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'''Chrysophanol''', also known as '''chrysophanic acid''', is a fungal isolate and a natural [[anthraquinone]].
'''Chrysophanol''', also known as '''chrysophanic acid''', is a fungal isolate and a natural [[anthraquinone]].

== Summary ==
Chrysophanol (other names; 1,8-dihydroxy-3-methyl-anthraquinone and chrysophanic acid) was found commonly within Chinese medicine and is a naturally occurring anthraquinone<ref name=":0">{{Cite journal|last=Xie|first=Long|last2=Tang|first2=Hailong|last3=Song|first3=Jiawen|last4=Long|first4=Jiaying|last5=Zhang|first5=Linlin|last6=Li|first6=Xiaofang|date=2019-10|title=Chrysophanol: a review of its pharmacology, toxicity and pharmacokinetics|url=https://pubmed.ncbi.nlm.nih.gov/31373015/|journal=The Journal of Pharmacy and Pharmacology|volume=71|issue=10|pages=1475–1487|doi=10.1111/jphp.13143|issn=2042-7158|pmid=31373015}}</ref> . Studies have been conducted on the benefits of chrysophanol and have found that it can aid in preventing cancer, diabetes, asthma, osteoporosis, retinal degeneration, Alzheimer’s disease, osteoarthritis, and atherosclerosis <ref name=":0" />.

Its most common effects are that on cancer growth/anti-tumour growth effects and neuroprotective properties.

== History ==
Chrysophanol was first noted from ''Rheum rhabarbarum'' which is a plant belonging to the Polygonaceae family <ref name=":1">{{Cite journal|last=Prateeksha|last2=Yusuf|first2=Mohd Aslam|last3=Singh|first3=Brahma N.|last4=Sudheer|first4=Surya|last5=Kharwar|first5=Ravindra N.|last6=Siddiqui|first6=Saba|last7=Abdel-Azeem|first7=Ahmed M.|last8=Fernandes Fraceto|first8=Leonardo|last9=Dashora|first9=Kavya|last10=Gupta|first10=Vijai K.|date=2019/2|title=Chrysophanol: A Natural Anthraquinone with Multifaceted Biotherapeutic Potential|url=https://www.mdpi.com/2218-273X/9/2/68|journal=Biomolecules|language=en|volume=9|issue=2|pages=68|doi=10.3390/biom9020068}}</ref>. It has since been discovered to be present in various families such as Liliaceae, Meliaceae, Asphodelaceae and Fabaceae among more <ref name=":1" />. As of 2019, it has been observed in 65 species from 14 genera, not just in plants but animals and microbes as well <ref name=":1" />.

== Uses ==
Chrysophanol has been shown to exhibit a variety of effects. It was shown in 2015 to lower cholesterol and triglyceride levels in zebrafish, as well as increase the frequency of peristalsis. This could therefore be used for lipid metabolic disorders in a clinical setting <ref name=":2">{{Cite journal|last=Chen|first=Kan|last2=Wang|first2=Chang-Qian|last3=Fan|first3=Yu-Qi|last4=Xie|first4=Yu-Shui|last5=Yin|first5=Zhao-Fang|last6=Xu|first6=Zuo-Jun|last7=Zhang|first7=Hui-Li|last8=Cao|first8=Jia-Tian|last9=Wang|first9=Yue|date=2015-07-15|title=Application of chrysophanol in zebrafish to reduce dietary introduced lipid and its possible mechanism|url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4565228/|journal=International Journal of Clinical and Experimental Medicine|volume=8|issue=7|pages=10558–10567|issn=1940-5901|pmc=4565228|pmid=26379845}}</ref>. Chrysophanol has also been shown to exhibit the same properties lipid lowering in rats in 2013 <ref name=":2" />.

