Bibenzyl Derivatives from Dendrobium nobile

doi:10.6023/cjoc201903035

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3289-3293.DOI: 10.6023/cjoc201903035 Previous Articles Next Articles

金钗石斛中联苄基衍生物化学成分研究

张茂生^a, 令狐浪^a, 张建永^a, 聂绪强^a, 李晓飞^b, 郭大乐^c, 肖世基^a^b*()

^a遵义医科大学药学院贵州遵义 563006
^b 贵州省兰科药用植物繁育及高效应用工程研究中心贵州遵义 563006
^c 成都中医药大学药学院成都 611137

收稿日期:2019-03-20 发布日期:2019-07-03
通讯作者: 肖世基 E-mail:xiaoshiji84@163.com
基金资助:
国家自然科学基金(31560102);贵州省科技重大专项子项目(黔科合重大专项字[2015]6010-2)

Bibenzyl Derivatives from Dendrobium nobile

Zhang Maosheng^a, Linghu Lang^a, Zhang Jianyong^a, Nie Xuqiang^a, Li Xiaofei^b, Guo Dale^c, Xiao Shiji^a^b*()

^a School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563006
^b Guizhou Provincial Research Center for the Propagation and Efficient Utilization of Medicinal Orchids, Zunyi, Guizhou 563006
^c School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137

Received:2019-03-20 Published:2019-07-03
Contact: Xiao Shiji E-mail:xiaoshiji84@163.com
Supported by:
the National Natural Science Foundation of China(31560102);the Key Technologies R & D Program of Guizhou Province(黔科合重大专项字[2015]6010-2)

1. .pdf(1013KB)

Abstract

By silica gel, MCI column chromatographic and preparative high performance liquid chromatography (HPLC) technologies, three new bibenzyl derivatives were isolated from the tubes of Dendrobium nobile. One racemic compound was further purified by chiral (HPLC) to obtain a pair of enantiomers 1a and 1b, and the absolute configurations of the enantiomers were confirmed using electronic circular dichroism (ECD) calculations. By using spectroscopic techniques including NMR and HR-ESIMS, the structures of compounds 1~3 were identified as didendronbiline A (1), dendronbiline B (2), and dendronbiline C(3).

Key words: dendrobium nobile, orchidaceae, bisbibenzyl, dendronbiline

Cite this article

Zhang Maosheng, Linghu Lang, Zhang Jianyong, Nie Xuqiang, Li Xiaofei, Guo Dale, Xiao Shiji. Bibenzyl Derivatives from Dendrobium nobile[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3289-3293.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

