Filicin

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
CAS Number	4482-83-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5060;
ChemSpider	170653;
ECHA InfoCard	100.022.516
EC Number	224-766-2;
KEGG	C10693;
PubChem CID	197044;
UNII	3OQ8CMM2OZ;
CompTox Dashboard (EPA)	DTXSID001101435 ;
	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,8-15H2,1-7H3 Key: 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−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]

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.^[3] Examples of filicins include:

Name(s)	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

^ "Filicin". TOXNET. U.S. National Library of Medicine.
^ 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.
^ Euw, J. v.; Lounasmaa, M.; Reichstein, T.; Widén, C.J. (1980). "Chemotaxonomy in Dryopteris and related fern genera". Studia Geobotanica. 1: 275–311.
^ 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.
^ ^a ^b 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.
^ ^a ^b Hisada, Sueo; Inoue, O.; Inagak, Isao (1973). "Phloroglucinol derivatives of Dryopteris sieboldii". Phytochemistry. 12 (8): 2055. doi:10.1016/s0031-9422(00)91535-8.
^ 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.

[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.

[Widen-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.

[Hisada-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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