It also has the potential to stimulate osteoblast differentiation <ref name=":3">{{Cite journal|last=Lim|first=Young-Ju|last2=Kim|first2=Kyeong-Min|last3=Jang|first3=Won-Gu|date=2021|title=Chrysophanol increases osteoblast differentiation via AMPK/Smad1/5/9 phosphorylation in vitro and in vivo|url=https://onlinelibrary.wiley.com/doi/abs/10.1111/1440-1681.13443|journal=Clinical and Experimental Pharmacology and Physiology|language=en|volume=48|issue=4|pages=515–523|doi=10.1111/1440-1681.13443|issn=1440-1681}}</ref>, as well as alleviate diabetic nephropathy <ref name=":4">{{Cite journal|last=Guo|first=Chuan|last2=Wang|first2=Yarong|last3=Piao|first3=Yuanlin|last4=Rao|first4=Xiangrong|last5=Yin|first5=Dehai|date=2020-11-16|title=Chrysophanol Inhibits the Progression of Diabetic Nephropathy via Inactivation of TGF-β Pathway|url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7678702/|journal=Drug Design, Development and Therapy|volume=14|pages=4951–4962|doi=10.2147/DDDT.S274191|issn=1177-8881|pmc=7678702|pmid=33235436}}</ref>. Furthermore, it can protect bronchial cells from cigarette smoke extract induced apoptosis <ref name=":5">{{Cite journal|last=Wu|first=Guorao|last2=Yuan|first2=Ting|last3=Zhu|first3=He|last4=Zhang|first4=Huilan|last5=Su|first5=Jiakun|last6=Guo|first6=Lei|last7=Zhou|first7=Qing|last8=Xiong|first8=Fei|last9=Yu|first9=Qilin|last10=Yang|first10=Ping|last11=Zhang|first11=Shu|date=2020-12-15|title=Chrysophanol protects human bronchial epithelial cells from cigarette smoke extract (CSE)-induced apoptosis|url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7811954/|journal=International Journal of Molecular Epidemiology and Genetics|volume=11|issue=3|pages=39–45|issn=1948-1756|pmc=7811954|pmid=33488953}}</ref>. Chrysophanol can also improve the condition of renal interstitial fibrosis <ref name=":6">{{Cite journal|date=2020-10-01|title=Chrysophanol ameliorates renal interstitial fibrosis by inhibiting the TGF-β/Smad signaling pathway|url=https://www.sciencedirect.com/science/article/abs/pii/S0006295220303130|journal=Biochemical Pharmacology|language=en|volume=180|pages=114079|doi=10.1016/j.bcp.2020.114079|issn=0006-2952}}</ref>.

Chrysophanol has also been used to inhibit T-Cell activation and protect mice from dextran sulphate sodium induced inflammatory bowel disease <ref name=":7">{{Cite journal|last=Lee|first=Hyun-Su|last2=Jeong|first2=Gil-Saeng|date=2021-03-17|title=Chrysophanol Attenuates Manifestations of Immune Bowel Diseases by Regulation of Colorectal Cells and T Cells Activation In Vivo|url=https://pubmed.ncbi.nlm.nih.gov/33802855/|journal=Molecules (Basel, Switzerland)|volume=26|issue=6|doi=10.3390/molecules26061682|issn=1420-3049|pmc=8002617|pmid=33802855}}</ref>. It was shown to have attenuated the pro-inflammatory cytokines that were present in the colon tissue due to sulphate sodium induced inflammatory bowel disease <ref name=":7" />.


== Mechanism of action ==
== Mechanism of action ==
Chrysophanol can alleviate diabetic nephropathy by inactivating TGF-β/EMT signalling <ref name=":4" />. It also has the potential to protect bronchial cells from cigarette smoke extract by repressing CYP1A expression which is usually produced due to excessive reactive oxygen species <ref name=":5" />. Chrysophanol can increase osteoblast differentiation by inducing AMP-activated protein kinase as well as Smad1/5/9 <ref name=":3" />. Chrysophanol acts to improve renal interstitial fibrosis by downregulating TGF-β1 and phospho-Smad3 and by upregulating Smad7 <ref name=":6" />.
⚫
Chrysophanol blocks the proliferation of colon cancer cells ''[[in vitro]]''.<ref>{{cite journal |pmid=21089180 |year=2011 |last1=Lee |first1=MS |last2=Cha |first2=EY |last3=Sul |first3=JY |last4=Song |first4=IS |last5=Kim |first5=JY |title=Chrysophanic acid blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway|volume=25 |issue=6 |pages=833–7| doi=10.1002/ptr.3323| journal=Phytotherapy Research}}</ref> It induces the necrosis of cells via a reduction in [[Adenosine triphosphate|ATP]] levels.<ref name=purinergic>{{cite journal|last=Burnstock|first=G|author2=Di Virgilio, F|title=Purinergic signalling and cancer |journal=[[Purinergic Signalling (journal)|Purinergic Signalling]] |date=Dec 2013 | volume=9 |issue=4 |pages=491–540 |pmid=23797685 |doi=10.1007/s11302-013-9372-5 |pmc=3889385}}</ref> Chrysophanol attenuates the effects of lead exposure in mice by reducing hippocampal neuronal cytoplasmic edema, enhancing mitochondrial crista fusion, significantly increasing memory and learning abilities, reducing lead content in blood, heart, brain, spleen, kidney and liver, promoting superoxide dismutase and glutathione peroxidase activities and reducing malondialdehyde level in the brain, kidney and liver.<ref>{{cite journal | pmid= 25206913| pmc= 4146226| year= 2014| last1= Zhang| first1= J| title= Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice| journal= Neural Regeneration Research| volume= 9| issue= 9| pages= 924–30| last2= Yan| first2= C| last3= Wang| first3= S| last4= Hou| first4= Y| last5= Xue| first5= G| last6= Zhang| first6= L| doi= 10.4103/1673-5374.133141}}</ref>

