拟康定乌头中新的二萜生物碱及其拒食活性

doi:10.6023/cjoc202111006

有机化学 ›› 2022, Vol. 42 ›› Issue (6): 1856-1862.DOI: 10.6023/cjoc202111006 上一篇下一篇

研究简报

拟康定乌头中新的二萜生物碱及其拒食活性

黄帅^a^,^b, 冯宇明^a, 任佳俐^a, 杨传轮^c, 陈琳^a^,^b^,^*(), 周先礼^a^,^b^,^*()

a 西南交通大学生命科学与工程学院成都 610031
b 西南交通大学宜宾研究院四川宜宾 644000
c 黄河三角洲京博化工研究院有限公司山东滨州 256500

收稿日期:2021-11-03 修回日期:2022-01-28 发布日期:2022-03-03
通讯作者: 陈琳, 周先礼
基金资助:
国家自然科学基金(21807089); 四川省应用基础项目(2021YJ0222); 四川省应用基础项目(2020YJ0288); 中央高校基本科研业务费专项(2682021CX085); 教育部产学合作协同育人(202102414025); 教育部产学合作协同育人(202102414026)

Diterpenoid Alkaloids from the Roots of Aconitum rockii and Their Antifeedant Activity

Shuai Huang^a^,^b, Yuming Feng^a, Jiali Ren^a, Chuanlun Yang^c, Lin Chen^a^,^b(), Xianli Zhou^a^,^b()

a School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
b Yibin Institute of Southwest, Jiaotong University, Yibin, Sichuan 644000
c Chambroad Chemical Industry Research Institute Co., Ltd, Binzhou, Shandong 256500

Received:2021-11-03 Revised:2022-01-28 Published:2022-03-03
Contact: Lin Chen, Xianli Zhou
Supported by:
National Natural Science Foundation of China(21807089); Science and Technology Support Programs of Sichuan Province(2021YJ0222); Science and Technology Support Programs of Sichuan Province(2020YJ0288); Fundamental Research Funds for Central Universities(2682021CX085); Industry-University Cooperation Collaborative Education Projects of Ministry of Education(202102414025); Industry-University Cooperation Collaborative Education Projects of Ministry of Education(202102414026)

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摘要/Abstract

为了发现更多结构新颖活性优异的二萜生物碱, 继续对拟康定乌头化学成分进行研究, 从其乙醇提取物中分离得到4个新化合物, 通过HR-ESI-MS, 1D和2D NMR等波谱技术鉴定了结构, 分别为rockidines A~C (1~3)和rockisine A (4). 同时考察了化合物1~4及前期分离得到的二萜生物碱(5~14)对甜菜夜蛾3龄幼虫的拒食活性, 结果表明化合物13的拒食活性较好(EC₅₀=0.13 mg/cm²).

关键词: 毛茛科, 拟康定乌头, 二萜生物碱, 拒食活性

As part of our ongoing research program toward discovering structurally intriguing and biologically important diterpenoid alkaloids from the Aconitum genera, four new diterpenoid alkaloids, including three C₁₉-diterpenoid alkaloids (rockidines A~C) and one C₂₀-diterpenoid alkaloid (rockisine A) were isolated from the roots of Aconitum rockii Fletcher et Lauener in this paper. Their structures were elucidated on the basis of spectroscopic analyses (HR-ESI-MS, NMR and IR). All the new compounds 1~4, alone with ten known compounds 5~14 isolated in our previous work, were evaluated for their antifeedant activities, and compound 13 showed highly potent antifeedant activity with an effective concentration for 50% feeding reduction (EC₅₀) at 0.13 mg/cm².

Key words: Ranunculaceae, Aconitum rockii, diterpenoid alkaloids, antifeedant activity

引用此文

黄帅, 冯宇明, 任佳俐, 杨传轮, 陈琳, 周先礼. 拟康定乌头中新的二萜生物碱及其拒食活性[J]. 有机化学, 2022, 42(6): 1856-1862.

Shuai Huang, Yuming Feng, Jiali Ren, Chuanlun Yang, Lin Chen, Xianli Zhou. Diterpenoid Alkaloids from the Roots of Aconitum rockii and Their Antifeedant Activity[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1856-1862.

