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

doi:10.6023/cjoc202111006

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1856-1862.DOI: 10.6023/cjoc202111006 Previous Articles Next Articles

NOTES

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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Abstract

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

Cite this article

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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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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[2]	Chen Lin, Wang Qian, Huang Shuai, Shan Lianhai, Gao Feng, Zhou Xianli. Diterpenoid Alkaloids from Aconitum leucostomum and Their Antifeedant Activity [J]. Chin. J. Org. Chem., 2017, 37(7): 1839-1843.
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