Chrysophanol can also aid in treatment for inflammatory bowel disease by inhibiting inflammation by targeting pro-inflammatory cytokines that are in tumour necrosis factor α <ref name=":7" />. It has also been shown that it inhibits the mitogen-activated protein kinase pathway <ref name=":7" />.

⚫
Chrysophanol blocks the proliferation of colon cancer cells ''[[in vitro]]''.<ref>{{cite journal |pmid=21089180 |year=2011 |last1=Lee |first1=MS |last2=Cha |first2=EY |last3=Sul |first3=JY |last4=Song |first4=IS |last5=Kim |first5=JY |title=Chrysophanic acid blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway|volume=25 |issue=6 |pages=833–7| doi=10.1002/ptr.3323| journal=Phytotherapy Research}}</ref> It induces the necrosis of cells via a reduction in [[Adenosine triphosphate|ATP]] levels.<ref name="purinergic">{{cite journal|last=Burnstock|first=G|author2=Di Virgilio, F|title=Purinergic signalling and cancer |journal=[[Purinergic Signalling (journal)|Purinergic Signalling]] |date=Dec 2013 | volume=9 |issue=4 |pages=491–540 |pmid=23797685 |doi=10.1007/s11302-013-9372-5 |pmc=3889385}}</ref> Chrysophanol attenuates the effects of lead exposure in mice by reducing hippocampal neuronal cytoplasmic edema, enhancing mitochondrial crista fusion, significantly increasing memory and learning abilities, reducing lead content in blood, heart, brain, spleen, kidney and liver, promoting superoxide dismutase and glutathione peroxidase activities and reducing malondialdehyde level in the brain, kidney and liver.<ref>{{cite journal | pmid= 25206913| pmc= 4146226| year= 2014| last1= Zhang| first1= J| title= Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice| journal= Neural Regeneration Research| volume= 9| issue= 9| pages= 924–30| last2= Yan| first2= C| last3= Wang| first3= S| last4= Hou| first4= Y| last5= Xue| first5= G| last6= Zhang| first6= L| doi= 10.4103/1673-5374.133141}}</ref>

== Drug Class ==
Chrysophanol can act as an antineoplastic drug. This has been shown in multiple organisms. It has been reported that chrysophanol causes necrosis-like cell death in renal cancer cells <ref name=":8">{{Cite journal|last=Choi|first=Joon-Seok|date=2016-06-30|title=Chrysophanic Acid Induces Necrosis but not Necroptosis in Human Renal Cell Carcinoma Caki-2 Cells|url=https://www.jcpjournal.org/journal/view.html?doi=10.15430/JCP.2016.21.2.81|journal=Journal of Cancer Prevention|language=en|volume=21|issue=2|pages=81–87|doi=10.15430/JCP.2016.21.2.81|pmc=PMC4933431|pmid=27390736}}</ref>. It also has expressed the capability to be classes as an ATC code A10 drug due to its effect on diabetic nephropathy as well as being able to lower lipid absorption <ref name=":2" /><ref name=":4" />.