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参考文献 26

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No.	1 (in CDCl₃)		2 (in CDCl₃)
No.	δ_H	δ_C,	δ_H	δ_C,
1	3.08~3.12, m	86.1, d	3.98, br.s	71.6, d
2	1.89~1.96 (m, H_α)	26.5, t	1.49~1.55 (m, H_α)	28.7, t
2	2.26~2.36 (m, H_β)	26.5, t	1.74~1.82 (m, H_β)	28.7, t
3	1.18~1.27 (m, H_α)	37.8, t	1.80~1.88 (m, H_α)	29.3, t
3	1.60~1.67 (m, H_β)	37.8, t	1.51~1.55 (m, H_β)	29.3, t
4	—	34.5, s	—	38.1, s
5	1.43 (d, J=7.2 Hz)	50.9, d	2.19~2.24, m	45.9, d
6	1.90~1.98 (m, H_α)	25.3, t	4.75 (d, J=8.0 Hz)	72.5, d
6	1.45~1.54 (m, H_β)	25.3, t	4.75 (d, J=8.0 Hz)	72.5, d
7	1.72~1.80, m	46.0, d	3.18, s	50.7, d
8	—	73.4, s	—	85.1, s
9	2.06~2.12, m	46.8, d	2.21~2.25, m	43.1, d
10	2.33 (t, J=5.2 Hz)	45.5, d	2.69~2.74, m	43.1, d
11	—	48.9, s	—	50.7, s
12	2.14~2.20 (m, H_α)	28.5, t	1.94~2.20 (m, H_α)	29.3, t
12	1.88~1.96 (m, H_β)	28.5, t	1.75~1.84 (m, H_β)	29.3, t
13	2.17~2.24, m	40.5, d	2.59 (t, J=8.0 Hz)	38.8, d
14	4.23 (d, J=5.2 Hz)	75.1, d	5.09 (t, J=4.0 Hz)	75.7, d
15	1.91~1.99 (m, H_α)	40.0, t	2.22~2.28 (m, H_α)	38.6, t
15	2.54~2.64 (m, H_β)	40.0, t	2.83~2.95 (m, H_β)	38.6, t
16	4.87 (t, J=9.6 Hz)	74.6, d	3.53 (t, J=8.0 Hz)	82.1, d
17	3.06, s	62.2, d	3.12, s	64.0, d
18	0.78, s	26.3, q	3.33 (d, J=8.4, H_α)	80.0, t
18	0.78, s	26.3, q	3.69 (d, J=8.4, H_β)	80.0, t
19	2.48 (d, J=12.0, H_α)	56.8, t	2.77 (d, J=11.4, H_α)	57.1, t
19	2.06 (d, J=12.0, H_β)	56.8, t	3.08 (d, J=11.4, H_β)	57.1, t
21	2.32~2.42 (m, H_a)	49.3, t	2.92~2.98 (m, H_a)	49.2, t
21	2.47~2.55 (m, H_b)	49.3, t	2.96~3.05 (m, H_b)	49.2, t
22	1.07 (t, J=6.8 Hz)	13.6 q	1.35 (t, J=6.8 Hz)	11.9, q
1-OMe	3.26, s	56.2, q	—
16-OMe	—	—	3.41, s	56.9, q
18-OMe	—	—	3.29, s	59.5, q
8-OAc	—	—	—	170.1, s
8-OAc	—	—	1.44, s	21.6, q
16-OAc	—	169.8, s	—
16-OAc	2.06, s	21.5, q	—
14-OCO	—	—	—	166.2, s
1'	—	—	—	130.1, s
2'/6'	—	—	8.02 (t, J=8.0 Hz)	128.7, d
3'/5'	—	—	7.42 (t, J=7.6 Hz)	129.7, d
4'	—	—	7.54 (t, J=7.6 Hz)	133.3, d

