Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113

doi:10.6023/cjoc202109021

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 896-900.DOI: 10.6023/cjoc202109021 Previous Articles Next Articles

NOTES

海南红树红榄李内生真菌Penicillium sclerotiorum HLL113次级代谢产物研究

杨静雨^a^,^b, 唐敏敏^a^,^b, 陈丽^a^,^b, 赖心怡^a^,^b, 卓欣^a^,^b, 周学明^a^,^b^,^*(), 陈光英^a^,^b^,^*()

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:2021-09-15 修回日期:2021-10-23 发布日期:2021-11-09
通讯作者: 周学明, 陈光英
基金资助:
国家自然科学基金(41866005); 国家自然科学基金(22177023); 海南省重大科技计划(ZDKJ202008); 海南省研究生创新研究(Hys2020-307)

Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113

Jing-Yu Yang^a^,^b, Min-Min Tang^a^,^b, Li Chen^a^,^b, Xin-Yi Lai^a^,^b, Xin Zhuo^a^,^b, Xue-Ming Zhou^a^,^b(), Guang-Ying Chen^a^,^b()

a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158
b Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2021-09-15 Revised:2021-10-23 Published:2021-11-09
Contact: Xue-Ming Zhou, Guang-Ying Chen
Supported by:
National Natural Science Foundation of China(41866005); National Natural Science Foundation of China(22177023); Key Science and Technology Program of Hainan Province(ZDKJ202008); Innovative Research Projects of Postgraduates in Hainan Universities(Hys2020-307)

1. .pdf(974KB)

Abstract

Two new furan derivatives, (2S,3S,5S)-2-(2-hydroxyethyl)-3-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran (1) and (2S,3S,5S)-2-allyl-3-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran (2), together with six known steroid compounds were isolated from Penicillium sclerotiorum HLL113. 6,9-Epoxy-ergosta-7,22-dien-3-ol (5) was isolated from the genus Penicillium for the first time. Their structures were elucidated on the basis of extensive spectroscopic methods. The test results of α-glucosidase inhibitory activity showed that (22E,4R)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (7) and derrisisoflavone K (8) have significant inhibitory activity.

Key words: Lumnitzera littorea, Penicillium sclerotiorum, secondary metabolite, furan derivative, inhibitory activity against α-glucosidase

Cite this article

Jing-Yu Yang, Min-Min Tang, Li Chen, Xin-Yi Lai, Xin Zhuo, Xue-Ming Zhou, Guang-Ying Chen. Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 896-900.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 26

