Chemical Constituents of Sinularia nanolobata from the South China Sea

doi:10.6023/cjoc202109004

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 891-895.DOI: 10.6023/cjoc202109004 Previous Articles Next Articles

NOTES

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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Abstract

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

Cite this article

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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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)

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)

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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