No.	1 (in CDCl₃)		2 (in CDCl₃)
No.	δ_H	δ_C,	δ_H	δ_C,
1	3.08~3.12, m	86.1, d	3.98, br.s	71.6, d
2	1.89~1.96 (m, H_α)	26.5, t	1.49~1.55 (m, H_α)	28.7, t
2	2.26~2.36 (m, H_β)	26.5, t	1.74~1.82 (m, H_β)	28.7, t
3	1.18~1.27 (m, H_α)	37.8, t	1.80~1.88 (m, H_α)	29.3, t
3	1.60~1.67 (m, H_β)	37.8, t	1.51~1.55 (m, H_β)	29.3, t
4	—	34.5, s	—	38.1, s
5	1.43 (d, J=7.2 Hz)	50.9, d	2.19~2.24, m	45.9, d
6	1.90~1.98 (m, H_α)	25.3, t	4.75 (d, J=8.0 Hz)	72.5, d
6	1.45~1.54 (m, H_β)	25.3, t	4.75 (d, J=8.0 Hz)	72.5, d
7	1.72~1.80, m	46.0, d	3.18, s	50.7, d
8	—	73.4, s	—	85.1, s
9	2.06~2.12, m	46.8, d	2.21~2.25, m	43.1, d
10	2.33 (t, J=5.2 Hz)	45.5, d	2.69~2.74, m	43.1, d
11	—	48.9, s	—	50.7, s
12	2.14~2.20 (m, H_α)	28.5, t	1.94~2.20 (m, H_α)	29.3, t
12	1.88~1.96 (m, H_β)	28.5, t	1.75~1.84 (m, H_β)	29.3, t
13	2.17~2.24, m	40.5, d	2.59 (t, J=8.0 Hz)	38.8, d
14	4.23 (d, J=5.2 Hz)	75.1, d	5.09 (t, J=4.0 Hz)	75.7, d
15	1.91~1.99 (m, H_α)	40.0, t	2.22~2.28 (m, H_α)	38.6, t
15	2.54~2.64 (m, H_β)	40.0, t	2.83~2.95 (m, H_β)	38.6, t
16	4.87 (t, J=9.6 Hz)	74.6, d	3.53 (t, J=8.0 Hz)	82.1, d
17	3.06, s	62.2, d	3.12, s	64.0, d
18	0.78, s	26.3, q	3.33 (d, J=8.4, H_α)	80.0, t
18	0.78, s	26.3, q	3.69 (d, J=8.4, H_β)	80.0, t
19	2.48 (d, J=12.0, H_α)	56.8, t	2.77 (d, J=11.4, H_α)	57.1, t
19	2.06 (d, J=12.0, H_β)	56.8, t	3.08 (d, J=11.4, H_β)	57.1, t
21	2.32~2.42 (m, H_a)	49.3, t	2.92~2.98 (m, H_a)	49.2, t
21	2.47~2.55 (m, H_b)	49.3, t	2.96~3.05 (m, H_b)	49.2, t
22	1.07 (t, J=6.8 Hz)	13.6 q	1.35 (t, J=6.8 Hz)	11.9, q
1-OMe	3.26, s	56.2, q	—
16-OMe	—	—	3.41, s	56.9, q
18-OMe	—	—	3.29, s	59.5, q
8-OAc	—	—	—	170.1, s
8-OAc	—	—	1.44, s	21.6, q
16-OAc	—	169.8, s	—
16-OAc	2.06, s	21.5, q	—
14-OCO	—	—	—	166.2, s
1'	—	—	—	130.1, s
2'/6'	—	—	8.02 (t, J=8.0 Hz)	128.7, d
3'/5'	—	—	7.42 (t, J=7.6 Hz)	129.7, d
4'	—	—	7.54 (t, J=7.6 Hz)	133.3, d

