Filicin

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).[1] Filicin has been studied for its anthelmintic activity.[2]

Filicin
Names
IUPAC name
2-Butanoyl-4-[[3-butanoyl-5-[(5-butanoyl-2,6-dihydroxy-3,3-dimethyl-4-oxocyclohexa-1,5-dien-1-yl)methyl]-2,4,6-trihydroxyphenyl]methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
Other names
Filixic acid BBB; Filixic acid
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.022.516
EC Number
  • 224-766-2
KEGG
UNII
  • 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,8-15H2,1-7H3
    Key: FRTCWDLFHSMTNW-UHFFFAOYSA-N
  • 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
C36H44O12
Molar mass 668.736 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

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.[3] 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[4]
Filixic acid ABP C33H38O12 626.66 57765-54-5 CID 73672225 from PubChem [5]
Filixic acid ABB C34H40O12 640.68 37318-24-4 CID 102574620 from PubChem Found in Dryopteris sieboldii[6]
Filixic acid PBP C34H40O12 640.68 51005-85-7 CID 20055092 from PubChem Found in Dryopteris sieboldii[6] and Dryopteris filix-mas
Filixic acid PBB C35H42O12 654.71 49582-09-4 CID 20055091 from PubChem [5]
Flavaspidic acid BB; Toxifren; Polystichocitrin; Glavaspidic acid C24H30O8 446.49 114-42-1 CID 8237 from PubChem Isolated from Dryopteris abbreviata[7]

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.
  5. Widén, C. J; Lounasmaa, M; Sarvela, J (1975). "Phloroglucinol derivatives of eleven Dryopteris species from Japan". Planta Medica. 28 (2): 144–64. 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.
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