Liriodenine (BioDeep_00000000915)

 

Secondary id: BioDeep_00000326798

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one

化学式: C17H9NO3 (275.0582)
中文名称: 鹅掌楸碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 29.72%

分子结构信息

SMILES: c1ccc2c(c1)c1c3c(ccnc3C2=O)cc2c1OCO2
InChI: InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

描述信息

Liriodenine is an oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities. It has a role as a metabolite, an antineoplastic agent, an antimicrobial agent, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.2.1.20 (alpha-glucosidase) inhibitor and an antifungal agent. It is a cyclic ketone, an oxacycle, an organic heteropentacyclic compound, an alkaloid antibiotic and an oxoaporphine alkaloid. It is functionally related to an aporphine.
Liriodenine is a natural product found in Magnolia mexicana, Annona purpurea, and other organisms with data available.
Liriodenine, also known as oxoushinsunine or micheline b, is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Liriodenine is practically insoluble (in water) and a strong basic compound (based on its pKa). Liriodenine can be found in cherimoya and custard apple, which makes liriodenine a potential biomarker for the consumption of these food products. Liriodenine is a bio-active isolate of the Chinese medicinal herb Zanthoxylum nitidum .

同义名列表

23 个代谢物同义名

3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one; 3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,9,11,14(19),15,17-octaen-13-one; 3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one; Noraporphin-7-one, 4,5,6,6a-tetradehydro-1,2-(methylenedioxy)-; Noraporphin-7-one,5,6,6a-tetradehydro-1,2-(methylenedioxy)-; 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one #; 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one; 8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-one; 8H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one; 4-27-00-06585 (Beilstein Handbook Reference); 8H-Benzo[g]-1,5,4-de]quinolin-8-one; Ushinsunine, oxo-; Spermatheridine; Spermatheridin; Oxoushinsunine; Oxoushinsunin; MEGxp0_001521; NCI60_042088; NCI60_001798; Liriodenine; Hiriodenine; Micheline B; Liriodenine



数据库引用编号

20 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)

