拟热带灵芝中杂萜类化学成分及其蛋白酪氨酸磷酸酶1B抑制活性

doi:10.6023/cjoc201905010

有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3264-3268.DOI: 10.6023/cjoc201905010 上一篇下一篇

研究简报

拟热带灵芝中杂萜类化学成分及其蛋白酪氨酸磷酸酶1B抑制活性

郭教岑^a^b, 马青云^b, 孔凡栋^b, 谢晴宜^b, 周丽曼^b, 丁琼^a, 吴友根^a*(), 赵友兴^b*()

^a海南大学园艺学院海口 570228
^b 中国热带农业科学院热带生物技术研究所海南省黎药资源天然产物研究与利用重点实验室海口 571101

收稿日期:2019-05-07 发布日期:2019-07-24
通讯作者: 吴友根,赵友兴 E-mail:wygeng2003@163.com;zhaoyouxing@itbb.org.cn
基金资助:
海南省自然科学基金(219MS078);海南省自然科学基金(2019CXTD411);现代农业产业技术体系建设专项(CARS-21);中国热带农业科学院基本科研业务(17CXTD-15);中国热带农业科学院基本科研业务(1630052016008)

Meroterpenoids from the Fruiting Bodies of Ganoderma ahmadii Steyaret and Their Protein Tyrosine Phosphatase 1B Inhibitory Activities

Guo Jiaocen^a^b, Ma Qingyun^b, Kong Fangdong^b, Xie Qingyi^b, Zhou Liman^b, Ding Qiong^a, Wu Yougen^a*(), Zhao Youxing^b*()

^a College of Horticulture, Hainan University, Haikou 570228
^b Hainan Key Laboratory for Research and Development of Natural Product from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences, Haikou 571101

Received:2019-05-07 Published:2019-07-24
Contact: Wu Yougen,Zhao Youxing E-mail:wygeng2003@163.com;zhaoyouxing@itbb.org.cn
Supported by:
the Natural Science Foundation of Hainan Province(219MS078);the Natural Science Foundation of Hainan Province(2019CXTD411);the China Agriculture Research System(CARS-21);the Central Public-interest Scientific Institution Basal Research Fund for Chinese Academy of Tropical Agricultural Sciences(17CXTD-15);the Central Public-interest Scientific Institution Basal Research Fund for Chinese Academy of Tropical Agricultural Sciences(1630052016008)

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摘要/Abstract

利用硅胶柱层析和半制备高效液相色谱（HPLC）等色谱分离技术对拟热带灵芝的化学成分进行分离纯化，从中分离得到了3个新的酚酸杂萜类化合物（ganoduriporols C~E）.运用NMR和HRESIMS等多种波谱技术鉴定了它们的结构.对所分离的化合物进行体外PTP1B抑制活性测试，结果显示所得化合物具有明显的蛋白酪氨酸磷酸酶1B（PTP1B）抑制活性，其IC₅₀值分别为19.1，17.8和29.6 μmol·L^-1.

关键词: 拟热带灵芝, 杂萜成分, PTP1B抑制活性

Three new meroterpenoids of ganoduriporols C~E were isolated from the fruiting bodies of Ganoderma ahmadii Steyaret by silica gel column, high performance liquid chromatography (HPLC) and other chromatography methods. Their structures were determined by spectroscopic techniques including NMR and HR-ESI-MS. Their inhibitory activities for protein tyrosine phosphatase 1B (PTP1B) in vitro were tested. The results showed that the three compounds had obvious PTP1B inhibitory activitiy with the IC₅₀ values of 19.1, 17.81, and 29.6 μmol·L^-1, respectively.

Key words: Ganoderma ahmadii Steyaret, meroterpenoid compound, PTP1B inhibitory effect

引用此文

郭教岑, 马青云, 孔凡栋, 谢晴宜, 周丽曼, 丁琼, 吴友根, 赵友兴. 拟热带灵芝中杂萜类化学成分及其蛋白酪氨酸磷酸酶1B抑制活性[J]. 有机化学, 2019, 39(11): 3264-3268.

Guo Jiaocen, Ma Qingyun, Kong Fangdong, Xie Qingyi, Zhou Liman, Ding Qiong, Wu Yougen, Zhao Youxing. Meroterpenoids from the Fruiting Bodies of Ganoderma ahmadii Steyaret and Their Protein Tyrosine Phosphatase 1B Inhibitory Activities[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3264-3268.

