MAIHEMUTI Abulikemu,WANG Lei,LI Jing,et al.Analysis of Effective Terpenoids in Xinjiang Pleurotus ferulae Against Esophageal Carcinoma by UPLC-Q/TOF-MS Technique[J].Chinese Journal of Experimental Traditional Medical Formulae,2021,27(10):93-101.
MAIHEMUTI Abulikemu,WANG Lei,LI Jing,et al.Analysis of Effective Terpenoids in Xinjiang Pleurotus ferulae Against Esophageal Carcinoma by UPLC-Q/TOF-MS Technique[J].Chinese Journal of Experimental Traditional Medical Formulae,2021,27(10):93-101. DOI: 10.13422/j.cnki.syfjx.20210149.
Analysis of Effective Terpenoids in Xinjiang Pleurotus ferulae Against Esophageal Carcinoma by UPLC-Q/TOF-MS Technique增强出版
By screening the activity of human esophageal cancer Eca109 cells, the ethyl acetate extract phase of
P. ferulae
ethanol extract (PFEP-E) was separated and purified by silica gel chromatography and preparative thin layer chromatography. Ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UPLC-Q/TOF-MS) combined with online network databases such as Metlin, MassBank, PubChem and related literature were used to identify the effective elution sites and analyze their contents.
Result
2
The elution fraction (Fr
2-3∶1
) of petroleum ether-ethyl acetate (3∶1) on the silica gel column had the strongest inhibitory activity on the proliferation of human esophageal cancer Eca109 cells. The component analysis showed that 24 effective terpenoids were identified under positive ion mode, and 28 effective terpenoids were identified under negative ion mode, a total of 52 terpenoids were identified, which were isolated from this edible fungus for the first time. Content of total terpenoids in Fr
2-3∶1
were 62.88 mg·g
-1
, including 2 monoterpenoids, 5 sesquiterpenoids, 15 diterpenoids and 30 triterpenoids, accounting for 1.32%, 12.04%, 47.55%, 39.09% of the total terpenoids, respectively. Diterpenoids and triterpenoids were the main components of the effective terpenoids in
P. ferulae
, accounting for 86.64% of the total terpenoids. Gibberellins were the main diterpenoids, accounting for 79.70% of the total diterpenoids, triterpenoids were mainly ganoderic acids, accounting for 29.25% of the total triterpenoids. The results of methyl thiazolyl tetrazolium (MTT) test showed that gibberellin A
3
and gibberellin A
5
had weak anti-esophageal cancer activity, while gypsogenin and oleanolic acid had strong anti-esophageal cancer activity.
Conclusion
2
The effective terpenoids of
P. ferulae
against esophageal cancer are triterpenoids mainly composed of ganoderic acids, which can provide theoretical basis for the development of terpenoids of
P. ferulae
as anti-tumor drugs and the development of functional foods, and help to effectively improve the additional output value of
WANG W L , CHEN K X , LIU Q , et al . Suppression of tumor growth by Pleurotus ferulae ethanol extract through induction of cell apoptosis,and inhibition of cell proliferation and migration [J]. PLoS One , 2014 , 9 ( 7 ): e102673 .
LI J Y , LI J Y , AIPIRE A , et al . The combination of Pleurotus ferulae water extract and CpG-ODN enhances the immune responses and antitumor efficacy of HPV peptides pulsed dendritic cell-based vaccine [J]. Vaccine , 2016 , 34 ( 31 ): 3568 - 3575 .
TSAI S Y , HUANG S J , LO S H , et al . Flavour components and antioxidant properties of several cultivated mushrooms [J]. Food Chem , 2009 , 113 ( 2 ): 578 - 584 .
ALAM N , YOON K N , LEE J S , et al . Consequence of the antioxidant activities and tyrosinase inhibitory effects of various extracts from the fruiting bodies of Pleurotus ferulae [J]. Saudi J Biol Sci , 2012 , 19 ( 1 ): 111 - 118 .
LI J Y , YUAN P F , WANG X H , et al . Purification,characterization and bioactivities of polysaccharides from Pleurotus ferulae [J]. Food Funct , 2017 , 8 ( 5 ): 1905 - 1914 .
YANG Y , FU C S , ZHOU F F , et al . Chemical composition,antioxidant and antitumor activities of sub-fractions of wild and cultivated Pleurotus ferulae ethanol extracts [J]. Peer J , 2018 , 6 : e6097 .
YANG Y , LUO X Y , MAYILA Y S , et al . Ergosterol peroxide from Pleurotus ferulae inhibits gastrointestinal tumor cell growth through induction of apoptosis via reactive oxygen species and endoplasmic reticulum stress [J]. Food Funct , 2020 , 11 ( 5 ): 4171 - 4184 .
SALVADOR J A R , LEAL A S , VALDEIRA A S , et al . Oleanane-,ursane-,and quinone methide friedelane-type triterpenoid derivatives:recent advances in cancer treatment [J]. Eur J Med Chem , 2017 , 142 : 95 - 130 .