== Chemical Structure and Production ==
Chrysophanol is naturally made by a variety of plant species. The most intake is from consumption of rhubarb. Chrysophanol is a chrysazin with a methyl substitute at C-3 and is a trihydroxyanthraquinone <ref name=":9">{{Cite web|last=PubChem|title=Chrysophanol|url=https://pubchem.ncbi.nlm.nih.gov/compound/10208|access-date=2021-05-31|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>.

== Drug interactions ==
Chrysophanol has been shown to be able to be co-administered with atorvastatin, to lower cholesterol levels <ref name=":2" />. This is due to the different mechanisms for each, with chrysophanol thought to bind to the stomach to disturb lipid absorption, while atorvastatin decreases cholesterol production in the liver <ref name=":2" />.

== Toxicity ==
Anthraquinones, chrysophanol derivatives among them, have been shown to be hepatotoxic <ref name=":10">{{Cite journal|last=Lin|first=Longfei|last2=Yuan|first2=Fang|last3=Liu|first3=Yuling|last4=Zhong|first4=Ming|last5=Xie|first5=Tanggui|last6=Ni|first6=Jian|last7=Li|first7=Hui|date=2019-12|title=Hepatotoxicity and mechanism study of chrysophanol-8-O-glucoside in vitro|url=https://pubmed.ncbi.nlm.nih.gov/31648163/|journal=Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie|volume=120|pages=109531|doi=10.1016/j.biopha.2019.109531|issn=1950-6007|pmid=31648163}}</ref>. They can cause apoptosis in normal human liver cells <ref name=":10" />. Chrysophanol derivatives such as chrysophanol-8-o-glucoside, have also been shown to possess anti-coagulant and anti-platelet properties <ref name=":11">{{Cite journal|last=Seo|first=Eun Ji|last2=Ngoc|first2=Tran Minh|last3=Lee|first3=Sun-Mee|last4=Kim|first4=Yeong Shik|last5=Jung|first5=Yi-Sook|date=2012|title=Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities|url=https://pubmed.ncbi.nlm.nih.gov/22302018/|journal=Journal of Pharmacological Sciences|volume=118|issue=2|pages=245–254|doi=10.1254/jphs.11123fp|issn=1347-8648|pmid=22302018}}</ref>. The derivatives also have potential to cause abnormal oxidative phosphorylation which can result in decreased mitochondrial membrane potential, as well as an increase in abundance of reactive oxygen species, and ultimately will lead to mitochondrial damage and eventual apoptosis <ref name=":10" />.

There is also evidence that chrysophanol could cause damage to DNA <ref name=":0" />. This has been demonstrated in two strains of Salmonella (strains TA 2637 and 1537)<ref name=":0" />. It is also important to note, that in treating liver cancer cells, it does so in a way that induced necrosis-like cell death <ref name=":12">{{Cite journal|last=Ni|first=Chien-Hang|last2=Chen|first2=Po-Yuan|last3=Lu|first3=Hsu-Feng|last4=Yang|first4=Jai-Sing|last5=Huang|first5=Hui-Ying|last6=Wu|first6=Shin-Hwar|last7=Ip|first7=Siu-Wan|last8=Wu|first8=Chin-Tung|last9=Chiang|first9=Su-Yin|last10=Lin|first10=Jaung-Geng|last11=Wood|first11=W. Gibson|date=2012-05|title=Chrysophanol-induced necrotic-like cell death through an impaired mitochondrial ATP synthesis in Hep3B human liver cancer cells|url=https://pubmed.ncbi.nlm.nih.gov/22644856/|journal=Archives of Pharmacal Research|volume=35|issue=5|pages=887–895|doi=10.1007/s12272-012-0514-z|issn=0253-6269|pmid=22644856}}</ref>. Necrosis damages the cellular environment, meaning that while it may treat potential issues, it can also damage the surrounding tissue <ref name=":12" />.


