Lapachol (BioDeep_00000002481)

 

Secondary id: BioDeep_00000180390, BioDeep_00000870842

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione

化学式: C15H14O3 (242.0943)
中文名称: 拉帕醇, 黄钟花醌
谱图信息: 最多检出来源 Viridiplantae(plant) 17.31%

分子结构信息

SMILES: CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
InChI: InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3

描述信息

Lapachol is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. It has a role as a plant metabolite, an antineoplastic agent, an antibacterial agent and an anti-inflammatory agent. It is a hydroxy-1,4-naphthoquinone and an olefinic compound.
NA is a natural product found in Plenckia populnea, Stereospermum colais, and other organisms with data available.
A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
D000970 - Antineoplastic Agents
[Raw Data] CB290_Lapachol_pos_40eV_CB000086.txt
[Raw Data] CB290_Lapachol_pos_50eV_CB000086.txt
[Raw Data] CB290_Lapachol_pos_10eV_CB000086.txt
[Raw Data] CB290_Lapachol_pos_30eV_CB000086.txt
[Raw Data] CB290_Lapachol_pos_20eV_CB000086.txt
[Raw Data] CB290_Lapachol_neg_10eV_000049.txt
[Raw Data] CB290_Lapachol_neg_20eV_000049.txt
[Raw Data] CB290_Lapachol_neg_40eV_000049.txt
[Raw Data] CB290_Lapachol_neg_50eV_000049.txt
[Raw Data] CB290_Lapachol_neg_30eV_000049.txt
Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].
Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

同义名列表

51 个代谢物同义名

4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione; 1,4-Naphthalenedione,2-hydroxy-3-(3-methyl-2-buten-1-yl)-; 2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione; 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione; 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)-; 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione; 2-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione; 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione; 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-; 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphtho-quinone; 2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone; 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone; 2-Hydroxy-3-(3-methyl-2-butenyl)naphthoquinone #; 4-08-00-02487 (Beilstein Handbook Reference); Cancer Chemother Rep (part 2) 4: 11 (1974); 1, 2-hydroxy-3-(3-methyl-2-butenyl)-; WLN: L66 BV EVJ CQ D2UY1&1; Zlut prirodni 16 [Czech]; Surinam greenheart wood; C.I. Natural Yellow 16; lapachol, sodium salt; Natural Yellow-?16; Spectrum5_001873; IPE-tobacco wood; Spectrum2_001451; Zlut prirodni 16; Spectrum3_000768; Bethabarra wood; Lapachoic acid; Lapachol, 98\\%; Oprea1_717083; DivK1c_000594; LAPACHOL [MI]; Lapachic acid; Lapachol wood; Tecomin (VAN); KBio3_001636; Tox21_202948; Taiguic acid; NCI60_000457; KBio1_000594; NCI60_000587; IDI1_000594; Greenhartin; Groenhartin; Greenharten; CAS-84-79-7; Taigu wood; Lapachol; Lapachol; Lapachol



数据库引用编号

55 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(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

