Brevione C

Brevione C
Names
	IUPAC name (2R,4'aS,6'aR,11'aR,11'bS)-3',4'a,6,7,7',11'a-hexamethylspiro[3H-furo[3,2-c]pyran-2,4'-5,6,6a,11b-tetrahydro-1H-cyclohepta[a]naphthalene]-4,9'-dione
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:205774;
ChemSpider	78436166; 26000631;
PubChem CID	139585565;
	InChI InChI=1S/C27H32O4/c1-15-13-19(28)9-11-25(5)21(15)10-12-26(6)22(25)8-7-16(2)27(26)14-20-23(31-27)17(3)18(4)30-24(20)29/h7,9,11,13,21-22H,8,10,12,14H2,1-6H3/t21-,22+,25-,26+,27-/m1/s1 Key: YIMHQYHZZQFOJT-YFSQZJJESA-N;
	SMILES CC1=CC[C@@H]2[C@@]([C@@]13CC4=C(O3)C(=C(OC4=O)C)C)(CC[C@H]5[C@]2(C=CC(=O)C=C5C)C)C;
Properties
Chemical formula	C27H32O4
Molar mass	420.549 g·mol−1
Appearance	Colorless solid
Melting point	247.7 °C (477.9 °F; 520.8 K) (decomposes)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Brevione C is a spiro diterpenoid fungal metabolite first isolated from Penicillium brevicompactum. Brevione C and related compounds have been shown to exhibit phytotoxic properties, while other members of the larger family of breviones may also act as cytotoxins or anti inflammatory agents.^[3]^[4] Originally extracted from biomaterial, a total synthesis route for brevione C, alongside breviones A and B, has been developed.^[2]^[4]

Proposed biosynthesis

The biosynthesis of brevione C is proposed to occur from precursor molecules originating from the mevalonate pathway for the diterpenic moiety, and a cyclic polyketide derivative originating from the acetate pathway.

Geranylgeranyl pyrophosphate is believed to condense with the cyclic polyketide derivative forming a universal precursor, which undergoes cyclization, oxidation and rearrangement steps to form the breviones B,A and C successively.^[4]

References

↑ PubChem. "Brevione C". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-07-07.
1 2 Yokoe, Hiromasa; Mitsuhashi, Chika; Matsuoka, Yoko; Yoshimura, Tomoyuki; Yoshida, Masahiro; Shishido, Kozo (2011-06-15). "Enantiocontrolled Total Syntheses of Breviones A, B, and C". Journal of the American Chemical Society. 133 (23): 8854–8857. Bibcode:2011JAChS.133.8854Y. doi:10.1021/ja202874d. ISSN 0002-7863. PMID 21557626. ^Supporting information p. 11
↑ Carrera, Ceferino; Chinchilla, Nuria; Fronczek, Frank R; Galindo, Juan CG; Macías, Francisco A (2015). "Structure–activity relationship studies of the phytotoxic properties of the diterpenic moiety of breviones". Pest Management Science. 71 (5): 701–711. Bibcode:2015PMSci..71..701C. doi:10.1002/ps.3831. hdl:10498/20319. ISSN 1526-4998. PMID 24839263.
1 2 3 Macías, Francisco A.; Varela, Rosa M.; Simonet, Ana M.; Cutler, Horace G.; Cutler, Stephen J.; Dugan, Frank M.; Hill, Robert A. (2000-12-01). "Novel Bioactive Breviane Spiroditerpenoids from Penicillium brevicompactum Dierckx". The Journal of Organic Chemistry. 65 (26): 9039–9046. doi:10.1021/jo0011078. ISSN 0022-3263. PMID 11149849.

[1] PubChem. "Brevione C". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-07-07.

[Yokoe-2] 1 2 Yokoe, Hiromasa; Mitsuhashi, Chika; Matsuoka, Yoko; Yoshimura, Tomoyuki; Yoshida, Masahiro; Shishido, Kozo (2011-06-15). "Enantiocontrolled Total Syntheses of Breviones A, B, and C". Journal of the American Chemical Society. 133 (23): 8854–8857. Bibcode:2011JAChS.133.8854Y. doi:10.1021/ja202874d. ISSN 0002-7863. PMID 21557626. ^Supporting information p. 11

[3] Carrera, Ceferino; Chinchilla, Nuria; Fronczek, Frank R; Galindo, Juan CG; Macías, Francisco A (2015). "Structure–activity relationship studies of the phytotoxic properties of the diterpenic moiety of breviones". Pest Management Science. 71 (5): 701–711. Bibcode:2015PMSci..71..701C. doi:10.1002/ps.3831. hdl:10498/20319. ISSN 1526-4998. PMID 24839263.

[EXTRACTION-4] 1 2 3 Macías, Francisco A.; Varela, Rosa M.; Simonet, Ana M.; Cutler, Horace G.; Cutler, Stephen J.; Dugan, Frank M.; Hill, Robert A. (2000-12-01). "Novel Bioactive Breviane Spiroditerpenoids from Penicillium brevicompactum Dierckx". The Journal of Organic Chemistry. 65 (26): 9039–9046. doi:10.1021/jo0011078. ISSN 0022-3263. PMID 11149849.

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