498 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 ANXA5, BCL2, BIRC5, CASP3, CASP8, CASP9, CCNB1, CCND1, CDK1, DDC, NOS3, TYR, VEGFA
Peripheral membrane protein 2 ANXA5, USO1
Endoplasmic reticulum membrane 3 BCL2, CDK1, RTN4
Nucleus 10 BCL2, BIRC5, CASP3, CASP8, CASP9, CCNB1, CCND1, CDK1, NOS3, VEGFA
cytosol 13 ANXA5, BCL2, BIRC5, CASP3, CASP8, CASP9, CCNB1, CCND1, CDK1, DDC, KCNN4, NOS3, USO1
centrosome 3 CCNB1, CCND1, CDK1
nucleoplasm 7 BIRC5, CASP3, CASP8, CCNB1, CCND1, CDK1, NOS3
Cell membrane 3 KCNN4, PTAFR, RTN4
Cytoplasmic side 1 RTN4
lamellipodium 1 CASP8
ruffle membrane 1 KCNN4
Multi-pass membrane protein 4 CACNA1E, KCNN4, PTAFR, RTN4
Golgi apparatus membrane 1 USO1
Synapse 2 CACNA1E, RTN4
cell junction 1 RTN4
cell surface 1 VEGFA
glutamatergic synapse 2 CASP3, RTN4
Golgi apparatus 3 NOS3, USO1, VEGFA
Golgi membrane 2 NOS3, USO1
lysosomal membrane 1 GAA
neuronal cell body 4 CACNA1E, CASP3, KCNN4, RTN4
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 USO1
Lysosome 2 GAA, TYR
plasma membrane 7 BCHE, CACNA1E, GAA, KCNN4, NOS3, PTAFR, RTN4
Membrane 10 ANXA5, BCL2, CACNA1E, CCNB1, CDK1, GAA, KCNN4, PTAFR, USO1, VEGFA
caveola 1 NOS3
extracellular exosome 4 ANXA5, CDK1, DDC, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 4 BCL2, RTN4, USO1, VEGFA
extracellular space 2 BCHE, VEGFA
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 NOS3, TYR, USO1
adherens junction 1 VEGFA
bicellular tight junction 1 CCND1
mitochondrion 4 BCL2, CASP8, CASP9, CDK1
protein-containing complex 4 BCL2, BIRC5, CASP8, CASP9
intracellular membrane-bounded organelle 2 GAA, TYR
postsynaptic density 2 CASP3, RTN4
Single-pass type I membrane protein 1 TYR
Secreted 3 BCHE, GAA, VEGFA
extracellular region 4 ANXA5, BCHE, GAA, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, CASP8
mitochondrial matrix 2 CCNB1, CDK1
Extracellular side 1 RTN4
anchoring junction 1 RTN4
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK1
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 1 ANXA5
Secreted, extracellular space, extracellular matrix 1 VEGFA
microtubule cytoskeleton 1 BIRC5
Melanosome membrane 1 TYR
midbody 2 BIRC5, CDK1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Golgi-associated vesicle 1 TYR
vesicle 1 KCNN4
Cell projection, lamellipodium 1 CASP8
Cell projection, ruffle membrane 1 KCNN4
pore complex 1 BCL2
Cytoplasm, cytoskeleton, spindle 1 BIRC5
focal adhesion 1 ANXA5
microtubule 1 BIRC5
spindle 1 BIRC5
extracellular matrix 1 VEGFA
collagen-containing extracellular matrix 1 ANXA5
secretory granule 1 VEGFA
interphase microtubule organizing center 1 BIRC5
Zymogen granule membrane 1 ANXA5
neuron projection 2 KCNN4, RTN4
mitotic spindle 1 CDK1
Chromosome 1 BIRC5
cytoskeleton 2 CASP8, NOS3
centriole 1 BIRC5
spindle pole 1 CCNB1
chromosome, telomeric region 1 CDK1
nuclear chromosome 1 BIRC5
blood microparticle 1 BCHE
fibrillar center 1 USO1
nuclear envelope 1 RTN4
Chromosome, centromere 1 BIRC5
Chromosome, centromere, kinetochore 1 BIRC5
microtubule organizing center 1 USO1
monoatomic ion channel complex 1 CACNA1E
tertiary granule membrane 2 GAA, PTAFR
Melanosome 1 TYR
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
cell body 1 CASP8
myelin sheath 1 BCL2
voltage-gated potassium channel complex 1 KCNN4
Golgi stack 1 USO1
secretory granule membrane 1 PTAFR
endoplasmic reticulum lumen 1 BCHE
transcription repressor complex 1 CCND1
platelet alpha granule lumen 1 VEGFA
voltage-gated calcium channel complex 1 CACNA1E
kinetochore 1 BIRC5
endocytic vesicle membrane 1 NOS3
transport vesicle 1 USO1
azurophil granule membrane 1 GAA
ER to Golgi transport vesicle membrane 1 USO1
nuclear envelope lumen 1 BCHE
apoptosome 1 CASP9
chromosome, centromeric region 1 BIRC5
outer kinetochore 1 CCNB1
vesicle membrane 1 ANXA5
chromosome passenger complex 1 BIRC5
cytoplasmic microtubule 1 BIRC5
ficolin-1-rich granule membrane 1 GAA
spindle microtubule 2 BIRC5, CDK1
survivin complex 1 BIRC5
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
cyclin-dependent protein kinase holoenzyme complex 2 CCND1, CDK1
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 2 CCNB1, CDK1
endothelial microparticle 1 ANXA5
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
cyclin D1-CDK4 complex 1 CCND1
[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
cyclin D1-CDK6 complex 1 CCND1
caspase complex 1 CASP9
endoplasmic reticulum tubular network 1 RTN4
endoplasmic reticulum tubular network membrane 1 RTN4
[Isoform a]: Endoplasmic reticulum membrane 1 RTN4
[Isoform b]: Endoplasmic reticulum membrane 1 RTN4
[Isoform C]: Endoplasmic reticulum membrane 1 RTN4


