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{{cs1 config|name-list-style=vanc}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 399512687 | verifiedrevid = 446181805
| ImageFile = (R,R)- and (S,S)-Anemonin Structural Formulae.png | ImageFile = Anemonin Structural Formulae.svg
| ImageSize = 240
| IUPACName = ''trans''-4,7-Dioxadispirododeca-1,9-diene-3,8-dione
| ImageAlt = Skeletal formula of anemonin
| ImageFile1 = Anemonin 3D ball.png
| ImageSize1 = 180
| ImageAlt1 = Ball-and-stick model of the anemonin molecule
| IUPACName = ''trans''-4,7-Dioxadispirododeca-1,9-diene-3,8-dione<br/>''trans''-1,7-Dioxadispirododeca-3,9-diene-2,8-dione<ref name="crc97">{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | pages=3–26 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}</ref>
| OtherNames = | OtherNames =
| Reference = <ref name="druglead" /> | Reference =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10064 | ChemSpiderID = 10064
| ChEMBL = 1972777
| SMILES1 = O=C\1OC3(/C=C/1)C/2(OC(=O)\C=C\2)CC3
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 508-44-1 | CASNo = 508-44-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G99XG5B674
| PubChem = 10496 | PubChem = 10496
| SMILES = C1CC2(C13C=CC(=O)O3)C=CC(=O)O2 | SMILES = C1CC2(C13C=CC(=O)O3)C=CC(=O)O2
Line 17: Line 26:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JLUQTCXCAFSSLD-UHFFFAOYSA-N}} | StdInChIKey = JLUQTCXCAFSSLD-UHFFFAOYSA-N}}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=10 | H=8 | O=4 | C=10 | H=8 | O=4
| Appearance = Colourless, odourless solid | Appearance = Colourless, odourless solid
| Density = 1.45g/cm<sup>3</sup> | Density = 1.45g/cm<sup>3</sup>
| MeltingPt = 158 °C | MeltingPtC = 158<ref name="crc97"/>
| MeltingPt_notes =
| BoilingPt = 535.7°C @ 760mmHg
| Boiling_notes = | BoilingPtC = 535.7
| BoilingPt_notes = @ 760mmHg
| Solubility = low | Solubility = low
| SolubleOther = soluble | SolubleOther = very soluble<ref name="crc97"/>
| Solvent = ]}} | Solvent = ]}}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| LD50 = 150 mg·kg<sup>−1</sup> (mouse, ]) | LD50 = 150 mg·kg<sup>−1</sup> (mouse, ])
| FlashPt = 300.7°C | FlashPtC = 300.7
| Autoignition = }} | AutoignitionPtC =
}}
}} }}
'''Anemonin''' is a tri-spirocyclic di] ] found in members of the buttercup family (]) such as '']'', '']'', '']'', '']'',<ref>{{cite journal |last1=Teodora |first1=Neag |last2=Neli Kinga |first2=Olag |last3=Daniela |first3=Hanganu |last4=Daniela |first4=Benedec |last5=Pripon |first5=Flavia |last6=Aurel |first6=Ardelean |last7=Claudia |first7=Toma |date=2018 |title=Anemonin Content of Four Different Ranunculus Species |journal=Pakistan Journal of Pharmaceutical Sciences |volume=31 |issue=5(Supplementary) |pages=2027–2032 |pmid=30393208 |url=https://pesquisa.bvsalud.org/portal/resource/pt/emr-199590}}</ref> and '']''.<ref name=":0">{{cite journal |vauthors=Kern JR, Cardellina JH |title=Native American medicinal plants. Anemonin from the horse stimulant ''Clematis hirsutissima''|journal=Journal of Ethnopharmacology |volume=8 |issue=1 |pages=121–123 |date=July 1983 |pmid=6632934 |doi=10.1016/0378-8741(83)90093-4}}</ref> Originally isolated in 1792 by M. Heyer,<ref name=":1">{{cite journal |vauthors=Moriarty RM, Romain CR, Karle IL, Karle J |date= July 1965 |title=The Structure of Anemonin |journal=Journal of the American Chemical Society |language=en |volume=87 |issue=14 |pages=3251–3252 |doi=10.1021/ja01092a047 |issn=0002-7863}}</ref> It is the ] product of the ] ].<ref name="TUGraz">{{cite web |title=Aktuelles aus der Natur |publisher=] |language=German |page=4 |date=2 April 2009 |url=http://www.orgc.tugraz.at/hoegroup/naturst/Akt_2009_04_02.pdf |access-date=27 November 2010 }}{{dead link|date=July 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> One of the likely active agents in plants used in Chinese medicine as an anti-inflammatory<ref name="Effect of anemonin on NO, ET-1 and">{{cite journal |vauthors=Duan H, Zhang Y, Xu J, Qiao J, Suo Z, Hu G, Mu X |title=Effect of anemonin on NO, ET-1 and ICAM-1 production in rat intestinal microvascular endothelial cells |journal=Journal of Ethnopharmacology |volume=104 |issue=3 |pages=362–366 |date=April 2006 |pmid=16257161 |doi=10.1016/j.jep.2005.09.034}}</ref> and Native American medicine as a horse stimulant,<ref name=":0" /> its unique biological properties give it pharmaceutical potential as an anti-inflammatory and cosmetic agent.
'''Anemonin''' is a compound found in plants of the ] (Ranunculaceae). It is the ] product of the ] ]<ref name="Hager" /> and is easily ]d to a ].<ref name="TUGraz" />
]


