Streptomyces griseofuscus

Azinomycins A and B (64 and 65 Scheme 11.5) [115, 116] were isolated in 1986 from Streptomyces griseofuscus at the SS pharmaceutical company in Japan and were found to have potent in vitro cytotoxicities [117] and to display significant in vivo antitumor activity [118]. Since their discovery [117] and structure determination [119], their unusual molecular framework has attracted the attention of many chemists interested in their mode of action and in developing synthetic approaches to them [115,116]. The first total synthesis of azinomycin A was achieved in 2000 by Coleman et al. [120]. 

Naphthoic acid component (23b) carzinophylin A (azinomycin B) Streptomyces safutchiroi (Streptomyces griseofuscus)... 

In 1986, azinomycins A (1) and B (2) were isolated from the culture broth of Streptomyces griseofuscus 842227. They exhibit potent antitumor activity against a number of different... 

Streptomyces grieolus (anisomycin), 46 Streptomyces griseofuscus (azinomycins AandB), 212 Streptomyces griseoporeus... 

Klebsiella pneumoniae [22] <13> Mycoplasma capricolum [26] <14> Streptomyces lividans [28] <15> Streptomyces coelicolor [28] <16> Streptomyces griseofuscus [28]... 

Zhang J, Marcin C, Shifflet MA, Salmon P, Brix T, Greasham R, Buckland BC, Chartrain M (1996) Development of a defined medium fermentation process for physostigmine production by Streptomyces griseofuscus. Appl Microbiol Biotechnol 44 568-575... 

Despite the fact that physostigmine is an important pharmaceutical, no reports have appeared on efforts to produce this alkaloid by means of plant cell cultures. Daoust (737) reported the fermentative production of physostigmine by means of the microorganism Streptomyces griseofuscus. Iwasa et al. (738) employed Streptomyces pseudogriseo-lus for the production of physostigmine. Murao and Hayashi (739) isolated physostigmine and its N-8 nor derivative from Streptomyces sp. AH-4. 

Azinomycins A and B are a functionally complex family of antitumor agents isolated from fermentation broths of Streptomyces griseofuscus [14, 15]. Actually, azi-nomycin B turned out to be identical to carzinophilin, an antitumor agent isolated in 1954 from Streptomyces sahachiroi [16]. The azinomycins exhibit cytotoxicity at submicrogram per milliliter concentrations and show antitumor activity in mouse... 

C31H53N3O11, Mr 623.62, colorless needles, mp. 217-222°C, [aJu +57.8° (CHCI3). Antitumor antibiotic from Streptomyces sahachiroi and 5. griseofuscus. 

C,oH 5CIN403, Mr 274.71 monohydrate hygroscopic, amorphous powder, mp. >119°C (decomp.), [aJu 94.6° (aq. CH3OH). A structurally unusual, antifun-gally active pyridazinium derivative isolated as the hydrochloride from cultures of Streptomyces violaceus-niger ssp. griseofuscus. 

---