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No.	1		2		3
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	157.2 (s)		157.2 (s)		156.5 (s)
2	121.3 (s)		121.3 (s)		120.4 (s)
3	115.8 (d)	7.12 (d, J＝2.9 Hz)	115.8 (d)	7.10 (d, J＝3.0 Hz)	115.6 (d)	7.32 (d, J＝2.5 Hz)
4	150.8 (s)		150.8 (s)		150.6 (s)
5	126.7 (d)	7.01 (dd, J＝9.0, 2.9 Hz)	126.7 (d)	6.99 (dd, J＝9.0, 3.0 Hz)	125.9 (d)	6.98 (dd, J＝9.0, 2.5 Hz)
6	119.9 (d)	6.81 (d, J＝9.0 Hz)	119.9 (d)	6.78 (d, J＝9.0 Hz)	119.7 (d)	6.75 (d, J＝9.0 Hz)
1'	198.8 (s)		198.8 (s)		204.3 (s)
2'	132.3 (d)	7.64 (s)	132.2 (d)	7.62 (s)	37.5 (t)	4.04 (s)
3'	146.9 (s)		146.5 (s)		127.4 (s)
4'	29.7 (t)	2.55 (t, J＝7.7 Hz)	29.7 (t)	2.52 (t, J＝7.0 Hz)	147.6 (d)	7.05 (t, J＝7.5 Hz)
5'	27.6 (t)	1.54~1.49 (m)	27.5 (t)	1.51~1.45, (m)	27.5 (t)	2.23~2.16 (m)
6'	31.3 (t)	1.40 (overlap), 1.28 (overlap)	31.3 (t)	1.33 (overlap), 1.25 (overlap)	30.8 (t)	1.54~1.1.48 (m), 1.39 (overlap)
7'	40.7 (d)	1.43~1.37 (m)	40.7 (d)	1.41~1.36 (m)	40.7 (d)	1.43~1.47 (m)
8'	31.7 (t)	1.40 (overlap), 1.28 (overlap)	31.7 (t)	1.33 (overlap), 1.25 (overlap)	31.4 (t)	1.39 (overlap), 1.27~1.31 (m)
9'	25.9 (t)	2.07~2.01 (m)	25.9 (t)	2.03~1.96 (m)	26.0 (t)	2.06~2.02 (m)
10'	130.8 (d)	5.46 (t, J＝7.3 Hz)	130.9 (d)	5.39 (t, J＝7.2 Hz)	130.5 (d)	5.43 (t, J＝7.1 Hz)
11'	131.5 (s)		131.3 (s)		131.6 (s)
12'	71.2 (t)	4.52 (s)	71.0 (t)	4.44 (s)	71.1 (t)	4.49 (s)
13'	14.1 (q)	1.66 (s)	14.1 (q)	1.57 (s)	14.1 (q)	1.63 (s)
14'	170.8 (s)		170.4 (s)		170.6 (s)
15'	65.4 (t)	3.40~3.44 (m)	65.4 (t)	3.41~3.37 (m)	65.1 (t)	3.46~3.42 (m)
1"	169.2 (s)		168.3 (s)		169.2 (s)
2"	115.2 (d)	6.30 (d, J＝15.8 Hz)	116.8 (d)	5.71 (d, J＝12.8 Hz)	115.1 (d)	6.29 (d, J＝16.0 Hz)
3"	146.5 (d)	7.57 (d, J＝15.8 Hz)	144.8 (d)	6.80 (d, J＝12.8 Hz)	146.5 (d)	7.56 (d, J＝16.0 Hz)
4"	127.1 (s)		127.7 (s)		127.1 (s)
5"/9"	131.2 (d)	7.42 (d, J＝8.5 Hz)	133.5 (d)	7.54 (d, J＝8.6 Hz)	131.2 (d)	7.42 (d, J＝8.1 Hz)
6"/8"	116.8 (d)	6.77 (d, J＝8.5 Hz)	115.8 (d)	6.68 (d, J＝8.6 Hz)	116.8 (d)	6.77 (d, J＝8.1 Hz)
7"	161.2 (s)		160.0 (s)		161.2 (s)