==References==
==References==
{{Reflist}}
{{Reflist}}Ref things


<ref>{{Cite journal|last=Trybus|first=Wojciech|last2=Król|first2=Teodora|last3=Trybus|first3=Ewa|last4=Stachurska|first4=Anna|last5=Król|first5=Grzegorz|date=2021|title=The potential antitumor effect of chrysophanol in relation to cervical cancer cells|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/jcb.29891|journal=Journal of Cellular Biochemistry|language=en|volume=122|issue=6|pages=639–652|doi=10.1002/jcb.29891|issn=1097-4644}}</ref><ref name=":1" /><ref name=":5" /><ref name=":10" /><ref name=":11" /><ref name=":2" /><ref name=":4" /><ref name=":3" /><ref name=":6" /><ref name=":9" /><ref name=":7" /><ref name=":8" />{{Purinergics}}
{{Purinergics}}


{{pharma-stub}}
{{pharma-stub}}

Revision as of 10:14, 31 May 2021

Chrysophanol
Names
Preferred IUPAC name
1,8-Dihydroxy-3-methylanthracene-9,10-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.885 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
    Key: LQGUBLBATBMXHT-UHFFFAOYSA-N
  • InChI=1/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
    Key: LQGUBLBATBMXHT-UHFFFAOYAW
  • CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
Properties
C15H10O4
Molar mass 254.241 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone.

Summary

Chrysophanol (other names; 1,8-dihydroxy-3-methyl-anthraquinone and chrysophanic acid) was found commonly within Chinese medicine and is a naturally occurring anthraquinone[1] . Studies have been conducted on the benefits of chrysophanol and have found that it can aid in preventing cancer, diabetes, asthma, osteoporosis, retinal degeneration, Alzheimer’s disease, osteoarthritis, and atherosclerosis [1].

Its most common effects are that on cancer growth/anti-tumour growth effects and neuroprotective properties.

History

Chrysophanol was first noted from Rheum rhabarbarum which is a plant belonging to the Polygonaceae family [2]. It has since been discovered to be present in various families such as Liliaceae, Meliaceae, Asphodelaceae and Fabaceae among more [2]. As of 2019, it has been observed in 65 species from 14 genera, not just in plants but animals and microbes as well [2].

Uses

Chrysophanol has been shown to exhibit a variety of effects. It was shown in 2015 to lower cholesterol and triglyceride levels in zebrafish, as well as increase the frequency of peristalsis. This could therefore be used for lipid metabolic disorders in a clinical setting [3]. Chrysophanol has also been shown to exhibit the same properties lipid lowering in rats in 2013 [3].

It also has the potential to stimulate osteoblast differentiation [4], as well as alleviate diabetic nephropathy [5]. Furthermore, it can protect bronchial cells from cigarette smoke extract induced apoptosis [6]. Chrysophanol can also improve the condition of renal interstitial fibrosis [7].

Chrysophanol has also been used to inhibit T-Cell activation and protect mice from dextran sulphate sodium induced inflammatory bowel disease [8]. It was shown to have attenuated the pro-inflammatory cytokines that were present in the colon tissue due to sulphate sodium induced inflammatory bowel disease [8].

Mechanism of action

Chrysophanol can alleviate diabetic nephropathy by inactivating TGF-β/EMT signalling [5]. It also has the potential to protect bronchial cells from cigarette smoke extract by repressing CYP1A expression which is usually produced due to excessive reactive oxygen species [6]. Chrysophanol can increase osteoblast differentiation by inducing AMP-activated protein kinase as well as Smad1/5/9 [4]. Chrysophanol acts to improve renal interstitial fibrosis by downregulating TGF-β1 and phospho-Smad3 and by upregulating Smad7 [7].

Chrysophanol can also aid in treatment for inflammatory bowel disease by inhibiting inflammation by targeting pro-inflammatory cytokines that are in tumour necrosis factor α [8]. It has also been shown that it inhibits the mitogen-activated protein kinase pathway [8].

Chrysophanol blocks the proliferation of colon cancer cells in vitro.[9] It induces the necrosis of cells via a reduction in ATP levels.[10] Chrysophanol attenuates the effects of lead exposure in mice by reducing hippocampal neuronal cytoplasmic edema, enhancing mitochondrial crista fusion, significantly increasing memory and learning abilities, reducing lead content in blood, heart, brain, spleen, kidney and liver, promoting superoxide dismutase and glutathione peroxidase activities and reducing malondialdehyde level in the brain, kidney and liver.[11]

Drug Class

Chrysophanol can act as an antineoplastic drug. This has been shown in multiple organisms. It has been reported that chrysophanol causes necrosis-like cell death in renal cancer cells [12]. It also has expressed the capability to be classes as an ATC code A10 drug due to its effect on diabetic nephropathy as well as being able to lower lipid absorption [3][5].