[1]	Carroll, A. R.; Copp, B. R.; Davis, R. A.; Keyzers, R. A.; Prinsep, M. R. Nat. Prod. Rep. 2021, 37, 175. doi: 10.1039/C9NP00069K
[2]	Cao, F.; Zhu, H.-J.; Sun, T.-T. Curr. Med. Chem. 2021, 28, 3568. doi: 10.2174/0929867327666201026150105
[3]	Song, C.-G.; Yang, J.; Zhang, M.-Z.; Ding, G.; Jia, C.-G.; Qin, J.-C.; Guo, L.-P. Chem. Biodiversity 2021, 18, e2001020.
[4]	Zhang, Y.; Chen, Y.-K.; Zhou, Y.; Zhang, J.-W.; Bai, H.; Zheng, C.-F. Front. Genet. 2020, 11, 584817. doi: 10.3389/fgene.2020.584817
[5]	Shi, S.-H.; Huang, Y.-L.; Zeng, K.; Tan, F.-X.; He, H.-H.; Huang, J.-Z.; Fu, Y.-X. Mol. Phylogenet. Evol. 2005, 34, 159. doi: 10.1016/j.ympev.2004.09.002
[6]	Saad, S.; Taher, M.; Susanti, D.; Qaralleh, H.; Rahim, N. A. B. A. Asian Pac. J. Trop. Med. 2011, 7, 523.
[7]	Feller, I. C.; Lovelock, C. E.; Berger, U.; Mckee, K. L.; Ball, M. C. Annu. Rev. Mar. Sci. 2010, 2, 395. pmid: 21141670
[8]	Xu, J. RSC Adv. 2015, 5, 841. doi: 10.1039/C4RA11756E
[9]	Luo, Q.; Peng, C.; Ye, B.-P. Chin. J. Pharm. Biotechnol. 2016, 23, 452. (in Chinese)
	(罗清, 彭程, 叶波平, 药物生物技术, 2016, 23, 452.)
[10]	Bai, M.; Zheng, C.-J.; Chen, G.-Y. J. Nat. Prod. 2021, 84, 2104. doi: 10.1021/acs.jnatprod.1c00050
[11]	Luo, Z.-W.; Tang, M.-M.; Zhou, X.-M.; Song, X.-M.; Yi, J.-L.; Zhang, B.; Yang, J.-Y.; Chen, G.-Y. Chem. Biodiversity 2021, 18, e2100027.
[12]	Bai, M.; Zheng, C.-J.; Nong, X.-H.; Zhou, X.-M.; Luo, Y.-P.; Chen, G.-Y. Mar. Drugs 2019, 17, 649. doi: 10.3390/md17120649
[13]	Bai, M.; Huang, G.-L.; Mei, R.-Q.; Wang, B.; Luo, Y.-P.; Nong, X.-H.; Chen, G.-Y.; Zheng, C.-J. Mar. Drugs 2019, 17, 433. doi: 10.3390/md17080433
[14]	Zhou, X.-M.; Zheng, C.-J.; Song, X.-M.; Tang, M.-M.; Yang, J.-Y.; Yang, X.; Peng, S.-J.; Cai, J.; Chen, G.-Y. Fitoterapia 2019, 139, 104400. doi: 10.1016/j.fitote.2019.104400
[15]	Bai, M.; Zheng, C.-J.; Huang, G.-L.; Mei, R.-Q.; Wang, B.; Luo, Y.-P.; Zheng, C.; Niu, Z.-G.; Chen, G.-Y. J. Nat. Prod. 2019, 82, 1155. doi: 10.1021/acs.jnatprod.8b00866
[16]	Chen, L.-L.; Wang, P.; Chen, H.-Q.; Guo, Z.-K.; Wang, H.; Dai, H.-F.; Mei, W.-L. Molecules 2017, 22, 261. doi: 10.3390/molecules22020261
[17]	Abdel-lateff, A.; Fisch, K. M.; Wright, A. D.; Koenig, G. M. Planta Med. 2003, 69, 831. pmid: 14598209
[18]	Zhang, P.-P.; Li, Y.-F.; Jia, C.-X; Lang, J.-J.; Niaz, S.-I.; Li, J.; Yuan, J.; Yu, J.-C.; Chen, S.-H.; Liu, L. RSC Adv. 2017, 7, 49910. doi: 10.1039/C7RA09859F
[19]	Deng, Q.; Li, G.; Sun, M.-Y.; Yang, X.-B.; Xu, J. Nat. Prod. Res. 2020, 34, 1404. doi: 10.1080/14786419.2018.1512993 pmid: 30417674
[20]	Shaker, S.; Sun, T.-T.; Wang, L.-Y.; Ma, W.-Z.; Wu, D.-L.; Guo, Y.-W.; Dong, J.; Chen, Y.-X.; Zhu, L.-P.; Yang, D.-P.; Li, H.-J.; Lan, W.-J. Nat. Prod. Res. 2021, 35, 41. doi: 10.1080/14786419.2019.1611816
[21]	Tian, M.-Q.; Li, J.-F.; Li, G.-H. Chem. Bioeng. 2015, 32, 29. (in Chinese)
	(田梦青, 李建芳, 李国红, 化学与生物工程, 2015, 32, 29.)
[22]	Zhang, X.; Geoffroy, P.; Miesch, M.; Julien-David, D.; Raul, F.; Aoude-Werner, D.; Marchioni, E. Steroids 2005, 70, 886. pmid: 16038957
[23]	Sun, S.-W.; Fu, J.; Zhou, H.-N.; Zhu, T.-J.; Li, D.-H.; Mao, W.-J.; Gu, Q.-Q. Chin. J. Mar. Drugs 2014, 33, 1. (in Chinese)
	(孙世伟, 付娟, 周会楠, 朱天骄, 李德海, 毛文君, 顾谦群, 中国海洋药物, 2014, 33, 1.)
[24]	Zhang, G.-W.; Ma, X.-Q.; Yan, S.-J.; Zeng, L.-M.; Su, J.-Y. Chem. J. Chin. Univ. 2005, 26, 81. (in Chinese)
	(张广文, 马祥全, 闫素君, 曾陇梅, 苏镜娱, 高等学校化学学报, 2005, 26, 81.)
[25]	Ma, K.; Han, J.-J.; Bao, L.; Wei, T.-Z.; Liu, H.-W. J. Nat. Prod. 2014, 77, 942. doi: 10.1021/np401026b
[26]	Jiang, Z.-H.; Chai, L.; Liu, Y.-P.; Qiu, H.-C.; Wang, T.-T.; Feng, X.-Y.; Wang, Y.-T.; Huang, Z.-H.; Liu, B.-M.; Fu, Y.-H. Phytochem. Lett. 2017, 22, 194. doi: 10.1016/j.phytol.2017.10.012