No.	1		2		3
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	157.2 (s)		157.2 (s)		156.5 (s)
2	121.3 (s)		121.3 (s)		120.4 (s)
3	115.8 (d)	7.12 (d, J＝2.9 Hz)	115.8 (d)	7.10 (d, J＝3.0 Hz)	115.6 (d)	7.32 (d, J＝2.5 Hz)
4	150.8 (s)		150.8 (s)		150.6 (s)
5	126.7 (d)	7.01 (dd, J＝9.0, 2.9 Hz)	126.7 (d)	6.99 (dd, J＝9.0, 3.0 Hz)	125.9 (d)	6.98 (dd, J＝9.0, 2.5 Hz)
6	119.9 (d)	6.81 (d, J＝9.0 Hz)	119.9 (d)	6.78 (d, J＝9.0 Hz)	119.7 (d)	6.75 (d, J＝9.0 Hz)
1'	198.8 (s)		198.8 (s)		204.3 (s)
2'	132.3 (d)	7.64 (s)	132.2 (d)	7.62 (s)	37.5 (t)	4.04 (s)
3'	146.9 (s)		146.5 (s)		127.4 (s)
4'	29.7 (t)	2.55 (t, J＝7.7 Hz)	29.7 (t)	2.52 (t, J＝7.0 Hz)	147.6 (d)	7.05 (t, J＝7.5 Hz)
5'	27.6 (t)	1.54~1.49 (m)	27.5 (t)	1.51~1.45, (m)	27.5 (t)	2.23~2.16 (m)
6'	31.3 (t)	1.40 (overlap), 1.28 (overlap)	31.3 (t)	1.33 (overlap), 1.25 (overlap)	30.8 (t)	1.54~1.1.48 (m), 1.39 (overlap)
7'	40.7 (d)	1.43~1.37 (m)	40.7 (d)	1.41~1.36 (m)	40.7 (d)	1.43~1.47 (m)
8'	31.7 (t)	1.40 (overlap), 1.28 (overlap)	31.7 (t)	1.33 (overlap), 1.25 (overlap)	31.4 (t)	1.39 (overlap), 1.27~1.31 (m)
9'	25.9 (t)	2.07~2.01 (m)	25.9 (t)	2.03~1.96 (m)	26.0 (t)	2.06~2.02 (m)
10'	130.8 (d)	5.46 (t, J＝7.3 Hz)	130.9 (d)	5.39 (t, J＝7.2 Hz)	130.5 (d)	5.43 (t, J＝7.1 Hz)
11'	131.5 (s)		131.3 (s)		131.6 (s)
12'	71.2 (t)	4.52 (s)	71.0 (t)	4.44 (s)	71.1 (t)	4.49 (s)
13'	14.1 (q)	1.66 (s)	14.1 (q)	1.57 (s)	14.1 (q)	1.63 (s)
14'	170.8 (s)		170.4 (s)		170.6 (s)
15'	65.4 (t)	3.40~3.44 (m)	65.4 (t)	3.41~3.37 (m)	65.1 (t)	3.46~3.42 (m)
1"	169.2 (s)		168.3 (s)		169.2 (s)
2"	115.2 (d)	6.30 (d, J＝15.8 Hz)	116.8 (d)	5.71 (d, J＝12.8 Hz)	115.1 (d)	6.29 (d, J＝16.0 Hz)
3"	146.5 (d)	7.57 (d, J＝15.8 Hz)	144.8 (d)	6.80 (d, J＝12.8 Hz)	146.5 (d)	7.56 (d, J＝16.0 Hz)
4"	127.1 (s)		127.7 (s)		127.1 (s)
5"/9"	131.2 (d)	7.42 (d, J＝8.5 Hz)	133.5 (d)	7.54 (d, J＝8.6 Hz)	131.2 (d)	7.42 (d, J＝8.1 Hz)
6"/8"	116.8 (d)	6.77 (d, J＝8.5 Hz)	115.8 (d)	6.68 (d, J＝8.6 Hz)	116.8 (d)	6.77 (d, J＝8.1 Hz)
7"	161.2 (s)		160.0 (s)		161.2 (s)

拟热带灵芝中杂萜类化学成分及其蛋白酪氨酸磷酸酶1B抑制活性

Meroterpenoids from the Fruiting Bodies of Ganoderma ahmadii Steyaret and Their Protein Tyrosine Phosphatase 1B Inhibitory Activities

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