Bohemic acid

Source: Wikipedia, the free encyclopedia.

Bohemic acid is a mixture of chemical compounds which is obtained through fermentation by

La Bohème and many individual components of the acid carry the names of characters from La Bohème. Most of those components are antitumor agents and anthracycline antibiotics active against Gram-positive bacteria
.

Synthesis and fractions

Bohemic acid is produced through fermentation by an actinobacteria species in the genus Actinosporangium (Actinoplanaceae) in the order Actinomycetales. Specifically, strain C36145 (ATCC 31127) produces bohemic acid. The acid can be extracted from the fermentation broth with methyl isobutyl ketone under neutral or slightly basic pH conditions, and the fats and oils are removed by washing with petroleum ether.[1]

antibiotics pyrromycin and cinerubin A and B, reveals several individual components of bohemic acid, including alcindoromycin, bohemamine, collinemycin, marcellomycin, mimimycin, musettamycin, rudolphomycin and schaunardimycin. Their names originate from the characters Alcindoro, Colline, Marcello, Mimì, Musetta, Rodolfo (Rudolph) and Schaunard of the Puccini opera La Bohème, and the acid itself and the bohemamine component carry the name of the opera.[1][2][3] The suffix -mycin is conventionally added to indicate antibiotics derived from actinobacteria[4][5] or fungi.[6]

Properties

The individual components of bohemic acid are orange-red solids, the color originating from an optical absorption band centered at about 490 nm. Marcellomycin and mimimycin, and collinemycin and musettamycin are

stereoisomers, that is they have the same chemical compositions; however, one C-H and one COOCH3 group exchange places. Those two groups are attached to the same carbon atom of one carbon ring, they are marked by the blue star in their structure in the table (C-H group is not shown).[7] Nearly all components of bohemic acid are anthracycline antibiotic agents active against Gram-positive bacteria, but not against Gram-negative bacteria, yeasts or fungi. The most potent component of the acid is rudolphomycin[1] and the least potent is schaunardimycin, which is about 10 times weaker than musettamycin and 20 times weaker than marcellomycin.[8] The original studies on the individual components of bohemic acid have tested them all for antitumor activity in mice, upon intraperitoneal injection.[1][8] Furthermore, the antitumor pharmacokinetics of marcellomycin in the human blood has been evaluated both in vitro and in vivo.[9][10][11][12]

The median lethal dose (LD50) of marcellomycin depends strongly on the animal and varies from a few mg/kg of body weight (dogs) to 20 mg/kg (Suiss-Webster mice, intravenal injection), the major site of toxicity being the gastrointestinal tract.[13] Bohemamine has several structural varieties and derivatives, such as bohemamine B (C14H20N2O3), bohemamine C (C14H21N2O3), and 5-chlorobohemamine C (C14H20ClN2O3). None of them showed antibiotic, antifungal or antitumor activity.[14][15]

Some components of bohemic acids[7]
Name Formula M.p., °C
CAS number
Structure
Alcindoromycin C41H53NO17 150 72586-21-1
Bohemamine C14H18N2O3 200 72926-12-6
Collinemycin C36H45NO14 140 72598-49-3
Marcellomycin C42H55NO17 175 63710-10-1
Mimimycin C42H55NO17 155 72657-06-8
Musettamycin C36H45NO14 160 63710-09-8
Rudolphomycin C42H52N2O16 170 69245-38-1
Schaunardimycin C35H43NO14 93423-02-0

The bottom fragment of rudolphomycin is a cyclic (sugar) compound with a chemical formula C6H8NO3 and a proposed trivial name rednose.[7]

References