文献列表

  • Shasank S Swain, Sanghamitra Pati, Tahziba Hussain. Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation. European journal of medicinal chemistry. 2022 Mar; 232(?):114173. doi: 10.1016/j.ejmech.2022.114173. [PMID: 35168150]
  • Quentin R R Coquerel, Fabien Démares, Werner J Geldenhuys, Anne-Marie Le Ray, Dimitri Bréard, Pascal Richomme, Christian Legros, Edmund Norris, Jeffrey R Bloomquist. Toxicity and mode of action of the aporphine plant alkaloid liriodenine on the insect GABA receptor. Toxicon : official journal of the International Society on Toxinology. 2021 Oct; 201(?):141-147. doi: 10.1016/j.toxicon.2021.08.019. [PMID: 34474068]
  • Emmanoel V Costa, Liviane do N Soares, Jamal da Silva Chaar, Valdenizia R Silva, Luciano de S Santos, Hector H F Koolen, Felipe M A da Silva, Josean F Tavares, Gokhan Zengin, Milena B P Soares, Daniel P Bezerra. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123714. [PMID: 34207059]
  • InWha Park, Hee Sun Byun, Gang Min Hur, MinKyun Na. Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation. Journal of natural products. 2021 05; 84(5):1598-1606. doi: 10.1021/acs.jnatprod.1c00146. [PMID: 33939429]
  • Yuan-Kun Zheng, Bao-Jun Su, Ya-Qi Wang, Heng-Shan Wang, Hai-Bing Liao, Dong Liang. New Tyramine- and Aporphine-Type Alkamides with NO Release Inhibitory Activities from Piper puberulum. Journal of natural products. 2021 04; 84(4):1316-1325. doi: 10.1021/acs.jnatprod.1c00055. [PMID: 33822610]
  • Renren Bai, Chuansheng Yao, Zhichao Zhong, Jiamin Ge, Ziqiang Bai, Xiangyang Ye, Tian Xie, Yuanyuan Xie. Discovery of natural anti-inflammatory alkaloids: Potential leads for the drug discovery for the treatment of inflammation. European journal of medicinal chemistry. 2021 Mar; 213(?):113165. doi: 10.1016/j.ejmech.2021.113165. [PMID: 33454546]
  • Douglas Costa Gontijo, Maria Fernanda Alves do Nascimento, Geraldo Célio Brandão, Alaíde Braga de Oliveira. Phytochemistry and antiplasmodial activity of Xylopia sericea leaves. Natural product research. 2020 Dec; 34(24):3526-3530. doi: 10.1080/14786419.2019.1577838. [PMID: 30810362]
  • Virayu Suthiphasilp, Wisanu Maneerat, Narawadee Rujanapun, Thidarat Duangyod, Rawiwan Charoensup, Suwanna Deachathai, Raymond J Andersen, Brian O Patrick, Stephen G Pyne, Surat Laphookhieo. α-Glucosidase inhibitory and nitric oxide production inhibitory activities of alkaloids isolated from a twig extract of Polyalthia cinnamomea. Bioorganic & medicinal chemistry. 2020 05; 28(10):115462. doi: 10.1016/j.bmc.2020.115462. [PMID: 32247751]
  • Taghreed A Majrashi, Fazila Zulfiqar, Amar G Chittiboyina, Zulfiqar Ali, Ikhlas A Khan. Isoquinoline alkaloids from Asimina triloba. Natural product research. 2019 Oct; 33(19):2823-2829. doi: 10.1080/14786419.2018.1504045. [PMID: 30453785]
  • Siddharth K Tripathi, Tao Xu, Qin Feng, Bharathi Avula, Xiaomin Shi, Xuewen Pan, Melanie M Mask, Scott R Baerson, Melissa R Jacob, Ranga Rao Ravu, Shabana I Khan, Xing-Cong Li, Ikhlas A Khan, Alice M Clark, Ameeta K Agarwal. Two plant-derived aporphinoid alkaloids exert their antifungal activity by disrupting mitochondrial iron-sulfur cluster biosynthesis. The Journal of biological chemistry. 2017 10; 292(40):16578-16593. doi: 10.1074/jbc.m117.781773. [PMID: 28821607]
