Quodlibet Naturopathics

Apigenin


Apigenin (4’,5,7-trihydroxyflavone) is a flavone that is the aglycone of several glycosides. It is a yellow crystalline solid that has been used to dye wool. Apigenin may contribute to the chemopreventive action of vegetables and fruits.[2] It was recently shown that apigenin induces a process called autophagia (a kind of cellular dormancy) that may well explain its chemopreventive properties, but at the same time it induces resistance against chemotherapy.[3] Apigenin is a potent inhibitor of CYP2C9,[4] an enzyme responsible for the metabolism of many pharmaceutical drugs in the body.

Apigenin has been shown to reverse the adverse effects of cyclosporin. Research has been conducted to study the effects of apigenin on reversal of cyclosporin-induced damage, and this was assessed by immunohistochemical estimation of expression of bcl-2, and estimation of apoptosis in histopathological sections.[5] Cyclosporine A enhances the expression of transforming growth factor-β in the rat kidney, which signifies accelerated apoptosis. Therefore, transforming growth factor-β and apoptotic index may be used to assess apigenin and its effect on cyclosporine A-induced renal damage.[6]

Apigenin acts as a monoamine transporter activator, one of the few chemicals demonstrated to possess this property.[7] Apigenin is a ligand for central benzodiazepine receptors that competitively inhibited the binding of flunitrazepam with a Ki of 4μM, exerting anxiolytic and slight sedative effects.[8]

Glycosides, formed by the derivatization of apigenin with sugars, include:

  1. Merck Index, 11th Edition, 763.
  2. CV Ferreira, GZ Gusto, AC Sousa, KC Queiroz, WF Zambuzzi, H Aoyama, MP Peppelenbosch (2006). "Natural compounds as a source of protein phosphatase inhibitors; application to the rational design of small-molecule derivatives.". Biochemie 88 (12): 1859–73. doi:10.1016/j.biochi.2006.08.007. PMID 17010496.
  3. RR Ruela-de-Sousa, GM Fuhler, N Blom, CV Ferreira, H Aoyama, MP Peppelenbosch (2010). "Cytotoxicity of apigenin on leukemia cell lines: implications for prevention and therapy". Cell Death and Disease 1 (e19): 1–11. doi:10.1038/cddis.2009.18. PMC 3032507. PMID 21364620.
  4. Si Dayong, Wang Y, Zhou Y-H, Guo Y, Wang J, Zhou H, Li Z-S, Fawcett JP (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metabolism and Disposition 37 (3): 629–634. doi:10.1124/dmd.108.023416. PMID 19074529.
  5. Srikumar Chakravarthi, Chong Fu Wen, HS Nagaraja (2009). "Apoptosis and expression of bcl-2 in cyclosporin induced renal damage and its reversal by beneficial effects of 4,5,7 - Trihydroxyflavone". Journal of Analytical Bio Science 32 (4): 320–327.
  6. Chong FW, Srikumar Chakravarthi, HS Nagaraja, PM Thanikachalam, Nagarajah Lee (2009). "Expression of Transforming Growth factor-β and determination of Apoptotic Index in histopathological sections for assessment of the effects of Apigenin (4',5',7'- trihydroxyflavone) on Cyclosporine A induced renal damage". Malaysian Journal of Pathology 31 (1): 35–43. PMID 19694312.
  7. Zhao, G; Qin, GW; Wang, J; Chu, WJ; Guo, LH (2010). "Functional activation of monoamine transporters by luteolin and apigenin isolated from the fruit of Perilla frutescens (L.) Britt". Neurochemistry international 56 (1): 168–76. doi:10.1016/j.neuint.2009.09.015. PMID 19815045.
  8. Viola H, Wasowski C, Levi de Stein M, Wolfman C, Silveira R, Dajas F, Medina JH, Paladini AC."Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects."



Apigenin may relate to these other naturopathic agents:


Apigenin is linked to these entities, through the following networks:

CASP3 CASP7 HIF1A MUC1 ODC ODC1 PROTEASOME


Apigenin references used by Quodlibet:
  1. Emerging glycolysis targeting and drug discovery from chinese medicine in cancer therapy.

    Evid Based Complement Alternat Med    2012;2012:873175


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KEGG COMPOUND: C01477
Entry
C01477                      Compound                               

Name
Apigenin;
4',5,7-Trihydroxyflavone;
5,7,4'-Trihydroxyflavone
Formula
C15H10O5
Exact mass
270.0528
Mol weight
270.2369
Structure
Mol fileKCF fileDB searchJmolKegDraw
Reaction
Enzyme
1.14.11.22      1.14.13.21      1.14.13.88      2.1.1.75        
2.4.1.81
Brite
Lipids [BR:br08002]
 PK  Polyketides
  PK12 Flavonoids
   PK1211 Flavones and Flavonols
    C01477  Apigenin
Phytochemical compounds [BR:br08003]
 Flavonoids
  Flavonoids
   Flavones
    C01477  Apigenin
BRITE hierarchy
Other DBs
CAS: 
520-36-5
PubChem: 
ChEBI: 
ChEMBL: 
LIPIDMAPS: 
KNApSAcK: 
PDB-CCD: 
3DMET: 
NIKKAJI: 
KCF data Show

ATOM        20
            1   C8y C    23.7905  -16.7751
            2   C8y C    23.7728  -15.3710
            3   C8y C    24.9031  -17.5151
            4   C8y C    22.4911  -17.4276
            5   O2x O    25.0138  -14.7185
            6   C8x C    22.5961  -14.6253
            7   C8x C    26.2141  -16.8683
            8   O5x O    24.9208  -18.9133
            9   C8x C    21.3785  -16.6877
            10  O1a O    22.4445  -18.8258
            11  C8y C    26.2024  -15.4701
            12  C8y C    21.3551  -15.2894
            13  C8y C    27.5132  -14.8118
            14  O1a O    20.1667  -14.5437
            15  C8x C    27.4898  -13.4135
            16  C8x C    28.6318  -15.5574
            17  C8x C    28.7308  -12.7551
            18  C8x C    29.8668  -14.8932
            19  C8y C    29.9135  -13.4951
            20  O1a O    31.1487  -12.8425
BOND        22
            1     1   2 1
            2     1   3 1
            3     1   4 2
            4     2   5 1
            5     2   6 2
            6     3   7 1
            7     3   8 2
            8     4   9 1
            9     4  10 1
            10    5  11 1
            11    6  12 1
            12   11  13 1
            13   12  14 1
            14   13  15 2
            15   13  16 1
            16   15  17 1
            17   16  18 2
            18   17  19 2
            19   19  20 1
            20    7  11 2
            21    9  12 2
            22   18  19 1

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