(S)-Boldine (BioDeep_00000000043)

 

Secondary id: BioDeep_00000397980

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

化学式: C19H21NO4 (327.1471)
中文名称: 波尔定, 波尔定碱
谱图信息: 最多检出来源 Viridiplantae(plant) 23.05%

分子结构信息

SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)OC)O
InChI: InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3

描述信息

Boldine is an aporphine alkaloid.
Boldine is a natural product found in Lindera umbellata, Damburneya salicifolia, and other organisms with data available.
See also: Peumus boldus leaf (part of).
(S)-Boldine is found in sweet bay. (S)-Boldine is an alkaloid from Sassafras and the leaves of Peumus boldus (boldo). (S)-Boldine is a flavouring ingredient.
Alkaloid from Sassafras and the leaves of Peumus boldus (boldo). Flavouring ingredient. (S)-Boldine is found in sweet bay.
D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents > D009466 - Neuromuscular Blocking Agents
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D020011 - Protective Agents > D000975 - Antioxidants
D000893 - Anti-Inflammatory Agents
D018501 - Antirheumatic Agents
Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1].
Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1].

同义名列表

44 个代谢物同义名

4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol; 4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-; 4H-Dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-; 4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-; 4H-Dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-; (6AS)-5,6,6A,7-TETRAHYDRO-1,10-DIMETHOXY-6-METHYL-4H-DIBENZO(DE,G)QUINOLINE-2,9-DIOL; (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol; 1,10-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol, (S)-; (S)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol; 5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol; Boldine, European Pharmacopoeia (EP) Reference Standard; 6a.alpha.-Aporphine-2,9-diol, 1,10-dimethoxy-; 5-21-06-00118 (Beilstein Handbook Reference); 6a-alpha-APORPHINE-2,9-DIOL, 1,10-DIMETHOXY-; 1,10-Dimethoxy-6a-.alpha.-aporphine-2,9-diol; 1,10-DIMETHOXY-6A.ALPHA.-APORPHINE-2,9-DIOL; 6aalpha-Aporphine-2,9-diol, 1,10-dimethoxy-; 1,10-Dimethoxy-6a-alpha-aporphine-2,9-diol; 1,10-dimethoxy-6aalpha-aporphine-2,9-diol; Boldine, analytical reference material; 2,9-Dihydroxy-1,10-dimethoxyaporphine; 1,10-Dimethoxy-2,9-dihydroxyaporphine; 2,6-dihydroxy-3,5-dimethoxyaporphine; Boldine, analytical standard; BOLDINE [EP MONOGRAPH]; BOLDINE (EP MONOGRAPH); Boldine chloroform; Aprophine alkaloid; Prestwick3_000600; ex Peumus boldus; BOLDINE [WHO-DD]; UNII-8I91GE2769; (S)-(+)-Boldine; (+)-(S)-Boldine; BPBio1_000528; BOLDINE [MI]; Prestwick_46; (S)-Boldine; (+)-Boldine; Uniboldina; 8I91GE2769; Boldine; Boldin; Boldine



数据库引用编号

21 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)

39 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 8 BCL2, CASP3, CDKN1A, GFAP, GJA1, NOS3, TERT, TNFSF11
Peripheral membrane protein 2 ACHE, GORASP1
Endoplasmic reticulum membrane 4 BCL2, GJA1, GJC1, PANX1
Nucleus 8 ACHE, BCL2, CASP3, CDKN1A, GJA1, MPO, NOS3, TERT
cytosol 8 ACP5, BCL2, CASP3, CDKN1A, GFAP, GJA1, NOS3, TERT
nuclear body 1 CDKN1A
nucleoplasm 7 CASP3, CDKN1A, GJA1, GJC1, MPO, NOS3, TERT
Cell membrane 7 ACHE, AGTR1, GJA1, GJC1, PANX1, TNF, TNFSF11
Cytoplasmic side 1 GORASP1
Multi-pass membrane protein 4 AGTR1, GJA1, GJC1, PANX1
Golgi apparatus membrane 1 GORASP1
Synapse 2 ACHE, GJC1
cell junction 1 GJA1
cell surface 3 ACHE, GJC1, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 4 ACHE, GJA1, GORASP1, NOS3
Golgi membrane 4 GJA1, GORASP1, INS, NOS3
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
Lysosome 2 ACP5, MPO