  • Takumi Shono, Naoki Ishikawa, Kazufumi Toume, Midori A Arai, Hyuma Masu, Takashi Koyano, Thaworn Kowithayakorn, Masami Ishibashi. Cerasoidine, a Bis-aporphine Alkaloid Isolated from Polyalthia cerasoides during Screening for Wnt Signal Inhibitors. Journal of natural products. 2016 08; 79(8):2083-8. doi: 10.1021/acs.jnatprod.6b00409. [PMID: 27490091]
  • Emmanoel V Costa, Maria Lúcia B Pinheiro, Beatriz Helena L N S Maia, Francisco A Marques, Ana Lúcia T G Ruiz, Gabriela M Marchetti, João Ernesto de Carvalho, Milena B P Soares, Cinara O S Costa, Alexandre F C Galvão, Norberto P Lopes, Hector H F Koolen, Daniel P Bezerra, Andersson Barison. 7,7-Dimethylaporphine and Other Alkaloids from the Bark of Guatteria friesiana. Journal of natural products. 2016 06; 79(6):1524-31. doi: 10.1021/acs.jnatprod.5b01037. [PMID: 27300257]
  • Noraziah Nordin, Nazia Abdul Majid, Najihah Mohd Hashim, Mashitoh Abd Rahman, Zalila Hassan, Hapipah Mohd Ali. Liriodenine, an aporphine alkaloid from Enicosanthellum pulchrum, inhibits proliferation of human ovarian cancer cells through induction of apoptosis via the mitochondrial signaling pathway and blocking cell cycle progression. Drug design, development and therapy. 2015; 9(?):1437-48. doi: 10.2147/dddt.s77727. [PMID: 25792804]
  • Yu-Lan Li, Qi-Pin Qin, Yan-Cheng Liu, Zhen-Feng Chen, Hong Liang. A platinum(II) complex of liriodenine from traditional Chinese medicine (TCM): Cell cycle arrest, cell apoptosis induction and telomerase inhibition activity via G-quadruplex DNA stabilization. Journal of inorganic biochemistry. 2014 Aug; 137(?):12-21. doi: 10.1016/j.jinorgbio.2014.04.001. [PMID: 24798373]
  • Huagang Liu, Jie Feng, Kan Feng, Maoxiang Lai. Optimization of the extraction conditions and quantification by RP-LC analysis of three alkaloids in Zanthoxylum nitidum roots. Pharmaceutical biology. 2014 Feb; 52(2):255-61. doi: 10.3109/13880209.2013.826244. [PMID: 24074362]
  • Marisol Castro-Moreno, Clara Leonor Tinoco-Ojangurén, Ma Del Rocío Cruz-Ortega, Alma Rosa González-Esquinca. Influence of seasonal variation on the phenology and liriodenine content of Annona lutescens (Annonaceae). Journal of plant research. 2013 Jul; 126(4):529-37. doi: 10.1007/s10265-013-0550-x. [PMID: 23389399]
  • Jong Hoon Ahn, Eun Sil Kim, Chul Lee, Soonok Kim, Soo-Hyun Cho, Bang Yeon Hwang, Mi Kyeong Lee. Chemical constituents from Nelumbo nucifera leaves and their anti-obesity effects. Bioorganic & medicinal chemistry letters. 2013 Jun; 23(12):3604-8. doi: 10.1016/j.bmcl.2013.04.013. [PMID: 23642481]
  • Patrick C Still, Bitna Yi, Tatiana F González-Cestari, Li Pan, Ryan E Pavlovicz, Hee-Byung Chai, Tran Ngoc Ninh, Chenglong Li, Djaja Djendoel Soejarto, Dennis B McKay, A Douglas Kinghorn. Alkaloids from Microcos paniculata with cytotoxic and nicotinic receptor antagonistic activities. Journal of natural products. 2013 Feb; 76(2):243-9. doi: 10.1021/np3007414. [PMID: 23327794]
