2753-30-2 Usage
Uses
1. Used in Anticancer Applications:
Gedunin is used as an anticancer agent for targeting various cancer cell lines, including breast, pancreatic, and colon cancer. It inhibits Hsp90 expression and induces apoptosis by targeting the sonic hedgehog pathway and other client proteins.
2. Used in Antimalarial Applications:
Gedunin is used as an antimalarial agent, displaying activity against Plasmodium falciparum, the parasite responsible for malaria.
3. Used in Anti-inflammatory Applications:
Gedunin is used as an anti-inflammatory agent, reducing edema formation, inflammatory cytokine production, and the accumulation of eosinophils and activated T lymphocytes in mouse models of inflammation.
4. Used in Drug Delivery Systems:
Gedunin can be potentially incorporated into drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes in various applications, including cancer treatment and inflammation management.
5. Used in Pharmaceutical Industry:
Gedunin is used as a research compound for studying the mechanisms of Hsp90 inhibition, apoptosis induction, and its potential applications in the development of novel therapeutics for cancer and inflammatory diseases.
6. Used in Natural Products Research:
Gedunin serves as a model compound for understanding the bioactive properties of natural products derived from plants, such as Azadirachta indica and Cedrela odorata, and their potential applications in medicine and pharmacology.
Biological Activity
Naturally occurring Hsp90 inhibitor. Induces Hsp90-dependent client protein degradation and displays antiproliferative activity in vitro (IC 50 values are 3.22, 8.84 and 16.8 μ M in SKBr3, MCF-7 and CaCo-2 cancer cell lines respectively). Also exhibits antimalarial activity against P. falciparum (IC 50 values are 0.14 and 3.1 μ M in parasite development and [ 3 H]-hypoxanthine uptake assays respectively).
in vitro
gedunin induces degradation of hsp90-dependent client protein and displays anti-proliferative activity in skbr3, caco-2 and mcf-7 cancer cell lines with ic50 of 3.22, 16.8 and 8.84 μm respectively1.
references
1. uddin sj, nahar l, shilpi ja, et al. gedunin, a limonoid from xylocarpus granatum, inhibits the growth of caco-2 colon cancer cell line in vitro. phytotherapy research : ptr. 2007;21(8):757-761.2. lee se, kim mr, kim jh, et al. antimalarial activity of anthothecol derived from khaya anthotheca (meliaceae). phytomedicine : international journal of phytotherapy and phytopharmacology. 2008;15(6-7):533-535.3. conte fp, ferraris fk, costa te, et al. effect of gedunin on acute articular inflammation and hypernociception in mice. molecules. 2015;20(2):2636-2657.
Check Digit Verification of cas no
The CAS Registry Mumber 2753-30-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,5 and 3 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2753-30:
(6*2)+(5*7)+(4*5)+(3*3)+(2*3)+(1*0)=82
82 % 10 = 2
So 2753-30-2 is a valid CAS Registry Number.
InChI:InChI=1/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21?,22-,25-,26+,27+,28-/m1/s1
2753-30-2Relevant academic research and scientific papers
Biocatalysis: Fungi mediated novel and selective 12β- or 17β-hydroxylation on the basic limonoid skeleton
Haldar, Saikat,Kolet, Swati P.,Thulasiram, Hirekodathakallu V.
supporting information, p. 1311 - 1317 (2013/06/27)
Basic limonoids carrying a 4,4,8-trimethyl-17-furanylsteroid skeleton are a class of triterpenoids and well-known for their insecticidal as well as a vast array of pharmacological activities. Rare and synthetically challenging 12β- and 17β-hydroxylation was achieved on the basic limonoid skeleton to produce a novel series of hydroxylated limonoids using fungi-mediated biocatalysis. The fungal system belonging to the genera of Mucor efficiently converted azadiradione, epoxyazadiradione, gedunin and their derivatives into corresponding 12β- and/or 17β-hydroxy derivatives. The position and stereochemistry of hydroxylation was determined by rigorous spectroscopic and crystallographic studies. This fungi-mediated stereo- and regio-selective hydroxylation process was highly efficient and mild enough to sustain chemically sensitive functional groups around the basic limonoid skeleton. Modifications of specific functional groups and variation in biocatalyst were shown to bring selectivity among 12β- or 17β-hydroxylation.
The Synthesis of a 1α,2α,3α-Triacetoxy Limonoid
Kehrli, Anne R. H.,Taylor, David A. H.,Niven, Margaret
, p. 2057 - 2065 (2007/10/02)
The report that Meerwein-Ponndorf reduction of gedunin (1a) gives 3α-hydroxy-3-deoxogedunin (2a) is wrong; the product is the 3β-epimer (2b). 3α-Acetoxy-7-deacetoxy-3-deoxo-7-oxgedunin (3c) was prepared by a stereospecific synthesis from cedrolide (1b), 7-deacetoxy-7-oxogedunin; osmium tetroxide oxidation then gave the 1,2α-glycol, isolated as the acetate (4a).Similarly, oxidation of the 3β-alcohol (3b) also gave the α-oriented glycol, as anticipated from the steric hindrance of the β-face of the molecule.Oxidation of the allylic alcohols (2b) or (3b), or of the allylic acetate (2d) with perbenzoic acid also takes place from the α-face of the molecule, giving the corresponding α-oxides (5a-c).The oxidation is pH sensitive; with a benzoate buffer the 7-oxo group in alcohol (3b) undergoes Baeyer-Villiger oxidation, giving the ε-lactone isolated as the acetate (6a).Opening of the oxide ring in the 3β,7α-diacetoxy oxide (5c) is complex.Identification of the products shows that the reaction involves participation by both the acetate groups.In contrast the 3β-acetoxy-7-oxo compound (5d) and the ε-lactone (6a) give the products of ring opening with assistance from the neighbouring acetate group, while the 3β-hydroxy compound (5b) gives the simple bromohydrin.
A New Limonoid Glycoside from the Stem Bark of Melia azedarach Linn.
Saxena, Meera,Srivastava, Santosh K.
, p. 1087 - 1088 (2007/10/02)
Chemical and spectral evidences are presented for characterizing a new limonoid glycoside as 7α-acetoxy-14β,15β-epoxy-gedunan-1-ene-3-O-β-D-glucopyranoside (I) isolated from the stem bark of Melia azedarach Linn.
