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Pedunculagin - Wikipedia

From Wikipedia, the free encyclopedia

Pedunculagin
Identifiers

CAS Number	7045-42-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:7948
ChEMBL	ChEMBL506204
ChemSpider	391045
KEGG	C10236
PubChem CID	442688
UNII	1KN18B7Y0X^Y
CompTox Dashboard (EPA)	DTXSID20990656
InChI InChI=1S/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34?/m1/s1 Key: IYMHVUYNBVWXKH-ZITZVVOASA-N InChI=1/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34?/m1/s1 Key: IYMHVUYNBVWXKH-ZITZVVOABK
SMILES c1c2c(c(c(c1O)O)O)-c3c(cc(c(c3O)O)O)C(=O)O[C@@H]4[C@@H](COC2=O)OC([C@H]5[C@H]4OC(=O)c6cc(c(c(c6-c7c(cc(c(c7O)O)O)C(=O)O5)O)O)O)O
Properties
Chemical formula	C₃₄H₂₄O₂₂
Molar mass	784.544 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

Natural occurrence

Pedunculagin is found in plants in orders in the clade Rosidae. It can be found the pericarp of pomegranates (Punica granatum), in the family Lythraceae, in the order Myrtales.^[1] It is also found in plants in the order Fagales such as walnuts (Juglans regia) in the family Juglandaceae,^[2] in Alnus sieboldiana^[3] and in the Manchurian alder (Alnus hirsuta var. microphylla), both species in the family Betulaceae^[4] and it is one of the main oak wood ellagitannins along with castalagin, vescalagin, grandinin and roburins A-E (genus Quercus, in the family Fagaceae).^[5] It is also found in the Indian gooseberry (Phyllanthus emblica), a plant in the family Phyllanthaceae, in the order Malpighiales.^[6]

Galloyl pedunculagin can be found in Platycarya strobilacea.^[7]

Research

Pedunculagin is a highly active carbonic anhydrase inhibitor in vitro.^[1]

Chemistry

A total synthesis of pedunculagin has been reported.^[8]

Pedunculagin is an isomer of terflavin B.

References

^ ^a ^b 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.
^ Cerdá, B. A.; Tomás-Barberán, F. A.; Espín, J. C. (2005). "Metabolism of Antioxidant and Chemopreventive Ellagitannins from Strawberries, Raspberries, Walnuts, and Oak-Aged Wine in Humans: Identification of Biomarkers and Individual Variability". Journal of Agricultural and Food Chemistry. 53 (2): 227–235. doi:10.1021/jf049144d. PMID 15656654.
^ Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, INIST 19467830 (abstract)
^ Lee, O.; Choi, M.; Ha, S.; Lee, G.; Kim, J.; Park, G.; Lee, M.; Choi, Y.; Kim, M.; Oh, C. H. (2010). "Effect of pedunculagin investigated by non-invasive evaluation on atopic-like dermatitis in NC/Nga mice". Skin Research and Technology. 16 (3): 371–377. doi:10.1111/j.1600-0846.2010.00443.x. PMID 20637007. S2CID 25752299.
^ Azorín-Ortuño, M. A.; Urbán, C.; Cerón, J. J.; Tecles, F.; Gil-Izquierdo, A.; Pallarés, F. J.; Tomás-Barberán, F. A.; Espín, J. C. (2008). "Safety Evaluation of an Oak-Flavored Milk Powder Containing Ellagitannins upon Oral Administration in the Rat". Journal of Agricultural and Food Chemistry. 56 (8): 2857–2865. doi:10.1021/jf8000857. PMID 18370397.
^ Bhattacharya, A.; Chatterjee, A.; Ghosal, S.; Bhattacharya, S. K. (1999). "Antioxidant activity of active tannoid principles of Emblica officinalis (amla)". Indian Journal of Experimental Biology. 37 (7): 676–680. PMID 10522157.
^ Ueno, T.; Miyanaga, T.; Kawakami, F.; Okano, M.; Tanaka, T.; Ohtsuki, K. (2002). "Further characterization of galloyl pedunculagin as an effective autophosphorylation inhibitor of C-kinase in vitro". Biological & Pharmaceutical Bulletin. 25 (11): 1401–1404. doi:10.1248/bpb.25.1401. hdl:10069/8378. PMID 12419947.
^ Feldman, K. S.; Smith, R. S. (1996). "Ellagitannin Chemistry. First Total Synthesis of the 2,3- and 4,6-Coupled Ellagitannin Pedunculagin". The Journal of Organic Chemistry. 61 (8): 2606–2612. doi:10.1021/jo952130+. PMID 11667089.

Types of ellagitannins

Moieties

Diphenolic acid : Hexahydroxydiphenic acid (HHDP)
Triphenolic acids : Nonahydroxytriphenic acid
Sanguisorbic acid
Valoneic acid
Tetraphenolic acids : Isoterchebulic acid
Terchebulinic acid

Lactones

Monomers

C-glycosidic ellagitannins

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Transformed ellagitannins

molecules with chebulic acid	Chebulagic acid Chebulinic acid
molecules with Elaeocarpusinic acid	Elaeocarpusin Helioscopin B Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)

Oligomers

Dimers: Agrimoniin; Cornusiin E (dimer of tellimagrandin II); Lambertianin A and B; Nobotanin B; Roburin A, B, C and D; Sanguiin H-6

Trimers: Lambertianin C; Raspberry ellagitannin

Tetramers: Lambertianin D; Nobotanin S

Pentamer: Melastoflorin A

Other

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