Grandinin - Misplaced Pages

Chemical compound

Grandinin
Identifiers

CAS Number	115166-32-0
3D model (JSmol)	Interactive image
PubChem CID	492392
CompTox Dashboard (EPA)	DTXSID101029292
SMILES C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)C8(C(C(C(O8)CO)O)O)O)OC(=O)C9=CC(=C(C(=C9C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O
Properties
Chemical formula	C₄₆H₃₄O₃₀
Molar mass	1066.748 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur). It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

It is a castalagin glycoside by binding of the pentose lyxose. It contains a nonahydroxytriphenic acid moiety.

It suppresses the phosphorylation of the epidermal growth factor receptor in human colon carcinoma cells.

References

^ Moharram, F. A.; Marzouk, M. S.; El-Toumy, S. A. A.; Ahmed, A. A. E.; Aboutabl, E. A. (2003). "Polyphenols of Melaleuca quinquenervia leaves – pharmacological studies of grandinin". Phytotherapy Research. 17 (7): 767–773. doi:10.1002/ptr.1214. PMID 12916075.
Mämmelä, P.; Savolainen, H.; Lindroos, L.; Kangas, J.; Vartiainen, T. (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A. 891 (1): 75–83. doi:10.1016/S0021-9673(00)00624-5. PMID 10999626.
^ Hofmann, T.; Glabasnia, A.; Schwarz, B.; Wisman, K. N.; Gangwer, K. A.; Hagerman, A. E. (2006). "Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-d-glucopyranose, Castalagin, and Grandinin". Journal of Agricultural and Food Chemistry. 54 (25): 9503–9509. doi:10.1021/jf062272c. PMC 2597504. PMID 17147439.
García-Estévez, I.; Escribano-Bailón, M. T.; Rivas-Gonzalo, J. N. C.; Alcalde-Eon, C. (2010). "Development of a fractionation method for the detection and identification of oak ellagitannins in red wines". Analytica Chimica Acta. 660 (1–2): 171–176. Bibcode:2010AcAC..660..171G. doi:10.1016/j.aca.2009.10.020. hdl:10366/141103. PMID 20103159.
Marinov, M. G.; Dimitrova, E. D.; Puech, J. -L. (1997). "Kinetics of ellagitannin extraction from oak wood using white wine". Journal of Wine Research. 8: 29–40. doi:10.1080/09571269708718095.
^ Fridrich, D.; Glabasnia, A.; Fritz, J.; Esselen, M.; Pahlke, G.; Hofmann, T.; Marko, D. (2008). "Oak Ellagitannins Suppress the Phosphorylation of the Epidermal Growth Factor Receptor in Human Colon Carcinoma Cells". Journal of Agricultural and Food Chemistry. 56 (9): 3010–3015. doi:10.1021/jf073427z. PMID 18419129., INIST 20325664

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

Growth factor receptor modulators

Angiopoietin

Agonists: Angiopoietin 1
Angiopoietin 4

Antagonists: Angiopoietin 2
Angiopoietin 3

Kinase inhibitors: Altiratinib
CE-245677
Rebastinib

Antibodies: Evinacumab (against angiopoietin 3)
Nesvacumab (against angiopoietin 2)

CNTF

Agonists: Axokine
CNTF
Dapiclermin

EGF (ErbB)

EGF (ErbB1/HER1)	Agonists: Amphiregulin Betacellulin EGF (urogastrone) Epigen Epiregulin Heparin-binding EGF-like growth factor (HB-EGF) Murodermin Nepidermin Transforming growth factor alpha (TGFα) Kinase inhibitors: Afatinib Agerafenib Brigatinib Canertinib Dacomitinib Erlotinib Gefitinib Grandinin Icotinib Lapatinib Neratinib Osimertinib Vandetanib WHI-P 154 Antibodies: Cetuximab Depatuxizumab Depatuxizumab mafodotin Futuximab Imgatuzumab Matuzumab Necitumumab Nimotuzumab Panitumumab Zalutumumab
ErbB2/HER2	Agonists: Unknown/none Antibodies: Ertumaxomab Pertuzumab Trastuzumab Trastuzumab deruxtecan Trastuzumab duocarmazine Trastuzumab emtansine Kinase inhibitors: Afatinib Lapatinib Mubritinib Neratinib Tucatinib
ErbB3/HER3	Agonists: Neuregulins (heregulins) (1, 2, 6 (neuroglycan C)) Antibodies: Duligotumab Patritumab Seribantumab
ErbB4/HER4	Agonists: Betacellulin Epigen Heparin-binding EGF-like growth factor (HB-EGF) Neuregulins (heregulins) (1, 2, 3, 4, 5 (tomoregulin, TMEFF))

FGF

FGFR1	Agonists: Ersofermin FGF (1, 2 (bFGF), 3, 4, 5, 6, 8, 10 (KGF2), 20) Repifermin Selpercatinib Trafermin Velafermin
FGFR2	Agonists: Ersofermin FGF (1, 2 (bFGF), 3, 4, 5, 6, 7 (KGF), 8, 9, 10 (KGF2), 17, 18, 22) Palifermin Repifermin Selpercatinib Sprifermin Trafermin Antibodies: Aprutumab Aprutumab ixadotin Kinase inhibitors: Infigratinib
FGFR3	Agonists: Ersofermin FGF (1, 2 (bFGF), 4, 8, 9, 18, 23) Selpercatinib Sprifermin Trafermin Antibodies: Burosumab (against FGF23)
FGFR4	Agonists: Ersofermin FGF (1, 2 (bFGF), 4, 6, 8, 9, 19) Trafermin
Unsorted	Agonists: FGF15/19

HGF (c-Met)

Agonists: Fosgonimeton
Hepatocyte growth factor

Potentiators: Dihexa (PNB-0408)

IGF

IGF-1

IGF-2

Agonists: Insulin-like growth factor-2 (somatomedin A)

Antibodies: Dusigitumab
Xentuzumab (against IGF-1 and IGF-2)

Others

Binding proteins: IGFBP (1, 2, 3, 4, 5, 6, 7)

Cleavage products/derivatives with unknown target: Glypromate (GPE, (1-3)IGF-1)
Trofinetide

LNGF (p75)

Antibodies: Against NGF: ABT-110 (PG110)
ASP-6294
Fasinumab
Frunevetmab
Fulranumab
MEDI-578
Ranevetmab
Tanezumab

Aptamers: Against NGF: RBM-004

Decoy receptors: LEVI-04 (p75-Fc)

PDGF

Agonists: Becaplermin
Platelet-derived growth factor (A, B, C, D)

RET (GFL)

GFRα1	Agonists: Glial cell line-derived neurotrophic factor (GDNF) Liatermin Kinase inhibitors: Vandetanib
GFRα2	Agonists: Neurturin (NRTN) Kinase inhibitors: Vandetanib
GFRα3	Agonists: Artemin (ARTN) Kinase inhibitors: Vandetanib
GFRα4	Agonists: Persephin (PSPN) Kinase inhibitors: Vandetanib
Unsorted	Kinase inhibitors: Agerafenib