Three New Phenanthraquinones from the Root of Dendrobium nobile

doi:10.6023/cjoc202012005

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2112-2115.DOI: 10.6023/cjoc202012005 Previous Articles Next Articles

NOTES

石斛根中三个新的菲醌类化合物

刘英豪^a^,^c, 林芳霞^a^,^c, 谭银丰^b, 杨静雨^a^,^c, 张斌^a^,^c, 周学明^a^,^c^,^*(), 宋鑫明^a^,^c^,^*()

a 海南师范大学化学与化工学院热带药用资源化学教育部重点实验室海口 571158
b 海南医学院海南省热带药用植物研究开发重点实验室海口 570216
c 海南师范大学化学与化工学院热带药用植物化学海南省重点实验室海口 571158

收稿日期:2020-12-01 修回日期:2020-12-28 发布日期:2021-02-07
通讯作者: 周学明, 宋鑫明
基金资助:
海南省自然科学基金(218QN234); 海南省热带药用植物研究开发重点实验室开放研究(KF202002); 国家自然科学基金(21662012); 国家自然科学基金(41866005); 以及教育部创新研究团队(IRT-16R19)

Three New Phenanthraquinones from the Root of Dendrobium nobile

Yinghao Liu^a^,^c, Fangxia Lin^a^,^c, Yinfeng Tan^b, Jingyu Yang^a^,^c, Bin Zhang^a^,^c, Xueming Zhou^a^,^c^,^*(), Xinming Song^a^,^c^,^*()

a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158
b Hainan Provincial Key Laboratory of Research and Development on Tropical Herbs, Hainan Medical College, Haikou 570216
c Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2020-12-01 Revised:2020-12-28 Published:2021-02-07
Contact: Xueming Zhou, Xinming Song
About author:
* Corresponding authors. E-mail: xueming2009211@126.com;
E-mail: sxm8646@163.com
Supported by:
Natural Science Foundation of Hainan Province(218QN234); Open Research Projects of Hainan Provincial Key Laboratory of Research and Development on Tropical Herbs(KF202002); National Natural Science Foundation of China(21662012); National Natural Science Foundation of China(41866005); Innovative Research Team Project of Ministry of Education(IRT-16R19)

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Abstract

Three new phenanthraquinones, phenanobiles A~C (1~3), together with two known phenanthraquinones 6,7-dihydroxy-2-methoxy-1,4-phenanthrenedione (4) and ephemeranthoquinone (5), were isolated from the root of Dendrobium nobile. Their structures were elucidated using comprehensive spectroscopic methods. The antitumor activities of compounds 1~5 were evaluated against three cancer cell lines (HL-60, A549 and MCF-7). Compounds 1~5 exhibited inhibitory effects against three cancer cell lines HeLa, MCF-7 and A549in vitro.

Key words: Dendrobium, Dendrobium nobile, phenanthraquinone, antitumor activity

Cite this article

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.

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Fig. & Tab. 4

References 12

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Position	1 (DMSO-d₆)		2 (DMSO-d₆)		3 (CD₃OD)
Position	δ_H (Jin Hz)	δ_C	δ_H (Jin Hz)	δ_C	δ_H (Jin Hz)	δ_C
1	—	182.9	—	180.2	—	183.3
2	—	156.3	—	156.9	—	169.4
3	6.90 (s, 1H)	112.6	6.94 (s, 1H)	111.3	5.93 (s, 1H)	109.0
4	—	182.9	—	188.2	—	189.6
4a	—	124.7	—	124.1	—	137.7
4b	—	125.5	—	124.9	—	122.6
5	8.99 (s, 1H)	109.9	8.87 (s, 1H)	105.6	7.94 (d, 9.2, 1H)	133.7
6	—	151.4	—	153.7	6.72 (dd, 9.2, 2.4, 1H)	115.2
7	—	149.8	—	152.1	—	161.4
8	7.26 (s, 1H)	110.7	7.20 (s, 1H)	107.2	6.71 (d, 2.4, 1H)	116.4
8a	—	128.9	—	128.3	—	138.8
9	8.02 (d, 8.8, 1H)	132.0	8.11 (d, 9.2, 1H)	131.4	2.63~2.68 (m, 2H)	21.7
10	7.84 (d, 8.8, 1H)	119.4	7.61 (d, 9.2, 1H)	118.7	2.73~2.77 (m, 2H)	29.1
10a	—	134.3	—	133.7	—	146.6
6-OMe	—	—	3.85 (s, 3H)	56.0	—	—
7-OMe	—	—	3.82 (s, 3H)	56.1	—	—

Position	1 (DMSO-d₆)		2 (DMSO-d₆)		3 (CD₃OD)
Position	δ_H (Jin Hz)	δ_C	δ_H (Jin Hz)	δ_C	δ_H (Jin Hz)	δ_C
1	—	182.9	—	180.2	—	183.3
2	—	156.3	—	156.9	—	169.4
3	6.90 (s, 1H)	112.6	6.94 (s, 1H)	111.3	5.93 (s, 1H)	109.0
4	—	182.9	—	188.2	—	189.6
4a	—	124.7	—	124.1	—	137.7
4b	—	125.5	—	124.9	—	122.6
5	8.99 (s, 1H)	109.9	8.87 (s, 1H)	105.6	7.94 (d, 9.2, 1H)	133.7
6	—	151.4	—	153.7	6.72 (dd, 9.2, 2.4, 1H)	115.2
7	—	149.8	—	152.1	—	161.4
8	7.26 (s, 1H)	110.7	7.20 (s, 1H)	107.2	6.71 (d, 2.4, 1H)	116.4
8a	—	128.9	—	128.3	—	138.8
9	8.02 (d, 8.8, 1H)	132.0	8.11 (d, 9.2, 1H)	131.4	2.63~2.68 (m, 2H)	21.7
10	7.84 (d, 8.8, 1H)	119.4	7.61 (d, 9.2, 1H)	118.7	2.73~2.77 (m, 2H)	29.1
10a	—	134.3	—	133.7	—	146.6
6-OMe	—	—	3.85 (s, 3H)	56.0	—	—
7-OMe	—	—	3.82 (s, 3H)	56.1	—	—

Compd.	IC₅₀/(μmol?L^–1)
Compd.	HL-60	A549	MCF-7
1	5.21±0.17	3.21±0.12	9.52±0.11
2	15.18±0.14	21.56±0.08	31.51±0.13
3	11.28±0.09	30.12±0.06	29.12±0.10
4	8.99±0.11	21.03±0.12	30.88±0.12
5	86±0.14	31.11±0.11	28.89±0.09
阿霉素	0.36±0.11	2.18±0.08	5.66±0.12

Compd.	IC₅₀/(μmol?L^–1)
Compd.	HL-60	A549	MCF-7
1	5.21±0.17	3.21±0.12	9.52±0.11
2	15.18±0.14	21.56±0.08	31.51±0.13
3	11.28±0.09	30.12±0.06	29.12±0.10
4	8.99±0.11	21.03±0.12	30.88±0.12
5	86±0.14	31.11±0.11	28.89±0.09
阿霉素	0.36±0.11	2.18±0.08	5.66±0.12

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石斛根中三个新的菲醌类化合物

Three New Phenanthraquinones from the Root of Dendrobium nobile

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