No.	3 (in CDCl₃)		4 (in CDCl₃)
No.	δ_H	δ_C,	δ_H	δ_C,
1	3.28~3.39, m	85.7, d	5.85 (d, J=8.0 Hz)	70.3, d
2	2.46~2.55 (m, H_α)	23.3, t	5.76~5.79, m	66.8, d
2	1.91~1.97 (m, H_β)	23.3, t	5.76~5.79, m	66.8, d
3	1.74~1.81 (m, H_α)	31.7, t	1.73 (dd, J=3.6, 4.0 Hz, H_α)	30.2, t
3	1.51~1.62 (m, H_β)	31.7, t	1.37 (s, H_β)	30.2, t
4	—	36.4, s	—	43.9, s
5	2.31, s	46.9, d	2.03, s	60.7, d
6	4.42 (d, J=6.0 Hz)	73.9, d	3.04, s	57.0, d
7	5.77 (d, J=5.6 Hz)	127.8, d	1.87 (dd, J=3.6, 4.0 Hz, H_α)	32.6, t
7	5.77 (d, J=5.6 Hz)	127.8, d	1.48~1.54 (m, H_β)	32.6, t
8	—	135.9, s	—	45.3, s
9	3.06 (d, J=9.2 Hz)	42.0, d	2.45 (dd, J=2.0, 2.4 Hz, H_α)	54.4, d
10	2.42~2.49, m	48.4, d	—	56.5, s
11	—	49.6, s	5.48 (d, J=12.0 Hz)	75.1, d
12	2.04~2.13 (m, H_α)	29.1, t	2.55 (d, J=2.0 Hz)	45.5, d
12	1.51~1.60 (m, H_β)	29.1, t	2.55 (d, J=2.0 Hz)	45.5, d
13	2.60~2.66, m	37.1, d	5.26~5.32, m	74.1, d
14	5.11, s	77.4, d	2.82 (dd, J=2.0, 2.4 Hz)	42.8, d
15	2.90~2.97 (m, H_α)	37.5, t	2.20~2.28 (m, H_α)	34.2, t
15	2.50~2.57 (m, H_β)	37.5, t	2.35~2.41 (m, H_β)	34.2, t
16	3.35, s	85.0, d	—	142.0, s
17	4.40, s	91.6, d	4.89 (s, H_a)	111.0, t
17	4.40, s	91.6, d	5.03 (s, H_b)	111.0, t
18	3.16 (d, J=9.2 Hz, H_α)	78.0, t	1.06, s	26.1, q
18	3.02 (s, H_β)	78.0, t	1.06, s	26.1, q
19	2.47 (s, H_α)	51.0, t	9.08, s	191.5, d
19	2.03 (d, J=12.8 Hz, H_β)	51.0, t	9.08, s	191.5, d
20	—	—	3.88, s	64.3, d
21	2.34~2.44 (m, H_α)	48.2, t	2.28, s	32.5, q
21	2.52~2.65 (m, H_β)	48.2, t	2.28, s	32.5, q
22	1.01 (t, J=7.2 Hz)	12.1, q	—	—
1-OMe	3.37, s	56.2, q	—	—
16-OMe	3.30, s	55.2, q	—	—
18-OMe	3.30, s	58.5, q	—	—
2-OCO	—	—	—	164.6, s
13-OCO	—	—	—	165.9, s
14-OCO	—	165.4, s	—	—
1-OAc	—	—	—	169.7, s
1-OAc	—	—	2.06, s	21.6, q
11-OAc	—	—	—	171.1, s
11-OAc	—	—	2.01, s	21.3, q
1'	—	121.2, s	—	128.8, s
2'/6'	7.87 (d, J=8.8 Hz)	130.9, d	7.76 (d, J=4.0 Hz)	129.2, d
3'/5'	6.73 (d, J=8.8 Hz)	114.1, d	7.28 (overlapped)	128.2, d
4'	—	159.6, s	7.45 (t, J=7.2 Hz)	132.8, d
1''	—	—	—	129.0, s
2''/6''	—	—	7.54 (d, J=1.2 Hz)	129.4, d
3''/5''	—	—	7.07 (t, J=8.0 Hz)	128.2, d
4''	—	—	7.28 (overlapped)	133.1, d

