Bicornin

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Bicornin
Bicornin.png
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
  • 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
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).

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]

Related Research Articles

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<span class="mw-page-title-main">Casuarictin</span> Chemical compound

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<i>Stachyurus</i> Genus of flowering plants in the family Stachyuraceae

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<span class="mw-page-title-main">Casuarinin</span> Chemical compound

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<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

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

<span class="mw-page-title-main">Luteic acid</span> Chemical compound

Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin.

<span class="mw-page-title-main">Alnusiin</span> Chemical compound

Alnusiin is an ellagitannin found in Alnus sieboldiana.

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Alnus sieboldiana is an alder species found on the islands of Honshū, Shikoku, and Suwanose-jima in Japan.

<span class="mw-page-title-main">Geraniin</span> Chemical compound

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).

<i>Nuphar japonica</i> Species of flowering plant

Nuphar japonica, known as East Asian yellow water-lily, is an aquatic plant species in the genus Nuphar found in Japan and the Korean Peninsula. It is endangered in Russia. The species was not accepted by The Plant List as of November 2013, which regarded it as an "unresolved name".

<span class="mw-page-title-main">Mallotusinic acid</span> Chemical compound

Mallotusinic acid is a hydrolysable tannin found in the bark of Mallotus japonicus. It is more generally present in Geraniales.

<i>Monochaetum multiflorum</i> Species of flowering plant

Monochaetum multiflorum is a flowering plant species in the genus Monochaetum indigenous to Colombia.

<span class="mw-page-title-main">Mallojaponin</span> Chemical compound

Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus. This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.

References

  1. ↑ 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 .{{cite journal}}: CS1 maint: multiple names: authors list (link) INIST   6780591
  2. ↑ 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 .{{cite journal}}: CS1 maint: multiple names: authors list (link) INIST   19467830
  3. ↑ 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.
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