  • Rosalind Pei Theng Kim, Vicky Bihud, Khalit Bin Mohamad, Kok Hoong Leong, Jamaludin Bin Mohamad, Fasihuddin Bin Ahmad, Hazrina Hazni, Noraini Kasim, Siti Nadiah Abdul Halim, Khalijah Awang. Cytotoxic and antioxidant compounds from the stem bark of Goniothalamus tapisoides Mat Salleh. Molecules (Basel, Switzerland). 2012 Dec; 18(1):128-39. doi: 10.3390/molecules18010128. [PMID: 23344192]
  • Zhen-Feng Chen, Yan-Cheng Liu, Yan Peng, Xue Hong, Hong-Hong Wang, Min-Min Zhang, Hong Liang. Synthesis, characterization, and in vitro antitumor properties of gold(III) compounds with the traditional Chinese medicine (TCM) active ingredient liriodenine. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry. 2012 Feb; 17(2):247-61. doi: 10.1007/s00775-011-0846-z. [PMID: 21960256]
  • I de la Cruz Chacón, A R González-Esquinca. Liriodenine alkaloid in Annona diversifolia during early development. Natural product research. 2012; 26(1):42-9. doi: 10.1080/14786419.2010.533373. [PMID: 21790492]
  • Yu-Hsuan Lan, Yann-Lii Leu, Yi-Ting Peng, Tran-Dinh Thang, Chia-Chen Lin, Bo-Ying Bao. The first bis-retrochalcone from Fissistigma latifolium. Planta medica. 2011 Dec; 77(18):2019-22. doi: 10.1055/s-0031-1280088. [PMID: 21850609]
  • Emmanoel Vilaça Costa, Maria Lúcia Belém Pinheiro, Afonso Duarte Leão de Souza, Andersson Barison, Francinete Ramos Campos, Rodrigo Hinojosa Valdez, Tânia Ueda-Nakamura, Benedito Prado Dias Filho, Celso Vataru Nakamura. Trypanocidal activity of oxoaporphine and pyrimidine-β-carboline alkaloids from the branches of Annona foetida Mart. (Annonaceae). Molecules (Basel, Switzerland). 2011 Nov; 16(11):9714-20. doi: 10.3390/molecules16119714. [PMID: 22113579]
  • Ziming Lv, Qingjian Zhang, Ruoyun Chen, Dequan Yu. [Alkaloids and anthraquinones from branches and leaves of uvaria kurzii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 May; 36(9):1190-2. doi: . [PMID: 21842647]
  • Emmanoel Vilaça Costa, Maria Lúcia B Pinheiro, Andersson Barison, Francinete R Campos, Marcos J Salvador, Beatriz Helena L N S Maia, Elaine C Cabral, Marcos N Eberlin. Alkaloids from the bark of Guatteria hispida and their evaluation as antioxidant and antimicrobial agents. Journal of natural products. 2010 Jun; 73(6):1180-3. doi: 10.1021/np100013r. [PMID: 20476748]
  • Yan-Cheng Liu, Zhen-Feng Chen, Li-Min Liu, Yan Peng, Xue Hong, Bin Yang, Hua-Gang Liu, Hong Liang, Chris Orvig. Divalent later transition metal complexes of the traditional chinese medicine (TCM) liriodenine: coordination chemistry, cytotoxicity and DNA binding studies. Dalton transactions (Cambridge, England : 2003). 2009 Dec; ?(48):10813-23. doi: 10.1039/b912553a. [PMID: 20023911]
  • Chen Li, Dongho Lee, Tyler N Graf, Sharnelle S Phifer, Yuka Nakanishi, Soedarsono Riswan, Fransisca M Setyowati, Achmad M Saribi, Djaja D Soejarto, Norman R Farnsworth, Joseph O Falkinham, David J Kroll, A Douglas Kinghorn, Mansukh C Wani, Nicholas H Oberlies. Bioactive constituents of the stem bark of Mitrephora glabra. Journal of natural products. 2009 Nov; 72(11):1949-53. doi: 10.1021/np900572g. [PMID: 19874044]
