Misplaced Pages

Filicin

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Filicin
Names
IUPAC name 2-Butanoyl-4--2,4,6-trihydroxyphenyl]methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
Other names Filixic acid BBB; Filixic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.022.516 Edit this at Wikidata
EC Number
  • 224-766-2
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C36H44O12/c1-8-11-20(37)23-27(41)16(14-18-29(43)24(21(38)12-9-2)33(47)35(4,5)31(18)45)26(40)17(28(23)42)15-19-30(44)25(22(39)13-10-3)34(48)36(6,7)32(19)46/h40-46H,8-15H2,1-7H3Key: FRTCWDLFHSMTNW-UHFFFAOYSA-N
SMILES
  • CCCC(=O)C1=C(C(=C(C(=C1O)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)C)O)O)CC3=C(C(C(=O)C(=C3O)C(=O)CCC)(C)C)O)O
Properties
Chemical formula C36H44O12
Molar mass 668.736 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Filicin is a chemical compound that has been isolated from ferns of the genus Dryopteris. It has been isolated from the male fern (Dryopteris filix-mas). Filicin has been studied for its anthelmintic activity.

Related compounds

A variety of chemically related compounds, sometimes referred to collectively as filicins, have also been isolated from ferns. Chemical analysis of filicins in fern extracts can assist in determining taxonomy. Examples of filicins include:

Name(s) Chemical structure Molecular formula Molecular weight (g/mol) CAS number PubChem Notes and
references
Filixic acid ABA C32H36O12 612.63 38226-84-5 CID 15081408 from PubChem First isolated from Dryopteris dickinsii
Filixic acid ABP C33H38O12 626.66 57765-54-5 CID 73672225 from PubChem
Filixic acid ABB C34H40O12 640.68 37318-24-4 CID 102574620 from PubChem Found in Dryopteris sieboldii
Filixic acid PBP C34H40O12 640.68 51005-85-7 CID 20055092 from PubChem Found in Dryopteris sieboldii and Dryopteris filix-mas
Filixic acid PBB C35H42O12 654.71 49582-09-4 CID 20055091 from PubChem
Flavaspidic acid BB; Toxifren; Polystichocitrin; Glavaspidic acid C24H30O8 446.49 114-42-1 CID 8237 from PubChem Isolated from Dryopteris abbreviata

References

  1. "Filicin". TOXNET. U.S. National Library of Medicine.
  2. Heikinheimo, R (1963). "Effect of filicin administered as an anthelmintic on the coagulation factors of the blood". Annales Medicinae Internae Fenniae. 52: 93–6. PMID 13953368.
  3. Euw, J. v.; Lounasmaa, M.; Reichstein, T.; Widén, C.J. (1980). "Chemotaxonomy in Dryopteris and related fern genera". Studia Geobotanica. 1: 275–311.
  4. Hisada, Sueo; Shiraishi, Koichi; Inagaki, Isao (1972). "Pharmaceutical studies on Japanese ferns containing phloroglucinol derivatives. 9 Constituents of Dryopteris dickinsii". Yakugaku Zasshi. 92 (9): 1124–1128. doi:10.1248/yakushi1947.92.9_1124. PMID 4674828.
  5. ^ Widén, C. J; Lounasmaa, M; Sarvela, J (1975). "Phloroglucinol derivatives of eleven Dryopteris species from Japan". Planta Medica. 28 (2): 144–64. doi:10.1055/s-0028-1097844. PMID 1197418.
  6. ^ Hisada, Sueo; Inoue, O.; Inagak, Isao (1973). "Phloroglucinol derivatives of Dryopteris sieboldii". Phytochemistry. 12 (8): 2055. doi:10.1016/s0031-9422(00)91535-8.
  7. Coşkun, Maksut; Sakushima, Akiyo; Nishibe, Sansei; Hisada, Sueo; Tanker, Nevin (1982). "A phloroglucinol derivative of Dryopteris abbreviata". Phytochemistry. 21 (6): 1453. doi:10.1016/0031-9422(82)80168-4.
Category: