Emetine (BioDeep_00000001955)

   

natural product


代谢物信息卡片


6,7,10,11-tetramethoxyemetan

  化学式: C29H40N2O4 (480.2988)
中文名称: 依米丁
  谱图信息: 最多检出来源 Viridiplantae(plant) 31.59%

分子结构信息

SMILES: CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
InChI: InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3


描述信息

A pyridoisoquinoline comprising emetam having methoxy substituents at the 6-, 7-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01A - Agents against amoebiasis and other protozoal diseases
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
D004791 - Enzyme Inhibitors > D011500 - Protein Synthesis Inhibitors
D005765 - Gastrointestinal Agents > D002400 - Cathartics
D005765 - Gastrointestinal Agents > D004639 - Emetics
D002491 - Central Nervous System Agents
Origin: Plant; Formula(Parent): C29H40N2O4; Bottle Name:Emetine dihydrochloride; PRIME Parent Name:Emetine; PRIME in-house No.:V0282; SubCategory_DNP: Isoquinoline alkaloids, Emetine alkaloids
Annotation level-1
Acquisition and generation of the data is financially supported by the Max-Planck-Society
IPB_RECORD: 2501; CONFIDENCE confident structure

同义名列表

54 个代谢物同义名

Emetine; 6,7,10,11-tetramethoxyemetan; Ipecac (Emetine); GNF-Pf-5190; YAT; Emetine; (-)-Emetine; (2S,3R,11bS)-2-(((1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo(a)quinolizine; (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine; (2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-2H-benzo[a]quinolizine; 2H-BENZO(A)QUINOLIZINE, 3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2-(((1R)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-ISOQUINOLINYL)METHYL)-, (2S,3R,11BS)-; 2H-BENZO(A)QUINOLIZINE, 3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2-((1,2,3,4-TETRAHYDRO-6,7-DIMET/; 2H-Benzo(a)quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-((1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl)-; 2H-Benzo[a]quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-(2S,3R,11bS)-; 6',7',10,11-tetrakis(methyloxy)emetan; 6',7',10,11-Tetramethoxy-emetan; 6',7',10,11-Tetramethoxy-emetan;Emetine;(-)-Emetine; 6',7',10,11-Tetramethoxyemetan; 6'',7'',10,11-tetramethoxyemetan; Amebicide (Salt/Mix); Bio1_000345; Bio1_000834; Bio1_001323; BPBio1_000396; Cephaeline methyl ether; Cephaline-O-methyl ether; Dihydrochloride, Emetine; Emetan, 6',7',10,11-tetramethoxy-; Emetin; Emetine (>90%); Emetine [BAN]; EMETINE [HSDB]; EMETINE [MI]; EMETINE [VANDF]; EMETINE [WHO-DD]; Emetine Dihydrochloride; Emetine dihydrochloride hydrate; Emetine hydrochloride; Emetine hydrochloride, European Pharmacopoeia (EP) Reference Standard; Emetine hydrochloride, United States Pharmacopeia (USP) Reference Standard; Emetinum; EMETINUM [HPUS]; Hydrochloride, Emetine; Ipecine; Lopac0_000460; Methyl cephaeline; Methylcephaeline; NCI60_002959; Prestwick3_000570; Purum (Salt/Mix); Tox21_110901; Tox21_110901_1; UNII-X8D5EPO80M; X8D5EPO80M



数据库引用编号

53 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(1)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