  • Emmanoel Vilaça Costa, Francisco A Marques, Maria Lúcia B Pinheiro, Nelissa P Vaz, Marta Cristina T Duarte, Camila Delarmelina, Raquel M Braga, Beatriz Helena L N Sales Maia. 7,7-Dimethylaporphine alkaloids from the stem of Guatteriopsis friesiana. Journal of natural products. 2009 Aug; 72(8):1516-9. doi: 10.1021/np800788n. [PMID: 19639965]
  • Cheng-Hui Yang, Ming-Jen Cheng, Shiow-Ju Lee, Cheng-Wei Yang, Hsun-Shuo Chang, Ih-Sheng Chen. Secondary metabolites and cytotoxic activities from the stem bark of Zanthoxylum nitidum. Chemistry & biodiversity. 2009 Jun; 6(6):846-57. doi: 10.1002/cbdv.200800107. [PMID: 19551734]
  • Zhen-Feng Chen, Yan-Cheng Liu, Li-Min Liu, Heng-Shan Wang, San-Hai Qin, Bo-Long Wang, He-Dong Bian, Bin Yang, Hoong-Kun Fun, Hua-Gang Liu, Hong Liang, Chris Orvig. Potential new inorganic antitumour agents from combining the anticancer traditional Chinese medicine (TCM) liriodenine with metal ions, and DNA binding studies. Dalton transactions (Cambridge, England : 2003). 2009 Jan; ?(2):262-72. doi: 10.1039/b813363h. [PMID: 19089006]
  • M Mukhlesur Rahman, Simin S Lopa, Golam Sadik, Harun-Or-Rashid, Robiul Islam, Proma Khondkar, A H M Khurshid Alam, Mohammad A Rashid. Antibacterial and cytotoxic compounds from the bark of Cananga odorata. Fitoterapia. 2005 Dec; 76(7-8):758-61. doi: 10.1016/j.fitote.2005.08.011. [PMID: 16242266]
  • Ihsan Ergün, M Cenk Akbostanci, Başol Canbakan, Bilge Koçer, Arzu Ensari, Gökhan Nergizoglu, Kenan Keven. Minimal change nephrotic syndrome with stiff-person syndrome: is there a link?. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2005 Jul; 46(1):e11-4. doi: 10.1053/j.ajkd.2005.03.009. [PMID: 15983949]
  • Wei-Luen Chang, Ching-Hu Chung, Yang-Chang Wu, Ming-Jai Su. The vascular and cardioprotective effects of liriodenine in ischemia-reperfusion injury via NO-dependent pathway. Nitric oxide : biology and chemistry. 2004 Dec; 11(4):307-15. doi: 10.1016/j.niox.2004.10.004. [PMID: 15604043]
  • Hui-Chiu Chang, Fang-Rong Chang, Yang-Chang Wu, Yung-Hsiung Lai. Anti-cancer effect of liriodenine on human lung cancer cells. The Kaohsiung journal of medical sciences. 2004 Aug; 20(8):365-71. doi: 10.1016/s1607-551x(09)70172-x. [PMID: 15473647]
  • Gildeci Alves de Lira, Lucimara Mariano de Andrade, Karina Chagas Florêncio, Marcelo Sobral da Silva, José Maria Barbosa-Filho, Emidio Vasconcelos Leitão da-Cunha. Roraimine: a bisbenzylisoquinoline alkaloid from Cissampelos sympodialis roots. Fitoterapia. 2002 Jul; 73(4):356-8. doi: 10.1016/s0367-326x(02)00089-8. [PMID: 12234585]
  • Zhizhen Zhang, Hala N ElSohly, Melissa R Jacob, David S Pasco, Larry A Walker, Alice M Clark. New sesquiterpenoids from the root of Guatteria multivenia. Journal of natural products. 2002 Jun; 65(6):856-9. doi: 10.1021/np0200717. [PMID: 12088427]
  • K S Chen, Y C Wu, C M Teng, F N Ko, T S Wu. Bioactive alkaloids from Illigera luzonensis. Journal of natural products. 1997 Jun; 60(6):645-7. doi: 10.1021/np9700735. [PMID: 9214740]