== Biosynthetic origins ==
The substance is named for the plant genus '']'', where it was first identified.<ref name="ChemOrgVerb" /> ] and ] properties have been described.<ref name="w-online" />
{{multiple image |direction=vertical |align=left

|image1=Protoanemonina.svg |caption1=Protoanemonin
⚫ == References ==
|image2=Ranunculin skeletal.svg |caption2=Ranunculin
{{reflist|refs=
<ref name="Hager">{{cite book|editor1-first=PH|editor1-last=List|editor2-first=L|editor2-last=Hörhammer|title=Hagers Handbuch der pharmazeutischen Praxis|edition=4|publisher=Springer Verlag|year=1979|language=German|isbn=3-540-07738-3}}</ref>
<ref name="TUGraz">{{cite web|url=http://www.orgc.tugraz.at/hoegroup/naturst/Akt_2009_04_02.pdf|title=Aktuelles aus der Natur|publisher=]|language=German|page=4|date=2 April 2009|accessdate=27 November 2010}}</ref>
<ref name="druglead">{{cite web|url=http://www.druglead.com/chemical/Anemonin.html|publisher=DrugLead|title=Anemonin|accessdate=27 November 2010}}</ref>
<ref name="ChemOrgVerb">, Carl Löwig {{de icon}}</ref>
<ref name="w-online">, Wissenschaft online {{de icon}}</ref>
}} }}
Anemonin is a ] formed from two protoanemonin subunits. Protoanemonin is formed from the enzymatic cleavage of ] upon crushing plant matter.<ref name=":1"/> When a plant from this family is injured, a β-glucosidase cleaves ranunculin, liberating protoanemonin from glucose as a defense mechanism.<ref>{{cite journal |last1=Pirvu |first1=Lucia |last2=Stefaniu |first2=Amalia |last3=Neagu |first3=Georgeta |last4=Pintilie |first4=Lucia |date=2022-01-01 |title=Studies on Anemone nemorosa L. extracts; polyphenols profile, antioxidant activity, and effects on Caco-2 cells by in vitro and in silico studies |journal=Open Chemistry |language=en |volume=20 |issue=1 |pages=299–312 |doi=10.1515/chem-2022-0137 |doi-access=free |issn=2391-5420}}</ref> This butenolide readily dimerizes in aqueous media to form a single cyclodimer.<ref name=":1"/>