29 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 13 ABCB1, BCL2, BCL2L1, CA1, CASP3, CTNNB1, HIF1A, MAPK14, MYC, PIK3CA, PPIA, RPS14, TNK1
Peripheral membrane protein 1 TNK1
Endoplasmic reticulum membrane 2 BCL2, HSP90B1
Mitochondrion membrane 1 BCL2L1
Nucleus 8 BCL2, CASP3, CTNNB1, HIF1A, HSP90B1, MAPK14, MYC, PPIA
cytosol 12 BCL2, BCL2L1, CA1, CASP3, CTNNB1, HIF1A, HSP90B1, MAPK14, PIK3CA, PPIA, PRF1, RPS14
nuclear body 1 HIF1A
centrosome 2 BCL2L1, CTNNB1
nucleoplasm 6 CASP3, CTNNB1, HIF1A, MAPK14, MYC, RPS14
RNA polymerase II transcription regulator complex 1 HIF1A
Cell membrane 4 ABCB1, CTNNB1, PRF1, TNF
Cytoplasmic side 1 BCL2L1
lamellipodium 2 CTNNB1, PIK3CA
Multi-pass membrane protein 3 ABCB1, CACNA1I, PRF1
Synapse 1 CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 2 ABCB1, TNF
glutamatergic synapse 3 CASP3, CTNNB1, MAPK14
Golgi membrane 1 INS
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 2 CASP3, TNF
presynaptic membrane 1 CTNNB1
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 BCL2L1
plasma membrane 8 ABCB1, CACNA1I, CTNNB1, IFNLR1, PIK3CA, PRF1, TNF, TNK1
synaptic vesicle membrane 1 BCL2L1
Membrane 11 ABCB1, BCL2, CACNA1I, CTNNB1, HSP90B1, IFNLR1, MYC, PPIA, PRF1, RPS14, TNK1
apical plasma membrane 1 ABCB1
basolateral plasma membrane 1 CTNNB1
extracellular exosome 6 ABCB1, CA1, CTNNB1, HSP90B1, PPIA, RPS14
endoplasmic reticulum 3 BCL2, BCL2L1, HSP90B1
extracellular space 4 IL6, INS, PPIA, TNF
perinuclear region of cytoplasm 3 CTNNB1, HSP90B1, PIK3CA
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, BCL2L1, MAPK14
protein-containing complex 6 BCL2, CTNNB1, HIF1A, HSP90B1, MYC, PPIA
postsynaptic density 2 CASP3, RPS14
Single-pass type I membrane protein 1 IFNLR1
Secreted 4 IL6, INS, PPIA, PRF1
extracellular region 7 HSP90B1, IL6, INS, MAPK14, PPIA, PRF1, TNF
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 2 BCL2, BCL2L1
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
transcription regulator complex 1 CTNNB1
motile cilium 1 HIF1A
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 1 TNF
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
nucleolus 2 MYC, RPS14
Wnt signalosome 1 CTNNB1
axon cytoplasm 1 HIF1A
midbody 1 HSP90B1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 PPIA
postsynaptic membrane 1 CTNNB1
Apical cell membrane 1 ABCB1
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 4 CTNNB1, HSP90B1, PPIA, RPS14
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
collagen-containing extracellular matrix 1 HSP90B1
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear speck 2 HIF1A, MAPK14
chromatin 2 HIF1A, MYC
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
Nucleus, nucleolus 2 MYC, RPS14
spindle pole 2 CTNNB1, MAPK14
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
nuclear envelope 1 MYC
Endomembrane system 1 CTNNB1
endosome lumen 2 INS, PRF1
Nucleus, nucleoplasm 1 MYC
Melanosome 1 HSP90B1
Nucleus speckle 1 HIF1A
euchromatin 2 CTNNB1, HIF1A
myelin sheath 1 BCL2
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 2 MAPK14, PPIA
secretory granule lumen 3 INS, MAPK14, PPIA
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 HSP90B1, IL6, INS
voltage-gated calcium channel complex 1 CACNA1I
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
transport vesicle 1 INS
RNA polymerase II transcription repressor complex 1 MYC
beta-catenin-TCF complex 1 CTNNB1
small-subunit processome 1 RPS14
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRF1
presynaptic active zone cytoplasmic component 1 CTNNB1
Sarcoplasmic reticulum lumen 1 HSP90B1
ribonucleoprotein complex 1 RPS14
protein-DNA complex 1 CTNNB1
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 MYC
cytosolic ribosome 1 RPS14
catenin complex 1 CTNNB1
endocytic vesicle lumen 1 HSP90B1
ribosome 1 RPS14
Myc-Max complex 1 MYC
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 HSP90B1
cytosolic small ribosomal subunit 1 RPS14
Cytolytic granule 1 PRF1
cytolytic granule lumen 1 PRF1
BAD-BCL-2 complex 1 BCL2
beta-catenin-TCF7L2 complex 1 CTNNB1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
small ribosomal subunit 1 RPS14
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
nucleoplasmic reticulum 1 MYC


