Chondromyces

Marine sponges of the genus Haliclona contain a diverse array of active secondary metabolites, including highly potent cytotoxic macrolides, e g., halichondrin and related compounds, Fig. (56) [468], and salicylihalamides A and B, Fig. (57) [469], New macrolides chemically related to salicylihalamides, apicularens A and B, were recently isolated from the myxobacteria Chondromyces sp. [470], From marine bacteria, other cytotoxic macrolides have been isolated, such as octalactin A, Fig. (58) and B, which have been shown as a cell cycle-specific anticancer drug [471], and swinholide, Fig. (59), isolated from symbiotic cyanobacteria with the marine sponge Theonella swinhoei [472]. 

The myxobacterium Chondromyces crocatus contains the novel chondrochlo-rens A (831) and B (832) (879). A marine Streptomyces species has afforded the manumycin antibiotics chinikomycins A (833) and B (834) (880). While inactive in antiviral, antimicrobial, and phytotoxicity screens, these chinikomycins display some cytotoxic activity. 

Jansen R, Kunze B, Reichenbach H, Hofle G (2003) Chondrochloren A and B, New (3-Amino Styrenes from Chondromyces crocatus (Myxobacteria). Eur J Org Chem 2684... 

Kunze B, Jansen R, Sasse F, Hofle G, Reichenbach (1995) Chondramides A-D, New Antifungal and Cytostatic Depsipeptides from Chondromyces crocatus (Myxobacteria). Production, Physico-Chemical and Biological Properties. J Antibiot 48 1262... 

Proteobacteria, Myxobacteria Chondromyces crocatus (chondramides A—D) [90]. F Basidiomycota Cortinarius violaceusa [5]. P Acanthaceae Aphelandra spp. (aphel-andrine, orantine [102]) Veronicaceae Chaenorhinum sp. [(S)-/ -Tyr chaenorhine, chaenorpine] [103]. 

Tyr substructures are, moreover, found within several peptidic antibiotics, for example the edeines 57 from Bacillus brevis, or within cyclodepsipeptides that have been isolated from marine sponges, for example jaspamides A-C 59 [106] or geo-diamolides H-I 58 [107] (Scheme 1.5.9). The chondramides 60 are closely related antibiotics that have been obtained from the myxobacterium Chondromyces croca-tus. Within the edeine biosynthesis D-/ -Tyr 9 seems to be a real precursor [89]. The biosynthesis of the jaspamides, the geodiamolides, or the chondramides has not yet been investigated. 

Figure 14 Biosynthesis of PKS-NRPS hybrid compounds in myxobacteria (b). Biosynthesis of chondramide D (34) in Chondromyces crocatus Cm c5. The DH domain from module 1 (marked with an asterisk) is most likely inactive. During the assembly of the chondramide backbone, an unusual extender unit - a /3-amino acid - is incorporated by NRPS module 6. The precursor is generated by the tyrosine amino mutase (TAM) CmdF, which converts L-tyrosine into R-/3-tyrosine (see box). The function of the terminal phosphoenolpyruvate synthase (PEP) domain is still unknown. Macrocyclization catalyzed by the TE domain yields chondramide C (40), which can be further transformed to the chlorinated derivative chondramide D (34). The halogenation process catalyzed by CmdE may also take place on the assembly line intermediate.

Kunze, B., Jansen, R., Sasse, R, Hofle, G., and Reichenbach, H. (1998). Apicularens A and B, new cytostatic macrolides from Chondromyces species (Myxobacteria) Production, physicochemical and biological properties. J. Antibiot. 51,1075-1080. 

Figure 7. Fruiting bodies of Myxobacteria. [a) Chondromyces pediculatus, [b] C. crocatus, [c] C. apiculatus, (d) Melittanglum boletus, (e) Myxococcus fulvus, [f] C. lanuginosus. Courtesy of Hans Reichenbach.

Overmann, J. et al (2016) Genome analysis of the fruiting body forming myxobacterium Chondromyces croca-tus reveals a high potential for natural product biosynthesis. Appl Environ. Microbiol, 82, 1945-1957. 

Chlamydomonas reinhardtii 606,607,609, 610,614-618,621-628 Chondromyces crocatus 457,465 chloramphenicol 513 Chlorella ellipsoidea 615 Chlorella protothecoides 628 Chlordla vulgaris 630 Chlorella zoofingensis 617 chloroplast genetic engineering... 

Present in various cooked foods. Prod, by Chondromyces crocatus. Liq. with peanut-like odour. Bpis 68-70° (as 1 1 mixt. with the 2,6-isomer), 1.4865. 

Among these Gram-negative bacteria, the genus Chondromyces crocatus holds a special place as it represents one of the most productive sources for... 

Rachid S, Krug D, Kunze B, Kochems I, Scharfe M, Zabriskie TM, Blocker H, Mueller R. Molecular and biochemical studies of chondramide formation-highly cytotoxic natural products from Chondromyces crocatus cm c5. Chem. Biol. 2006 13 667-681. 

Dialkylpyrazines (examples) Chondromyces crocatus Dickschat et al., 2005b... 

Dickschat J.S., Reichenbach, H., Wagner-Dobler, L, and Schulz, S. (2005b) Novel pyrazines from the myxobacterium Chondromyces crocatus and marine bacteria. Eur. J. Org. Chem., 4141—4153. 

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