References 18

[1]	Zhang H. Y. Zhang Z. Y. The Chinese Traditional Medicine Resource Records Beijing Science Press 1994
	张惠源张志英中国中药资源志要北京科学出版社 1994
[2]	Xu J. Han Q. B. Li S. L. Wang X. N. Zhao Z. Z. Chen H. B. Phytochem. Rev. 2013 12 341. doi: 10.1007/s11101-013-9310-8
[3]	Zhang X. Q. Zhao T. M. Liu J. Zhao R. X. Zheng S. G. Ze C. Hu Y. D. Chin. Tradit. Herb. Drugs 2018 49 3174. doi: 10.7501/j.issn.0253-2670.2018.13.033
	张雪琴赵庭梅刘静赵若茜郑世刚淳泽胡亚东中草药 2018 49 3174. doi: 10.7501/j.issn.0253-2670.2018.13.033
[4]	Yang H. Sung S. H. Kim Y. C. J. Nat. Prod. 2007 70 1925. doi: 10.1021/np070423f
[5]	Zhou X. M. Zheng C. J. Gan L. S. Chen G. Y. Zhang X. P. Song X. P. Li G. L. Sun C. G. J. Nat. Prod. 2016 79 1791. doi: 10.1021/acs.jnatprod.6b00252
[6]	Xiao S. J. Liu Z. Zhang M. S. Chen Y. Z. Nie X. Q. Zhang J. Y. He Y. Q. Shi J. S. Acta Pharm. Sin. 2016 51 1117.
	肖世基刘珍张茂生陈永正聂绪强张建永何芋岐石京山药学学报 2016 51 1117.
[7]	Xiao S. J. Qian Y. Zhang L. Tang Y. F. Zhu X. M. Zhou H. X. Zhao Z. N. Zhang M. S. Xu D. L. Chin. Tradit. Herb. Drugs 2016 47 2972. doi: 10.7501/j.issn.0253-2670.2016.17.002
	肖世基钱怡张良唐艳芬朱雪梅周惠黠赵忠能张茂生徐德林中草药 2016 47 2972. doi: 10.7501/j.issn.0253-2670.2016.17.002
[8]	Xiang T. Uno T. Ogino F. Ai C. Duo J. Sankawa U. Chem. Pharm. Bull. 2005 53 1204. doi: 10.1248/cpb.53.1204
[9]	Lee D. Cuendet M. Vigo J. S. Graham J. G. Cabieses F. Fong H. H. Pezzuto J. M. Kinghorn A. D. Org. Lett. 2001 3 2169. doi: 10.1021/ol015985j
[10]	Liu Q. F. Chen W. L. Tang J. Zhao W. M. Helv. Chim. Acta 2007 90 1745. doi: 10.1002/hlca.200790183
[11]	Yang D. Cheng Z. Q. Yang L. Hou B. Yang J. Li X. N. Zi C. T. Dong F. W. Liu Z. H. Zhou J. Ding Z. T. Hu J. M. J. Nat. Prod. 2018 81 227. doi: 10.1021/acs.jnatprod.7b00150
[12]	Li Y. Wang C. L. Zhao H. J. Guo S. X. J. Asian Nat. Prod. Res. 2014 16 1035. doi: 10.1080/10286020.2014.967230
[13]	Li Y. Wang C. L. Wang Y. J. Wang F. F. Guo S. X. Yang J. S. Xiao P. G. Chem. Pharm. Bull. 2009 57 997. doi: 10.1248/cpb.57.997
[14]	Termentzi A. Zervou M. Kokkalou E. Food Chem. 2009 116 371. doi: 10.1016/j.foodchem.2009.02.019
[15]	Jiang S. Wang K. Lou H. Y. Yi P. Zhang N. Zhou M. Song Z. Q. Wang W. Wu M. K. Pan W. D. Phytochemistry 2019 162 216. doi: 10.1016/j.phytochem.2019.03.022
[16]	Xiao S. J. He D. H. Fang D. M. Chen F. Ding L. S. Zhou Y. Helv. Chim. Acta 2014 97 499. doi: 10.1002/hlca.201300208
[17]	Guo D. L. Li X. H. Feng D. Jin M. Y. Cao Y. M. Cao Z. X. Gu Y. C. Geng Z. Deng F. Deng Y. Molecules 2018 23 1709. doi: 10.3390/molecules23071709
[18]	Liu H. S. Zhu G. L. Zhao S. G. Fu P. Zhu W. M. Chin. J. Org. Chem. 2019 39 507. doi: 10.6023/cjoc201806045
	刘海珊朱国良赵水鸽付鹏朱伟明有机化学 2019 39 507. doi: 10.6023/cjoc201806045

No.	1^a		2^b		3^a
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1		148.7		149.8		148.5
2		131.7		132.6		131.2
3		143.6		145.2		144.3
4	6.57 (br s)	109.3	6.43 (d, 1.8)	110.2	6.52 (d, 1.8)	109.7
5		134.3		134.7		134.5
6	6.37 (br s)	104.8	6.46 (d, 1.8)	106.0	6.34 (d, 1.8)	104.9
7	2.82~2.93 (m)	37.6	2.76~2.85 (m)	38.3	2.81~2.91 (m)	37.7
8	2.82~2.93 (m)	38.0	2.76~2.85 (m)	38.6	2.81~2.91 (m)	38.1
9		143.4		144.5		143.4
10	6.77 (br s)	114.2	6.72 (br s)	116.3	6.74 (br s)	114.5
11		159.4		158.3		159.8
12	6.75 (br d, 8.0)	111.2	6.65 (br d, 7.7)	113.7	6.75 (br d, 7.6)	111.3
13	7.22 (br t, 8.0)	129.2	7.09 (br t, 7.7)	130.1	7.21 (br t, 7.6)	129.5
14	6.81 (br d, 8.0)	120.9	6.71 (br d, 7.7)	120.5	6.79 (br d, 7.6)	121.0
1′		146.5		146.3		147.5
2′		132.5		135.1		135.4
3′		144.0		149.0		147.5
4′	6.09 (br s)	103.0	6.67 (d, 2.0)	103.8	6.68 (s)	104.3
5′		127.8		128.9		127.5
6′	6.46 (br s)	108.4	6.65 (d, 2.0)	109.4	6.68 (s)	104.3
7′	4.73 (d, 8.0)	80.5	4.88 (d, 7.9)	77.2	4.96 (d, 8.2)	76.6
8′	4.82 (d, 8.0)	80.5	3.95~4.02 (m)	79.3	3.97~3.99 (m)	78.5
9′		137.9	3.49~3.55 (m), 3.75~3.77 (m)	61.9	3.56 (dd, 12.6, 5.6), 3.90 (dd, 12.6, 2.7)	61.7
10′	6.66 (br s)	112.9
11′		159.6
12′	6.78 (br d, 8.0)	114.2
13′	7.15 (br t, 8.0)	129.3
14′	6.66 (br d, 8.0)	120.1
1-OCH₃	3.84 (s)	56.1	3.79 (s)	56.3	3.80 (s)	56.2
11-OCH₃	3.71 (s)	55.3			3.85 (s)	55.3
1'-OCH₃	3.81 (s)	56.2			3.92 (s)	56.6
3'-OCH₃			3.84 (s)	56.6	3.92 (s)	56.6
11'-OCH₃	3.67 s	55.2