83 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 7 CASP3, CAT, NQO1, PKM, PLA2G12A, TLR2, VEGFA
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 6 CYP1B1, FMO1, FMO3, FMO4, FMO5, HSP90B1
Nucleus 6 CASP3, HSP90B1, NQO1, PARP1, PKM, VEGFA
cytosol 9 CASP3, CAT, DHODH, FMO5, HSP90B1, IL1B, NQO1, PARP1, PKM
dendrite 1 NQO1
nuclear body 1 PARP1
nucleoplasm 3 CASP3, DHODH, PARP1
Cell membrane 2 C5AR1, TNF
Multi-pass membrane protein 1 C5AR1
Synapse 1 NQO1
cell surface 3 TLR2, TNF, VEGFA
glutamatergic synapse 1 CASP3
Golgi apparatus 2 TLR2, VEGFA
mitochondrial inner membrane 1 DHODH
neuronal cell body 3 CASP3, NQO1, TNF
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 3 IL1B, NQO1, PARP1
Lysosome 1 IL1B
plasma membrane 4 C5AR1, CSF2, TLR2, TNF
Membrane 8 CAT, CYP1B1, DHODH, HSP90B1, NQO1, PARP1, TLR2, VEGFA
basolateral plasma membrane 1 C5AR1
extracellular exosome 3 CAT, HSP90B1, PKM
endoplasmic reticulum 5 FMO1, FMO3, FMO5, HSP90B1, VEGFA
extracellular space 5 CSF2, CXCL8, IL1B, TNF, VEGFA
perinuclear region of cytoplasm 1 HSP90B1
adherens junction 1 VEGFA
mitochondrion 5 CAT, CYP1B1, DHODH, PARP1, PKM
protein-containing complex 3 CAT, HSP90B1, PARP1
intracellular membrane-bounded organelle 4 CAT, CSF2, CYP1B1, FMO3
Microsome membrane 4 CYP1B1, FMO3, FMO4, FMO5
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TLR2
Secreted 5 CSF2, CXCL8, IL1B, PLA2G12A, VEGFA
extracellular region 9 CAT, CSF2, CXCL8, HSP90B1, IL1B, PKM, PLA2G12A, TNF, VEGFA
Single-pass membrane protein 4 DHODH, FMO1, FMO3, FMO4
mitochondrial matrix 1 CAT
transcription regulator complex 1 PARP1
external side of plasma membrane 1 TNF
Extracellular vesicle 1 PKM
Secreted, extracellular space, extracellular matrix 1 VEGFA
cytoplasmic vesicle 1 C5AR1
nucleolus 1 PARP1
midbody 1 HSP90B1
apical part of cell 1 C5AR1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 PKM
Mitochondrion inner membrane 1 DHODH
Membrane raft 2 TLR2, TNF
focal adhesion 2 CAT, HSP90B1
extracellular matrix 1 VEGFA
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 HSP90B1, PKM
secretory granule 2 IL1B, VEGFA
receptor complex 1 TLR2
cilium 1 PKM
chromatin 1 PARP1
Cytoplasmic vesicle, phagosome membrane 1 TLR2
cell projection 1 TLR2
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 TLR2
Chromosome 1 PARP1
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
Melanosome 1 HSP90B1
cell body 1 TLR2
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 2 CAT, PKM
secretory granule lumen 2 CAT, PKM
secretory granule membrane 2 C5AR1, TLR2
endoplasmic reticulum lumen 2 FMO1, HSP90B1
platelet alpha granule lumen 1 VEGFA
Secreted, extracellular exosome 1 IL1B
Sarcoplasmic reticulum lumen 1 HSP90B1
protein-DNA complex 1 PARP1
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 PKM
Toll-like receptor 1-Toll-like receptor 2 protein complex 1 TLR2
Toll-like receptor 2-Toll-like receptor 6 protein complex 1 TLR2
granulocyte macrophage colony-stimulating factor receptor complex 1 CSF2
site of DNA damage 1 PARP1
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
endoplasmic reticulum chaperone complex 1 HSP90B1
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yujing Zhao, Jingjie An, Zhihong Dang, Jianglong Guo, Zhanlin Gao, Shujie Ma, Yaofa Li. Identification of highly active compounds from insecticidal plant Oroxylum indicum L. (Vent.) and the induction of apoptosis by lapachol on Sf9 cells. In vitro cellular & developmental biology. Animal. 2023 Nov; ?(?):. doi: 10.1007/s11626-023-00821-y. [PMID: 37966689]
