Filicin

Last updated
Filicin
Filicin.svg
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
PubChem CID
UNII
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

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]

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 Filixic acid ABA.svg C32H36O12612.6338226-84-5 CID 15081408 from PubChem First isolated from Dryopteris dickinsii [4]
Filixic acid ABP Filixic acid ABP.svg C33H38O12626.6657765-54-5 CID 73672225 from PubChem [5]
Filixic acid ABB Filixic acid ABB.svg C34H40O12640.6837318-24-4 CID 102574620 from PubChem Found in Dryopteris sieboldii [6]
Filixic acid PBP Filixic acid PBP.svg C34H40O12640.6851005-85-7 CID 20055092 from PubChem Found in Dryopteris sieboldii [6] and Dryopteris filix-mas
Filixic acid PBB Filixic acid PBB.svg C35H42O12654.7149582-09-4 CID 20055091 from PubChem [5]
Flavaspidic acid BB; Toxifren; Polystichocitrin; Glavaspidic acid Flavaspidic acid BB.svg C24H30O8446.49114-42-1 CID 8237 from PubChem Isolated from Dryopteris abbreviata [7]

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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. 1 2 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. 1 2 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.