plasma membrane 10 ACHE, AGTR1, GJA1, GJC1, NOS3, PANX1, TERT, TNF, TNFRSF11B, TNFSF11
Membrane 6 ACHE, ACP5, AGTR1, BCL2, PANX1, TNFSF11
apical plasma membrane 1 GJA1
caveola 1 NOS3
extracellular exosome 1 MPO
endoplasmic reticulum 4 BCL2, GJA1, GJC1, PANX1
extracellular space 7 ACHE, CXCL8, INS, MPO, TNF, TNFRSF11B, TNFSF11
perinuclear region of cytoplasm 3 ACHE, CDKN1A, NOS3
gap junction 3 GJA1, GJC1, PANX1
intercalated disc 2 GJA1, GJC1
mitochondrion 2 BCL2, GJA1
protein-containing complex 3 BCL2, CDKN1A, PANX1
intracellular membrane-bounded organelle 2 GJA1, MPO
postsynaptic density 1 CASP3
Secreted 5 ACHE, CXCL8, INS, TNFRSF11B, TNFSF11
extracellular region 7 ACHE, CXCL8, INS, MPO, TNF, TNFRSF11B, TNFSF11
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
astrocyte end-foot 1 GFAP
Extracellular side 1 ACHE
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
nucleolus 2 CDKN1A, TERT
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
Membrane raft 2 GJA1, TNF
pore complex 1 BCL2
focal adhesion 1 GJA1
cis-Golgi network 1 GORASP1
extracellular matrix 1 TNFRSF11B
mitochondrial nucleoid 1 TERT
basement membrane 1 ACHE
Nucleus, PML body 1 TERT
PML body 1 TERT
secretory granule 1 MPO
Cell junction, gap junction 2 GJA1, GJC1
connexin complex 2 GJA1, GJC1
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 2 GFAP, GJA1
lateral plasma membrane 1 GJA1
nuclear speck 1 TERT
receptor complex 1 TNFRSF11B
cell projection 1 GFAP
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
Nucleus, nucleolus 1 TERT
Chromosome, telomere 1 TERT
chromosome, telomeric region 1 TERT
Lipid-anchor, GPI-anchor 1 ACHE
endosome lumen 1 INS
Nucleus, nucleoplasm 1 TERT
Golgi-associated vesicle membrane 1 GJA1
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
cell body 1 GFAP
side of membrane 1 ACHE
myelin sheath 1 BCL2
intermediate filament cytoskeleton 1 GFAP
azurophil granule 1 MPO
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
tight junction 1 GJA1
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
nuclear telomere cap complex 1 TERT
RNA-directed RNA polymerase complex 1 TERT
telomerase catalytic core complex 1 TERT
telomerase holoenzyme complex 1 TERT
TERT-RMRP complex 1 TERT
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
cell-cell contact zone 1 GJA1
cyclin-dependent protein kinase holoenzyme complex 1 CDKN1A
cytoplasmic side of lysosomal membrane 1 GFAP
bleb 1 PANX1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
BAD-BCL-2 complex 1 BCL2
PCNA-p21 complex 1 CDKN1A
[Isoform H]: Cell membrane 1 ACHE
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Devaraj Ezhilarasan, Karthik Shree Harini, Munusamy Karthick, Prathap Lavanya. Boldine protects against carbon tetrachloride-induced chronic liver injury by regulating NF-κB signaling pathway. Journal of biochemical and molecular toxicology. 2024 Apr; 38(4):e23691. doi: 10.1002/jbt.23691. [PMID: 38500399]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Devaraj Ezhilarasan, Subramanian Raghunandhakumar. Boldine treatment protects acetaminophen-induced liver inflammation and acute hepatic necrosis in mice. Journal of biochemical and molecular toxicology. 2021 Apr; 35(4):e22697. doi: 10.1002/jbt.22697. [PMID: 33393705]
  • Izabela Natalia Faria Gomes, Ana Gabriela Silva, Gustavo Fernando de Frazao Lima, Tamara Ribeiro Longatti, Lucas Fernandes Do Carmo, Jose Augusto Ferreira Perez Villar, Arali Aparecida Da Costa Araujo, Ralph Gruppi Tome, Helio Batista Dos Santos, Rosy Iara Maciel De Azambuja Ribeiro. Alkaloid and phenolic compounds of Xylopia aromatica inhibits tumor growth by down-regulating matrix metalloproteinase-2 (MMP-2) expression. Pakistan journal of pharmaceutical sciences. 2021 Mar; 34(2):599-606. doi: ". [PMID: 34275835]
