Lonomycins
Title: Lonomycins
Literature References: Polyether antibiotics active against gram-positive bacteria, esp. coccidia. The major component is lonomycin A (initially named lonomycin). Lonomycin B and C are minor congeners. Isoln from Streptomyces ribosidificus strain TM-481 as sodium salt: M. Shibata et al., JP Kokai 75 49495 (1975 to Taisho Pharm.), C.A. 83, 191339p (1975); S. Omura et al., J. Antibiot. 29, 15 (1976). Identity of A with antibiotic DE-3936; fermentation, isolation, physicochemical properties and biological activity: M. Ohshima et al., ibid. 354. Structure of A: N. Otake, M. Koenuma, Tetrahedron Lett. 1975, 4147; C. Riche, C. Pascard-Billy, Chem. Commun. 1975, 951; of B, C: H. Seto et al., J. Antibiot. 31, 929 (1978); T. Mizutani et al., ibid. 33, 1224 (1980). 13C-NMR spectrum of A: H. Seto et al., ibid. 979. Ionophorous activity of A: M. Mitani, N. Otake, ibid. 31, 750 (1978). Cardiovascular effects of A: K. Kaneko et al., Res. Commun. Chem. Pathol. Pharmacol. 67, 17 (1990); K. Tsuchida et al., Arch. Int. Pharmacodyn. 314, 25 (1991). Total synthesis of A: D. A. Evans et al., J. Am. Chem. Soc. 117, 3448 (1995).
Properties: Sodium salts are sol in lower alcohols, acetone, ethyl acetate, benzene, chloroform, ether. Slightly sol in n-hexane, petr ether. Insol in water.
 
Derivative Type: Lonomycin A
CAS Registry Number: 58785-63-0
Additional Names: Antibiotic DE-3936; emericid
Molecular Formula: C44H76O14
Molecular Weight: 829.07
Percent Composition: C 63.74%, H 9.24%, O 27.02%
Properties: Colorless prisms from benzene-petr ether, mp 109-114°. [a]D20 +66.6° (c = 1 in CHCl3); [a]D23 +57.5° (c = 0.40 in CH2Cl2). pKa¢ (66% acetone) 5.9. Sol in most organic solvents. Insol in water.
Melting point: mp 109-114°
pKa: pKa¢ (66% acetone) 5.9
Optical Rotation: [a]D20 +66.6° (c = 1 in CHCl3); [a]D23 +57.5° (c = 0.40 in CH2Cl2)
 
Derivative Type: Lonomycin A sodium salt
CAS Registry Number: 58845-80-0
Molecular Formula: C44H75NaO14
Molecular Weight: 851.05
Percent Composition: C 62.10%, H 8.88%, Na 2.70%, O 26.32%
Properties: Colorless prisms from benzene-petr ether, mp 173-176° (dec) (Ohshima); also reported as mp 188-189° (Omura). [a]D25 +49.8° (c = 1 in CH3OH), [a]D25 +67.0° (c = 1 in CHCl3) (Ohshima); also reported as [a]D25 +47° (c = 1 in CH3OH) (Omura). LD50 in mice (mg/kg): 45.8 orally; 13.0 i.p.; 37.5 s.c. (Ohshima).
Melting point: mp 173-176° (dec) (Ohshima); mp 188-189° (Omura)
Optical Rotation: [a]D25 +49.8° (c = 1 in CH3OH); [a]D25 +67.0° (c = 1 in CHCl3); [a]D25 +47° (c = 1 in CH3OH) (Omura)
Toxicity data: LD50 in mice (mg/kg): 45.8 orally; 13.0 i.p.; 37.5 s.c. (Ohshima)
 
Derivative Type: Lonomycin B sodium salt
Molecular Formula: C44H75NaO14
Molecular Weight: 851.05
Percent Composition: C 62.10%, H 8.88%, Na 2.70%, O 26.32%
Properties: White prisms from n-hexane-benzene, mp 181-182°. [a]D +48.2° (c = 0.5 in CH3OH).
Melting point: mp 181-182°
Optical Rotation: [a]D +48.2° (c = 0.5 in CH3OH)
 
Derivative Type: Lonomycin C sodium salt
Molecular Formula: C43H73NaO14
Molecular Weight: 837.02
Percent Composition: C 61.70%, H 8.79%, Na 2.75%, O 26.76%
Properties: White prisms from n-hexane-benzene, mp 186-187°. [a]D +49.2° (c = 0.5 in CH3OH).
Melting point: mp 186-187°
Optical Rotation: [a]D +49.2° (c = 0.5 in CH3OH)

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