中国南海矮小短指软珊瑚(Sinularia nanolobata)的化学成分研究

doi:10.6023/cjoc202109004

有机化学 ›› 2022, Vol. 42 ›› Issue (3): 891-895.DOI: 10.6023/cjoc202109004 上一篇下一篇

研究简报

中国南海矮小短指软珊瑚(Sinularia nanolobata)的化学成分研究

曾子溶^a^,^b, 张梦梦^b, 王鸿^a, 李佳^b, 郭跃伟^a^,^b^,^c^,^*(), 苏明智^c^,^*()

a 浙江工业大学长三角绿色制药协同创新中心杭州 310014
b 中国科学院上海药物研究所新药研究国家重点实验室上海 201203
c 中科环渤海(烟台)药物高等研究院山东烟台 264000

收稿日期:2021-09-01 修回日期:2021-09-27 发布日期:2021-11-17
通讯作者: 郭跃伟, 苏明智
基金资助:
国家重点研发计划(2018YFC0310903); 国家自然科学基金(81991521); 中国科学院上海药物研究所新药研究国家重点实验室项目(SIMM2103ZZ-06); 浙江省“万人计划”科技创新领军人才(2019R52009)

Chemical Constituents of Sinularia nanolobata from the South China Sea

Zirong Zeng^a^,^b, Mengmeng Zhang^b, Hong Wang^a, Jia Li^b, Yuewei Guo^a^,^b^,^c(), Mingzhi Su^c()

a Yangtze River Delta Green Pharmaceutical Collaborative Innovation Center, Zhejiang University of Technology, Hangzhou 310014
b State Key Laboratory of New Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
c Bohai rim Advanced Research Institute for Drug Discovery, Yantai, Shandong 264000

Received:2021-09-01 Revised:2021-09-27 Published:2021-11-17
Contact: Yuewei Guo, Mingzhi Su
Supported by:
National Key Research and Development Program(2018YFC0310903); National Natural Science Foundation of China(81991521); Project of State Key Laboratory of Drug Research/Shanghai Institute of Materia Medica(SIMM2103ZZ-06); Zhejiang Province “Ten Thousand Talents Program” Science and Technology Innovation Leading Talent Project(2019R52009)

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摘要/Abstract

运用硅胶柱色谱、凝胶柱色谱和高效液相色谱等分离技术, 对中国南海西瑁岛矮小短指软珊瑚的丙酮提取物中的化学成分进行了系统研究, 从中分离得到10个化合物, 并采用多种波谱技术确定了这些化合物的化学结构. 分别鉴定为罗伯塔特(1)、(17R)-loba-8,10,13(15)-triene-17,18-diol (2)、α-生育醌(3)、(1E,3Z,7E,11R,12R)-11-羟基-12-甲氧基-1-异丙基-4,8,12-三甲基-环十四碳-1,3,7-三烯(4)、(+)-(1E,3E,7E,11R,12S)-11,12-epoxy-11,12-dihydrocembrene-C (5)、(1E,3E,7R,8S,11E)-7,8-环氧-1-异丙基-4,8,12-三甲基-环十四碳-1,3,11-三烯(6)、24-亚甲基-胆固醇(7)、孕烯醇酮(8)、3β,6α,11-三羟基-24-亚甲基-9,11-断-5α-胆甾-7-烯-9-酮(9), Sinugrandisterol A (10). 其中化合物1为新的异戊烯基榄烷型二萜化合物. 生物活性实验结果表明, 化合物3对蛋白酪氨酸磷酸酶1B (PTP1B)的酶活力具有较好的抑制活性, 其IC₅₀为(4.83±2.35) μmol/L, 提示该化合物在治疗糖尿病和肥胖症的药物开发中具有一定的潜力.