  • Nirmala Subramaniam, Pugazhendhi Kannan, Jagan Sundaram, Ashok Mari, Sathesh K Velli, Sharmila Salam, Palanisamy Krishnan, Gopalakrishnan Balaraman, Devaki Thiruvengadam. Potential Chemopreventive Role of Boldine Against Hepatocellular Carcinoma via Modulation of Cell Cycle Proteins in Rat Model. Anti-cancer agents in medicinal chemistry. 2021; 21(18):2546-2552. doi: 10.2174/1871520621666210203102854. [PMID: 33535961]
  • Thaise Boeing, Luisa Natália Bolda Mariano, Ana Caroline Dos Santos, Bianca Tolentino, Angela Cadorin Vargas, Priscila de Souza, Luciane Angela Nottar Nesello, Luísa Mota da Silva. Gastroprotective effect of the alkaloid boldine: Involvement of non-protein sulfhydryl groups, prostanoids and reduction on oxidative stress. Chemico-biological interactions. 2020 Aug; 327(?):109166. doi: 10.1016/j.cbi.2020.109166. [PMID: 32531310]
  • Luis A Cea, Gabriela Fernández, Guisselle Arias-Bravo, Mario Castillo-Ruiz, Rosalba Escamilla, María C Brañes, Juan C Sáez. Blockade of Hemichannels Normalizes the Differentiation Fate of Myoblasts and Features of Skeletal Muscles from Dysferlin-Deficient Mice. International journal of molecular sciences. 2020 Aug; 21(17):. doi: 10.3390/ijms21176025. [PMID: 32825681]
  • Xiufang Liang, Yunan Xiang, Yanling Li, Ping Feng, Yongping Qin, Xianrong Lai. A rapid method for simultaneous quantification of berberine, berbamine, magnoflorine and berberrubine in mouse serum using UPLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Apr; 1142(?):122040. doi: 10.1016/j.jchromb.2020.122040. [PMID: 32145638]
  • Nirmala Subramaniam, Pugazhendhi Kannan, Ashokkumar K, Devaki Thiruvengadam. Hepatoprotective effect of boldine against diethylnitrosamine-induced hepatocarcinogenesis in wistar rats. Journal of biochemical and molecular toxicology. 2019 Dec; 33(12):e22404. doi: 10.1002/jbt.22404. [PMID: 31593341]
  • Wanderson Fernando Mello de Souza, Xavier Maia Mariano, Júlia Lima Isnard, Gisele Santos de Souza, Ana Luísa de Souza Gomes, Rutheneia José Tavares de Carvalho, Cristiane Barbosa Rocha, César Luis Siqueira Junior, Ricardo Felipe Alves Moreira. Evaluation of the volatile composition, toxicological and antioxidant potentials of the essential oils and teas of commercial Chilean boldo samples. Food research international (Ottawa, Ont.). 2019 10; 124(?):27-33. doi: 10.1016/j.foodres.2018.12.059. [PMID: 31466647]
  • Gonzalo I Gómez, Victoria Velarde. Boldine Improves Kidney Damage in the Goldblatt 2K1C Model Avoiding the Increase in TGF-β. International journal of molecular sciences. 2018 Jun; 19(7):. doi: 10.3390/ijms19071864. [PMID: 29941815]
  • Gonzalo Fuentes-Barros, Sebastián Castro-Saavedra, Leonel Liberona, Williams Acevedo-Fuentes, Cristian Tirapegui, César Mattar, Bruce K Cassels. Variation of the alkaloid content of Peumus boldus (boldo). Fitoterapia. 2018 Jun; 127(?):179-185. doi: 10.1016/j.fitote.2018.02.020. [PMID: 29454020]
  • Fatma Gizem Avci, Nihat Alpagu Sayar, Berna Sariyar Akbulut. An OMIC approach to elaborate the antibacterial mechanisms of different alkaloids. Phytochemistry. 2018 May; 149(?):123-131. doi: 10.1016/j.phytochem.2017.12.023. [PMID: 29494814]
  • Xinyao Yang, Xiaoli Gao, Yuan Cao, Qiang Guo, Shanshan Li, Zhixiang Zhu, Yunfang Zhao, Pengfei Tu, Xingyun Chai. Anti-Inflammatory Effects of Boldine and Reticuline Isolated from Litsea cubeba through JAK2/STAT3 and NF-κB Signaling Pathways. Planta medica. 2018 Jan; 84(1):20-25. doi: 10.1055/s-0043-113447. [PMID: 28651290]
  • Adam Kostelnik, Miroslav Pohanka. Inhibition of Acetylcholinesterase and Butyrylcholinesterase by a Plant Secondary Metabolite Boldine. BioMed research international. 2018; 2018(?):9634349. doi: 10.1155/2018/9634349. [PMID: 29850593]
