Geraniin

chemical compound

DBpedia resource is: http://dbpedia.org/resource/Geraniin

Abstract is: Geraniin is a dehydroellagitannin found in geraniums. It is found for instance in Geranium thunbergii, which is one of the most popular folk medicines and also an official antidiarrheic drug in Japan. It can also be found in the rind of Nephelium lappaceum (rambutan). It mediates apoptosis by cleavage of focal adhesion kinase through up-regulation of Fas ligand expression in human melanoma cells. Geraniin has also been shown to possess immunomodularity properties, as it inhibits tumor necrosis factor-alpha, and NF-κB in ovarian cancer cells. Geraniin was studied for its anticancer activity and shown to target apoptosis via inactivation of PI3K/Akt/mTOR signaling pathway involving NF-κB when treated against HT-29 human colorectal adenocarcinoma cells. It is formed with one hexahydroxydiphenic acid unit, one modified hexahydroxydiphenic acid unit (dehydrohexahydroxydiphenic acid or DHHDP) and one gallic acid unit linked to a glucose molecule. It is forming an equilibrium mixture of six-membered hemi-ketal and five-membered hemi-ketal forms. Chebulagic acid is formed from geraniin through a glutathione-mediated conversion.

C₄₁H₂₈O₂₇

Geraniin is …
instance of (P31):
type of chemical entityQ113145171

sublass of (P279):
CID 338147Q104667359

External links are
P233canonical SMILESC1C2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C7C(=CC(=O)C(C7(O)O)(O6)O)C(=O)O3)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
P231CAS Registry Number60976-49-0
P683ChEBI ID5328
P592ChEMBL IDCHEMBL506069
P661ChemSpider ID10270376
P646Freebase ID/m/0k3nkty
P234InChIInChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2/t18-,23+,30-,32+,33-,39+,41+/m1/s1
P235InChIKeyJQQBXPCJFAKSPG-SVYIMCMUSA-N
P2017isomeric SMILESC1[C@@H]2[C@@H]3[C@@H]([C@H]([C@@H](O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5[C@@H]7C(=CC(=O)[C@@](C7(O)O)(O6)O)C(=O)O3)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
P665KEGG IDC10230
P2064KNApSAcK IDC00002926
P6366Microsoft Academic ID2779241620
P9405NMRShiftDB structure ID20175821
P2840NSC number359346
P11199Probes And Drugs IDPD124374
P662PubChem CID3001497
P11089UniChem compound ID123555

P703found in taxonLotus corniculatusQ29907
Euphorbia hirtaQ36177
Erodium cicutariumQ157726
Parthenocissus tricuspidataQ157979
Erodium moschatumQ159800
Acer tataricumQ162728
Geranium sibiricumQ163088
Acalypha hispidaQ163528
Euphorbia helioscopiaQ148889
Geum japonicumQ164367
Euphorbia maculataQ177322
Spondias mombinQ794969
Euphorbia nutansQ798313
Phyllanthus emblicaQ310050
Acer maximowiczianumQ1038831
Phyllanthus urinariaQ1131974
Nymphaea tetragonaQ244009
Terminalia catappaQ271179
Cercidiphyllum japonicumQ526549
Triadica sebiferaQ702175
Euphorbia tirucalliQ883685
Euphorbia prostrataQ1023705
Acalypha wilkesianaQ1377693
Vernicia fordiiQ1422363
Carpinus laxifloraQ4147190
Geranium thunbergiiQ5236828
Elaeocarpus sylvestrisQ5367459
Acalypha australisQ6676255
Tamarix chinensisQ6825364
Bischofia javanicaQ8248272
Coriaria japonicaQ8340253
Acer nikoenseQ9578385
Quercus gambeliiQ2266358
Geum aleppicumQ2585830
Phyllanthus sellowianusQ10349256
Phyllanthus tenellusQ10882137
Excoecaria kawakamiiQ10893561
Phyfnnvik eyyfnQ2719836
Geum macrophyllumQ2917893
Excoecaria agallochaQ5419710
Geranium viscosissimumQ5549882
Euphorbia thymifoliaQ10904925
Macaranga sinensisQ10915064
Macaranga tanariusQ3020630
Acalypha indicaQ3339634
Phyllanthus flexuosusQ15247375
Acalypha poiretiiQ15286864
Erodium glaucophyllumQ15327345
Nymphaea pygmaeaQ21396688
Antidesma montanum var. montanumQ25119230
Euphorbia scordiifoliaQ15389558
Heterocentron subtriplinerviumQ15389920
Acer ginnalaQ15634290
Euphorbia jolkiniiQ10936724
Euphorbia makinoiQ10958092
Mallotus philippinensisQ104253278
Phyllanthus amarusQ11034878
Mallotus repandusQ11076094
Phyllanthus virgatusQ11178012
Euphorbia supinaQ12605986
Euphorbia humifusaQ12847854
Euphorbia watanabeiQ14937068
Geranium rectumQ15227519
Mallotus japonicusQ15236078
Phyllanthus myrtifoliusQ15246934
P2067mass952.081796
P3364stereoisomer ofJQQBXPCJFAKSPG-DBBVXFTCSA-NQ105133602
JQQBXPCJFAKSPG-OTYJEXDISA-NQ105133603