== Chemical structure and proposed mechanism of formation ==
⚫ ]
Despite multiple possibilities, ] of the solid anemonin has revealed that the two rings exclusively possess a ''trans'' relationship.<ref>{{cite journal |last1=Karle |first1=I. L. |last2=Karle |first2=J. |date=1966-04-10 |title=The crystal and molecular structure of anemonin, C10H8O4 |url=https://scripts.iucr.org/cgi-bin/paper?S0365110X66001233 |journal=Acta Crystallographica |language=en |volume=20 |issue=4 |pages=555–559 |doi=10.1107/S0365110X66001233 |bibcode=1966AcCry..20..555K |issn=0365-110X}}</ref> The central cyclobutane ring was found to be bent to a ] of 152°. ] reveals that the central ring is also twisted 9-11°.<ref>{{cite journal |last1=Lustig |first1=Ernest |last2=Moriarty |first2=Robert M. |date=July 1965 |title=The Estimation of the Angle of Twist for a Cyclobutane Derivative by Nuclear Magnetic Resonance |journal=Journal of the American Chemical Society |language=en |volume=87 |issue=14 |pages=3252–3253 |doi=10.1021/ja01092a048 |issn=0002-7863}}</ref>
⚫ ]


The highly selective formation of the head-to-head dimer has been rationalized through the stability of a proposed diradical intermediate; the resulting radicals after an initial carbon-carbon bond forming step are delocalized through the ] system.<ref name=":1" /> These proposed radicals could also be stabilized through the ], as they are situated between the enone and sp3-hybridized oxygen of the butenolides.


Destabilizing dipole-dipole interactions are proposed to disfavor the transition state where the two butenolide rings adopt a ''cis'' conformation, leading to selectivity of a ''trans'' relationship between the lactone rings.<ref name=":1" />
{{heterocyclic-stub}}


The formation of anemonin from protoanemonin is most likely a photochemical process. When Kataoka et. al compared the dimerization of protoanemonin in the presence and absence of radiation from a mercury lamp, they found a 75% yield with radiation and a very poor yield without radiation. It is not mentioned whether light was excluded from this control reaction; the low yield of anemonin may arise from visible light-mediated dimerization of protoanemonin.<ref>{{cite journal |last1=Kataoka |first1=Hiroshi |last2=Yamada |first2=Kazutoshi |last3=Sugiyama |first3=Noboru |date=November 1965 |title=The Photo-synthesis of Anemonin from Protoanemonin |journal=Bulletin of the Chemical Society of Japan |language=en |volume=38 |issue=11 |pages=2027 |doi=10.1246/bcsj.38.2027 |issn=0009-2673|doi-access=free }}</ref>
]