No.	1^a		2^b		3^a
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1		148.7		149.8		148.5
2		131.7		132.6		131.2
3		143.6		145.2		144.3
4	6.57 (br s)	109.3	6.43 (d, 1.8)	110.2	6.52 (d, 1.8)	109.7
5		134.3		134.7		134.5
6	6.37 (br s)	104.8	6.46 (d, 1.8)	106.0	6.34 (d, 1.8)	104.9
7	2.82~2.93 (m)	37.6	2.76~2.85 (m)	38.3	2.81~2.91 (m)	37.7
8	2.82~2.93 (m)	38.0	2.76~2.85 (m)	38.6	2.81~2.91 (m)	38.1
9		143.4		144.5		143.4
10	6.77 (br s)	114.2	6.72 (br s)	116.3	6.74 (br s)	114.5
11		159.4		158.3		159.8
12	6.75 (br d, 8.0)	111.2	6.65 (br d, 7.7)	113.7	6.75 (br d, 7.6)	111.3
13	7.22 (br t, 8.0)	129.2	7.09 (br t, 7.7)	130.1	7.21 (br t, 7.6)	129.5
14	6.81 (br d, 8.0)	120.9	6.71 (br d, 7.7)	120.5	6.79 (br d, 7.6)	121.0
1′		146.5		146.3		147.5
2′		132.5		135.1		135.4
3′		144.0		149.0		147.5
4′	6.09 (br s)	103.0	6.67 (d, 2.0)	103.8	6.68 (s)	104.3
5′		127.8		128.9		127.5
6′	6.46 (br s)	108.4	6.65 (d, 2.0)	109.4	6.68 (s)	104.3
7′	4.73 (d, 8.0)	80.5	4.88 (d, 7.9)	77.2	4.96 (d, 8.2)	76.6
8′	4.82 (d, 8.0)	80.5	3.95~4.02 (m)	79.3	3.97~3.99 (m)	78.5
9′		137.9	3.49~3.55 (m), 3.75~3.77 (m)	61.9	3.56 (dd, 12.6, 5.6), 3.90 (dd, 12.6, 2.7)	61.7
10′	6.66 (br s)	112.9
11′		159.6
12′	6.78 (br d, 8.0)	114.2
13′	7.15 (br t, 8.0)	129.3
14′	6.66 (br d, 8.0)	120.1
1-OCH₃	3.84 (s)	56.1	3.79 (s)	56.3	3.80 (s)	56.2
11-OCH₃	3.71 (s)	55.3			3.85 (s)	55.3
1'-OCH₃	3.81 (s)	56.2			3.92 (s)	56.6
3'-OCH₃			3.84 (s)	56.6	3.92 (s)	56.6
11'-OCH₃	3.67 s	55.2

金钗石斛中联苄基衍生物化学成分研究

Bibenzyl Derivatives from Dendrobium nobile

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 4

References 18

Related Articles 3

Recommended Articles

Metrics

Comments

[1]	Yinghao Liu, Fangxia Lin, Yinfeng Tan, Jingyu Yang, Bin Zhang, Xueming Zhou, Xinming Song. Three New Phenanthraquinones from the Root of Dendrobium nobile [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2112-2115.
[2]	Xiao Shiji, Xu Delin, Zhang Maosheng, Lin hulang, Ding Lisheng, Zhou Shuyong, Zhou Yan. A Novel Phenanthrene-1,2-dione from Bletilla striata [J]. Chin. J. Org. Chem., 2016, 36(3): 638-641.
[3]	LI MANFEI;XU GUOJUN;WU HOUMING;PINGTIAN YIZHENG;DAN YUZHENGWU. Chemical constituents of the essential oil from dendrobium nobile lindl [J]. Chin. J. Org. Chem., 1991, 11(2): 219-220.