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Showing NP-Card for Kaempferol 3-O-beta-D-galactopyranoside (NP0338365)

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Record Information
Version2.0
Created at2024-09-11 15:05:38 UTC
Updated at2024-09-11 15:05:38 UTC
NP-MRD IDNP0338365
Secondary Accession NumbersNone
Natural Product Identification
Common NameKaempferol 3-O-beta-D-galactopyranoside
DescriptionKaempferol 3-O-beta-D-galactopyranoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-O-beta-D-galactopyranoside was first documented in 2007 (PMID: 18081103). Based on a literature review a significant number of articles have been published on Kaempferol 3-O-beta-D-galactopyranoside (PMID: 25935545) (PMID: 20600691) (PMID: 38695332) (PMID: 26382913) (PMID: 21954556) (PMID: 21834640).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)


  Mrv2104 05262317372D          

 32 35  0  0  0  0            999 V2000
 9999.6268 9999.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.054210000.5272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4842 9997.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1982 9997.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6268 9999.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6248 9997.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0542 9996.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.198210003.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2013 9999.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.771710002.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.201910002.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.487410001.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.487410000.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.201810000.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.484310003.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.769910003.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055410003.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055410002.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.769810001.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.484310002.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627710002.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913410001.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913410000.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627710000.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.342110000.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.342110001.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0549 9999.0948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3404 9998.6823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3404 9997.8572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0549 9997.4448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7694 9997.8572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7694 9998.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 26 25  2  0  0  0  0
 26 18  1  0  0  0  0
 22 11  2  0  0  0  0
 14 23  2  0  0  0  0
  1 24  2  0  0  0  0
 25  2  1  0  0  0  0
 15  8  1  0  0  0  0
 12 10  1  0  0  0  0
 14  9  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
 31 32  1  0  0  0  0
 27  2  1  6  0  0  0
 31  3  1  6  0  0  0
 30  7  1  6  0  0  0
 29  6  1  6  0  0  0
 28  5  1  1  0  0  0
M  END
Download

3D MOL for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)

Download
3D SDF for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)

  Mrv2104 05262317372D          

 32 35  0  0  0  0            999 V2000
 9999.6268 9999.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.054210000.5272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4842 9997.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1982 9997.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6268 9999.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6248 9997.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0542 9996.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.198210003.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2013 9999.6980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.771710002.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.201910002.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.487410001.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.487410000.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.201810000.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.484310003.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.769910003.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055410003.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055410002.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.769810001.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.484310002.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627710002.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913410001.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913410000.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627710000.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.342110000.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.342110001.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0549 9999.0948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3404 9998.6823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3404 9997.8572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0549 9997.4448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7694 9997.8572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7694 9998.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 26 25  2  0  0  0  0
 26 18  1  0  0  0  0
 22 11  2  0  0  0  0
 14 23  2  0  0  0  0
  1 24  2  0  0  0  0
 25  2  1  0  0  0  0
 15  8  1  0  0  0  0
 12 10  1  0  0  0  0
 14  9  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
 31 32  1  0  0  0  0
 27  2  1  6  0  0  0
 31  3  1  6  0  0  0
 30  7  1  6  0  0  0
 29  6  1  6  0  0  0
 28  5  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0338365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21+/s2

> <INCHI_KEY>
JPUKWEQWGBDDQB-AISPFLNMNA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.49898866066892

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <JCHEM_LOGP>
0.15873002566666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.869704355311086

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3723484229657545

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98109237118166

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
107.29459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
trifolin

