Highly Modified Lanostane Triterpenes from the Wood-Rot Basidiomycete Ganoderma colossus: Comparative Chemical Investigations of Natural and Artificially Cultivated Fruiting Bodies and Mycelial Cultures

被引:13
作者
Isaka, Masahiko [1 ]
Chinthanom, Panida [1 ]
Choeyklin, Rattaket [1 ]
Thummarukcharoen, Tuksaporn [2 ]
Rachtawee, Pranee [1 ]
Sappan, Malipan [1 ]
Srichomthong, Kitlada [1 ]
Fujii, Ryoma [3 ]
Kawashima, Kyohei [3 ]
Mori, Seiji [3 ]
机构
[1] Natl Ctr Genet Engn & Biotechnol BIOTEC, Klongluang 12120, Pathumthani, Thailand
[2] Natl Biobank Thailand NBT, Klongluang 12120, Pathumthani, Thailand
[3] Ibaraki Univ, Inst Quantum Beam Sci, Mito, Ibaraki 3108512, Japan
来源
JOURNAL OF NATURAL PRODUCTS | 2020年 / 83卷 / 07期
关键词
METABOLITES; LACTONES;
D O I
10.1021/acs.jnatprod.9b00947
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The wood-rot basidiomycete Ganoderma colossus has been chemically investigated. Comparative analyses of the natural fruiting body, artificially cultivated fruiting bodies, and mycelial cultures resulted in the isolation, in total, of 13 new highly modified lanostanes, ganocolossusins A-H (1-8) and ganoder-malactones T-X (9-13), together with 23 known compounds (14-36). There were significant overlaps of the same compounds among the three different states of the fungal materials. Ganocolossusin D (4) displayed the most potent antimalarial activity against Plasmodium falciparum K1 (multi-drug-resistant strain) with an IC50 value of 2.4 mu M, while it was noncytotoxic to Vero cells at 50 mu g/mL.
引用
收藏
页码:2066 / 2075
页数:10
相关论文
共 26 条
[1]   Secondary metabolites from Ganoderma [J].
Baby, Sabulal ;
Johnson, Anil John ;
Govindan, Balaji .
PHYTOCHEMISTRY, 2015, 114 :66-101
[2]   GFN2-xTB-An Accurate and Broadly Parametrized Self-Consistent Tight-Binding Quantum Chemical Method with Multipole Electrostatics and Density-Dependent Dispersion Contributions [J].
Bannwarth, Christoph ;
Ehlert, Sebastian ;
Grimme, Stefan .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2019, 15 (03) :1652-1671
[3]   Improved green fluorescent protein reporter gene-based microplate screening for antituberculosis compounds by utilizing an acetamidase promoter [J].
Changsen, C ;
Franzblau, SG ;
Palittapongarnpim, P .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2003, 47 (12) :3682-3687
[4]   Colossolactone H, a new Ganoderma triterpenoid exhibits cytotoxicity and potentiates drug efficacy of gefitinib in lung cancer [J].
Chen, Su-Yu ;
Chang, Chao-Lin ;
Chen, Teng-Hai ;
Chang, Ya-Wen ;
Lin, Shwu-Bin .
FITOTERAPIA, 2016, 114 :81-91
[5]   QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE [J].
DESJARDINS, RE ;
CANFIELD, CJ ;
HAYNES, JD ;
CHULAY, JD .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :710-718
[6]   Anti-HIV-1 protease activity of lanostane triterpenes from the Vietnamese mushroom Ganoderma colossum [J].
El Dine, Riham Salah ;
El Halawany, Ali M. ;
Ma, Chao-Mei ;
Hattori, Masao .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (06) :1022-1026
[7]   New lanostane triterpene lactones from the Vietnamese mushroom Ganoderma colossum (FR.) C. F. BAKER [J].
El Dine, Riham Salah ;
El Halawany, Ali Mahmoud ;
Nakamura, Norio ;
Ma, Chao-Mei ;
Hattori, Masao .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (05) :642-646
[8]  
Frisch M. J., 2016, Gaussian 16 Revision C. 01
[9]   A Robust and Accurate Tight-Binding Quantum Chemical Method for Structures, Vibrational Frequencies, and Noncovalent Interactions of Large Molecular Systems Parametrized for All spd-Block Elements (Z=1-86) [J].
Grimme, Stefan ;
Bannwarth, Christoph ;
Shushkov, Philip .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2017, 13 (05) :1989-2009
[10]  
Hunt L, 1999, BIOTECHNOL BIOENG, V65, P201, DOI 10.1002/(SICI)1097-0290(19991020)65:2<201::AID-BIT10>3.0.CO