  • Hongyan Zhao, Huihui Xu, Senyan Qiao, Cheng Lu, Gui Wang, Meijie Liu, Baosheng Guo, Yong Tan, Dahong Ju, Cheng Xiao. Boldine isolated from Litsea cubeba inhibits bone resorption by suppressing the osteoclast differentiation in collagen-induced arthritis. International immunopharmacology. 2017 Oct; 51(?):114-123. doi: 10.1016/j.intimp.2017.08.013. [PMID: 28826044]
  • Cecilia M Peralta, Cecilia Henestrosa, Raúl A Gil, Liliana P Fernández, Gimena Acosta. Novel spectrofluorimetric method for boldine alkaloid determination in herbal drugs and phytopharmaceuticals. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2017 Sep; 184(?):101-108. doi: 10.1016/j.saa.2017.04.039. [PMID: 28486201]
  • Isabel Cristina Salama, Cristina Arrais-Lima, Wagner Welber Arrais-Silva. Evaluation of Boldine Activity against Intracellular Amastigotes of Leishmania amazonensis. The Korean journal of parasitology. 2017 Jun; 55(3):337-340. doi: 10.3347/kjp.2017.55.3.337. [PMID: 28719960]
  • Pavel Tomšík, Stanislav Mičuda, Darina Muthná, Eva Čermáková, Radim Havelek, Emil Rudolf, Miloš Hroch, Zuzana Kadová, Martina Řezáčová, Jana Ćmielová, Pavel Živný. Boldine Inhibits Mouse Mammary Carcinoma In Vivo and Human MCF-7 Breast Cancer Cells In Vitro. Planta medica. 2016 Nov; 82(16):1416-1424. doi: 10.1055/s-0042-113611. [PMID: 27611982]
  • Matheus Chimelo Bianchini, Claudia Ortiz Alves Gularte, Dandara Fidélis Escoto, Geovana Pereira, Mateus Cristofari Gayer, Rafael Roehrs, Félix Alexandre Antunes Soares, Robson L Puntel. Peumus boldus (Boldo) Aqueous Extract Present Better Protective Effect than Boldine Against Manganese-Induced Toxicity in D. melanogaster. Neurochemical research. 2016 Oct; 41(10):2699-2707. doi: 10.1007/s11064-016-1984-z. [PMID: 27350578]
  • Azeana Zahari, Abdulwali Ablat, Noridayu Omer, Mohd Azlan Nafiah, Yasodha Sivasothy, Jamaludin Mohamad, Mohammad Niyaz Khan, Khalijah Awang. Ultraviolet-visible study on acid-base equilibria of aporphine alkaloids with antiplasmodial and antioxidant activities from Alseodaphne corneri and Dehaasia longipedicellata. Scientific reports. 2016 Feb; 6(?):21517. doi: 10.1038/srep21517. [PMID: 26898753]
  • Jolana Cermanova, Zuzana Kadova, Marie Zagorova, Milos Hroch, Pavel Tomsik, Petr Nachtigal, Zdenka Kudlackova, Petr Pavek, Michaela Dubecka, Martina Ceckova, Frantisek Staud, Tomas Laho, Stanislav Micuda. Boldine enhances bile production in rats via osmotic and farnesoid X receptor dependent mechanisms. Toxicology and applied pharmacology. 2015 May; 285(1):12-22. doi: 10.1016/j.taap.2015.03.004. [PMID: 25771127]
  • Sakineh Kazemi Noureini, Fatemeh Tanavar. Boldine, a natural aporphine alkaloid, inhibits telomerase at non-toxic concentrations. Chemico-biological interactions. 2015 Apr; 231(?):27-34. doi: 10.1016/j.cbi.2015.02.020. [PMID: 25746354]
  • Rong-Jie Zeng, Yu Li, Jian-Zhong Chen, Gui-Xin Chou, Yu Gao, Jing-Wei Shao, Lee Jia, Sheng-Dong Wu, Shui-Sheng Wu. A novel UPLC-MS/MS method for sensitive quantitation of boldine in plasma, a potential anti-inflammatory agent: application to a pharmacokinetic study in rats. Biomedical chromatography : BMC. 2015 Mar; 29(3):459-64. doi: 10.1002/bmc.3297. [PMID: 25065486]
  • Sakineh Kazemi Noureini, Michael Wink. Dose-dependent cytotoxic effects of boldine in HepG-2 cells-telomerase inhibition and apoptosis induction. Molecules (Basel, Switzerland). 2015 Feb; 20(3):3730-43. doi: 10.3390/molecules20033730. [PMID: 25719742]
  • Ian Tietjen, Fidele Ntie-Kang, Philip Mwimanzi, Pascal Amoa Onguéné, Margaret A Scull, Thomas Oyebode Idowu, Abiodun Oguntuga Ogundaini, Luc Mbaze Meva'a, Berhanu M Abegaz, Charles M Rice, Kerstin Andrae-Marobela, Mark A Brockman, Zabrina L Brumme, David Fedida. Screening of the Pan-African natural product library identifies ixoratannin A-2 and boldine as novel HIV-1 inhibitors. PloS one. 2015; 10(4):e0121099. doi: 10.1371/journal.pone.0121099. [PMID: 25830320]