关键词: 中国南海, 矮小短指软珊瑚, 异戊烯基榄烷型二萜, PTP1B抑制活性

A new prenylelemane-type diterpenoid named lobatate (1), together with nine known compounds, namely (17R)- loba-8,10,13(15)-triene-17,18-diol (2), α-tocopherolquinone (3), (1E,3Z,7E,11R,12R)-11-hydroxy-12-methoxy-1-isopropyl- 4,8,12-trimethyl-cyclotetradeca-1,3,7-triene (4), (+)-(1E,3E,7E,11R,12S)-11,12-epoxy-11,12-dihydrocembrene-C (5), (1E,3E, 7R,8S,11E)-7,8-epoxy-1-isopropyl-4,8,12-trimethyl-cyclotetradeca-1,3,11-triene (6), 24-methylene-cholesterol (7), pregnenolone (8), 3β,6α,11-trihydroxy-24-methylene-9,11-seco-5α-cholest-7-en-9-one (9), sinugrandisterol A (10), was isolated from the soft coral Sinularia nanolobata, which were collected from the Ximao Island, Sanya, South China Sea. Their structures were elucidated using comprehensive spectroscopic methods. The biological activity experiment result showed that compound 3 significantly inhibited the enzymatic activity of protein tyrosine phosphatase-1B (PTP1B) with the IC₅₀ value of (4.83± 2.35) μmol/L. The result indicated that compound 3 has a promising potential on the drug discovery of anti-diabetes and anti- obesity.

Key words: south china sea, Sinularia nanolobata, prenylelemane-type diterpene, protein tyrosine phosphatase-1B (PTP1B) inhibitory activity

引用此文

曾子溶, 张梦梦, 王鸿, 李佳, 郭跃伟, 苏明智. 中国南海矮小短指软珊瑚(Sinularia nanolobata)的化学成分研究[J]. 有机化学, 2022, 42(3): 891-895.

Zirong Zeng, Mengmeng Zhang, Hong Wang, Jia Li, Yuewei Guo, Mingzhi Su. Chemical Constituents of Sinularia nanolobata from the South China Sea[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 891-895.

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图/表 4

图1. 化合物1~10的化学结构

Figure 1. Chemical structure of compounds 1~10

No.	δ_H (J in Hz)	δ_C
1		40.0 (C)
2	1.97~2.03 (m)	53.0 (CH)
3a	1.97~2.03 (m)	33.1 (CH₂)
3b	1.56~1.57 (m)
4	1.86~1.92 (m)	47.7 (CH)
5a	1.49~1.52 (m)	27.0 (CH₂)
5b	1.42~1.48 (m)
6a	1.42~1.48 (m)	40.1 (CH₂)
6b	1.42~1.48 (m)
7	1.00 (s)	16.8 (CH₃)
8	5.81 (dd, 17.4)	150.6 (CH)
9a	4.91 (d, 1.4)	109.9 (CH₂)
9b	4.89 (d, 1.4)
10		148.0 (C)
11a	4.81 (s)	112.1 (CH₂)
11b	4.58 (s)
12	1.70 (s)	24.9 (CH₃)
13		140.6 (C)
14	1.60 (s)	14.6 (CH₃)
15	5.13 (t, 7.1)	122.0 (CH)
16a 16b 17a 17b 18 19 20 21	1.97~2.03 (m) 1.66~1.69 (m) 1.71~1.76 (m) 1.42~1.48 (m) 2.45 (q, 7.0) 1.15 (d, 7.0) 3.67 (s)	25.6 (CH₂) 34.0 (CH₂) 39.2 (CH) 17.2 (CH₃) 177.5 (C) 51.6 (OCH₃)

表1. 化合物1的1H NMR (500 MHz)和13C NMR (125 MHz)数据(CDCl3)

Table 1. 1H NMR (500 MHz) and 13C NMR (125 MHz) data of compound 1 in CDCl3

图2. 化合物1的主要的1H-1H COSY、HMBC以及NOESY相关信号

Figure 2. 1H-1H COSY, HMBC and NOESY correlations of compound 1

图3. 使用QM-NMR方法在PCM/mPW1PW91/6-31+G**水平上对实验与计算的1b构型的13C NMR化学位移的回归分析

Figure 3. Regression analysis of experimental versus calculated 13C NMR chemical shifts of 1b configuration at the PCM/mPW1- PW91/6-31+G** level using QM-NMR method The linear fitting is shown as a red line (diagonal)

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中国南海矮小短指软珊瑚(Sinularia nanolobata)的化学成分研究

Chemical Constituents of Sinularia nanolobata from the South China Sea

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