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

doi:10.6023/cjoc201905010

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3264-3268.DOI: 10.6023/cjoc201905010 Previous Articles Next Articles

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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Abstract

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

Cite this article

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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Fig. & Tab. 3

References 18

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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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