  • G J Chang, M H Wu, Y C Wu, M J Su. Electrophysiological mechanisms for antiarrhythmic efficacy and positive inotropy of liriodenine, a natural aporphine alkaloid from Fissistigma glaucescens. British journal of pharmacology. 1996 Aug; 118(7):1571-83. doi: 10.1111/j.1476-5381.1996.tb15577.x. [PMID: 8842417]
  • S Chuliá, M A Noguera, M D Ivorra, D Cortes, M P D'Ocón. Vasodilator effects of liriodenine and norushinsunine, two aporphine alkaloids isolated from Annona cherimolia, in rat aorta. Pharmacology. 1995 Jun; 50(6):380-7. doi: 10.1159/000139307. [PMID: 7568337]
  • G G Harrigan, A A Gunatilaka, D G Kingston, G W Chan, R K Johnson. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea. Journal of natural products. 1994 Jan; 57(1):68-73. doi: 10.1021/np50103a009. [PMID: 8158166]
  • L Xu, K Li, N Sun, J Kong. [Alkaloids of Annona reticulata L]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1992 May; 17(5):295-6 inside backcover. doi: ". [PMID: 1418565]
  • I O Mondranondra, C T Che, A M Rimando, S Vajrodaya, H H Fong, N R Farnsworth. Sesquiterpene lactones and other constituents from a cytotoxic extract of Michelia floribunda. Pharmaceutical research. 1990 Dec; 7(12):1269-72. doi: 10.1023/a:1015937921880. [PMID: 2095565]
  • T Nozaka, I Morimoto, M Ishino, S Natori. Mutagenic principles in Sinomeni Caulis et Rhizoma. II. The mutagenicity of liriodenine in the basic fraction of the methanol extract. Chemical & pharmaceutical bulletin. 1988 Jun; 36(6):2259-62. doi: 10.1248/cpb.36.2259. [PMID: 3240460]
  • A M Clark, E S Watson, M K Ashfaq, C D Hufford. In vivo efficacy of antifungal oxoaporphine alkaloids in experimental disseminated candidiasis. Pharmaceutical research. 1987 Dec; 4(6):495-8. doi: 10.1023/a:1016479622383. [PMID: 3508563]
  • N Ruangrungsi, A Rivepiboon, G L Lange, M Lee, C P Decicco, P Picha, K Preechanukool. Constituents of Paramichelia baillonii: a new antitumor germacranolide alkaloid. Journal of natural products. 1987 Sep; 50(5):891-6. doi: 10.1021/np50053a020. [PMID: 3437284]
  • K Murai, M Yamanaka, K Akagi, M Anai, T Mukai, T Omae. Purification and properties of deoxyribonuclease from human urine. Biochimica et biophysica acta. 1978 Jan; 517(1):186-94. doi: 10.1016/0005-2787(78)90046-1. [PMID: 23831]
  • M Sano. Subcellular localizations of guanylate cyclase and 3',5'-cyclic nucleotide phosphodiesterase in sea urchin sperm. Biochimica et biophysica acta. 1976 Apr; 428(2):525-31. doi: 10.1016/0304-4165(76)90061-1. [PMID: 6049]
  • P Szylman, O S Better, C Chaimowitz, A Rosler. Role of hyperkalemia in the metabolic acidosis of isolated hypoaldosteronism. The New England journal of medicine. 1976 Feb; 294(7):361-5. doi: 10.1056/nejm197602122940703. [PMID: 1674]
  • A Koj, J Chudzik, A Dubin. Substrate specificity and modifications of the active centre of elastase-like neutral proteinases from horse blood leucocytes. The Biochemical journal. 1976 Feb; 153(2):397-402. doi: 10.1042/bj1530397. [PMID: 6009]