Bicornin : Wikipedia, the free encyclopedia

Bicornin

Bicornin
Identifiers

CAS Number	124854-12-2
3D model (JSmol)	Interactive image
ChemSpider	28190824
PubChem CID	71308161
CompTox Dashboard (EPA)	DTXSID40745428
InChI InChI=1S/C48H32O30/c49-17-1-11(2-18(50)29(17)58)42(65)76-40-38-26(72-48(78-44(67)13-5-21(53)31(60)22(54)6-13)41(40)77-43(66)12-3-19(51)30(59)20(52)4-12)10-71-45(68)16-9-23(55)32(61)35(64)36(16)73-37-25(57)8-14-27(34(37)63)28-15(47(70)74-38)7-24(56)33(62)39(28)75-46(14)69/h1-9,26,38,40-41,48-64H,10H2/t26-,38-,40-,41-,48+/m1/s1 Key: DOTJYWQAPHIAIF-TWNAEOARSA-N InChI=1/C48H32O30/c49-17-1-11(2-18(50)29(17)58)42(65)76-40-38-26(72-48(78-44(67)13-5-21(53)31(60)22(54)6-13)41(40)77-43(66)12-3-19(51)30(59)20(52)4-12)10-71-45(68)16-9-23(55)32(61)35(64)36(16)73-37-25(57)8-14-27(34(37)63)28-15(47(70)74-38)7-24(56)33(62)39(28)75-46(14)69/h1-9,26,38,40-41,48-64H,10H2/t26-,38-,40-,41-,48+/m1/s1 Key: DOTJYWQAPHIAIF-TWNAEOARBX
SMILES c1c(cc(c(c1O)O)O)C(=O)O[C@@H]2[C@H]3[C@@H](COC(=O)c4cc(c(c(c4Oc5c(cc6c(c5O)c7c(cc(c(c7oc6=O)O)O)C(=O)O3)O)O)O)O)O[C@H]([C@@H]2OC(=O)c8cc(c(c(c8)O)O)O)OC(=O)c9cc(c(c(c9)O)O)O
Properties
Chemical formula	C₄₈H₃₂O₃₀
Molar mass	1088.754 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

Chemical compound

Bicornin is an ellagitannin found in plants of the order Myrtales, including Trapa bicornis (water caltrop)^[1] and Syzygium aromaticum (clove).^[2]

The molecule contains a luteic acid group.^[3]

References

^ Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K and Okuda T (1989). "Bicornin, a new hydrolyzable tannin from Trapa bicornis, and revised structure of alnusiin". Heterocycles. 29 (5): 861–864. doi:10.3987/COM-89-4951 (inactive 2024-03-30).{{cite journal}}: CS1 maint: DOI inactive as of March 2024 (link) CS1 maint: multiple names: authors list (link) INIST 6780591
^ Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T (1989). "Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group". Chemical and Pharmaceutical Bulletin. 37 (10): 2655–2660. doi:10.3987/COM-11-12392 (inactive 2024-03-12).{{cite journal}}: CS1 maint: DOI inactive as of March 2024 (link) CS1 maint: multiple names: authors list (link) INIST 19467830
^ Yoshida, Takashi; Yazaki, Kazufumi; Memon, Muhammad Usman; Maruyama, Izumi; Kurokawa, Kenji; Shingu, Tetsuro; Okuda, Takuo (1989). "Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group". Chemical and Pharmaceutical Bulletin. 37 (10): 2655–2660. doi:10.1248/cpb.37.2655.

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)