Azadiradione
Chemical compound
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
ChEBI
ChEMBL
ChemSpider
MeSH
azadiradione
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
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
C 28 H 34 O 5
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).
Chemical compound
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 .