From Wikipedia, the free encyclopedia
Punicalagin
Names
Other names
2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-
gallagyl -D-glucose
α-punicalagin
β-punicalagin
Identifiers
ChEMBL
KEGG
C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C4C5=C3C(=O)OC6=C(C(=C(C7=C(C(=C(C=C7C(=O)O1)O)O)O)C(=C56)C(=O)O4)O)O)O)O)O)O)O)C8C(OC(=O)C9=CC(=C(C(=C9C1=C(C(=C(C=C1C(=O)O8)O)O)O)O)O)O)C=O)O
Properties
C48 H28 O30
Molar mass
1084.71 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Punicalagin (Pyuni-cala-jen ) is an
ellagitannin , a type of
phenolic compound . It is found as alpha and beta isomers in
pomegranates (Punica granatum ),
Terminalia catappa ,
Terminalia myriocarpa ,
[1] and in
Combretum molle , the velvet bushwillow, a plant species found in South Africa.
[2] These three genera are all
Myrtales and the last two are both
Combretaceae .
Research
Punicalagins are water-soluble and
hydrolyze into smaller phenolic compounds, such as
ellagic acid .
There were no toxic effects in rats on a 6% diet of punicalagins for 37 days.
[3] In laboratory research, punicalagins had
carbonic anhydrase inhibitor activity.
[4]
See also
References
^ Marzouk, M. S. A.; El-Toumy, S. A. A.; Moharram, F. A.; Shalaby, N. M.; Ahmed, A. A. (2002).
"Pharmacologically Active Ellagitannins from Terminalia myriocarpa" . Planta Medica . 68 (6): 523–527.
doi :
10.1055/s-2002-32549 .
PMID
12094296 .
^ Asres, K.; Bucar, F.; Knauder, E.; Yardley, V.; Kendrick, H.; Croft, S. L. (2001).
"In vitro antiprotozoal activity of extract and compounds from the stem bark of Combretum molle" . Phytotherapy Research . 15 (7): 613–617.
doi :
10.1002/ptr.897 .
PMID
11746844 .
S2CID
24511496 .
^ Cerdá, B; Cerón, J. J; Tomás-Barberán, F. A; Espín, J. C (2003).
"Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic" . Journal of Agricultural and Food Chemistry . 51 (11): 3493–501.
doi :
10.1021/jf020842c .
PMID
12744688 .
^ Satomi, H.; Umemura, K.; Ueno, A.; Hatano, T.; Okuda, T.; Noro, T. (1993).
"Carbonic anhydrase inhibitors from the pericarps of Punica granatum L" . Biological & Pharmaceutical Bulletin . 16 (8): 787–790.
doi :
10.1248/bpb.16.787 .
PMID
8220326 .
Moieties Lactones Monomers
Acetonyl geraniin
Alnusiin
Bicornin
Carlesiin
Casuarictin
Emblicanin A and
B
Euscaphinin
Galloyl pedunculagin
Grandinin
Helioscopinin B
Jolkinin
Lagerstannin A ,
B and
C
Macranganin
Myrobalanitannin
Nupharin A ,
B ,
C ,
D ,
E and
F
Pedunculagin
Punicalagin
Punigluconin
Phyllanemblinin A ,
B ,
C ,
D ,
E and
F
Punicalin
Roburin E
Rugosin E
Sanguiin H-5
Stenophyllanin A ,
B and
C
Strictinin
Tellimagrandin I and
II
Teracatain
Terchebulin
Terflavin A and
B
Tergallic acid
Tergallic acid dilactone
Oligomers Other