Kiiacylphnols A-H, eight undescribed polycyclic polyprenylated acylphloroglucinols with anticancer activities from Hypericum przewalskii Maxim

被引:4
作者
Duan, Yulin [1 ]
Hu, Ping [1 ]
Guo, Yi [1 ]
Bu, Pengfei [1 ]
Shi, Zhengyi [1 ]
Cao, Yunfang [1 ]
Zhang, Yeting [1 ]
Hu, Hong [1 ]
Tong, Qingyi [1 ]
Qi, Changxing [1 ]
Zhang, Yonghui [1 ]
机构
[1] Huazhong Univ Sci & Technol, Sch Pharm, Tongji Med Coll, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
Hypericum przewalskii Maxim; Hypericaceae; Polycyclic polyprenylated acylphloroglucinols; Cytotoxic activity;
D O I
10.1016/j.phytochem.2022.113166
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Kiiacylphnols A-H, eight previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs), along with two known congeners (hyperforcinol F and oxepahyperforin), were obtained from Hypericum przewalskii Maxim. The structures of these metabolites were confirmed by spectroscopic analyses, quantum-chemical 1H and 13C NMR calculations with DP4+ analyses, electronic circular dichroism (ECD) comparisons and calculations. Kiiacylphnols A and B were the first [3.3.1]-type PPAPs with an unusual octahydrooxireno[2,3-i]chromene scaffold bearing a rare 6/6/6/3 ring system. More significantly, kiiacylphnol A and oxepahyperforin displayed cytotoxicity against acute myeloid leukemia and diffuse large B-cell lymphoma cell lines by inducing cell apoptosis.
引用
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页数:11
相关论文
共 17 条
[1]   Garcinol Exhibits Anti-Neoplastic Effects by Targeting Diverse Oncogenic Factors in Tumor Cells [J].
Aggarwal, Vaishali ;
Tuli, Hardeep Singh ;
Kaur, Jagjit ;
Aggarwal, Diwakar ;
Parashar, Gaurav ;
Parashar, Nidarshana Chaturvedi ;
Kulkarni, Samruddhi ;
Kaur, Ginpreet ;
Sak, Katrin ;
Kumar, Manoj ;
Ahn, Kwang Seok .
BIOMEDICINES, 2020, 8 (05)
[2]  
Billard C, 2013, CURR CANCER DRUG TAR, V13, P1
[3]   Structural diversity and biological activities of phloroglucinol derivatives from Hypericum species [J].
Bridi, Henrique ;
Meirelles, Gabriela de Carvalho ;
von Poser, Gilsane Lino .
PHYTOCHEMISTRY, 2018, 155 :203-232
[4]   Polycyclic Polyprenylated Acylphloroglucinols and Chromone O-Glucosides from Hypericum henryi subsp uraloides [J].
Chen, Xuan-Qin ;
Li, Yan ;
Cheng, Xiao ;
Wang, Kou ;
He, Juan ;
Pan, Zheng-Hong ;
Li, Ming-Ming ;
Peng, Li-Yan ;
Xu, Gang ;
Zhao, Qin-Shi .
CHEMISTRY & BIODIVERSITY, 2010, 7 (01) :196-204
[5]   Polycyclic polyprenylated acylphloroglucinols [J].
Ciochina, Roxana ;
Grossman, Robert B. .
CHEMICAL REVIEWS, 2006, 106 (09) :3963-3986
[6]  
Duan Y., 2019, ORG BIOMOL CHEM
[7]   (±)-hyperzewalsins A-D, four pairs of nor-monocyclic polyprenylated acylphloroglucinols with immunosuppressive activity from hypericum przewalskii maxim [J].
Duan, Yulin ;
Bu, Pengfei ;
Xie, Shuangshuang ;
Guo, Yi ;
Shi, Zhengyi ;
Qi, Changxing ;
Zhang, Yonghui .
PHYTOCHEMISTRY, 2021, 187
[8]   Highly functionalized cyclohexanone-monocyclic polyprenylated acylphloroglucinols from Hypericum perforatum induce leukemia cell apoptosis [J].
Guo, Yi ;
Tong, Qingyi ;
Zhang, Na ;
Duan, Xueyan ;
Cao, Yunfang ;
Zhu, Hucheng ;
Xie, Shuangshuang ;
Yang, Jing ;
Zhang, Jinwen ;
Liu, Yanfei ;
Xue, Yongbo ;
Zhang, Yonghui .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (06) :817-824
[9]   Bicyclic polyprenylated acylphloroglucinols and their derivatives: structural modification, structure-activity relationship, biological activity and mechanism of action [J].
Phang, Yeelin ;
Wang, Xueying ;
Lu, Yue ;
Fu, Wenwei ;
Zheng, Changwu ;
Xu, Hongxi .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 205
[10]   Global Cancer Incidence and Mortality Rates and Trends-An Update [J].
Torre, Lindsey A. ;
Siegel, Rebecca L. ;
Ward, Elizabeth M. ;
Jemal, Ahmedin .
CANCER EPIDEMIOLOGY BIOMARKERS & PREVENTION, 2016, 25 (01) :16-27