ICM0201, a new inhibitor of osteoclastogenesis from Cunninghamella sp. F-1490. I. Taxonomy, fermentation, isolation and biological activities.

@article{Inoue2003ICM0201AN,
  title={ICM0201, a new inhibitor of osteoclastogenesis from Cunninghamella sp. F-1490. I. Taxonomy, fermentation, isolation and biological activities.},
  author={Hiroyuki Inoue and Hiroyuki Kumagai and Michiyo Osono and Motoko Matsufuji and Tomohiro Sameshima and Naoto Kawamura and Tetsuya Someno and Masaaki Ishizuka and Tomio Takeuchi},
  journal={The Journal of antibiotics},
  year={2003},
  volume={56 3},
  pages={
          209-13
        }
}
In the course of screening for inhibitors of osteoclastogenesis, a new substance designated as ICM0201 was isolated from a fermentation broth of Cunninghamella sp. F-1490. ICM0201 inhibited the formation of osteoclasts in mouse bone marrow cells with an IC50 value of 0.78 microg/ml and showed weak cytotoxicity against bone marrow cells. 
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ICM0201, a new inhibitor of osteoclastogenesis from Cunninghamella sp. F-1490. II. Structure determination and synthesis.
TLDR
The structure of ICM0201 was determined to be (3S,10aR)-3, 4a-dihydroxy-2,3,4,4a-tetrahydro-2H-pyrano[3,2-b]benzo[e]morpholine-9-carboxylic acid by spectroscopic analyses and chemical studies.
Small-molecule natural products: new structures, new activities.
Microbial metabolites and derivatives targeted at inflammation and bone diseases therapy: chemistry, biological activity and pharmacology
TLDR
Recent advances in the chemistry and analysis of inhibitors of prostaglandin release or other functional molecules of immune cells, as well as inducers of osteoblast differentiation are described, including biological and pharmacological activities.
ICM0201, a New Inhibitor of Osteoclastogenesis form Cunninghamella sp. F‐1490. Part 1. Taxonomy, Fermentation, Isolation and Biological Activities.

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ICM0201, a new inhibitor of osteoclastogenesis from Cunninghamella sp. F-1490. II. Structure determination and synthesis.
TLDR
The structure of ICM0201 was determined to be (3S,10aR)-3, 4a-dihydroxy-2,3,4,4a-tetrahydro-2H-pyrano[3,2-b]benzo[e]morpholine-9-carboxylic acid by spectroscopic analyses and chemical studies.
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