Grandinin

Chemical compound

Grandinin
Identifiers

CAS Number	115166-32-0^Y
3D model (JSmol)	Interactive image
PubChem CID	492392
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	1066.74 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves^[1] and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).^[2] It shows antioxydant activity.^[1] It is an astringent compound.^[3] It is also found in wine, red^[4] or white,^[5] aged in oak barrels.

It is a castalagin glycoside^[6] by binding of the pentose lyxose.^[3] It contains a nonahydroxytriphenic acid moiety.

It suppresses the phosphorylation of the epidermal growth factor receptor in human colon carcinoma cells.^[6]

References

^ ^a ^b Polyphenols of Melaleuca quinquenervia leaves - pharmacological studies of grandinin. Moharram F. A., Marzouk M. S., El-Toumy S. A. A., Ahmed A. A. E. and Aboutabl E. A., Phytotherapy Research, Volume 17 Issue 7, Pages 767-773, doi:10.1002/ptr.1214
^ 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.
^ ^a ^b 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.
^ ^a ^b 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

Ellagic acid
Gallagic acid
Gallagic acid dilactone
Luteic acid
Sanguisorbic acid dilactone
Valoneic acid dilactone

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

C-glycosidic ellagitannins

Castalagin (Vescalagin)
Castalin
Casuariin
Casuarinin
Punicacortein A, B, C and D

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Alnicortin
Euphorbin A
Euphorscopin
Excoecarianin
Geraniin
Granatin A and B
Helioscopinin A
Mallotusinic acid
Supinanin
Terchebin

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)

Kinase inhibitors: Altiratinib
AM7
AMG-458
Amuvatinib
BMS-777607
Cabozantinib
Capmatinib
Crizotinib
Foretinib
Golvatinib
INCB28060
JNJ-38877605
K252a
MK-2461
PF-04217903
PF-2341066
PHA-665752
SU-11274
Tivantinib
Volitinib

IGF

IGF-1	Agonists: des(1-3)IGF-1 Insulin-like growth factor-1 (somatomedin C) IGF-1 LR3 Insulin-like growth factor-2 (somatomedin A) Insulin Mecasermin Mecasermin rinfabate Kinase inhibitors: BMS-754807 Linsitinib NVP-ADW742 NVP-AEW541 OSl-906 Antibodies: AVE-1642 Cixutumumab Dalotuzumab Figitumumab Ganitumab Robatumumab R1507 Teprotumumab Xentuzumab (against IGF-1 and IGF-2)
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^NTR)

Antagonists: ALE-0540
Dexamethasone
EVT-901 (SAR-127963)
Testosterone

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^NTR-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

SCF (c-Kit)

Agonists: Ancestim
Stem cell factor

TGFβ

See here instead.

Trk

TrkA	Agonists: Amitriptyline BNN-20 BNN-27 Cenegermin DHEA DHEA-S Gambogic amide NGF Tavilermide Antagonists: ALE-0540 Dexamethasone FX007 Testosterone Negative allosteric modulators: VM-902A Kinase inhibitors: Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib Milciclib ONO-4474 ONO-5390556 PLX-7486 Rebastinib SNA-120 (pegylated K252a)) Antibodies: Against TrkA: GBR-900; Against NGF: ABT-110 (PG110) ASP-6294 Fasinumab Frunevetmab Fulranumab MEDI-578 Ranevetmab Tanezumab Aptamers: Against NGF: RBM-004 Decoy receptors: ReN-1820 (TrkAd5)
TrkB	Agonists: 3,7-DHF 3,7,8,2'-THF 4'-DMA-7,8-DHF 7,3'-DHF 7,8-DHF 7,8,2'-THF 7,8,3'-THF Amitriptyline BDNF BNN-20 Deoxygedunin Deprenyl Diosmetin DMAQ-B1 HIOC LM22A-4 N-Acetylserotonin NT-3 NT-4 Norwogonin (5,7,8-THF) R7 R13 TDP6 Antagonists: ANA-12 Cyclotraxin B Gossypetin (3,5,7,8,3',4'-HHF) Ligands: DHEA Kinase inhibitors: Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib ONO-4474 ONO-5390556 PLX-7486
TrkC	Agonists: BNN-20 DHEA NT-3 Kinase inhibitors: Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib ONO-4474 ONO-5390556 PLX-7486