Verticillins
Title: Verticillins
Literature References: Three antibiotics, verticillins A, B and C, produced by a species of Verticillium (strain TM-759), an imperfect fungus isolated from a basidiocarp of Coltricia cinnamomea (Polystictus cinnamomeus). Isoln, IR, NMR spectra of verticillin A: Katagiri et al., J. Antibiot. 23, 420 (1970); see also Chepenko et al., C.A. 78, 156654n (1973). Structure: Minato et al., Chem. Commun. 1971, 44. Structure of verticillins A, B and C and absolute configuration of verticillins A and B: eidem, J. Chem. Soc. Perkin Trans. 1 1973, 1819. Synthetic studies: Häusler, Schmidt, Ber. 107, 2804 (1974); Schmidt et al., ibid. 2816.
 
Derivative Type: Verticillin A
CAS Registry Number: 32164-16-2
Molecular Formula: C30H28N6O6S4
Molecular Weight: 696.84
Percent Composition: C 51.71%, H 4.05%, N 12.06%, O 13.78%, S 18.41%
Properties: Pale yellow plates from chloroform, C30H28N6O6S4.CHCl3, mp 199-213° (dec); pale yellow needles from pyridine, C30H28N6O6S4.2/3C5H5N, mp 202-217° (dec); pale yellow amorphous powder from tetrahydrofuran, mp 203-214° (dec). [a]D +703.7° (c = 0.422 in dioxane). uv max (dioxane): 306 nm (e 5960). LD50 i.p. in mice: 7.6 mg/kg (Katagiri).
Melting point: mp 199-213° (dec); mp 202-217° (dec); mp 203-214° (dec)
Optical Rotation: [a]D +703.7° (c = 0.422 in dioxane)
Absorption maximum: uv max (dioxane): 306 nm (e 5960)
Toxicity data: LD50 i.p. in mice: 7.6 mg/kg (Katagiri)
 
Derivative Type: Verticillin B
CAS Registry Number: 52212-86-9
Molecular Formula: C30H28N6O7S4
Molecular Weight: 712.84
Percent Composition: C 50.55%, H 3.96%, N 11.79%, O 15.71%, S 17.99%
Properties: The mono-3-hydroxymethyl analog of verticillin A. Pale yellow prisms from chloroform, mp 230-233° (dec). [a]D21 +704.7° (c = 0.493 in dioxane). uv max (dioxane): 306 nm (e 5600).
Melting point: mp 230-233° (dec)
Optical Rotation: [a]D21 +704.7° (c = 0.493 in dioxane)
Absorption maximum: uv max (dioxane): 306 nm (e 5600)
 
Derivative Type: Verticillin C
Molecular Formula: C30H28N6O7S5
Molecular Weight: 744.90
Percent Composition: C 48.37%, H 3.79%, N 11.28%, O 15.04%, S 21.52%
Properties: Differs from verticillin B by having a trisulfide rather than disulfide bridge in one of the two dioxopiperazine rings. Pale yellow amorphous powder from methanol-water, mp 230-235° (dec). [a]D21 +765.0° (c = 0.506 in dioxane). uv max (dioxane): 303 nm (e 5500).
Melting point: mp 230-235° (dec)
Optical Rotation: [a]D21 +765.0° (c = 0.506 in dioxane)
Absorption maximum: uv max (dioxane): 303 nm (e 5500)

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