Journal
JOURNAL OF NATURAL PRODUCTS
Volume 83, Issue 8, Pages 2477-2482Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c00441
Keywords
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [15K01803]
- University of the Ryukyus Strategic Research Grant
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research
- BINDS) from the Japan Agency for Medical Research and Development (AMED) [JP19am0101099]
- Grants-in-Aid for Scientific Research [15K01803] Funding Source: KAKEN
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We discovered that majusculamide A (1) and majusculamide B (2), isolated from a marine cyanobacterium collected in Okinawa, induced osteoblast differentiation in MC3T3-E1 cells. Although majusculamide A (1) has a different configuration only at the C-19 stereocenter, bearing a methyl group, compared to majusculamide B (2), the effect of 1 was stronger than that of 2. We synthesized some analogues of the majusculamides (3-15) and evaluated osteogenic activities of these analogues. The structure-activity relationship study of majusculamide analogues suggested that the number of methyls and configuration at C-19 and the nature of the substituent at C-20 of majusculamide A (1) may be important for the osteoblast differentiation-inducing effect of 1.
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