12. QUINONES: STRUCTURE AND DISTRIBUTION
673
TABLE IV
BACTERIAL SOURCES OF VITAMIN K
a
Species
Azotobacter vinelandii
Bacillus brevis
B. cereus
B. mesentei icus
B. mycoides
B. subtilis
B. vulgatus
Bacterium aerogenes
B. flexneri
B. friedlanderi
B. proteus
Chromatium sp.
Erythrobacillus prodigiosus
Escherichia coli
Fishmeal
Mycobacterium phlei
M. tuberculosis
M. smegmatis
Salmonella typhosa
Sarcina lutea
Staphylococcus aureus
Streptomyces griseus
Method of identification
6
UV
P
CT
UV
CT
CT
CT
CT
CT
CT
CT
UV
CT
CT, UV
P
0
P
UV
CT
CT
CT
UV
Compound
—
^2(35)
—
—
—
—
—
—
K2(30), K2(35)
—
K 2 (45)
—
—
—
References
(83)
(181)
(173)
(83)
(173)
(173)
(173)
(173)
(173)
(173)
(173)
(83)
(173)
(83, 173)
(180, 183)
(177, 185)
(m) (83)
(173)
(173)
(173)
(83)
a More recent information will be found in reference 173a.
b Abbreviations: CT, chick test; O, isolated as an oil; P, isolated in crystalline form;
UV, ultraviolet absorption.
species by means of its characteristic ultraviolet absorption, before
and after reduction with potassium borohydride.
One of the species studied by Almquist was Mycobacterium tuberculosis, from which Anderson and Newmann (174) had previously isolated
phthiocol (3-hydroxy-2-methyl-l,4-naphthoquinone) by alkaline extraction of the acetone-soluble fraction of the lipids. This was found to have
antihemorrhagic activity and because the first compound to be used
successfully in vitamin K therapy (175). Phthiocol has also been obtained from Corynebacterium diphtheriae (176), but this, the first bacterial quinone to be positively identified, is almost certainly an artifact.
Snow et al. (177) were unable to detect phthiocol in fresh extracts of
M. tuberculosis but they did obtain a yellow oil having vitamin K properties, which gave phthiocol on alkaline hydrolysis. The possibility that
phthiocol might arise from vitamin K under alkaline conditions had
previously been suggested by Fieser et al. (178), who found that allylquinones in general react in this way, the allyl group being replaced by
673
TABLE IV
BACTERIAL SOURCES OF VITAMIN K
a
Species
Azotobacter vinelandii
Bacillus brevis
B. cereus
B. mesentei icus
B. mycoides
B. subtilis
B. vulgatus
Bacterium aerogenes
B. flexneri
B. friedlanderi
B. proteus
Chromatium sp.
Erythrobacillus prodigiosus
Escherichia coli
Fishmeal
Mycobacterium phlei
M. tuberculosis
M. smegmatis
Salmonella typhosa
Sarcina lutea
Staphylococcus aureus
Streptomyces griseus
Method of identification
6
UV
P
CT
UV
CT
CT
CT
CT
CT
CT
CT
UV
CT
CT, UV
P
0
P
UV
CT
CT
CT
UV
Compound
—
^2(35)
—
—
—
—
—
—
K2(30), K2(35)
—
K 2 (45)
—
—
—
References
(83)
(181)
(173)
(83)
(173)
(173)
(173)
(173)
(173)
(173)
(173)
(83)
(173)
(83, 173)
(180, 183)
(177, 185)
(m) (83)
(173)
(173)
(173)
(83)
a More recent information will be found in reference 173a.
b Abbreviations: CT, chick test; O, isolated as an oil; P, isolated in crystalline form;
UV, ultraviolet absorption.
species by means of its characteristic ultraviolet absorption, before
and after reduction with potassium borohydride.
One of the species studied by Almquist was Mycobacterium tuberculosis, from which Anderson and Newmann (174) had previously isolated
phthiocol (3-hydroxy-2-methyl-l,4-naphthoquinone) by alkaline extraction of the acetone-soluble fraction of the lipids. This was found to have
antihemorrhagic activity and because the first compound to be used
successfully in vitamin K therapy (175). Phthiocol has also been obtained from Corynebacterium diphtheriae (176), but this, the first bacterial quinone to be positively identified, is almost certainly an artifact.
Snow et al. (177) were unable to detect phthiocol in fresh extracts of
M. tuberculosis but they did obtain a yellow oil having vitamin K properties, which gave phthiocol on alkaline hydrolysis. The possibility that
phthiocol might arise from vitamin K under alkaline conditions had
previously been suggested by Fieser et al. (178), who found that allylquinones in general react in this way, the allyl group being replaced by