Thelephantins

Last updated
Thelephantins
Thelephantin A.svg
Thelephantin B.svg
Thelephantin C.svg
Thelephantin D.svg
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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]

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Pulvinone Chemical compound

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<i>Hydnellum</i> Genus of fungi in the family Bankeraceae

Hydnellum is a genus of tooth fungi in the family Bankeraceae. Widely distributed in the Northern Hemisphere, the genus contains around 40 species. The fruitbodies of its members grow by slowly enveloping nearby bits of grass and vegetation. There is great variability in the form of Hydnellum fruitbodies, which are greatly influenced by environmental conditions such as rainfall and humidity, drying winds, and temperature. They are too tough and woody to eat comfortably. Several species have become the focus of increasing conservation concern following widespread declines in abundance.

<i>Hydnellum aurantiacum</i>

Hydnellum aurantiacum is an inedible fungus, commonly known as the orange spine or orange Hydnellum for its reddish orange or rusty red colored fruit bodies. Like other tooth fungi, it bears a layer of spines rather than gills on the underside of the cap. Due to substantial declines in sightings, this species is listed as critically endangered in the United Kingdom.

<i>Polyozellus</i> Genus of fungus

Polyozellus is a fungal genus in the family Thelephoraceae, a grouping of mushrooms known collectively as the leathery earthfans. A monotypic genus, it contains the single species Polyozellus multiplex, first described in 1899, and commonly known as the blue chanterelle, the clustered blue chanterelle, or, in Alaska, the black chanterelle. The distinctive fruit body of this species comprises blue- to purple-colored clusters of vase- or spoon-shaped caps with veiny wrinkles on the undersurface that run down the length of the stem.

<i>Thelephora</i> Genus of fungi

Thelephora is a genus of fungi in the family Thelephoraceae. The genus has a widespread distribution and contains about 50 species. Fruit bodies of species are leathery, usually brownish at maturity, and range in shape from coral-like tufts to having distinct caps. Almost all species in the genus are thought to be inedible, but Thelephora ganbajun is a gourmet fungus in Yunnan province of southwest China.

Haematopodin Chemical compound

Haematopodin is the more stable breakdown product of Haematopodin B. Both compounds are found in the mushroom Mycena haematopus, although haematopodin only occurs in trace amounts in fresh fruit bodies. Similar pigments, known as batzellins and damirones, have been found in sea sponges. A chemical synthesis for haematopodin was reported in 1996. Key steps in the synthesis involved the addition of 3-[(2,4-dimethoxybenzyl)amino]-1-propanol to the indolo-6,7-quinone and cyclization of the resulting adduct with trifluoroacetic acid.

Ustalic acid Chemical compound

Ustalic acid is a naturally occurring chemical compound found in the poisonous mushroom Tricholoma ustale.

Variegatic acid Chemical compound

Variegatic acid is an orange pigment found in some mushrooms. It is responsible for the bluing reaction seen in many bolete mushrooms when they are injured. When mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions, specifically chinonmethid anions. It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form is variegatorubin, similar to xerocomorubin.

Norbadione A Chemical compound

Norbadione A is a pigment found in the bay bolete mushroom. A polyphenol, norbadione A is related to a family of mushroom pigments known as pulvinic acids. The molecule has also been reported as a potassium salt from the mushrooms Pisolithus tinctorius and Chalciporus piperatus.

Xerocomorubin Chemical compound

Xerocomorubin is a pigment from the fungus order Boletales. It is the oxidized form of isoxerocomic acid. Air oxidation is responsible its formation, and it oxidizes faster to a similar pulvinic acid type pigment oxidized variant, variegatorubin. The long wavelength has an absorption at 497 nm, 106 nm higher than its precursor isoxerocomic acid. Synthesis experiments have shown tetra-acetylation by acetic anhydride and sulfuric acid. Although xerocomorubin and variegatorubin give off the same deep red color and could simultaneously occur in a mushroom, extracts from the deep red colored mushroom Boletus rubellus Krombh. identified only variegatorubin by thin layer chromatography (TLC), leading to the question the natural abundance of xerocomorubin.

<i>Thelephora terrestris</i>

Thelephora terrestris is an inedible species of fungus in the Basidiomycota phylum. It is commonly known by the name Common Fiber Vase because of its circular and overlapping cap. As well, it has also been called the Earthfan fungus.

References

  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)