  • Yi Yang, Jian Sheng, Yongjia Sheng, Jin Wang, Xiaohong Zhou, Wenyan Li, Yun Kong. Lapachol treats non-alcoholic fatty liver disease by modulating the M1 polarization of Kupffer cells via PKM2. International immunopharmacology. 2023 May; 120(?):110380. doi: 10.1016/j.intimp.2023.110380. [PMID: 37244116]
  • Nilson Nicolau Junior, Igor Andrade Santos, Bruno Amaral Meireles, Mariana Sant'Anna Pereira Nicolau, Igor Rodrigues Lapa, Renato Santana Aguiar, Ana Carolina Gomes Jardim, Diego Pandeló José. In silico evaluation of lapachol derivatives binding to the Nsp9 of SARS-CoV-2. Journal of biomolecular structure & dynamics. 2022 08; 40(13):5917-5931. doi: 10.1080/07391102.2021.1875050. [PMID: 33478342]
  • 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]
  • Nico Linzner, Verena Nadin Fritsch, Tobias Busche, Quach Ngoc Tung, Vu Van Loi, Jörg Bernhardt, Jörn Kalinowski, Haike Antelmann. The plant-derived naphthoquinone lapachol causes an oxidative stress response in Staphylococcus aureus. Free radical biology & medicine. 2020 10; 158(?):126-136. doi: 10.1016/j.freeradbiomed.2020.07.025. [PMID: 32712193]
  • Maria Fernanda Alves do Nascimento, Tatiane Freitas Borgati, Larissa Camila Ribeiro de Souza, Carlos Alberto Tagliati, Alaíde Braga de Oliveira. In silico, in vitro and in vivo evaluation of natural Bignoniaceous naphthoquinones in comparison with atovaquone targeting the selection of potential antimalarial candidates. Toxicology and applied pharmacology. 2020 08; 401(?):115074. doi: 10.1016/j.taap.2020.115074. [PMID: 32464218]
  • Ali Alaiye, Ercan Kaya, Mehmet Özgür Pınarbaşlı, Nuşin Harmancı, Cafer Yıldırım, Dilek Burukoğlu Dönmez, Cemal Cingi. An Experimental Comparison of the Analgesic and Anti-Inflammatory Effects of Safflower Oil, Benzydamine HCl, and Naproxen Sodium. Journal of medicinal food. 2020 Aug; 23(8):862-869. doi: 10.1089/jmf.2019.0157. [PMID: 32216647]
  • Lucas Bonfim Marques, Flaviano Melo Ottoni, Mauro Cunha Xavier Pinto, Juliana Martins Ribeiro, Fernanda S de Sousa, Ricardo Weinlich, Nathalia Cruz de Victo, Jaffar Kisitu, Anna-Katharina Holzer, Marcel Leist, Ricardo José Alves, Elaine Maria Souza-Fagundes. Lapachol acetylglycosylation enhances its cytotoxic and pro-apoptotic activities in HL60 cells. Toxicology in vitro : an international journal published in association with BIBRA. 2020 Jun; 65(?):104772. doi: 10.1016/j.tiv.2020.104772. [PMID: 31935485]
  • Frederico A V Castro, Gabriel F M de Souza, Marcos D Pereira. Characterization of lapachol cytotoxicity: contribution of glutathione depletion for oxidative stress in Saccharomyces cerevisiae. Folia microbiologica. 2020 Feb; 65(1):197-204. doi: 10.1007/s12223-019-00722-2. [PMID: 31183610]
  • A F D Di Stefano, M M Radicioni, A Vaccani, G Caccia, F Focanti, E Salvatori, F Pelacchi, R Picollo, M T Rosignoli, S Olivieri, G Bovi, A Comandini. Phase I Study in Healthy Women of a Novel Antimycotic Vaginal Ovule Combining Econazole and Benzydamine. Infectious diseases in obstetrics and gynecology. 2020; 2020(?):7201840. doi: 10.1155/2020/7201840. [PMID: 32410819]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Pooja Vyas, Dinesh Kumar Yadav, Poonam Khandelwal. Tectona grandis (teak) - A review on its phytochemical and therapeutic potential. Natural product research. 2019 Aug; 33(16):2338-2354. doi: 10.1080/14786419.2018.1440217. [PMID: 29506390]
