金钗石斛中联苄基衍生物化学成分研究

doi:10.6023/cjoc201903035

有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3289-3293.DOI: 10.6023/cjoc201903035 上一篇下一篇

研究简报

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)

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摘要/Abstract

通过硅胶和MCI柱色谱以及制备液相色谱等分离方法从金钗石斛中分离得到3个联苄基类衍生物，其中化合物1为外消旋的双联苄基衍生物，进一步通过手性拆分得到一对对映异构体1a和1b，通过计算所得的电子圆二色谱（ECD）谱图与实测的ECD谱图进行比较得出1a和1b的绝对构型.经高分辨质谱和核磁共振等波谱技术确立化合物1~3的结构分别为二聚体石斛素A（1）、金钗石斛素B（2）和金钗石斛素C（3）.

关键词: 金钗石斛, 兰科, 联苄基衍生物, 金钗石斛素

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

引用此文

张茂生, 令狐浪, 张建永, 聂绪强, 李晓飞, 郭大乐, 肖世基. 金钗石斛中联苄基衍生物化学成分研究[J]. 有机化学, 2019, 39(11): 3289-3293.

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.

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参考文献 18

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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

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