Chemical Structure and Production

Chrysophanol is naturally made by a variety of plant species. The most intake is from consumption of rhubarb. Chrysophanol is a chrysazin with a methyl substitute at C-3 and is a trihydroxyanthraquinone [13].

Drug interactions

Chrysophanol has been shown to be able to be co-administered with atorvastatin, to lower cholesterol levels [3]. This is due to the different mechanisms for each, with chrysophanol thought to bind to the stomach to disturb lipid absorption, while atorvastatin decreases cholesterol production in the liver [3].

Toxicity

Anthraquinones, chrysophanol derivatives among them, have been shown to be hepatotoxic [14]. They can cause apoptosis in normal human liver cells [14]. Chrysophanol derivatives such as chrysophanol-8-o-glucoside, have also been shown to possess anti-coagulant and anti-platelet properties [15]. The derivatives also have potential to cause abnormal oxidative phosphorylation which can result in decreased mitochondrial membrane potential, as well as an increase in abundance of reactive oxygen species, and ultimately will lead to mitochondrial damage and eventual apoptosis [14].

There is also evidence that chrysophanol could cause damage to DNA [1]. This has been demonstrated in two strains of Salmonella (strains TA 2637 and 1537)[1]. It is also important to note, that in treating liver cancer cells, it does so in a way that induced necrosis-like cell death [16]. Necrosis damages the cellular environment, meaning that while it may treat potential issues, it can also damage the surrounding tissue [16].