文献列表

  • Mohibullah Shah, Ramsha Yamin, Iqra Ahmad, Gang Wu, Zainab Jahangir, Amen Shamim, Haq Nawaz, Umar Nishan, Riaz Ullah, Essam A Ali, Sheheryar, Ke Chen. In-silico evaluation of natural alkaloids against the main protease and spike glycoprotein as potential therapeutic agents for SARS-CoV-2. PloS one. 2024; 19(1):e0294769. doi: 10.1371/journal.pone.0294769. [PMID: 38175855]
  • Kun Zhang, Ke Wang, Chaoguo Zhang, Xiuli Teng, Dan Li, Mingwei Chen. Exploring the potential mechanism of emetine against coronavirus disease 2019 combined with lung adenocarcinoma: bioinformatics and molecular simulation analyses. BMC cancer. 2022 Jun; 22(1):687. doi: 10.1186/s12885-022-09763-2. [PMID: 35733175]
  • Juhyeon Son, Sang Yeol Lee. Emetine exerts anticancer effects in U2OS human osteosarcoma cells via activation of p38 and inhibition of ERK, JNK, and β-catenin signaling pathways. Journal of biochemical and molecular toxicology. 2021 Oct; 35(10):e22868. doi: 10.1002/jbt.22868. [PMID: 34338395]
  • Ming-Cheng Lee, Yin-Kai Chen, Jyy-Jih Tsai-Wu, Yih-Jen Hsu, Bor-Ru Lin. Zinc supplementation augments the suppressive effects of repurposed NF-κB inhibitors on ACE2 expression in human lung cell lines. Life sciences. 2021 Sep; 280(?):119752. doi: 10.1016/j.lfs.2021.119752. [PMID: 34171382]
  • Edin Muratspahić, Nataša Tomašević, Shahrooz Nasrollahi-Shirazi, Jasmin Gattringer, Fabiola Susanna Emser, Michael Freissmuth, Christian W Gruber. Plant-Derived Cyclotides Modulate κ-Opioid Receptor Signaling. Journal of natural products. 2021 08; 84(8):2238-2248. doi: 10.1021/acs.jnatprod.1c00301. [PMID: 34308635]
  • Ram Kumar, Mohammad Afsar, Nitin Khandelwal, Yogesh Chander, Thachamvally Riyesh, Ramesh Kumar Dedar, Baldev R Gulati, Yash Pal, Sanjay Barua, Bhupendra N Tripathi, Tanweer Hussain, Naveen Kumar. Emetine suppresses SARS-CoV-2 replication by inhibiting interaction of viral mRNA with eIF4E. Antiviral research. 2021 05; 189(?):105056. doi: 10.1016/j.antiviral.2021.105056. [PMID: 33711336]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Sayed S Sohrab, Mohd Suhail, Mohammad A Kamal, Esam I Azhar. Natural Products Homoharringtonine and Emetine Alkaloids as SARS-CoV-2 Treatment Options. Current pharmaceutical design. 2021; 27(32):3444-3453. doi: 10.2174/1381612826666201210121858. [PMID: 33302852]
  • Namrta Choudhry, Xin Zhao, Dan Xu, Mark Zanin, Weisan Chen, Zifeng Yang, Jianxin Chen. Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). Journal of medicinal chemistry. 2020 11; 63(22):13205-13227. doi: 10.1021/acs.jmedchem.0c00626. [PMID: 32845145]
  • Dario Cattaneo, Dario Cattaneo, Cristina Gervasoni, Mario Corbellino, Massimo Galli, Agostino Riva, Cristina Gervasoni, Emilio Clementi, Emilio Clementi. Does lopinavir really inhibit SARS-CoV-2?. Pharmacological research. 2020 08; 158(?):104898. doi: 10.1016/j.phrs.2020.104898. [PMID: 32438034]
  • Aleksandr Ianevski, Rouan Yao, Mona Høysæter Fenstad, Svetlana Biza, Eva Zusinaite, Tuuli Reisberg, Hilde Lysvand, Kirsti Løseth, Veslemøy Malm Landsem, Janne Fossum Malmring, Valentyn Oksenych, Sten Even Erlandsen, Per Arne Aas, Lars Hagen, Caroline H Pettersen, Tanel Tenson, Jan Egil Afset, Svein Arne Nordbø, Magnar Bjørås, Denis E Kainov. Potential Antiviral Options against SARS-CoV-2 Infection. Viruses. 2020 06; 12(6):. doi: 10.3390/v12060642. [PMID: 32545799]
  • Ka-Tim Choy, Alvina Yin-Lam Wong, Prathanporn Kaewpreedee, Sin Fun Sia, Dongdong Chen, Kenrie Pui Yan Hui, Daniel Ka Wing Chu, Michael Chi Wai Chan, Peter Pak-Hang Cheung, Xuhui Huang, Malik Peiris, Hui-Ling Yen. Remdesivir, lopinavir, emetine, and homoharringtonine inhibit SARS-CoV-2 replication in vitro. Antiviral research. 2020 06; 178(?):104786. doi: 10.1016/j.antiviral.2020.104786. [PMID: 32251767]
