Structure Database (LMSD)

Common Name
Bergamottin
Systematic Name
Synonyms
  • 5-Geranyloxypsoralen
LM ID
LMPK12160611
Formula
C21H22O4
Exact Mass
Calculate m/z
338.15181
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Other Flavonoids [PK1216]

Biological Context

Bergamottin is a furanocoumarin found in grapefruit juice and lemon, lime, and bergamot oils that has diverse biological activities.1 In vitro, bergamottin inhibits migration and invasion of HT-1080 fibrosarcoma cells at sub-cytotoxic concentrations via inhibition of matrix metalloproteinase-9 (MMP-9) expression.2 It shows antiproliferative activity against HepG2 liver, HL-60 leukemia, and BGC-823 gastric cancer cell lines in a dose-dependent manner and induces cell death of CHO cells following near ultraviolet irradiation.1,3 Bergamottin inhibits the cytochrome P450 isoform 3A4 (CYP3A4; Ki = 7.7 μM) and is a mixed inhibitor of simvastatin drug metabolism (Ki = 174 μM).4,5 It also increases glucose consumption in HepG2 cells in a dose-dependent manner.3

This information has been provided by Cayman Chemical

References

1. Ashwood-Smith, M.J., Ceska, O., Warrington, P.J., et al. The photobiological activity of 5-geranoxypsoralen and its photoproducts. Photochem. Photobiol. 55(4), 529-532 (1992).
1. Ashwood-Smith, M.J., Ceska, O., Warrington, P.J., et al. The photobiological activity of 5-geranoxypsoralen and its photoproducts. Photochem. Photobiol. 55(4), 529-532 (1992).
2. Hwang, Y.P., Yun, H.J., Choi, J.H., et al. Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expression. Mol. Nutr. Food Res. 54(7), 977-990 (2010).
2. Hwang, Y.P., Yun, H.J., Choi, J.H., et al. Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expression. Mol. Nutr. Food Res. 54(7), 977-990 (2010).
3. Liu, Y., Ren, C., Cao, Y., et al. Characterization and purification of bergamottin from Citrus grandis (L.) Osbeck cv. Yongjiazaoxiangyou and its antiproliferative activity and effect on glucose consumption in HepG2 cells. Molecules 22(7), (2017).
3. Liu, Y., Ren, C., Cao, Y., et al. Characterization and purification of bergamottin from Citrus grandis (L.) Osbeck cv. Yongjiazaoxiangyou and its antiproliferative activity and effect on glucose consumption in HepG2 cells. Molecules 22(7), (2017).
4. He, K., Iyer, K.R., Hayes, R.N., et al. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 11(4), 252-259 (1998).
4. He, K., Iyer, K.R., Hayes, R.N., et al. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 11(4), 252-259 (1998).
5. Le Goff-Klein, N., Koffel, J.C., Jung, L., et al. In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice. Eur. J. Pharm. Sci. 18(1), 31-35 (2003).
5. Le Goff-Klein, N., Koffel, J.C., Jung, L., et al. In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice. Eur. J. Pharm. Sci. 18(1), 31-35 (2003).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Citrus bergamia (#380129)
Magnoliopsida (#3398)
Uber Bergamottin und über die Auffindung von Limettin im Bergamottol (XXXIV. Mitteil. uber naturliche Cumarine),
Ber, 1937

String Representations

InChiKey (Click to copy)
DBMJZOMNXBSRED-OQLLNIDSSA-N
InChi (Click to copy)
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
SMILES (Click to copy)
C1(OC/C=C(/CC/C=C(\C)/C)\C)=C2C(OC(=O)C=C2)=CC2=C1C=CO2

Other Databases

Wikipedia
Bergamottin
CHEBI ID
70476
PubChem CID
5471349
Cayman ID
10009439
PDB ID
HJJ

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 3
Aromatic Rings 3
Rotatable Bonds 6
Van der Waals Molecular Volume 316.12
Topological Polar Surface Area 52.58
Hydrogen Bond Donors
Hydrogen Bond Acceptors 4
logP 6.80
Molar Refractivity 100.77

Admin

Created at
22nd Aug 2024
Updated at
23rd Aug 2024