Position	1		2
Position	δ_H (MeOH-d₄)	δ_C (CDCl₃)	δ_H (MeOH-d₄)	δ_C (CDCl₃)
2	—	84.5 (C)	—	87.6 (C)
3	3.61 (dd, J=10.0, 2.0 Hz)	77.6 (CH)	3.83 (dd, J=8.4, 5.6 Hz)	75.5 (CH)
4	1.20~1.26 (m), 1.81~1.89 (m)	26.4 (CH₂)	1.84~1.90 (m), 2.18~2.25 (m)	34.7 (CH₂)
5	3.78 (dd, J=9.2, 6.0 Hz)	87.4 (CH)	3.92 (dd, J=5.6, 3.2 Hz)	83.4 (CH)
6	1.66~1.72 (m), 2.01~2.09 (m)	34.8 (CH₂)	5.88 (dd, J=17.2, 10.8 Hz)	142.1 (CH)
7	3.44 (dd, J=11.2, 9.6 Hz) 3.86 (dd, J=11.2, 1.6 Hz)	47.2 (CH₂)	5.04 (dd, J=10.8, 1.6 Hz) 5.24 (dd, J=17.2, 1.6 Hz)	112.9 (CH₂)
8	1.12 (s)	24.2 (CH₃)	1.24 (s)	21.1 (CH₃)
9	—	70.7 (C)	—	71.8 (C)
10	1.18 (s)	22.5 (CH₃)	1.14 (s)	26.2 (CH₃)
11	1.21 (s)	27.7 (CH₃)	1.26 (s)	27.7 (CH₃)

Position	1		2
Position	δ_H (MeOH-d₄)	δ_C (CDCl₃)	δ_H (MeOH-d₄)	δ_C (CDCl₃)
2	—	84.5 (C)	—	87.6 (C)
3	3.61 (dd, J=10.0, 2.0 Hz)	77.6 (CH)	3.83 (dd, J=8.4, 5.6 Hz)	75.5 (CH)
4	1.20~1.26 (m), 1.81~1.89 (m)	26.4 (CH₂)	1.84~1.90 (m), 2.18~2.25 (m)	34.7 (CH₂)
5	3.78 (dd, J=9.2, 6.0 Hz)	87.4 (CH)	3.92 (dd, J=5.6, 3.2 Hz)	83.4 (CH)
6	1.66~1.72 (m), 2.01~2.09 (m)	34.8 (CH₂)	5.88 (dd, J=17.2, 10.8 Hz)	142.1 (CH)
7	3.44 (dd, J=11.2, 9.6 Hz) 3.86 (dd, J=11.2, 1.6 Hz)	47.2 (CH₂)	5.04 (dd, J=10.8, 1.6 Hz) 5.24 (dd, J=17.2, 1.6 Hz)	112.9 (CH₂)
8	1.12 (s)	24.2 (CH₃)	1.24 (s)	21.1 (CH₃)
9	—	70.7 (C)	—	71.8 (C)
10	1.18 (s)	22.5 (CH₃)	1.14 (s)	26.2 (CH₃)
11	1.21 (s)	27.7 (CH₃)	1.26 (s)	27.7 (CH₃)

Compound	IC₅₀/(µmol•mL^–1)
1	2009.566
2	1851.642
3	1910.011
4	1467.279
5	1791.437
6	1472.091
7	861.211
8	940.376
阿卡波糖	1954.935

Compound	IC₅₀/(µmol•mL^–1)
1	2009.566
2	1851.642
3	1910.011
4	1467.279
5	1791.437
6	1472.091
7	861.211
8	940.376
阿卡波糖	1954.935

海南红树红榄李内生真菌Penicillium sclerotiorum HLL113次级代谢产物研究

Study on the Secondary Metabolites of Endophytic Penicillium sclerotiorum HLL113

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 26

Related Articles 7

Recommended Articles

Metrics

Comments

[1]	Bingwen Zhang, Yuqi Lin, Yanqing Xue, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. Study on Secondary Metabolites from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 4003-4007.
[2]	Xibin Wu, Yinfeng Tan, Jiling Yi, Xinming Song, Jingyu Yang, Xueming Zhou, Guangying Chen. Study on Bioactive Secondary Metabolites from Penicillium herquei JX4 [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1251-1254.
[3]	Weinü Zeng, Guolei Huang, Bin Wang, Jin Cai, Caijuan Zheng. Secondary Metabolites and Bioactivities of Penicillium sp. Sourced from Mangrove from 2007 to 2020 [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4255-4278.
[4]	Yu Shuyan, Gao Lihong, Lan Hongbing, Qian Hengyu, Yin Zhigang, Shang Yongjia. Recent Progress in the Reactions of Aurone-Derived Azadienes [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2714-2724.
[5]	Li Baolin. Furan Derivatives: An Emerging Class of Organic Semiconductors [J]. Chin. J. Org. Chem., 2015, 35(12): 2487-2506.
[6]	Zheng Caijuan, Huang Guolei, Tang Xiongzhao, Wang Deneng, Gong Xiaolu, Zhang Qiang, Song Xiaoping, Chen Guangying. Secondary Metabolites and Antibacterial Activities of a Bruguiera sexangula var. Rhynchopetala-Derived Fungus Penicillium sp. (J41221) [J]. Chin. J. Org. Chem., 2014, 34(6): 1172-1176.
[7]	Zhao Yunhui, Liu Wenjie, Sun Xingwen, Lin Guoqiang. A Novel Strategy for the Synthesis of Benzofuran Derivatives [J]. Chin. J. Org. Chem., 2012, 32(10): 1919-1924.