  • Ioanna A Anastasiou, Ioanna Eleftheriadou, Anastasios Tentolouris, Dimitrios Tsilingiris, Nikolaos Tentolouris. In Vitro Data of Current Therapies for SARS-CoV-2. Current medicinal chemistry. 2020; 27(27):4542-4548. doi: 10.2174/0929867327666200513075430. [PMID: 32400323]
  • Petter I Andersen, Klara Krpina, Aleksandr Ianevski, Nastassia Shtaida, Eunji Jo, Jaewon Yang, Sandra Koit, Tanel Tenson, Veijo Hukkanen, Marit W Anthonsen, Magnar Bjoras, Magnus Evander, Marc P Windisch, Eva Zusinaite, Denis E Kainov. Novel Antiviral Activities of Obatoclax, Emetine, Niclosamide, Brequinar, and Homoharringtonine. Viruses. 2019 10; 11(10):. doi: 10.3390/v11100964. [PMID: 31635418]
  • Godwin Akpeko Dziwornu, Stephanie Kamunya, Tando Ntsabo, Kelly Chibale. Novel antimycobacterial C-21 amide derivatives of the antibiotic fusidic acid: synthesis, pharmacological evaluation and rationalization of media-dependent activity using molecular docking studies in the binding site of human serum albumin. MedChemComm. 2019 Jun; 10(6):961-969. doi: 10.1039/c9md00161a. [PMID: 31303994]
  • Celia Bustos-Brito, Pedro Joseph-Nathan, Eleuterio Burgueño-Tapia, Diego Martínez-Otero, Antonio Nieto-Camacho, Fernando Calzada, Lilian Yépez-Mulia, Baldomero Esquivel, Leovigildo Quijano. Structure and Absolute Configuration of Abietane Diterpenoids from Salvia clinopodioides: Antioxidant, Antiprotozoal, and Antipropulsive Activities. Journal of natural products. 2019 05; 82(5):1207-1216. doi: 10.1021/acs.jnatprod.8b00952. [PMID: 31063376]
  • Faridoon, Dumisani Mnkandhla, Michelle Isaacs, Heinrich C Hoppe, Perry T Kaye. Synthesis and evaluation of substituted 4-arylimino-3-hydroxybutanoic acids as potential HIV-1 integrase inhibitors. Bioorganic & medicinal chemistry letters. 2018 04; 28(6):1067-1070. doi: 10.1016/j.bmcl.2018.02.020. [PMID: 29482943]
  • Sonja Krstin, Tamer Mohamed, Xiaojuan Wang, Michael Wink. How do the alkaloids emetine and homoharringtonine kill trypanosomes? An insight into their molecular modes of action. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2016 Dec; 23(14):1771-1777. doi: 10.1016/j.phymed.2016.10.008. [PMID: 27912879]
  • Rupkatha Mukhopadhyay, Sujayita Roy, Rajkumar Venkatadri, Yu-Pin Su, Wenjuan Ye, Elena Barnaeva, Lesley Mathews Griner, Noel Southall, Xin Hu, Amy Q Wang, Xin Xu, Andrés E Dulcey, Juan J Marugan, Marc Ferrer, Ravit Arav-Boger. Efficacy and Mechanism of Action of Low Dose Emetine against Human Cytomegalovirus. PLoS pathogens. 2016 06; 12(6):e1005717. doi: 10.1371/journal.ppat.1005717. [PMID: 27336364]
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  • Celia Bustos-Brito, Mariano Sánchez-Castellanos, Baldomero Esquivel, José S Calderón, Fernando Calzada, Lilian Yépez-Mulia, Pedro Joseph-Nathan, Gabriel Cuevas, Leovigildo Quijano. ent-Kaurene Glycosides from Ageratina cylindrica. Journal of natural products. 2015 Nov; 78(11):2580-7. doi: 10.1021/acs.jnatprod.5b00488. [PMID: 26517282]
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  • Ana Luiza Chaves Valadão, Celina Monteiro Abreu, Juliana Zanatta Dias, Pablo Arantes, Hugo Verli, Amilcar Tanuri, Renato Santana de Aguiar. Natural Plant Alkaloid (Emetine) Inhibits HIV-1 Replication by Interfering with Reverse Transcriptase Activity. Molecules (Basel, Switzerland). 2015 Jun; 20(6):11474-89. doi: 10.3390/molecules200611474. [PMID: 26111177]
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  • Celia Bustos-Brito, Mariano Sánchez-Castellanos, Baldomero Esquivel, José S Calderón, Fernando Calzada, Lilian Yepez-Mulia, Angelina Hernández-Barragán, Pedro Joseph-Nathan, Gabriel Cuevas, Leovigildo Quijano. Structure, absolute configuration, and antidiarrheal activity of a thymol derivative from Ageratina cylindrica. Journal of natural products. 2014 Feb; 77(2):358-63. doi: 10.1021/np400964w. [PMID: 24502360]
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