Thelephantins

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Thelephantins
Thelephantin A.svg
Thelephantin B.svg
Thelephantin C.svg
Thelephantin D.svg
Identifiers
3D model (JSmol)
ChemSpider
  • A: InChI=1S/C29H24O9/c1-2-3-22(33)37-27-23(16-4-10-19(30)11-5-16)26(35)28(38-29(36)18-8-14-21(32)15-9-18)24(25(27)34)17-6-12-20(31)13-7-17/h4-15,30-32,34-35H,2-3H2,1H3
    Key: CNDDIRNNJHDZCC-UHFFFAOYSA-N
  • B: InChI=1S/C31H28O9/c1-2-3-4-5-24(35)39-29-25(18-6-12-21(32)13-7-18)28(37)30(40-31(38)20-10-16-23(34)17-11-20)26(27(29)36)19-8-14-22(33)15-9-19/h6-17,32-34,36-37H,2-5H2,1H3
    Key: PVJPNBBVZSBLLI-UHFFFAOYSA-N
  • C: InChI=1S/C32H30O9/c1-17(2)18(3)16-25(36)40-30-26(19-4-10-22(33)11-5-19)29(38)31(41-32(39)21-8-14-24(35)15-9-21)27(28(30)37)20-6-12-23(34)13-7-20/h4-15,17-18,33-35,37-38H,16H2,1-3H3
    Key: IXNCXNGAGCSAMG-UHFFFAOYSA-N
  • D: InChI=1S/C30H26O8/c1-2-6-23(33)37-29-25(19-9-13-21(31)14-10-19)28(36)30(38-24(34)17-18-7-4-3-5-8-18)26(27(29)35)20-11-15-22(32)16-12-20/h3-5,7-16,31-32,35-36H,2,6,17H2,1H3
    Key: WQRIEKDUHJQWLC-UHFFFAOYSA-N
  • A: CCCC(=O)OC1=C(C(=C(C(=C1O)C2=CC=C(C=C2)O)OC(=O)C3=CC=C(C=C3)O)O)C4=CC=C(C=C4)O
  • B: CCCCCC(=O)OC1=C(C(=C(C(=C1C2=CC=C(C=C2)O)O)OC(=O)C3=CC=C(C=C3)O)C4=CC=C(C=C4)O)O
  • C: CC(C)C(C)CC(=O)OC1=C(C(=C(C(=C1C2=CC=C(C=C2)O)O)OC(=O)C3=CC=C(C=C3)O)C4=CC=C(C=C4)O)O
  • D: CCCC(=O)OC1=C(C(=C(C(=C1C2=CC=C(C=C2)O)O)OC(=O)CC3=CC=CC=C3)C4=CC=C(C=C4)O)O
Properties
C29H24O9
Molar mass 516.502 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thelephantins are a group of pigments found in the inedible mushroom Thelephora aurantiotincta. Chemically, they are classified as polyphenols and terphenyl derivatives.

Three variants (thelephantin A, B, C) have been elucidated by high-resolution 2D nuclear magnetic resonance, mass spectroscopy, infrared and ultraviolet spectra as well as an acetylated congener of thelephantin A.[1][2] The structure of telephantin G was revised and confirmed by total synthesis.[3]

References[edit]

  1. ^ Quang DN, Hashimoto T, Nukada M, Yamamoto I, Hitaka Y, Tanaka M, Asakawa Y. Thelephantins A, B and C: three benzoyl p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta. Phytochemistry. 2003 Jan;62(1):109-13.
  2. ^ Gill, M., and Steglich, W. (1987) Pigments of fungi (Macromycetes). Prog Chem Org Nat Prod 51: 1–317.
  3. ^ Yue Qi Ye, Hiroyuki Koshino, Jun-ichi Onose, Chiemi Negishi, Kunie Yoshikawa, Naoki Abe, and Shunya Takahashi (2009). "Structural Revision of Thelephantin G by Total Synthesis and the Inhibitory Activity against TNF-α Production". J. Org. Chem. 74 (12): 4642–4645. doi:10.1021/jo900638b. PMID 19453155.{{cite journal}}: CS1 maint: multiple names: authors list (link)