BI X X , HAN L , QU T G , et al . Anti-inflammatory effects,SAR,and action mechanism of monoterpenoids from Radix Paeoniae Alba on LPS-stimulated RAW264.7 cells [J]. Molecules , 2017 , 22 ( 5 ): 715 .
MAFUD A C , SILVA M P N , MONTEIRO D C , et al . Structural parameters,molecular properties,and biological evaluation of some terpenes targeting Schistosoma mansoni parasite [J]. Chem Biol Interact , 2016 , 244 : 129 - 139 .
GALLE M , CRESPO R , KLADNIEW B R , et al . Suppression by geraniol of the growth of A549 human lung adenocarcinoma cells and inhibition of the mevalonate pathway in culture and in vivo :potential use in cancer chemotherapy [J]. Nutr Cancer , 2014 , 66 ( 5 ): 888 - 895 .
XIE W , HAN C , ZHENG Z Q , et al . Determination of gibberellin A 3 residue in fruit samples by liquid chromatography-tandem mass spectrometry [J]. Food Chem , 2011 , 127 ( 2 ): 890 - 892 .
MODUGNO F , RIBECHINI E , COLOMBINI M P . Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry [J]. Rapid Commun Mass Sp , 2010 , 20 ( 11 ): 1787 - 1800 .
PANG N , MALIKE D , LIU H . Simultaneous determination of main bioactive components in Rosa multiflora Thunb. and their fragmentation study by LC-MS [J]. Chromatographia , 2009 , 70 ( 7 ): 1253 - 1257 .
GILL B S , NAVGEET A , KUMAR S . Ganoderic acid targeting multiple receptors in cancer:in silico and in vitro study [J]. Tumor Biol , 2016 , 37 ( 10 ): 14271 - 14290 .
WENG C J , CHAU C F , HEIEH Y S , et al . Lucidenic acid inhibits PMA-induced invasion of human hepatoma cells through inactivating MAPK/ERK signal transduction pathway and reducing binding activities of NF-kappaB and AP-1 [J]. Carcinogenesis , 2008 , 29 ( 1 ): 147 - 156 .
CHEN N H , LIU J W , ZHONG J J . Ganoderic acid T inhibits tumor invasion in vitro and in vivo through inhibition of MMP expression [J]. Pharmacol Rep , 2010 , 62 ( 1 ): 150 - 163 .
SHAO C S , ZHOU X H , ZHENG X X , et al . Ganoderic acid D induces synergistic autophagic cell death except for apoptosis in ESCC cells [J]. J Ethnopharmacol , 2020 , 262 : 113213 .
TANG Y , WU H , SHAO B Z , et al . Celosins inhibit atherosclerosis in ApoE -/- mice and promote autophagy flow [J]. J Ethnopharmacol , 2018 , 215 : 74 - 82 .
ZOU L , ZHANG Y , LI W , et al . Comparison of chemical profiles,anti-inflammatory activity,and UPLC-Q-TOF/MS-based metabolomics in endotoxic fever rats between synthetic borneol and natural borneol [J]. Molecules , 2017 , 22 ( 9 ): 1446 .
BI E X , LIU D Q , LI Y X , et al . Oridonin induces growth inhibition and apoptosis in human gastric carcinoma cells by enhancement of p53 expression and function [J]. Braz J Med Biol Res , 2018 , 51 ( 12 ): e7599 .
MA B , ZHANG H , WANG Y , et al . Corosolic acid,a natural triterpenoid,induces ER stress-dependent apoptosis in human castration resistant prostate cancer cells via activation of IRE-1/JNK,PERK/CHOP and TRIB3 [J]. J Exp Clin Cancer Res , 2018 , 37 ( 1 ): 210 .
Advances in Chemical Constituents and Pharmacological Action of Tinosporae Radix
Analysis of Effect of Characteristic Processing with Rice-washed Water on Volatile Components in Raw and Bran-fried Products of Atractylodis Macrocephalae Rhizoma by HS-GC-MS
Metabolic Analysis of Tongfengding Capsules in vivo Based on Sequential Metabolism
Analysis of Differences of Volatile Components in Atractylodis Rhizoma Before and After Processing with Rice-washed Water by HS-GC-MS
Radiosensitization Effect and Mechanism of Xuefu Zhuyutang on Transplanted Esophageal Carcinoma in Nude Mice
Related Author
WANG Jingjing
YANG Ruwei
XIE Yongyan
XU Ziwei
WANG Shuaikang
CHEN Liping
LAN Daoyuan
GUO Qiujin
Related Institution
The Third Xiangya Hospital of Central South University
Jiangxi Provincial Key Laboratory of Pharmacology of Traditional Chinese Medicine
School of Pharmacy, Jiangxi University of Chinese Medicine
Jiangxi University of Chinese Medicine
Institute of Information on Traditional Chinese Medicine,China Academy of Chinese Medical Sciences