Ingenol (BioDeep_00000000247)

   

PANOMIX_OTCML-2023 natural product PANOMIX_OTCML-2025


代谢物信息卡片


1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR-(1A.ALPHA.,2.BETA.,5.BETA.,5A.BETA.,6.BETA.,8A.ALPHA.,9.ALPHA.,10A.ALPHA.))-

  化学式: C20H28O5 (348.1937)
中文名称: 巨大戟醇
  谱图信息: 最多检出来源 Viridiplantae(otcml) 21.18%

Reviewed

Last reviewed on 2025-06-03.

Cite this Page

Ingenol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/ingenol (retrieved 2026-01-13) (BioDeep RN: BioDeep_00000000247). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC1=CC23C(=O)C(C=C(CO)C(O)C2(O)C1O)C1C(CC3C)C1(C)C
InChI: InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3


描述信息

Ingenol is a tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer). It is a tetracyclic diterpenoid and a cyclic terpene ketone.
Ingenol is a natural product found in Euphorbia villosa, Euphorbia illirica, and other organisms with data available.
Ingenol is a PKC activator, with a Ki of 30 μM, with antitumor activity.
Ingenol is a PKC activator, with a Ki of 30 μM, with antitumor activity.

同义名列表

25 个代谢物同义名

1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR-(1A.ALPHA.,2.BETA.,5.BETA.,5A.BETA.,6.BETA.,8A.ALPHA.,9.ALPHA.,10A.ALPHA.))-; 1aalpha,2alpha,5beta,5abeta,6beta,beta,9 alpha, 10,10aalpha-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8aalpha-methano cyclopenta(a)cyclopropa(e)cyclodecen-11-one; 1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR,2S,5R,5AR,6S,8AS,9R,10AR)-; (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one; (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0(1),?.0(1)?,(1)(2)]pentadeca-2,7-dien-15-one; (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one; VEBVPUXQAPLADL-POYOOMFHSA-N; BCBcMAP01_000158; INGENOL [WHO-DD]; UNII-IC77UZI9G8; INGENOL, (+)-; INGENOL [MI]; SMP1_000044; (+)-Ingenol; (-)-Ingenol; IC77UZI9G8; Ingenol; CID 3719; Ingenol; (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta(a)cyclopropa(e)(10)annulen-11-one; (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo(7.5.1.01,5.010,12)pentadeca-2,7-dien-15-one; 1a alpha,2 alpha,5 beta,5a beta,6 beta,beta,9 alpha, 10,10a alpha-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a alpha-methano cyclopenta(a)cyclopropa(e)cyclodecen-11-one; 1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR-(1AALPHA,2BETA,5BETA,5ABETA,6BETA,8AALPHA,9ALPHA,10AALPHA))-; 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-; 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome()

BioCyc()

PlantCyc()

代谢反应

个相关的代谢反应过程信息。

Reactome()

BioCyc()

WikiPathways()

Plant Reactome()

INOH()

PlantCyc()

COVID-19 Disease Map()

PathBank()

PharmGKB()

