Antiproliferative Sorbicillinoids From the Deep-Sea-Derived Penicillium allii-sativi

被引:13
作者
Xie, Chun-Lan [1 ,2 ]
Zhang, Duo [1 ]
Lin, Ting [1 ]
He, Zhi-Hui [2 ]
Yan, Qing-Xiang [2 ]
Cai, Qi [1 ]
Zhang, Xiao-Kun [1 ]
Yang, Xian-Wen [2 ]
Chen, Hai-Feng [1 ]
机构
[1] Xiamen Univ, Sch Pharmaceut Sci, Xiamen, Peoples R China
[2] Minist Nat Resources, Inst Oceanog 3, Key Lab Marine Biogenet Resources, Xiamen, Peoples R China
基金
中国国家自然科学基金;
关键词
deep-sea; fungi; sorbicillinoids; cell cycle; cytotoxicities;
D O I
10.3389/fmicb.2020.636948
中图分类号
Q93 [微生物学];
学科分类号
071005 ; 100705 ;
摘要
Two new (1-2) and three known (3-5) sorbicillinoids were isolated from the deep-sea-derived fungus Penicillium allii-sativi MCCC 3A00580. Compounds 1 and 2, named sorbicatechols C and D, were two new hybrid dihydrosorbillinoids. Their structures were established mainly by spectroscopic analyses and electronic circular dichroism (ECD) calculations. All five isolates were tested for antiproliferative activities against four tumor cell lines of MCF-7, HT-29, HuH-7, and LNCap. Compounds 2 and 5 inhibited HT-29 cells in a good dose-dependent manner. Mechanism investigation uncovered that they could significantly induce cell cycle G2-M phase arresting by increasing the protein levels of p-H3 and cyclin B1.
引用
收藏
页数:6
相关论文
共 17 条
[1]   The biosynthesis of bisorbicillinoids: evidence for a biosynthetic route from bisorbicillinol to bisorbibutenolide and bisorbicillinolide [J].
Abe, N ;
Yamamoto, K ;
Arakawa, T ;
Hirota, A .
CHEMICAL COMMUNICATIONS, 2001, (01) :23-24
[2]   Identification of the quinol metabolite "sorbicillinol", a key intermediate postulated in bisorbicillinoid biosynthesis [J].
Abe, N ;
Sugimoto, O ;
Tanji, K ;
Hirota, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) :12606-12607
[3]   Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis [J].
al Fahad, Ahmed ;
Abood, Amira ;
Fisch, Katja M. ;
Osipow, Anna ;
Davison, Jack ;
Avramovic, Marija ;
Butts, Craig P. ;
Piel, Joern ;
Simpson, Thomas J. ;
Cox, Russell J. .
CHEMICAL SCIENCE, 2014, 5 (02) :523-527
[4]   The sorbicillinoid family of natural products: Isolation, biosynthesis, and synthetic studies [J].
Harned, Andrew M. ;
Volp, Kelly A. .
NATURAL PRODUCT REPORTS, 2011, 28 (11) :1790-1810
[5]   CELL-CYCLE CONTROL AND CANCER [J].
HARTWELL, LH ;
KASTAN, MB .
SCIENCE, 1994, 266 (5192) :1821-1828
[6]  
HWANG A, 1995, J BIOL CHEM, V270, P28419
[7]   Diels-Alder Reactions During the Biosynthesis of Sorbicillinoids [J].
Kahlert, Lukas ;
Bassiony, Eman F. ;
Cox, Russell J. ;
Skellam, Elizabeth J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) :5816-5822
[8]   Sorbicillin analogues and related dimeric compounds from Penicillium notatum [J].
Maskey, RP ;
Grün-Wollny, I ;
Laatsch, H .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (06) :865-870
[9]   Sorbicillinoids From the Fungus Ustilaginoidea virens and Their Phytotoxic, Cytotoxic, and Antimicrobial Activities [J].
Meng, Jiajia ;
Gu, Gan ;
Dang, Pengqin ;
Zhang, Xuping ;
Wang, Weixuan ;
Dai, Jungui ;
Liu, Yang ;
Lai, Daowan ;
Zhou, Ligang .
FRONTIERS IN CHEMISTRY, 2019, 7
[10]   Sorbicillinoids from Fungi and Their Bioactivities [J].
Meng, Jiajia ;
Wang, Xiaohan ;
Xu, Dan ;
Fu, Xiaoxiang ;
Zhang, Xuping ;
Lai, Daowan ;
Zhou, Ligang ;
Zhang, Guozhen .
MOLECULES, 2016, 21 (06)