Reverse relations

stereoisomer of (P3364)
Q105133602JQQBXPCJFAKSPG-DBBVXFTCSA-N
Q105133603JQQBXPCJFAKSPG-OTYJEXDISA-N

main subject (P921)
Q104386895Amariin, a di-dehydrohexahydroxydiphenoyl hydrolysable tannin from Phyllanthus amarus
Q44631251Antibacterial Polyphenol from Erodium glaucophyllum
Q104666741Antimicrobial constituents of the leaves ofAcalypha wilkesiana and Acalypha hispida
Q43141915Antioxidant activities and xanthine oxidase inhibitory effects of extracts and main polyphenolic compounds obtained from Geranium sibiricum L.
Q31156240Antioxidant, anti-semicarbazide-sensitive amine oxidase, and anti-hypertensive activities of geraniin isolated from Phyllanthus urinaria
Q34260496Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents
Q59306707Antiviral ellagitannins from Spondias mombin
Q28371886Antiviral tannins from two Phyllanthus species
Q104911534Bergenin derivatives from Mallotus japonicus
Q104387302Bischofianin, a dimeric dehydroellagitannin from Bischofia javanica
Q54263524Chemical and Pharmaceutical Studies on Medicinal Plants in Paraguay, Geraniin, an Angiotensin-Converting Enzyme Inhibitor from "Paraparai Mi," Phyllanthus niruri
Q47178716Chemical and preliminary analgesic evaluation of geraniin and furosin isolated from Phyllanthus sellowianus.
Q104909788Constituents of Geranium thunbergii SIEB. et Zucc. XV. Modified Dehydroellagitannins, Geraniinic Acids B and C, and Phyllathusiin F.
Q104394128Constituents of Geranium thunbergii Sieb. et Zucc. Part 14. Structures of didehydrogeraniin, furosinin, and furosin
Q105133597Constituents of Geranium thunbergii Sieb. et Zucc. XIII Isolation of water-soluble tannins by centrifugal partition chromatography, and biomimetic synthesis of elaeocarpusin.
Q64098610Efficacy of geraniin on dengue virus type-2 infected BALB/c mice
Q79860295Flavonoids from Acalypha indica
Q105009479Gemins D, E and F, ellagitannins from Geum japonicum
Q105133598Geraniin, a Hydrolyzable Tannin fromNymphaea tetragonaGeorgi (Nymphaeaceae)
Q104387285Hydrolysable tannins from Euphorbia thymifolia
Q44438129Inhibition of wild-type human immunodeficiency virus and reverse transcriptase inhibitor-resistant variants by Phyllanthus amarus
Q45848617Inhibitory effect of tannins on reverse transcriptase from RNA tumor virus
Q39422932Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L.
Q104850307Phenolic compounds from Acalypha australis
Q33956559Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica
Q104838259Structure and antiherpetic activity among the Tannins
Q44951445Structure and biogenesis of jolkinin, a highly oxygenated ellagitannin from Euphorbia jolkinii
Q47415266Studies on dental caries prevention by traditional medicines. VIII. Inhibitory effect of various tannins on glucan synthesis by glucosyltransferase from Streptococcus mutans
Q70583751Studies on the activities of tannins and related compounds from medicinal plants and drugs. IV. Effects of various extracts of Geranii herba and geraniin on liver injury and lipid metabolism in rats fed peroxidized oil
Q105006977Tannin production in Sapium sebiferum callus cultures
Q104850061Tannin production in cell cultures of Sapium sebiferum
Q104850347Tannin production in hairy root culture of Geranium thunbergii
Q104848016Tanning substances ofGeranium rectum
Q104911525Tannins and Flavonoids from the Erodium cicutarium Herb
Q104387295Tannins and Related Polyphenols of Euphorbiaceous Plants. IX. Hydrolyzable Tannins with 1C4 Glucose Core from Phyllanthus flexuosus MUELL. ARG.
Q104386809Tannins and Related Polyphenols of Euphorbiaceous Plants. VII. Tirucallins A, B and Euphorbin F, Monomeric and Dimeric ellagitannins from Euphorbia tirucalli L.
Q104386813Tannins and Related Polyphenols of Euphorbiaceous Plants. XII. Euphorbins G and H, New Dimeric Hydrolyzable Tannins from Euphorbia prostrata and Euphorbia makinoi.