31 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 10 BCL2, CASP3, CCL5, CCND1, CCR5, CXCR4, PIK3CA, PRKCD, PRKX, PTEN
Peripheral membrane protein 1 PRKCD
Endoplasmic reticulum membrane 2 BCL2, CD4
Nucleus 8 BCL2, CASP3, CCND1, H2AX, JUN, PRKCD, PRKX, PTEN
cytosol 7 BCL2, CASP3, CCND1, PIK3CA, PRKCD, PRKCQ, PTEN
centrosome 2 CCND1, H2AX
nucleoplasm 7 CASP3, CCND1, H2AX, JUN, PRKCD, PRKX, PTEN
RNA polymerase II transcription regulator complex 1 JUN
Cell membrane 6 CCR5, CD4, CD8A, CXCR4, PRKCD, TNF
lamellipodium 1 PIK3CA
Multi-pass membrane protein 2 CCR5, CXCR4
Synapse 1 PRKCD
cell junction 1 CXCR4
cell surface 3 CCR5, CXCR4, TNF
glutamatergic synapse 1 CASP3
lysosomal membrane 1 EGF
neuronal cell body 2 CASP3, TNF
Lysosome 1 CXCR4
endosome 1 CCR5
plasma membrane 10 CCR5, CD4, CD8A, CXCR4, EGF, PIK3CA, PRKCD, PRKCQ, PTEN, TNF
Membrane 5 BCL2, CCR5, CXCR4, EGF, PRKCD
apical plasma membrane 1 PTEN
extracellular exosome 4 CXCR4, EGF, H2AX, PRKCD
endoplasmic reticulum 2 BCL2, PRKCD
extracellular space 6 CCL2, CCL5, EGF, IL6, THPO, TNF
perinuclear region of cytoplasm 2 PIK3CA, PRKCD
bicellular tight junction 1 CCND1
intercalated disc 1 PIK3CA
mitochondrion 2 BCL2, PRKCD
protein-containing complex 2 BCL2, CXCR4
postsynaptic density 2 CASP3, PTEN
Single-pass type I membrane protein 2 CD4, CD8A
Secreted 4 CCL2, CCL5, IL6, THPO
extracellular region 9 CCL2, CCL5, CD8A, EGF, IL6, PRKCD, PTEN, THPO, TNF
cytoplasmic side of plasma membrane 1 PTEN
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
[Isoform 2]: Secreted 1 CD8A
anchoring junction 1 CXCR4
transcription regulator complex 1 JUN
centriolar satellite 1 PRKCQ
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 5 CCR5, CD4, CD8A, CXCR4, TNF
dendritic spine 1 PTEN
cytoplasmic vesicle 1 CXCR4
Early endosome 2 CD4, CXCR4
cell-cell junction 1 PRKCD
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 PRKCD
Membrane raft 2 CD4, TNF
pore complex 1 BCL2
Cell projection, dendritic spine 1 PTEN
Nucleus, PML body 1 PTEN
PML body 1 PTEN
nuclear speck 1 H2AX
Late endosome 1 CXCR4
receptor complex 1 CD8A
Cell projection, neuron projection 1 PTEN
neuron projection 2 PRKCD, PTEN
chromatin 1 JUN
cell leading edge 1 CXCR4
cell projection 1 PTEN
phagocytic cup 1 TNF
Chromosome 1 H2AX
nuclear chromosome 1 JUN
site of double-strand break 1 H2AX
Endomembrane system 1 PRKCD
euchromatin 1 JUN
replication fork 1 H2AX
myelin sheath 1 BCL2
plasma membrane raft 1 CD8A
endoplasmic reticulum lumen 2 CD4, IL6
nuclear matrix 1 PRKCD
transcription repressor complex 1 CCND1
male germ cell nucleus 1 H2AX
platelet alpha granule lumen 1 EGF
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
XY body 1 H2AX
Schmidt-Lanterman incisure 1 PTEN
azurophil granule lumen 1 PRKCD
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
condensed nuclear chromosome 1 H2AX
clathrin-coated endocytic vesicle membrane 2 CD4, EGF
Synapse, synaptosome 1 PRKCD
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 CD8A
nucleosome 1 H2AX
site of DNA damage 1 H2AX
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
transcription factor AP-1 complex 1 JUN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 2 CD4, CD8A
interleukin-6 receptor complex 1 IL6
myelin sheath adaxonal region 1 PTEN
BAD-BCL-2 complex 1 BCL2
cyclin D1-CDK4 complex 1 CCND1
[Isoform alpha]: Secreted 1 PTEN
endolysosome 1 PRKCD
cyclin D1-CDK6 complex 1 CCND1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Han-Xiang Liu, Yu-Song Zhang, Shi-Kang Zhou, Yi Zhang, Li Zhang. [Optimization of parameters for stir-frying of Kansui Radix with vinegar based on conversion of toxic components]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Jun; 48(11):2958-2967. doi: 10.19540/j.cnki.cjcmm.20230303.301. [PMID: 37381956]