  • J Walstab, C Wohlfarth, R Hovius, S Schmitteckert, R Röth, F Lasitschka, M Wink, H Bönisch, B Niesler. Natural compounds boldine and menthol are antagonists of human 5-HT3 receptors: implications for treating gastrointestinal disorders. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society. 2014 Jun; 26(6):810-20. doi: 10.1111/nmo.12334. [PMID: 24708203]
  • Daniéli Gerhardt, Gabriela Bertola, Fabrícia Dietrich, Fabrício Figueiró, Alfeu Zanotto-Filho, José Cláudio Moreira Fonseca, Fernanda Bueno Morrone, Carlos Henrique Barrios, Ana Maria O Battastini, Christianne G Salbego. Boldine induces cell cycle arrest and apoptosis in T24 human bladder cancer cell line via regulation of ERK, AKT, and GSK-3β. Urologic oncology. 2014 Jan; 32(1):36.e1-9. doi: 10.1016/j.urolonc.2013.02.012. [PMID: 24239461]
  • Darina Muthna, Jana Cmielova, Pavel Tomsik, Martina Rezacova. Boldine and related aporphines: from antioxidant to antiproliferative properties. Natural product communications. 2013 Dec; 8(12):1797-800. doi: . [PMID: 24555301]
  • Miloš Hroch, Stanislav Mičuda, Jolana Cermanová, Jaroslav Chládek, Pavel Tomšík. Development of an HPLC fluorescence method for determination of boldine in plasma, bile and urine of rats and identification of its major metabolites by LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Oct; 936(?):48-56. doi: 10.1016/j.jchromb.2013.07.009. [PMID: 23973534]
  • Romina Hernández-Salinas, Alejandra Z Vielma, Marlene N Arismendi, Mauricio P Boric, Juan C Sáez, Victoria Velarde. Boldine prevents renal alterations in diabetic rats. Journal of diabetes research. 2013; 2013(?):593672. doi: 10.1155/2013/593672. [PMID: 24416726]
  • Eduardo Sobarzo-Sánchez, Patricio González Soto, Cristóbal Valdés Rivera, Georgina Sánchez, María Eliana Hidalgo. Applied biological and physicochemical activity of isoquinoline alkaloids: oxoisoaporphine and boldine. Molecules (Basel, Switzerland). 2012 Sep; 17(9):10958-70. doi: 10.3390/molecules170910958. [PMID: 22971581]
  • P L Falé, F Amaral, P J Amorim Madeira, M Sousa Silva, M H Florêncio, F N Frazão, M L M Serralheiro. Acetylcholinesterase inhibition, antioxidant activity and toxicity of Peumus boldus water extracts on HeLa and Caco-2 cell lines. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Aug; 50(8):2656-62. doi: 10.1016/j.fct.2012.04.049. [PMID: 22617353]
  • Abbas Mollataghi, Emilie Coudiere, A Hamid A Hadi, Mat Ropi Mukhtar, Khalijah Awang, Marc Litaudon, Athar Ata. Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species. Fitoterapia. 2012 Mar; 83(2):298-302. doi: 10.1016/j.fitote.2011.11.009. [PMID: 22119096]
  • Veysel Kenan Çelık, Zeynep Deniz Şahın, İsmail Sari, Sevtap Bakir. Comparison of oxidant/antioxidant, detoxification systems in various tissue homogenates and mitochondria of rats with diabetes induced by streptozocin. Experimental diabetes research. 2012; 2012(?):386831. doi: 10.1155/2012/386831. [PMID: 22536214]
  • Pius S Fasinu, Patrick J Bouic, Bernd Rosenkranz. An overview of the evidence and mechanisms of herb-drug interactions. Frontiers in pharmacology. 2012; 3(?):69. doi: 10.3389/fphar.2012.00069. [PMID: 22557968]
  • Alessandra Russo, Venera Cardile, Silvia Caggia, Germán Gunther, Nicolas Troncoso, Juan Garbarino. Boldo prevents UV light and nitric oxide-mediated plasmid DNA damage and reduces the expression of Hsp70 protein in melanoma cancer cells. The Journal of pharmacy and pharmacology. 2011 Sep; 63(9):1219-29. doi: 10.1111/j.2042-7158.2011.01320.x. [PMID: 21827495]
