Azadiradione

Azadiradione
Names
	IUPAC name [(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
	Other names 24-Norchola-1,14,20,22-tetraene-3,16-dione, 7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,17alpha)-
Identifiers
CAS Number	26241-51-0 [ChemSpider];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67280;
ChEMBL	ChEMBL1215754;
ChemSpider	25044638;
MeSH	azadiradione
PubChem CID	12308714;
CompTox Dashboard (EPA)	DTXSID40949106 ;
	InChI InChI=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 Key: KWAMDQVQFVBEAU-HMWIRDDCSA-N;
	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;
Properties
Chemical formula	C28H34O5
Molar mass	450.575 g·mol−1
Density	1.2±0.1 g/cm3
Vapor pressure	0.0±1.5 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 siamensis, 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.^[1]

Research suggests azadiradione may have properties that fight microbes (bacteria, fungi, viruses),^[2] reduce inflammation, protect cells from damage,^[3] and even have anti-cancer effects.^[4]^[5]^[6]^[7]

Azadiradione may also act as a natural pesticide, potentially controlling some insects and pests.^[8]

References

^ Sakib, Raiyan; Caruso, Francesco; Belli, Stuart; Rossi, Miriam (2023-11-18). "Azadiradione, a Component of Neem Oil, Behaves as a Superoxide Dismutase Mimic When Scavenging the Superoxide Radical, as Shown Using DFT and Hydrodynamic Voltammetry". Biomedicines. 11 (11): 3091. doi:10.3390/biomedicines11113091. ISSN 2227-9059. PMC 10669394. PMID 38002091.
^ Amankwa, Charles E.; Kodati, Bindu; Donkor, Nina; Acharya, Suchismita (2023). "Therapeutic Potential of Antioxidants and Hybrid TEMPOL Derivatives in Ocular Neurodegenerative Diseases: A Glimpse into the Future". Biomedicines. 11 (11): 2959. doi:10.3390/biomedicines11112959. ISSN 2227-9059. PMC 10669210. PMID 38001960.
^ Priya, P. Snega; Kumar, Rajendran Saravana; Gawwad, Mohamed Ragab Abdel; Alarjani, Khaloud Mohammed; Elshikhe, Mohamed S; Namasivayam, S. Karthick Raja; Arockiaraj, Jesu (2023-07-01). "Azadiradione (AZD) neem biomass derived limonoid: extraction, characterization, and potential biological activities with special reference to anti-microbial and anti-cancer activities". South African Journal of Botany. 158: 405–416. doi:10.1016/j.sajb.2023.05.042. ISSN 0254-6299.
^ Patel, Shradha M.; Nagulapalli Venkata, Kalyan C.; Bhattacharyya, Piyali; Sethi, Gautam; Bishayee, Anupam (2016). "Potential of neem (Azadirachta indica L.) for prevention and treatment of oncologic diseases". Seminars in Cancer Biology. 40–41: 100–115. doi:10.1016/j.semcancer.2016.03.002. ISSN 1096-3650. PMID 27019417.
^ Setzer, W. N.; Setzer, M. C. (2003). "Plant-derived triterpenoids as potential antineoplastic agents". Mini Reviews in Medicinal Chemistry. 3 (6): 540–556. doi:10.2174/1389557033487854. ISSN 1389-5575. PMID 12871157.
^ Subapriya, R.; Nagini, S. (2005). "Medicinal properties of neem leaves: a review". Current Medicinal Chemistry. Anti-Cancer Agents. 5 (2): 149–146. doi:10.2174/1568011053174828. ISSN 1568-0118. PMID 15777222.
^ Biswas, Kausik; Chattopadhyay, Ishita; Banerjee, Ranajit K.; Bandyopadhyay, Uday (2002). "Biological activities and medicinal properties of neem (Azadirachta indica)". Current Science. 82 (11): 1336–1345. ISSN 0011-3891. JSTOR 24106000.
^ Lin, Meihong; Yang, Sifan; Huang, Jiguang; Zhou, Lijuan (2021-12-09). "Insecticidal Triterpenes in Meliaceae: Plant Species, Molecules and Activities: Part Ⅰ (Aphanamixis-Chukrasia)". International Journal of Molecular Sciences. 22 (24): 13262. doi:10.3390/ijms222413262. ISSN 1422-0067. PMC 8704831. PMID 34948062.

[1] Sakib, Raiyan; Caruso, Francesco; Belli, Stuart; Rossi, Miriam (2023-11-18). "Azadiradione, a Component of Neem Oil, Behaves as a Superoxide Dismutase Mimic When Scavenging the Superoxide Radical, as Shown Using DFT and Hydrodynamic Voltammetry". Biomedicines. 11 (11): 3091. doi:10.3390/biomedicines11113091. ISSN 2227-9059. PMC 10669394. PMID 38002091.

[2] Amankwa, Charles E.; Kodati, Bindu; Donkor, Nina; Acharya, Suchismita (2023). "Therapeutic Potential of Antioxidants and Hybrid TEMPOL Derivatives in Ocular Neurodegenerative Diseases: A Glimpse into the Future". Biomedicines. 11 (11): 2959. doi:10.3390/biomedicines11112959. ISSN 2227-9059. PMC 10669210. PMID 38001960.

[3] Priya, P. Snega; Kumar, Rajendran Saravana; Gawwad, Mohamed Ragab Abdel; Alarjani, Khaloud Mohammed; Elshikhe, Mohamed S; Namasivayam, S. Karthick Raja; Arockiaraj, Jesu (2023-07-01). "Azadiradione (AZD) neem biomass derived limonoid: extraction, characterization, and potential biological activities with special reference to anti-microbial and anti-cancer activities". South African Journal of Botany. 158: 405–416. doi:10.1016/j.sajb.2023.05.042. ISSN 0254-6299.

[4] Patel, Shradha M.; Nagulapalli Venkata, Kalyan C.; Bhattacharyya, Piyali; Sethi, Gautam; Bishayee, Anupam (2016). "Potential of neem (Azadirachta indica L.) for prevention and treatment of oncologic diseases". Seminars in Cancer Biology. 40–41: 100–115. doi:10.1016/j.semcancer.2016.03.002. ISSN 1096-3650. PMID 27019417.

[5] Setzer, W. N.; Setzer, M. C. (2003). "Plant-derived triterpenoids as potential antineoplastic agents". Mini Reviews in Medicinal Chemistry. 3 (6): 540–556. doi:10.2174/1389557033487854. ISSN 1389-5575. PMID 12871157.

[6] Subapriya, R.; Nagini, S. (2005). "Medicinal properties of neem leaves: a review". Current Medicinal Chemistry. Anti-Cancer Agents. 5 (2): 149–146. doi:10.2174/1568011053174828. ISSN 1568-0118. PMID 15777222.

[7] Biswas, Kausik; Chattopadhyay, Ishita; Banerjee, Ranajit K.; Bandyopadhyay, Uday (2002). "Biological activities and medicinal properties of neem (Azadirachta indica)". Current Science. 82 (11): 1336–1345. ISSN 0011-3891. JSTOR 24106000.

[8] Lin, Meihong; Yang, Sifan; Huang, Jiguang; Zhou, Lijuan (2021-12-09). "Insecticidal Triterpenes in Meliaceae: Plant Species, Molecules and Activities: Part Ⅰ (Aphanamixis-Chukrasia)". International Journal of Molecular Sciences. 22 (24): 13262. doi:10.3390/ijms222413262. ISSN 1422-0067. PMC 8704831. PMID 34948062.

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