  • Afam A Okoye, Rémi Fromentin, Hiroshi Takata, Jessica H Brehm, Yoshinori Fukazawa, Bryan Randall, Marion Pardons, Vincent Tai, Jun Tang, Jeremy Smedley, Michael Axthelm, Jeffrey D Lifson, Louis J Picker, David Favre, Lydie Trautmann, Nicolas Chomont. The ingenol-based protein kinase C agonist GSK445A is a potent inducer of HIV and SIV RNA transcription. PLoS pathogens. 2022 01; 18(1):e1010245. doi: 10.1371/journal.ppat.1010245. [PMID: 35041707]
  • Qiao Zhang, Yong-Hui Ju, Yi Zhang, Kan Wang, Min Zhang, Pei-Dong Chen, Wei-Feng Yao, Yu-Ping Tang, Jian-Hua Wu, Li Zhang. The water expelling effect evaluation of 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol and ingenol on H22 mouse hepatoma ascites model and their content differences analysis in Euphorbia kansui before and after stir-fried with vinegar by UPLC. Journal of ethnopharmacology. 2021 Mar; 267(?):113507. doi: 10.1016/j.jep.2020.113507. [PMID: 33098970]
  • Jared P Taylor, Lucas H Armitage, Daniel L Aldridge, Melanie N Cash, Mark A Wallet. Harmine enhances the activity of the HIV-1 latency-reversing agents ingenol A and SAHA. Biology open. 2020 12; 9(12):. doi: 10.1242/bio.052969. [PMID: 33234703]
  • Viviane Aline Oliveira Silva, Marcela Nunes Rosa, Aline Tansini, Olga Martinho, Amilcar Tanuri, Adriane Feijó Evangelista, Adriana Cruvinel Carloni, João Paulo Lima, Luiz Francisco Pianowski, Rui Manuel Reis. Semi-Synthetic Ingenol Derivative from Euphorbia tirucalli Inhibits Protein Kinase C Isotypes and Promotes Autophagy and S-phase Arrest on Glioma Cell Lines. Molecules (Basel, Switzerland). 2019 Nov; 24(23):. doi: 10.3390/molecules24234265. [PMID: 31771098]
  • Qiao Zhang, Yi Zhang, Shi-Kang Zhou, Kan Wang, Min Zhang, Pei-Dong Chen, Wei-Feng Yao, Yu-Ping Tang, Jian-Hua Wu, Li Zhang. Toxicity Reduction of Euphorbia kansui Stir-Fried with Vinegar Based on Conversion of 3-O-(2'E,4'Z-Decadi-enoyl)-20-O-acetylingenol. Molecules (Basel, Switzerland). 2019 Oct; 24(20):. doi: 10.3390/molecules24203806. [PMID: 31652602]
  • He Yang, Xian Li, Xinyi Yang, Panpan Lu, Yanan Wang, Zhengtao Jiang, Hanyu Pan, Lin Zhao, Yuqi Zhu, Inam Ullah Khan, Yinzhong Shen, Hongzhou Lu, Tong Zhang, Guochun Jiang, Zhongjun Ma, Hao Wu, Huanzhang Zhu. Dual effects of the novel ingenol derivatives on the acute and latent HIV-1 infections. Antiviral research. 2019 09; 169(?):104555. doi: 10.1016/j.antiviral.2019.104555. [PMID: 31295520]
  • Ya-Si Huang, Yan Lu, Chin-Ho Chen, Kuo-Hsiung Lee, Dao-Feng Chen. Potent Anti-HIV Ingenane Diterpenoids from Euphorbia ebracteolata. Journal of natural products. 2019 06; 82(6):1587-1592. doi: 10.1021/acs.jnatprod.9b00088. [PMID: 31184480]
  • Raymond J Andersen, Fidele Ntie-Kang, Ian Tietjen. Natural product-derived compounds in HIV suppression, remission, and eradication strategies. Antiviral research. 2018 10; 158(?):63-77. doi: 10.1016/j.antiviral.2018.07.016. [PMID: 30063970]
  • Qingbo Liu, Wei Li, Li Huang, Yoshihisa Asada, Susan L Morris-Natschke, Chin-Ho Chen, Kuo-Hsiung Lee, Kazuo Koike. Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui. European journal of medicinal chemistry. 2018 Aug; 156(?):618-627. doi: 10.1016/j.ejmech.2018.07.020. [PMID: 30031972]
  • Tibor Béres, Klaus Dragull, Jiří Pospíšil, Danuše Tarkowská, Martin Dančák, Ondřej Bíba, Petr Tarkowski, Karel Doležal, Miroslav Strnad. Quantitative Analysis of Ingenol in Euphorbia species via Validated Isotope Dilution Ultra-high Performance Liquid Chromatography Tandem Mass Spectrometry. Phytochemical analysis : PCA. 2018 Jan; 29(1):23-29. doi: 10.1002/pca.2711. [PMID: 28786149]
  • Gordana Krstić, Boban Anđelković, Young Hae Choi, Vlatka Vajs, Tatjana Stević, Vele Tešević, Dejan Gođevac. Metabolic changes in Euphorbia palusrtis latex after fungal infection. Phytochemistry. 2016 Nov; 131(?):17-25. doi: 10.1016/j.phytochem.2016.08.005. [PMID: 27553715]
  • Xiaojing Yan, Li Zhang, Yudan Cao, Weifeng Yao, Yuping Tang, Anwei Ding. An Ingenol Derived from Euphorbia kansui Induces Hepatocyte Cytotoxicity by Triggering G0/G1 Cell Cycle Arrest and Regulating the Mitochondrial Apoptosis Pathway in Vitro. Molecules (Basel, Switzerland). 2016 Jun; 21(6):. doi: 10.3390/molecules21060813. [PMID: 27338329]
