Gancochlearols E - I, meroterpenoids from Ganoderma cochlear against COX-2 and triple negative breast cancer cells and the absolute configuration assignment of ganomycin K

被引:13
作者
Li, Yan-Peng [1 ]
Jiang, Xiao-Ting [1 ]
Qin, Fu-Ying [1 ]
Zhang, Hao-Xing [1 ]
Cheng, Yong-Xian [1 ,2 ]
机构
[1] Shenzhen Univ, Coll Life Sci & Oceanog, Sch Pharmaceut Sci, Shenzhen 518060, Peoples R China
[2] Shenzhen Univ, Marshall Lab Biomed Engn, Shenzhen 518060, Peoples R China
基金
中国国家自然科学基金;
关键词
Ganoderma cochlear; Meroterpenoids; COX-2; TNBC; EMT; TRITERPENOIDS;
D O I
10.1016/j.bioorg.2021.104706
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
Five new meroterpenoids, gancochlearols E - I (1, 3-6), and one compound ganomycin K (2) were isolated from the fruiting bodies of G. cochlear. Their structures were assigned by 1D and 2D NMR, MS, and CD analysis. Rh-2(OCOCF3)(4)-induced ECD method was used to clarify the absolute configuration of secondary alcohol in 1 and 2. Biochemical evaluation showed that all the isolates significantly inhibit COX-2 enzyme in vitro with the IC50 values range from 1.03 mu M to 2.71 mu M. Further cellular assay revealed that (+)-3 and (-)-6 could suppress metastatic phenotype of triple-negative breast cancer (TNBC) cells via impeding the epithelial-mesenchymal transition (EMT).
引用
收藏
页数:7
相关论文
共 27 条
[1]   Anticancer and Anti-Inflammatory Properties of Ganoderma lucidum Extract Effects on Melanoma and Triple-Negative Breast Cancer Treatment [J].
Barbieri, Antonio ;
Quagliariello, Vincenzo ;
Del Vecchio, Vitale ;
Falco, Michela ;
Luciano, Antonio ;
Amruthraj, Nagoth Joseph ;
Nasti, Guglielmo ;
Ottaiano, Alessandro ;
Berretta, Massimiliano ;
Iaffaioli, Rosario Vincenzo ;
Arra, Claudio .
NUTRIENTS, 2017, 9 (03)
[2]   Meroterpenoid enantiomers from Ganoderma sinensis [J].
Cao, Wen-Wen ;
Luo, Qi ;
Cheng, Yong-Xian ;
Wang, Shu-Mei .
FITOTERAPIA, 2016, 110 :110-115
[3]   Antitumour, Antimicrobial, Antioxidant and Antiacetylcholinesterase Effect of Ganoderma Lucidum Terpenoids and Polysaccharides: A Review [J].
Cor, Darija ;
Knez, Zeljko ;
Hrncic, Masa Knez .
MOLECULES, 2018, 23 (03)
[4]   [Rh2(OCOCF3)4] as an auxiliary chromophore in chiroptical studies on steroidal alcohols [J].
Frelek, J ;
Szczepek, WJ .
TETRAHEDRON-ASYMMETRY, 1999, 10 (08) :1507-1520
[5]   CIRCULAR-DICHROISM .93. DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ALCOHOLS, OLEFINS, EPOXIDES, AND ETHERS FROM THE CD OF THEIR INSITU COMPLEXES WITH [RH2(O2CCF3)4] [J].
GERARDS, M ;
SNATZKE, G .
TETRAHEDRON-ASYMMETRY, 1990, 1 (04) :221-236
[6]   Chemical Components of Ganoderma [J].
Gong, Ting ;
Yan, Renyi ;
Kang, Jie ;
Chen, Ruoyun .
GANODERMA AND HEALTH: BIOLOGY, CHEMISTRY AND INDUSTRY, 2019, 1181 :59-106
[7]   Highly Modified Lanostane Triterpenes from the Wood-Rot Basidiomycete Ganoderma colossus: Comparative Chemical Investigations of Natural and Artificially Cultivated Fruiting Bodies and Mycelial Cultures [J].
Isaka, Masahiko ;
Chinthanom, Panida ;
Choeyklin, Rattaket ;
Thummarukcharoen, Tuksaporn ;
Rachtawee, Pranee ;
Sappan, Malipan ;
Srichomthong, Kitlada ;
Fujii, Ryoma ;
Kawashima, Kyohei ;
Mori, Seiji .
JOURNAL OF NATURAL PRODUCTS, 2020, 83 (07) :2066-2075
[8]   STRUCTURES OF GANODERIC ACID-A AND ACID-B, 2 NEW LANOSTANE TYPE BITTER TRITERPENES FROM GANODERMA-LUCIDUM (FR) KARST [J].
KUBOTA, T ;
ASAKA, Y ;
MIURA, I ;
MORI, H .
HELVETICA CHIMICA ACTA, 1982, 65 (02) :611-619
[9]   Ling Zhi-8 reduces lung cancer mobility and metastasis through disruption of focal adhesion and induction of MDM2-mediated Slug degradation [J].
Lin, Tung-Yi ;
Hsu, Hsien-Yeh .
CANCER LETTERS, 2016, 375 (02) :340-348
[10]   The natural compound GL22, isolated from Ganoderma mushrooms, suppresses tumor growth by altering lipid metabolism and triggering cell death [J].
Liu, Ge ;
Wang, Kai ;
Kuang, Shan ;
Cao, Ruobing ;
Bao, Li ;
Liu, Rui ;
Liu, Hongwei ;
Sun, Chaomin .
CELL DEATH & DISEASE, 2018, 9