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Record Information
Version2.0
Created at2022-09-12 09:47:55 UTC
Updated at2022-09-12 09:47:55 UTC
NP-MRD IDNP0327320
Secondary Accession NumbersNone
Natural Product Identification
Common Namediosmine
DescriptionDiosmin, also known as barosmin or daflon, belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. This leads to a reduction in the release of inflammatory mediators, principally oxygen free radicals and prostaglandins (PGE2, PGF2a). Diosmin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Diosmin is found, on average, in the highest concentration within a few different foods, such as hyssops, peppermints, and lemons. Diosmin has also been detected, but not quantified in, several different foods, such as green vegetables, mandarin orange (clementine, tangerine), rosemaries, spearmints, and sweet oranges. This could make diosmin a potential biomarker for the consumption of these foods. The enhanced version of diosmin, Vasculera, is sold as a medical food product. Furthermore, diosmin with hesperidine decreases the diameter of lymphatic capillaries and the intralymphatic pressure. It is also speculated that diosmin might have potential in the treatment of neurodegenerative diseases, such as Alzheimer's disease, and its anti-inflammatory and anti-apoptotic activity has been demonstrated in neuronal cells, in vitro. It is an oral phlebotropic drug used in the treatment of venous disease, i.E., Chronic venous insufficiency (CVI) including spider and varicose veins, leg swelling (edema), stasis dermatitis and venous ulcers. diosmine is found in Abies nephrolepis, Citrus limon, Helichrysum arenarium, Hyssopus officinalis, Linaria macroura, Lomelosia caucasica, Meehania urticifolia, Mentha piperita, Mentha spicata, Scutellaria baicalensis and Sechium edule. diosmine was first documented in 2011 (PMID: 21477647). ,However, diosmin products have been used in Europe for over 40 years with no safety issues.
Structure
Thumb
Synonyms
ValueSource
5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinosideHMDB
BarosminHMDB
DaflonHMDB
Diosmetin 7-O-rutinosideHMDB
Diosmetin 7-rutinosideHMDB
Diosmetin-7-O-rutinosideHMDB
DiosmilHMDB
Diosmin, ban, innHMDB
DiosmineHMDB
DiosminumHMDB
DiovenorHMDB
FlebostenHMDB
Luteolin 4'-methyl ether 7-rutinosideHMDB
RiovenHMDB
SalinigricoflavonolosideHMDB
ToveneHMDB
Ven-detrexHMDB
Veno-VHMDB
VenosmineHMDB
Chemical FormulaC28H32O15
Average Mass608.5447 Da
Monoisotopic Mass608.17412 Da
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one
Traditional Namediosmine
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(OC1OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C1O)C=C2O
InChI Identifier
InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3
InChI KeyGZSOSUNBTXMUFQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies nephrolepisLOTUS Database
Citrus limonLOTUS Database
Helichrysum arenariumLOTUS Database
Hyssopus officinalis L.LOTUS Database
Linaria macrouraLOTUS Database
Lomelosia caucasicaLOTUS Database
Meehania urticifoliaLOTUS Database
Mentha piperitaLOTUS Database
Mentha spicataLOTUS Database
Scutellaria baicalensisLOTUS Database
Sechium eduleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.08ALOGPS
logP-0.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.39 m³·mol⁻¹ChemAxon
Polarizability59.9 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0029548
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000693
KNApSAcK IDC00004362
Chemspider ID4510141
KEGG Compound IDC10039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiosmin
METLIN IDNot Available
PubChem Compound5353588
PDB IDNot Available
ChEBI ID1188022
Good Scents IDNot Available
References
General References
  1. Dholakiya SL, Benzeroual KE: Protective effect of diosmin on LPS-induced apoptosis in PC12 cells and inhibition of TNF-alpha expression. Toxicol In Vitro. 2011 Aug;25(5):1039-44. doi: 10.1016/j.tiv.2011.04.003. Epub 2011 Apr 6. [PubMed:21477647 ]
  2. LOTUS database [Link]