Azadiradione

Last updated
Azadiradione
Azadiradione.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
MeSH azadiradione
PubChem CID
  • 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
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).

Azadiradione is a naturally occurring compound found in several plants, most notably the neem tree ( Azadirachta indica ). It is a tetracyclic triterpenoid.

Contents

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. [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

  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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.