  • Omotayo Owomofoyon Erejuwa, Siti Amrah Sulaiman, Mohd Suhaimi Ab Wahab, Sirajudeen Kuttulebbai Nainamohammed Salam, Md Salzihan Md Salleh, Sunil Gurtu. Comparison of antioxidant effects of honey, glibenclamide, metformin, and their combinations in the kidneys of streptozotocin-induced diabetic rats. International journal of molecular sciences. 2011 Jan; 12(1):829-43. doi: 10.3390/ijms12010829. [PMID: 21340016]
  • Siu Kuin Wong, Yau Yan Lim, Noor Rain Abdullah, Fariza Juliana Nordin. Assessment of antiproliferative and antiplasmodial activities of five selected Apocynaceae species. BMC complementary and alternative medicine. 2011 Jan; 11(?):3. doi: 10.1186/1472-6882-11-3. [PMID: 21232161]
  • Kyoung Ah Kang, Jin Sook Kim, Rui Zhang, Mei Jing Piao, Young Hee Maeng, Mi Young Kang, In Kyung Lee, Bum Joon Kim, Jin Won Hyun. KIOM-4 Protects against Oxidative Stress-Induced Mitochondrial Damage in Pancreatic β-cells via Its Antioxidant Effects. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):978682. doi: 10.1093/ecam/neq007. [PMID: 21799698]
  • Rui Zhang, Jin Sook Kim, Kyoung Ah Kang, Mei Jing Piao, Ki Cheon Kim, Jin Won Hyun. Protective Mechanism of KIOM-4 in Streptozotocin-Induced Pancreatic β-Cells Damage Is Involved in the Inhibition of Endoplasmic Reticulum Stress. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):. doi: 10.1155/2011/231938. [PMID: 20924496]
  • M J Simirgiotis, G Schmeda-Hirschmann. Direct identification of phenolic constituents in Boldo Folium (Peumus boldus Mol.) infusions by high-performance liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry. Journal of chromatography. A. 2010 Jan; 1217(4):443-9. doi: 10.1016/j.chroma.2009.11.014. [PMID: 20022332]
  • Bangning Yu, Carla Cook, Nalini Santanam. The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells. Journal of medicinal food. 2009 Oct; 12(5):1074-83. doi: 10.1089/jmf.2008.0230. [PMID: 19857072]
  • J Fernández, P Lagos, P Rivera, E Zamorano-Ponce. Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver. Phytotherapy research : PTR. 2009 Jul; 23(7):1024-7. doi: 10.1002/ptr.2746. [PMID: 19145575]
  • Mat Ropi Mukhtar, Ahmad Nazif Aziz, Noel F Thomas, A Hamid A Hadi, Marc Litaudon, Khalijah Awang. Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis. Molecules (Basel, Switzerland). 2009 Mar; 14(3):1227-33. doi: 10.3390/molecules14031227. [PMID: 19325519]
  • Lip Yong Chung, Mee Wah Lo, Muhammad Rais Mustafa, Swee Hock Goh, Zamrie Imiyabir. 5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis. Phytotherapy research : PTR. 2009 Mar; 23(3):330-4. doi: 10.1002/ptr.2627. [PMID: 18844258]
  • Zheng Han, Yunliang Zheng, Na Chen, Lianjun Luan, Changxin Zhou, Lishe Gan, Yongjiang Wu. Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2008 Nov; 1212(1-2):76-81. doi: 10.1016/j.chroma.2008.10.017. [PMID: 18951552]
  • Tzong-Cherng Chi, Shoei-Sheng Lee, Ming-Jai Su. Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats. Planta medica. 2006 Oct; 72(13):1175-80. doi: 10.1055/s-2006-947199. [PMID: 16924583]
  • Carlos Basalo, Tobias Mohn, Matthias Hamburger. Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction. Planta medica. 2006 Oct; 72(12):1157-62. doi: 10.1055/s-2006-947193. [PMID: 16924586]
  • Qizhi Zhao, Yimin Zhao, Kejun Wang. Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen. Journal of ethnopharmacology. 2006 Jul; 106(3):408-13. doi: 10.1016/j.jep.2006.01.019. [PMID: 16513307]
  • Emuri Abe, Jean-Claude Alvarez. Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method. Therapeutic drug monitoring. 2006 Jun; 28(3):407-12. doi: 10.1097/01.ftd.0000211828.11350.77. [PMID: 16778727]
  • Qi-Zhi Zhao, Yi-Min Zhao, Ke-Jun Wang. [Alkaloids from the root of Lindera angustifolia]. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Oct; 40(10):931-4. doi: . [PMID: 16408812]