Q103783168Tannins and Related Polyphenols of Euphorbiaceous Plants. XIV. Euphorbin I, a New Dimeric Hydrolyzable Tannin from Euphorbia watanabei.
Q104389187Tannins and Related Polyphenols of Melastomataceous Plants. III. Nobotanins G, H and I, Dimeric Hydrolyzable Tannins from Heterocentron roseum.
Q104850211Tannins and related compounds from Erodium moschatum (L.) L'Her
Q104387289Tannins and related compounds. CV. Monomeric and dimeric hydrolyzable tannins having a dehydrohexahydroxydiphenoyl group, supinanin, euphorscopin, euphorhelin and jolkianin, from euphorbia species.
Q104387276Tannins and related compounds. LXXVI. Isolation and characterization of cercidinins A and B and cuspinin, unusual 2,3-(R)-hexahydroxydiphenoyl glucoses from Cercidiphyllum japonicum and Castanopsis cuspidata var. sieboldii.
Q34476748Tannins and related compounds. LXXXIV. Isolation and characterization of five new hydrolyzable tannins from the bark of Mallotus japonicus
Q104387280Tannins and related compounds. LXXXVII. Isolation and characterization of four new hydrolyzable tannins from the leaves of Mallotus repandus.
Q104387281Tannins and related compounds. LXXXVIII. Isolation and characterization of hydrolyzable tannins from Mallotus japonicus (Thunb.) Mueller-Arg. and M. philippinensis (Lam.) Mueller-Arg.
Q56530881Tannins and related compounds. Part 37. Isolation and structure elucidation of elaeocarpusin, a novel ellagitannin from Elaeocarpus sylvestris var. Ellipticus
Q104387282Tannins and related compounds. XCII. Isolation and characterization of cyanogenic ellagitannins, aleurinins A and B, and a related O-glycosidic ellagitannin, aleurinin C, from Aleurites fordii Hemsley.
Q104387283Tannins and related compounds. XCIV. Isolation and characterization of seven new hydrolyzable tannins from the leaves of Macaranga tanarius (L.) Muell. et Arg.
Q57405992Tannins and related compounds. XCV. Isolation and characterization of helioscopinins and helioscopins, four new hydrolyzable tannins from Euphorbia helioscopia L. (1)
Q104386710Tannins and related compounds. XCVI. Structures of macaranins and macarinins, new hydrolyzable tannins possessing macaranoyl and tergalloyl ester groups, from the leaves of Macaranga sinensis (Baill.) Muell.-Arg.
Q104387284Tannins and related compounds. XCVIII. Structures of three new dimeric ellagitannins, excoecarianin and excoecarinins A and B, isolated from the leaves of Excoecaria kawakamii Hayata.
Q105007053Tannins and related compounds. XLII. Isolation and characterization of four new hydrolyzable tannins, terflavins A and B, tergallagin and tercatain from the leaves of Terminalia catappa L.
Q104850352Tannins and related polyphenols of euphorbiaceous plants. IV. Euphorbins A and B, novel dimeric dehydroellagitannins from Euphorbia hirta L.
Q104386808Tannins and related polyphenols of euphorbiaceous plants. VIII. Eumaculin A and eusupinin A, and accomapanying polyphenols from Euphorbia maculata L. and E. supina Rafin.
Q72791066Tannins and related polyphenols of euphorbiaceous plants. XI. Three new hydrolyzable tannins and a polyphenol glucoside from Euphorbia humifusa
Q104393819Tannins of Coriaria japonica A. Gray. I Coriariins A and B, new dimeric and monomeric hydrolyzable tannins.
Q100145845Tannins of Euphorbiaceous Plants. X. Antidesmin A, a New Dimeric Hydrolyzable Tannin from Antidesma pentandrum var. barbatum.
Q104975289Tannins of aceraceous plants. Part II. Gallotannins having a 1,5-anhydro-D-glucitol core and some ellagitannins from Acer species.
Q77449903Tannins, flavonol sulfonates, and a norlignan from phyllanthus virgatus
Q104850361The ellagitannin geraniin and its hydrolysis products isolated as insect growth inhibitors from semi-arid land plants
Q104386714Two New Ellagitannin Metabolites, Carpinusin and Carpinusin from Carpinus laxiflora
Q104850273Two Tannins from Phyllanthus tenellus