]
== Pharmaceutical potential ==
]
Anemonin possesses anti-inflammatory properties rather than the ] properties of its parent monomer. Numerous studies have demonstrated anemonin’s potential in treating ],<ref>{{cite journal | vauthors = Jiang L, Chi C, Yuan F, Lu M, Hu D, Wang L, Liu X | title = Anti-inflammatory effects of anemonin on acute ulcerative colitis via targeted regulation of protein kinase C-θ | journal = Chinese Medicine | volume = 17 | issue = 1 | pages = 39 | date = March 2022 | pmid = 35346284 | pmc = 8962473 | doi = 10.1186/s13020-022-00599-3 | doi-access = free }}</ref> ],<ref>{{cite journal | vauthors = Jia D, Han B, Yang S, Zhao J | title = Anemonin alleviates nerve injury after cerebral ischemia and reperfusion (i/r) in rats by improving antioxidant activities and inhibiting apoptosis pathway | journal = Journal of Molecular Neuroscience | volume = 53 | issue = 2 | pages = 271–279 | date = June 2014 | pmid = 24443273 | doi = 10.1007/s12031-013-0217-z | s2cid = 255492187 }}</ref> and ].<ref name=":2">{{cite journal | vauthors = Hou H, Peng Q, Wang S, Zhang Y, Cao J, Deng Y, Wang Y, Sun WC, Wang HB | display-authors = 6 | title = Anemonin Attenuates RANKL-Induced Osteoclastogenesis and Ameliorates LPS-Induced Inflammatory Bone Loss in Mice ''via'' Modulation of NFATc1 | journal = Frontiers in Pharmacology | volume = 10 | pages = 1696 | date = 2020 | pmid = 32116686 | doi = 10.3389/fphar.2019.01696 | pmc = 7025528 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Wang Z, Huang J, Zhou S, Luo F, Xu W, Wang Q, Tan Q, Chen L, Wang J, Chen H, Chen L, Xie Y, Du X | display-authors = 6 | title = Anemonin attenuates osteoarthritis progression through inhibiting the activation of IL-1β/NF-κB pathway | journal = Journal of Cellular and Molecular Medicine | volume = 21 | issue = 12 | pages = 3231–3243 | date = December 2017 | pmid = 28643466 | pmc = 5706500 | doi = 10.1111/jcmm.13227 }}</ref> Its activity against ]-related inflammation<ref name=":2" /><ref>{{cite journal | vauthors = Xiao K, Cao ST, Jiao LE, Lin FH, Wang L, Hu CH | title = Anemonin improves intestinal barrier restoration and influences TGF-β1 and EGFR signaling pathways in LPS-challenged piglets | journal = Innate Immunity | volume = 22 | issue = 5 | pages = 344–352 | date = July 2016 | pmid = 27189428 | doi = 10.1177/1753425916648223 | s2cid = 12372791 | doi-access = free }}</ref> and ] production<ref>{{cite journal | vauthors = Lee TH, Huang NK, Lai TC, Yang AT, Wang GJ | title = Anemonin, from Clematis crassifolia, potent and selective inducible nitric oxide synthase inhibitor | journal = Journal of Ethnopharmacology | volume = 116 | issue = 3 | pages = 518–527 | date = March 2008 | pmid = 18281171 | doi = 10.1016/j.jep.2007.12.019 }}</ref><ref name="Effect of anemonin on NO, ET-1 and"/> contribute to its pharmaceutical potential. Anemonin also displays inhibition of ] production in human ]s with mild cytotoxicity.<ref>{{cite journal | vauthors = Huang YH, Lee TH, Chan KJ, Hsu FL, Wu YC, Lee MH | title = Anemonin is a natural bioactive compound that can regulate tyrosinase-related proteins and mRNA in human melanocytes | journal = Journal of Dermatological Science | volume = 49 | issue = 2 | pages = 115–123 | date = February 2008 | pmid = 17766092 | doi = 10.1016/j.jdermsci.2007.07.008 }}</ref>
]

Given its skin permeability in ethanolic solutions<ref>{{cite journal | vauthors = Ning Y, Rao Y, Yu Z, Liang W, Li F | title = Skin permeation profile and anti-inflammatory effect of anemonin extracted from weilingxian | journal = Die Pharmazie | volume = 71 | issue = 3 | pages = 134–138 | date = March 2016 | pmid = 27183707 | url = https://pubmed.ncbi.nlm.nih.gov/27183707/ }}</ref> and its anti-inflammatory and anti-pigmentation properties, anemonin may be a good candidate for topical formulations as arthritis medications or cosmetics. An extraction method with the potential for industrial-scale preparations of anemonin may provide inroads to drug development.<ref>{{cite patent|number=CN101759706B|title=Method for manufacturing anemonin|gdate=2012-01-11|invent1=王琳|invent2=范淦彬|url=https://patents.google.com/patent/CN101759706B/en}}</ref>

⚫ == References ==
{{Reflist}}

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