  • Cristina Flors, Chantal Prat, Rafael Suau, Francisco Nájera, Santi Nonell. Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine. Photochemistry and photobiology. 2005 Jan; 81(1):120-4. doi: 10.1562/2004-07-23-ra-243. [PMID: 15493958]
  • Leelavinothan Pari, Muniappan Latha. Protective role of Scoparia dulcis plant extract on brain antioxidant status and lipidperoxidation in STZ diabetic male Wistar rats. BMC complementary and alternative medicine. 2004 Nov; 4(?):16. doi: 10.1186/1472-6882-4-16. [PMID: 15522116]
  • Sara Hoet, Caroline Stévigny, Sébastien Block, Frederik Opperdoes, Pierre Colson, Brigitte Baldeyrou, Amélie Lansiaux, Christian Bailly, Joëlle Quetin-Leclercq. Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases. Planta medica. 2004 May; 70(5):407-13. doi: 10.1055/s-2004-818967. [PMID: 15124084]
  • N Santanam, M Penumetcha, H Speisky, S Parthasarathy. A novel alkaloid antioxidant, Boldine and synthetic antioxidant, reduced form of RU486, inhibit the oxidation of LDL in-vitro and atherosclerosis in vivo in LDLR(-/-) mice. Atherosclerosis. 2004 Apr; 173(2):203-10. doi: 10.1016/j.atherosclerosis.2003.12.035. [PMID: 15064093]
  • Kristina Jenett-Siems, Carola Kraft, Karsten Siems, Jasmin Jakupovic, Pablo N Solis, Mahabir P Gupta, Ulrich Bienzle. Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora. Phytochemistry. 2003 Jun; 63(4):377-81. doi: 10.1016/s0031-9422(03)00098-0. [PMID: 12770583]
  • G Schmeda-Hirschmann, J A Rodriguez, C Theoduloz, S L Astudillo, G E Feresin, A Tapia. Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo"). Free radical research. 2003 Apr; 37(4):447-52. doi: 10.1080/1071576031000090000. [PMID: 12747739]
  • Felicia Loghin, Abdeslam Chagraoui, Marcelo Asencio, Etienne Comoy, Hernan Speisky, Bruce K Cassels, Philippe Protais. Effects of some antioxidative aporphine derivatives on striatal dopaminergic transmission and on MPTP-induced striatal dopamine depletion in B6CBA mice. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2003 Feb; 18(2):133-40. doi: 10.1016/s0928-0987(02)00253-1. [PMID: 12594006]
  • Fiorenza Rancan, Stefania Rosan, Kirsten Boehm, Ernesto Fernández, M Eliana Hidalgo, Wanda Quihot, Cecilia Rubio, Fritz Boehm, Helmut Piazena, Ute Oltmanns. Protection against UVB irradiation by natural filters extracted from lichens. Journal of photochemistry and photobiology. B, Biology. 2002 Nov; 68(2-3):133-9. doi: 10.1016/s1011-1344(02)00362-7. [PMID: 12468208]
  • Manfrid Eltze, Thomas Grebe, Martin C Michel, Peter Czyborra, Brigitte Ullrich. Affinity profile at alpha(1)- and alpha(2)-adrenoceptor subtypes and in vitro cardiovascular actions of (+)-boldine. European journal of pharmacology. 2002 May; 443(1-3):151-68. doi: 10.1016/s0014-2999(02)01591-1. [PMID: 12044805]
  • Y Y Jang, J H Song, Y K Shin, E S Han, C S Lee. Protective effect of boldine on oxidative mitochondrial damage in streptozotocin-induced diabetic rats. Pharmacological research. 2000 Oct; 42(4):361-71. doi: 10.1006/phrs.2000.0705. [PMID: 10987997]
  • I Jiménez, A Garrido, R Bannach, M Gotteland, H Speisky. Protective effects of boldine against free radical-induced erythrocyte lysis. Phytotherapy research : PTR. 2000 Aug; 14(5):339-43. doi: 10.1002/1099-1573(200008)14:5<339::aid-ptr585>3.0.co;2-t. [PMID: 10925398]
  • I Jiménez, H Speisky. Biological disposition of boldine: in vitro and in vivo studies. Phytotherapy research : PTR. 2000 Jun; 14(4):254-60. doi: 10.1002/1099-1573(200006)14:4<254::aid-ptr582>3.0.co;2-m. [PMID: 10861968]
  • E R Almeida, A M Melo, H Xavier. Toxicological evaluation of the hydro-alcohol extract of the dry leaves of Peumus boldus and boldine in rats. Phytotherapy research : PTR. 2000 Mar; 14(2):99-102. doi: 10.1002/(sici)1099-1573(200003)14:2<99::aid-ptr600>3.0.co;2-4. [PMID: 10685105]