  • Merve Harman, Nimet Ovayolu, Ozlem Ovayolu. The effect of three different solutions on preventing oral mucositis in cancer patients undergoing stem cell transplantation: a non-randomized controlled trial: A Turkish study - NON-RANDOMISED TRIAL. JPMA. The Journal of the Pakistan Medical Association. 2019 Jun; 69(6):811-816. doi: ". [PMID: 31189287]
  • S E Miranda, J A Lemos, R S Fernandes, F M Ottoni, R J Alves, A Ferretti, D Rubello, V N Cardoso, A L Branco de Barros. Technetium-99m-labeled lapachol as an imaging probe for breast tumor identification. Revista espanola de medicina nuclear e imagen molecular. 2019 May; 38(3):167-172. doi: 10.1016/j.remn.2018.10.006. [PMID: 30679039]
  • Iasmin Aparecida Cunha Araújo, Renata Cristina de Paula, Ceres Luciana Alves, Karen Ferraz Faria, Marco Miguel de Oliveira, Gabriela Gonçalves Mendes, Eliane Martins Ferreira Abdias Dias, Raul Rio Ribeiro, Alaíde Braga de Oliveira, Sydnei Magno da Silva. Efficacy of lapachol on treatment of cutaneous and visceral leishmaniasis. Experimental parasitology. 2019 Apr; 199(?):67-73. doi: 10.1016/j.exppara.2019.02.013. [PMID: 30797783]
  • Yasuhiro Uno, Makiko Shimizu, Hiromi Yoda, Hiroshi Yamazaki. Expression and metabolic activity of flavin-containing monooxygenase 1 in cynomolgus macaque kidney. Journal of medical primatology. 2019 02; 48(1):51-53. doi: 10.1111/jmp.12385. [PMID: 30252147]
  • Hauke Löcken, Cinzia Clamor, Klaus Müller. Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells. Journal of natural products. 2018 07; 81(7):1636-1644. doi: 10.1021/acs.jnatprod.8b00247. [PMID: 30003778]
  • Luciana Romão, Vanessa P do Canto, Paulo A Netz, Vivaldo Moura-Neto, Ângelo C Pinto, Cristian Follmer. Conjugation with polyamines enhances the antitumor activity of naphthoquinones against human glioblastoma cells. Anti-cancer drugs. 2018 07; 29(6):520-529. doi: 10.1097/cad.0000000000000619. [PMID: 29561308]
  • Miho Yamazaki-Nishioka, Makiko Shimizu, Hiroshi Suemizu, Megumi Nishiwaki, Marina Mitsui, Hiroshi Yamazaki. Human plasma metabolic profiles of benzydamine, a flavin-containing monooxygenase probe substrate, simulated with pharmacokinetic data from control and humanized-liver mice. Xenobiotica; the fate of foreign compounds in biological systems. 2018 Feb; 48(2):117-123. doi: 10.1080/00498254.2017.1288280. [PMID: 28145791]
  • Tadatoshi Tanino, Toru Bando, Akira Komada, Yukie Nojiri, Yuna Okada, Yukari Ueda, Eiichi Sakurai. Hepatic Flavin-Containing Monooxygenase 3 Enzyme Suppressed by Type 1 Allergy-Produced Nitric Oxide. Drug metabolism and disposition: the biological fate of chemicals. 2017 11; 45(11):1189-1196. doi: 10.1124/dmd.117.076570. [PMID: 28760731]
  • Therese Ellendorff, Reto Brun, Marcel Kaiser, Jandirk Sendker, Thomas J Schmidt. PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp. Molecules (Basel, Switzerland). 2015 May; 20(6):10082-94. doi: 10.3390/molecules200610082. [PMID: 26035104]
  • Silvia Castrignanò, Gianfranco Gilardi, Sheila J Sadeghi. Human flavin-containing monooxygenase 3 on graphene oxide for drug metabolism screening. Analytical chemistry. 2015 Mar; 87(5):2974-80. doi: 10.1021/ac504535y. [PMID: 25630629]
  • Tomomi Taniguchi-Takizawa, Makiko Shimizu, Toshiyuki Kume, Hiroshi Yamazaki. Benzydamine N-oxygenation as an index for flavin-containing monooxygenase activity and benzydamine N-demethylation by cytochrome P450 enzymes in liver microsomes from rats, dogs, monkeys, and humans. Drug metabolism and pharmacokinetics. 2015 Feb; 30(1):64-9. doi: 10.1016/j.dmpk.2014.09.006. [PMID: 25760531]