References

  1. ^ a b c d Xie, Long; Tang, Hailong; Song, Jiawen; Long, Jiaying; Zhang, Linlin; Li, Xiaofang (2019-10). "Chrysophanol: a review of its pharmacology, toxicity and pharmacokinetics". The Journal of Pharmacy and Pharmacology. 71 (10): 1475–1487. doi:10.1111/jphp.13143. ISSN 2042-7158. PMID 31373015. {{cite journal}}: Check date values in: |date= (help)
  2. ^ a b c Prateeksha; Yusuf, Mohd Aslam; Singh, Brahma N.; Sudheer, Surya; Kharwar, Ravindra N.; Siddiqui, Saba; Abdel-Azeem, Ahmed M.; Fernandes Fraceto, Leonardo; Dashora, Kavya; Gupta, Vijai K. (2019/2). "Chrysophanol: A Natural Anthraquinone with Multifaceted Biotherapeutic Potential". Biomolecules. 9 (2): 68. doi:10.3390/biom9020068. {{cite journal}}: Check date values in: |date= (help)CS1 maint: unflagged free DOI (link)
  3. ^ a b c d e Chen, Kan; Wang, Chang-Qian; Fan, Yu-Qi; Xie, Yu-Shui; Yin, Zhao-Fang; Xu, Zuo-Jun; Zhang, Hui-Li; Cao, Jia-Tian; Wang, Yue (2015-07-15). "Application of chrysophanol in zebrafish to reduce dietary introduced lipid and its possible mechanism". International Journal of Clinical and Experimental Medicine. 8 (7): 10558–10567. ISSN 1940-5901. PMC 4565228. PMID 26379845.
  4. ^ a b Lim, Young-Ju; Kim, Kyeong-Min; Jang, Won-Gu (2021). "Chrysophanol increases osteoblast differentiation via AMPK/Smad1/5/9 phosphorylation in vitro and in vivo". Clinical and Experimental Pharmacology and Physiology. 48 (4): 515–523. doi:10.1111/1440-1681.13443. ISSN 1440-1681.
  5. ^ a b c Guo, Chuan; Wang, Yarong; Piao, Yuanlin; Rao, Xiangrong; Yin, Dehai (2020-11-16). "Chrysophanol Inhibits the Progression of Diabetic Nephropathy via Inactivation of TGF-β Pathway". Drug Design, Development and Therapy. 14: 4951–4962. doi:10.2147/DDDT.S274191. ISSN 1177-8881. PMC 7678702. PMID 33235436.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  6. ^ a b Wu, Guorao; Yuan, Ting; Zhu, He; Zhang, Huilan; Su, Jiakun; Guo, Lei; Zhou, Qing; Xiong, Fei; Yu, Qilin; Yang, Ping; Zhang, Shu (2020-12-15). "Chrysophanol protects human bronchial epithelial cells from cigarette smoke extract (CSE)-induced apoptosis". International Journal of Molecular Epidemiology and Genetics. 11 (3): 39–45. ISSN 1948-1756. PMC 7811954. PMID 33488953.
  7. ^ a b "Chrysophanol ameliorates renal interstitial fibrosis by inhibiting the TGF-β/Smad signaling pathway". Biochemical Pharmacology. 180: 114079. 2020-10-01. doi:10.1016/j.bcp.2020.114079. ISSN 0006-2952.
  8. ^ a b c d Lee, Hyun-Su; Jeong, Gil-Saeng (2021-03-17). "Chrysophanol Attenuates Manifestations of Immune Bowel Diseases by Regulation of Colorectal Cells and T Cells Activation In Vivo". Molecules (Basel, Switzerland). 26 (6). doi:10.3390/molecules26061682. ISSN 1420-3049. PMC 8002617. PMID 33802855.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  9. ^ Lee, MS; Cha, EY; Sul, JY; Song, IS; Kim, JY (2011). "Chrysophanic acid blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway". Phytotherapy Research. 25 (6): 833–7. doi:10.1002/ptr.3323. PMID 21089180.
  10. ^ Burnstock, G; Di Virgilio, F (Dec 2013). "Purinergic signalling and cancer". Purinergic Signalling. 9 (4): 491–540. doi:10.1007/s11302-013-9372-5. PMC 3889385. PMID 23797685.
  11. ^ Zhang, J; Yan, C; Wang, S; Hou, Y; Xue, G; Zhang, L (2014). "Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice". Neural Regeneration Research. 9 (9): 924–30. doi:10.4103/1673-5374.133141. PMC 4146226. PMID 25206913.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  12. ^ Choi, Joon-Seok (2016-06-30). "Chrysophanic Acid Induces Necrosis but not Necroptosis in Human Renal Cell Carcinoma Caki-2 Cells". Journal of Cancer Prevention. 21 (2): 81–87. doi:10.15430/JCP.2016.21.2.81. PMC 4933431. PMID 27390736.{{cite journal}}: CS1 maint: PMC format (link)
  13. ^ PubChem. "Chrysophanol". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-05-31.
  14. ^ a b c Lin, Longfei; Yuan, Fang; Liu, Yuling; Zhong, Ming; Xie, Tanggui; Ni, Jian; Li, Hui (2019-12). "Hepatotoxicity and mechanism study of chrysophanol-8-O-glucoside in vitro". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 120: 109531. doi:10.1016/j.biopha.2019.109531. ISSN 1950-6007. PMID 31648163. {{cite journal}}: Check date values in: |date= (help)
  15. ^ Seo, Eun Ji; Ngoc, Tran Minh; Lee, Sun-Mee; Kim, Yeong Shik; Jung, Yi-Sook (2012). "Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities". Journal of Pharmacological Sciences. 118 (2): 245–254. doi:10.1254/jphs.11123fp. ISSN 1347-8648. PMID 22302018.
  16. ^ a b Ni, Chien-Hang; Chen, Po-Yuan; Lu, Hsu-Feng; Yang, Jai-Sing; Huang, Hui-Ying; Wu, Shin-Hwar; Ip, Siu-Wan; Wu, Chin-Tung; Chiang, Su-Yin; Lin, Jaung-Geng; Wood, W. Gibson (2012-05). "Chrysophanol-induced necrotic-like cell death through an impaired mitochondrial ATP synthesis in Hep3B human liver cancer cells". Archives of Pharmacal Research. 35 (5): 887–895. doi:10.1007/s12272-012-0514-z. ISSN 0253-6269. PMID 22644856. {{cite journal}}: Check date values in: |date= (help)

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  1. ^ Trybus, Wojciech; Król, Teodora; Trybus, Ewa; Stachurska, Anna; Król, Grzegorz (2021). "The potential antitumor effect of chrysophanol in relation to cervical cancer cells". Journal of Cellular Biochemistry. 122 (6): 639–652. doi:10.1002/jcb.29891. ISSN 1097-4644.
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