  • I W Reiniger, C Ribeiro da Silva, I Felzenszwalb, J C de Mattos, J F de Oliveira, F J da Silva Dantas, R J Bezerra, A Caldeira-de-Araújo, M Bernardo-Filho. Boldine action against the stannous chloride effect. Journal of ethnopharmacology. 1999 Dec; 68(1-3):345-8. doi: 10.1016/s0378-8741(99)00120-8. [PMID: 10624900]
  • M Gotteland, I Jimenez, O Brunser, L Guzman, S Romero, B K Cassels, H Speisky. Protective effect of boldine in experimental colitis. Planta medica. 1997 Aug; 63(4):311-5. doi: 10.1055/s-2006-957689. [PMID: 9270374]
  • C M Teng, C M Hsueh, Y L Chang, F N Ko, S S Lee, K C Liu. Antiplatelet effects of some aporphine and phenanthrene alkaloids in rabbits and man. The Journal of pharmacy and pharmacology. 1997 Jul; 49(7):706-11. doi: 10.1111/j.2042-7158.1997.tb06096.x. [PMID: 9255715]
  • M Böhlke, H Guinaudeau, C K Angerhofer, V Wongpanich, D D Soejarto, N R Farnsworth, G A Mora, L J Poveda. Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark. Journal of natural products. 1996 Jun; 59(6):576-80. doi: 10.1021/np960195h. [PMID: 8786363]
  • S W Sun, S S Lee, H M Huang. Determination of lauraceous aporphine alkaloids by high-performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 1996 Jun; 14(8-10):1383-7. doi: 10.1016/0731-7085(95)01715-1. [PMID: 8818061]
  • M J Priston, G J Sewell. Novel liquid chromatographic assay for the low-level determination of apomorphine in plasma. Journal of chromatography. B, Biomedical applications. 1996 May; 681(1):161-7. doi: 10.1016/0378-4347(95)00534-x. [PMID: 8798925]
  • R Bannach, A Valenzuela, B K Cassels, L J Nunez-Vergara, H Speisky. Cytoprotective and antioxidant effects of boldine on tert-butyl hydroperoxide-induced damage to isolated hepatocytes. Cell biology and toxicology. 1996 Apr; 12(2):89-100. doi: 10.1007/bf00143359. [PMID: 8738478]
  • J Hu, H Speisky, I A Cotgreave. The inhibitory effects of boldine, glaucine, and probucol on TPA-induced down regulation of gap junction function. Relationships to intracellular peroxides, protein kinase C translocation, and connexin 43 phosphorylation. Biochemical pharmacology. 1995 Nov; 50(10):1635-43. doi: 10.1016/0006-2952(95)02055-1. [PMID: 7503766]
  • P Kringstein, A I Cederbaum. Boldine prevents human liver microsomal lipid peroxidation and inactivation of cytochrome P4502E1. Free radical biology & medicine. 1995 Mar; 18(3):559-63. doi: 10.1016/0891-5849(94)e0138-9. [PMID: 9101247]
  • R González-Cabello, H Speisky, R Bannach, A Valenzuela, J Fehér, P Gergely. Effects of boldine on cellular immune functions in vitro. Journal of investigational allergology & clinical immunology. 1994 May; 4(3):139-45. doi: . [PMID: 7981884]
  • H Speisky, B K Cassels. Boldo and boldine: an emerging case of natural drug development. Pharmacological research. 1994 Jan; 29(1):1-12. doi: 10.1016/1043-6618(94)80093-6. [PMID: 8202440]
  • H Speisky, B K Cassels, S Nieto, A Valenzuela, L J Nuñez-Vergara. Determination of boldine in plasma by high-performance liquid chromatography. Journal of chromatography. 1993 Feb; 612(2):315-9. doi: 10.1016/0378-4347(93)80179-8. [PMID: 8468391]
  • A I Cederbaum, E Kukiełka, H Speisky. Inhibition of rat liver microsomal lipid peroxidation by boldine. Biochemical pharmacology. 1992 Nov; 44(9):1765-72. doi: 10.1016/0006-2952(92)90070-y. [PMID: 1333206]
  • H Speisky, B K Cassels, E A Lissi, L A Videla. Antioxidant properties of the alkaloid boldine in systems undergoing lipid peroxidation and enzyme inactivation. Biochemical pharmacology. 1991 Jun; 41(11):1575-81. doi: 10.1016/0006-2952(91)90156-y. [PMID: 2043147]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]