Azadiradione
{{Short description|Chemical compound}}
{{chembox
| Name = Azadiradione
| ImageFile = Azadiradione.svg
| ImageSize = 250px
| OtherNames = 24-Norchola-1,14,20,22-tetraene-3,16-dione, 7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,17alpha)-
| IUPACName = [(5R,7R,8R,9R,10R,13S,17R)-17-(Furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
| Section1 = {{Chembox Identifiers
| 3DMet =
| Abbreviations =
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| CASNo = 26241-51-0
| CASNo_Ref = {{Cascite|correct|ChemSpider}}
| ChEBI = 67280
| ChEMBL = 1215754
| ChemSpiderID = 25044638
| EINECS =
| EC_number =
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| Gmelin =
| StdInChI = 1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24-,26-,27-,28-/m1/s1
| StdInChIKey = KWAMDQVQFVBEAU-HMWIRDDCSA-N
| KEGG =
| MeSHName = azadiradione
| PubChem = 12308714
| RTECS =
| SMILES = CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1(C4=CC(=O)[C@H]([C@@]4(CC3)C)C5=COC=C5)C)C
| UNNumber =
}}
| Section2 = {{Chembox Properties
| Appearance =
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| Density = 1.2±0.1 g/cm3
| C = 28 | H = 34 | O = 5
| MeltingPt =
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| VaporPressure = 0.0±1.5 mmHg
}}
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Azadiradione is a naturally occurring compound found in several plants, most notably the neem tree (Azadirachta indica). It is a tetracyclic triterpenoid.
Sources
Azadiradione is the principal active ingredient in neem oil, which is extracted from the seeds of the neem tree. Smaller quantities of azadiradione can also be found in other plants like Cedrela odorata (Spanish cedar), Chisocheton spp., Xylocarpus granatum (cannonball mangrove) and Azalea indica (common azalea).
Applications
Azadiradione acts as an antioxidant and has been used in traditional medicine in Asia, Africa and the Middle East for ages.{{Cite journal |last1=Sakib |first1=Raiyan |last2=Caruso |first2=Francesco |last3=Belli |first3=Stuart |last4=Rossi |first4=Miriam |date=2023-11-18 |title=Azadiradione, a Component of Neem Oil, Behaves as a Superoxide Dismutase Mimic When Scavenging the Superoxide Radical, as Shown Using DFT and Hydrodynamic Voltammetry |journal=Biomedicines |volume=11 |issue=11 |pages=3091 |doi=10.3390/biomedicines11113091 |doi-access=free |issn=2227-9059 |pmid=38002091|pmc=10669394 }}
Research suggests azadiradione may have properties that fight microbes (bacteria, fungi, viruses),{{Cite journal |last1=Amankwa |first1=Charles E. |last2=Kodati |first2=Bindu |last3=Donkor |first3=Nina |last4=Acharya |first4=Suchismita |date=2023 |title=Therapeutic Potential of Antioxidants and Hybrid TEMPOL Derivatives in Ocular Neurodegenerative Diseases: A Glimpse into the Future |journal=Biomedicines |language=en |volume=11 |issue=11 |pages=2959 |doi=10.3390/biomedicines11112959 |issn=2227-9059 |doi-access=free|pmid=38001960 |pmc=10669210 }} reduce inflammation, protect cells from damage,{{Cite journal |last1=Priya |first1=P. Snega |last2=Kumar |first2=Rajendran Saravana |last3=Gawwad |first3=Mohamed Ragab Abdel |last4=Alarjani |first4=Khaloud Mohammed |last5=Elshikhe |first5=Mohamed S |last6=Namasivayam |first6=S. Karthick Raja |last7=Arockiaraj |first7=Jesu |date=2023-07-01 |title=Azadiradione (AZD) neem biomass derived limonoid: extraction, characterization, and potential biological activities with special reference to anti-microbial and anti-cancer activities |url=https://www.sciencedirect.com/science/article/pii/S0254629923002995 |journal=South African Journal of Botany |volume=158 |pages=405–416 |doi=10.1016/j.sajb.2023.05.042 |issn=0254-6299|url-access=subscription }} and even have anti-cancer effects.{{Cite journal |last1=Patel |first1=Shradha M. |last2=Nagulapalli Venkata |first2=Kalyan C. |last3=Bhattacharyya |first3=Piyali |last4=Sethi |first4=Gautam |last5=Bishayee |first5=Anupam |date=2016 |title=Potential of neem (Azadirachta indica L.) for prevention and treatment of oncologic diseases |url=https://pubmed.ncbi.nlm.nih.gov/27019417/ |journal=Seminars in Cancer Biology |volume=40-41 |pages=100–115 |doi=10.1016/j.semcancer.2016.03.002 |issn=1096-3650 |pmid=27019417}}{{Cite journal |last1=Setzer |first1=W. N. |last2=Setzer |first2=M. C. |date=2003 |title=Plant-derived triterpenoids as potential antineoplastic agents |url=https://pubmed.ncbi.nlm.nih.gov/12871157/ |journal=Mini Reviews in Medicinal Chemistry |volume=3 |issue=6 |pages=540–556 |doi=10.2174/1389557033487854 |issn=1389-5575 |pmid=12871157}}{{Cite journal |last1=Subapriya |first1=R. |last2=Nagini |first2=S. |date=2005 |title=Medicinal properties of neem leaves: a review |url=https://pubmed.ncbi.nlm.nih.gov/15777222/ |journal=Current Medicinal Chemistry. Anti-Cancer Agents |volume=5 |issue=2 |pages=149–146 |doi=10.2174/1568011053174828 |issn=1568-0118 |pmid=15777222}}{{Cite journal |last1=Biswas |first1=Kausik |last2=Chattopadhyay |first2=Ishita |last3=Banerjee |first3=Ranajit K. |last4=Bandyopadhyay |first4=Uday |date=2002 |title=Biological activities and medicinal properties of neem (Azadirachta indica) |url=https://www.jstor.org/stable/24106000 |journal=Current Science |volume=82 |issue=11 |pages=1336–1345 |jstor=24106000 |issn=0011-3891}}
Azadiradione may also act as a natural pesticide, potentially controlling some insects and pests.{{Cite journal |last1=Lin |first1=Meihong |last2=Yang |first2=Sifan |last3=Huang |first3=Jiguang |last4=Zhou |first4=Lijuan |date=2021-12-09 |title=Insecticidal Triterpenes in Meliaceae: Plant Species, Molecules and Activities: Part Ⅰ (Aphanamixis-Chukrasia) |journal=International Journal of Molecular Sciences |volume=22 |issue=24 |pages=13262 |doi=10.3390/ijms222413262 |issn=1422-0067 |pmc=8704831 |pmid=34948062 |doi-access=free}}