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)
Download
PDB for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0    8665.9708666.103   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.6358667.651   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8671.3048661.898   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.6378662.670   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8665.9708664.979   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8665.9668661.894   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8668.6358660.353   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8672.6378673.055   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8663.3098666.103   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8660.6418670.744   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8663.3108670.736   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9768669.967   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.9768668.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3108667.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.3048672.284   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.9708673.054   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.6378672.283   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.6378670.744   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.9708669.974   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3048670.744   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8665.9728670.736   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8664.6388669.967   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8664.6388668.427   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8665.9728667.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8667.3058668.427   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.3058669.967   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.6368664.977   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.3028664.207   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8667.3028662.667   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8668.6368661.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8669.9708662.667   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8669.9708664.207   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   25   27                                                       
CONECT    3    4   31                                                       
CONECT    4    3                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8   15                                                            
CONECT    9   14                                                            
CONECT   10   12                                                            
CONECT   11   12   22                                                       
CONECT   12   11   13   10                                                  
CONECT   13   12   14                                                       
CONECT   14   13   23    9                                                  
CONECT   15   16   20    8                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   22   26                                                       
CONECT   22   23   21   11                                                  
CONECT   23   22   24   14                                                  
CONECT   24   23   25    1                                                  
CONECT   25   24   26    2                                                  
CONECT   26   21   25   18                                                  
CONECT   27   28   32    2                                                  
CONECT   28   27   29    5                                                  
CONECT   29   28   30    6                                                  
CONECT   30   29   31    7                                                  
CONECT   31   30   32    3                                                  
CONECT   32   27   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Download
3D PDB for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)
Download
SMILES for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O
Download
INCHI for NP0338365 (Kaempferol 3-O-beta-D-galactopyranoside)
InChI=1/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21+/s2
Download
View in JSmol
Synonyms
ValueSource
Kaempferol 3-O-b-D-galactopyranosideGenerator
Kaempferol 3-O-β-D-galactopyranosideGenerator
Chemical FormulaC21H20O11
Average Mass448.3800 Da
Monoisotopic Mass448.10056 Da
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nametrifolin
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21+/s2
InChI KeyJPUKWEQWGBDDQB-AISPFLNMNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid-3-O-glycosides  
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Hexose monosaccharide
    • 

  • Chromone
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP0.16ChemAxon
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.29 m³·mol⁻¹ChemAxon
Polarizability42.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wubshet SG, Moresco HH, Tahtah Y, Brighente IMC, Staerk D: High-resolution bioactivity profiling combined with HPLC-HRMS-SPE-NMR: alpha-Glucosidase inhibitors and acetylated ellagic acid rhamnosides from Myrcia palustris DC. (Myrtaceae). Phytochemistry. 2015 Aug;116:246-252. doi: 10.1016/j.phytochem.2015.04.004. Epub  2015 Apr 30. [PubMed:25935545  ] 
  2. Vitalini S, Braca A, Passarella D, Fico G: New flavonol glycosides from Aconitum burnatii Gayer and Aconitum variegatum L. Fitoterapia. 2010 Oct;81(7):940-7. doi: 10.1016/j.fitote.2010.06.012. Epub 2010  Jun 20. [PubMed:20600691  ] 
  3. Iradukunda Y, Kang JY, Zhao XB, Fu XK, Nsanzamahoro S, Ha W, Shi YP: Triple Sensing Modes for Triggered beta-Galactosidase Activity Assays Based on Kaempferol-Deduced Silicon Nanoparticles and Biological Imaging of MCF-7 Breast Cancer Cells. ACS Appl Bio Mater. 2024 May 20;7(5):3154-3163. doi: 10.1021/acsabm.4c00185. Epub  2024 May 2. [PubMed:38695332  ] 
  4. Samy MN, Hamed AN, Sugimoto S, Otsuka H, Kamel MS, Matsunami K: Officinalioside, a new lignan glucoside from Borago officinalis L. Nat Prod Res. 2016;30(8):967-72. doi: 10.1080/14786419.2015.1088540. Epub 2015  Sep 18. [PubMed:26382913  ] 
  5. Yi Y, Wu X, Wang Y, Ye WC, Zhang QW: [Studies on the flavonoids from the flowers of Hylocereus undatus]. Zhong Yao Cai. 2011 May;34(5):712-6. [PubMed:21954556  ] 
  6. Wong KC, Hag Ali DM, Boey PL: Chemical constituents and antibacterial activity of Melastoma malabathricum L. Nat Prod Res. 2012;26(7):609-18. doi: 10.1080/14786419.2010.538395. Epub 2011 Aug  11. [PubMed:21834640  ] 
  7. da Silva I, Diaz JG, Gonzalez-platas J: Structure determination of monohydrated trifolin (kaempferol 3-O-beta-D-galactopyranoside) from laboratory powder diffraction data. J Pharm Sci. 2011 Apr;100(4):1588-93. doi: 10.1002/jps.22379. Epub 2010 Nov 24. [PubMed:24081478  ] 
  8. Liu L, Li AL, Zhao MB, Tu PF: Tetralones and flavonoids from Pyrola calliantha. Chem Biodivers. 2007 Dec;4(12):2932-7. doi: 10.1002/cbdv.200790242. [PubMed:18081103  ]