No.	3 (in CDCl₃)		4 (in CDCl₃)
No.	δ_H	δ_C,	δ_H	δ_C,
1	3.28~3.39, m	85.7, d	5.85 (d, J=8.0 Hz)	70.3, d
2	2.46~2.55 (m, H_α)	23.3, t	5.76~5.79, m	66.8, d
2	1.91~1.97 (m, H_β)	23.3, t	5.76~5.79, m	66.8, d
3	1.74~1.81 (m, H_α)	31.7, t	1.73 (dd, J=3.6, 4.0 Hz, H_α)	30.2, t
3	1.51~1.62 (m, H_β)	31.7, t	1.37 (s, H_β)	30.2, t
4	—	36.4, s	—	43.9, s
5	2.31, s	46.9, d	2.03, s	60.7, d
6	4.42 (d, J=6.0 Hz)	73.9, d	3.04, s	57.0, d
7	5.77 (d, J=5.6 Hz)	127.8, d	1.87 (dd, J=3.6, 4.0 Hz, H_α)	32.6, t
7	5.77 (d, J=5.6 Hz)	127.8, d	1.48~1.54 (m, H_β)	32.6, t
8	—	135.9, s	—	45.3, s
9	3.06 (d, J=9.2 Hz)	42.0, d	2.45 (dd, J=2.0, 2.4 Hz, H_α)	54.4, d
10	2.42~2.49, m	48.4, d	—	56.5, s
11	—	49.6, s	5.48 (d, J=12.0 Hz)	75.1, d
12	2.04~2.13 (m, H_α)	29.1, t	2.55 (d, J=2.0 Hz)	45.5, d
12	1.51~1.60 (m, H_β)	29.1, t	2.55 (d, J=2.0 Hz)	45.5, d
13	2.60~2.66, m	37.1, d	5.26~5.32, m	74.1, d
14	5.11, s	77.4, d	2.82 (dd, J=2.0, 2.4 Hz)	42.8, d
15	2.90~2.97 (m, H_α)	37.5, t	2.20~2.28 (m, H_α)	34.2, t
15	2.50~2.57 (m, H_β)	37.5, t	2.35~2.41 (m, H_β)	34.2, t
16	3.35, s	85.0, d	—	142.0, s
17	4.40, s	91.6, d	4.89 (s, H_a)	111.0, t
17	4.40, s	91.6, d	5.03 (s, H_b)	111.0, t
18	3.16 (d, J=9.2 Hz, H_α)	78.0, t	1.06, s	26.1, q
18	3.02 (s, H_β)	78.0, t	1.06, s	26.1, q
19	2.47 (s, H_α)	51.0, t	9.08, s	191.5, d
19	2.03 (d, J=12.8 Hz, H_β)	51.0, t	9.08, s	191.5, d
20	—	—	3.88, s	64.3, d
21	2.34~2.44 (m, H_α)	48.2, t	2.28, s	32.5, q
21	2.52~2.65 (m, H_β)	48.2, t	2.28, s	32.5, q
22	1.01 (t, J=7.2 Hz)	12.1, q	—	—
1-OMe	3.37, s	56.2, q	—	—
16-OMe	3.30, s	55.2, q	—	—
18-OMe	3.30, s	58.5, q	—	—
2-OCO	—	—	—	164.6, s
13-OCO	—	—	—	165.9, s
14-OCO	—	165.4, s	—	—
1-OAc	—	—	—	169.7, s
1-OAc	—	—	2.06, s	21.6, q
11-OAc	—	—	—	171.1, s
11-OAc	—	—	2.01, s	21.3, q
1'	—	121.2, s	—	128.8, s
2'/6'	7.87 (d, J=8.8 Hz)	130.9, d	7.76 (d, J=4.0 Hz)	129.2, d
3'/5'	6.73 (d, J=8.8 Hz)	114.1, d	7.28 (overlapped)	128.2, d
4'	—	159.6, s	7.45 (t, J=7.2 Hz)	132.8, d
1''	—	—	—	129.0, s
2''/6''	—	—	7.54 (d, J=1.2 Hz)	129.4, d
3''/5''	—	—	7.07 (t, J=8.0 Hz)	128.2, d
4''	—	—	7.28 (overlapped)	133.1, d

Compd.	EC₅₀/(mg•cm^–2)	95% confidence limits
1	4.03	3.05~5.72
2	0.32	0.15~0.51
3	0.79	0.52~1.06
4	24.13	13.17~79.15
5	7.08	3.94~30.59
6	0.64	0.16~1.15
7	4.46	3.68~6.21
8	0.38	0.02~0.88
9	0.24	0.24~0.55
10	7.43	4.29~26.12
11	0.61	0.12~1.16
12	0.42	0.15~0.72
13	0.13	0.01~0.38
14	0.35	0.13~0.60
AZA^a	0.02	0.01~0.08

拟康定乌头中新的二萜生物碱及其拒食活性

Diterpenoid Alkaloids from the Roots of Aconitum rockii and Their Antifeedant Activity

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