J=12.8, 2.0 Hz, 3-H), 3.55(1H, m, 3_a-H), 3.65(1H, m, 3_b-H), 4.85(1H, d, J=7.2 Hz, 1″'-H), 3.74(6H, s, 3', 3″-OCH₃)		83.3(C2), 60.6(C3), 58.9(C3_a),80.5(C4), 39.5(C4_a), 134.4.1(C1'), 111.0(C2'), 146.8(C3'), 145.6(C4'), 115.3(C5'), 119.1(C6'),132.1(C1″), 115.0(C2″),147.3(C3″), 144.9(C4'), 114.7(C5″), 121.7(C6″), 100.7(C1″'), 73.0(C2″'), 76.9(C3″'), 69.2(C4″'), 76.9(C5″'), 60.1(C6″'), 55.6(3'-OCH₃), 55.7(3″-OCH₃)
Compd.		¹H NMR(400 MHz, DMSO-d₆ ), δ			¹³C NMR(100 MHz, DMSO-d₆ ), δ
7	6.66(4H, s, 2, 6, 2', 6'-H), 4.67(2H, d, J=3.2 Hz, 7, 7'-H), 4.19(2H, dd, J=9.0, 6.0 Hz, 9_e, 9'_e-H), 3.82(2H, dd, J=9.0, 6.0 Hz, 9_a, 9'_a-H), 3.76(12H, s, 4-OMe), 3.03(2H, m, 8, 8-H') 4.89(2H, m, 1″,1″'-H)			133.7(C1,1'), 104.2(C2, 6, 2', 6'), 152.6(C3, 5, 3', 5'), 137.1(C4, 4'), 85.1(C7, 7'), 53.6(C8, 8'), 71.3(C9, 9'), 102.7(C1″, 1″'), 74.1(C2″, 2″'), 76.5(C3″, 3″'), 69.9(C4″, 4″'), 77.2(C5″, 5″'), 60.9(C6″, 6″'), 56.4(3, 5, 3', 5'-OMe)