  • Xin Shu, Xi-Wen Jiang, Brian Chi-Yan Cheng, Shuang-Cheng Ma, Guang-Ying Chen, Zhi-Ling Yu. Ultra-performance liquid chromatography-quadrupole/time-of-flight mass spectrometry analysis of the impact of processing on toxic components of Kansui Radix. BMC complementary and alternative medicine. 2016 Feb; 16(?):73. doi: 10.1186/s12906-016-1039-7. [PMID: 26912002]
  • Jin Woo Lee, Chul Lee, Qinghao Jin, Hari Jang, Dongho Lee, Ha-Jin Lee, Jong Won Shin, Sang Bae Han, Jin Tae Hong, Youngsoo Kim, Mi Kyeong Lee, Bang Yeon Hwang. Diterpenoids from the Roots of Euphorbia fischeriana with Inhibitory Effects on Nitric Oxide Production. Journal of natural products. 2016 Jan; 79(1):126-31. doi: 10.1021/acs.jnatprod.5b00789. [PMID: 26702644]
  • Daniele C Cary, Koh Fujinaga, B Matija Peterlin. Euphorbia Kansui Reactivates Latent HIV. PloS one. 2016; 11(12):e0168027. doi: 10.1371/journal.pone.0168027. [PMID: 27977742]
  • Louis-Félix Nothias-Scaglia, Isabelle Schmitz-Afonso, Franck Renucci, Fanny Roussi, David Touboul, Jean Costa, Marc Litaudon, Julien Paolini. Insights on profiling of phorbol, deoxyphorbol, ingenol and jatrophane diterpene esters by high performance liquid chromatography coupled to multiple stage mass spectrometry. Journal of chromatography. A. 2015 Nov; 1422(?):128-139. doi: 10.1016/j.chroma.2015.09.092. [PMID: 26522744]
  • Jing Gao, Lan Gao, Li Zhang, Weifeng Yao, Yudan Cao, Beihua Bao, Anwei Ding. 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol induces apoptosis in intestinal epithelial cells of rats via mitochondrial pathway. Journal of ethnopharmacology. 2015 Nov; 174(?):331-8. doi: 10.1016/j.jep.2015.08.036. [PMID: 26318745]
  • Guochun Jiang, Erica A Mendes, Philipp Kaiser, Sumathi Sankaran-Walters, Yuyang Tang, Mariana G Weber, Greg P Melcher, George R Thompson, Amilcar Tanuri, Luiz F Pianowski, Joseph K Wong, Satya Dandekar. Reactivation of HIV latency by a newly modified Ingenol derivative via protein kinase Cδ-NF-κB signaling. AIDS (London, England). 2014 Jul; 28(11):1555-66. doi: 10.1097/qad.0000000000000289. [PMID: 24804860]
  • Hong-Bing Wang, Wei Chen, Ying-Ying Zhang, Xiao-Yang Wang, Li-Ping Liu, Ling-Jiang Tong, Yi Chen. Four new diterpenoids from the roots of Euphorbia fischeriana. Fitoterapia. 2013 Dec; 91(?):211-216. doi: 10.1016/j.fitote.2013.09.003. [PMID: 24042072]
  • Hong-Ying Wang, Jun-Song Wang, Dan-Dan Wei, Xiao-Bing Wang, Jun Luo, Ming-Hua Yang, Ling-Yi Kong. Bioactivity-guided isolation of antiproliferative diterpenoids from Euphorbia kansui. Phytotherapy research : PTR. 2012 Jun; 26(6):853-9. doi: 10.1002/ptr.3640. [PMID: 22095916]
  • Imam Bakhsh Baloch, Musa Kaleem Baloch. Isolation and characterisation of new bio-active compounds from Euphorbia cornigera: cytotoxic ingenol esters. Natural product research. 2012; 26(20):1857-63. doi: 10.1080/14786419.2011.616507. [PMID: 22007629]
  • Imam Bakhsh Baloch, Musa Kaleem Baloch. Isolation and characterization of cytotoxic compounds from Euphorbia cornigera Boiss. Journal of Asian natural products research. 2010 Nov; 12(11):985-91. doi: 10.1080/10286020.2010.512007. [PMID: 21061221]
  • Norimitsu Morioka, Joynal Md Abdin, Katsuya Morita, Tomoya Kitayama, Yoshihiro Nakata, Toshihiro Dohi. The regulation of glycine transporter GLYT1 is mainly mediated by protein kinase Calpha in C6 glioma cells. Neurochemistry international. 2008 Dec; 53(6-8):248-54. doi: 10.1016/j.neuint.2008.08.002. [PMID: 18778746]
  • S M Zayed, M Farghaly, H Taha, R Gminski, E Hecker. Dietary cancer risk from conditional cancerogens in produce of livestock fed on species of spurge (Euphorbiaceae). III. Milk of lactating goats fed on the skin irritant herb Euphorbia peplus is polluted by tumor promoters of the ingenane diterpene ester type. Journal of cancer research and clinical oncology. 1998; 124(6):301-6. doi: 10.1007/s004320050173. [PMID: 9692836]