  • Mahnaz Sahebjamee, Arash Mansourian, Mohammad Hajimirzamohammad, Haji Mirza Mohammad Mohammad, Mohsen Taghi Zadeh, Reza Bekhradi, Ali Kazemian, Soheila Manifar, Sajjad Ashnagar, Kiavash Doroudgar. Comparative Efficacy of Aloe vera and Benzydamine Mouthwashes on Radiation-induced Oral Mucositis: A Triple-blind, Randomised, Controlled Clinical Trial. Oral health & preventive dentistry. 2015; 13(4):309-15. doi: 10.3290/j.ohpd.a33091. [PMID: 25431805]
  • Marek Smoluch, Przemyslaw Mielczarek, Edward Reszke, Gary M Hieftje, Jerzy Silberring. Determination of psychostimulants and their metabolites by electrochemistry linked on-line to flowing atmospheric pressure afterglow mass spectrometry. The Analyst. 2014 Sep; 139(17):4350-5. doi: 10.1039/c3an02067c. [PMID: 25010982]
  • Tatiana Hadjieva, Eva Cavallin-Ståhl, Margareta Linden, Fredrik Tiberg. Treatment of oral mucositis pain following radiation therapy for head-and-neck cancer using a bioadhesive barrier-forming lipid solution. Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer. 2014 Jun; 22(6):1557-62. doi: 10.1007/s00520-014-2117-3. [PMID: 24442926]
  • Serena Fiorito, Francesco Epifano, Céline Bruyère, Véronique Mathieu, Robert Kiss, Salvatore Genovese. Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives. Bioorganic & medicinal chemistry letters. 2014 Jan; 24(2):454-7. doi: 10.1016/j.bmcl.2013.12.049. [PMID: 24374273]
  • Giselle Tamayo-Castillo, Víctor Vásquez, María Isabel Ríos, María Victoria Rodríguez, Godofredo Solano, Susana Zacchino, Mahabir P Gupta. Isolation of major components from the roots of Godmania aesculifolia and determination of their antifungal activities. Planta medica. 2013 Dec; 79(18):1749-55. doi: 10.1055/s-0033-1351025. [PMID: 24356871]
  • Jin-Jian Lu, Jiao-Lin Bao, Guo-Sheng Wu, Wen-Shan Xu, Ming-Qing Huang, Xiu-Ping Chen, Yi-Tao Wang. Quinones derived from plant secondary metabolites as anti-cancer agents. Anti-cancer agents in medicinal chemistry. 2013 Mar; 13(3):456-63. doi: . [PMID: 22931417]
  • Ramon Lavado, Rosaura Aparicio-Fabre, Daniel Schlenk. Effects of salinity acclimation on the pesticide-metabolizing enzyme flavin-containing monooxygenase (FMO) in rainbow trout (Oncorhynchus mykiss). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2013 Jan; 157(1):9-15. doi: 10.1016/j.cbpc.2012.08.004. [PMID: 22981832]
  • Ricardo Q Aucélio, Ana I Peréz-Cordovés, Juliano L Xavier Lima, Aurélio Baird B Ferreira, Ana M Esteva Guas, Andrea R da Silva. Determination of lapachol in the presence of other naphthoquinones using 3MPA-CdTe quantum dots fluorescent probe. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Jan; 100(?):155-60. doi: 10.1016/j.saa.2012.04.020. [PMID: 22591798]
  • Beatrice Nyanchama Kiage-Mokua, Nils Roos, Jürgen Schrezenmeir. Lapacho tea (Tabebuia impetiginosa) extract inhibits pancreatic lipase and delays postprandial triglyceride increase in rats. Phytotherapy research : PTR. 2012 Dec; 26(12):1878-83. doi: 10.1002/ptr.4659. [PMID: 22431070]
  • Cristina Theoduloz, Ivanna Bravo Carrión, Mariano Walter Pertino, Daniela Valenzuela, Guillermo Schmeda-Hirschmann. Potential gastroprotective effect of novel cyperenoic acid/quinone derivatives in human cell cultures. Planta medica. 2012 Nov; 78(17):1807-12. doi: 10.1055/s-0032-1315389. [PMID: 23047252]
  • Michael Niehues, Valéria Priscila Barros, Flávio da Silva Emery, Marcelo Dias-Baruffi, Marilda das Dores Assis, Norberto Peporine Lopes. Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds. European journal of medicinal chemistry. 2012 Aug; 54(?):804-12. doi: 10.1016/j.ejmech.2012.06.042. [PMID: 22796040]
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