Inhibitory effects of sesquiterpene lactones from the Indonesian marine sponge Lamellodysidea cf. herbacea on bone morphogenetic protein-induced osteoblastic differentiation. (1st March 2021)

• Record Type: Journal Article
• Authors: Ohte, Satoshi; Yamazaki, Hiroyuki; Takahashi, Ohgi; Rotinsulu, Henki; Wewengkang, Defny S.; Sumilat, Deiske A.; Abdjul, Delfly B.; Maarisit, Wilmar; Kapojos, Magie M.; Zhang, Huiping; Hayashi, Fumiaki; Namikoshi, Michio; Katagiri, Takenobu; Tomoda, Hiroshi; Uchida, Ryuji
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 35(2021)
• Publication Date: 2021-03-01
• Subjects: bicyclolamellolactone A -- Sesquiterpene lactone -- Marine sponge Lamellodysidea cf. herbacea -- Bone morphogenic protein-induced alkaline phosphatase -- Fibrodysplasia ossificans progressive; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2021.127783
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A new unique sesquiterpene lactone, bicyclolamellolactone A (1 ), was isolated together with two known monocyclofarnesol-type sesquiterpenes, lamellolactones A (2 ) and B (3 ), from the Indonesian marine sponge Lamellodysidea sp. (cf. L. herbacea ). The planar structure of 1 was assigned based on its spectroscopic data (1D and 2D NMR, HRESIMS, UV, and IR spectra). The relative and absolute configuration of 1 was determined by comparison of its calculated and experimental electronic circular dichroism spectra in combination with NOESY correlations. Compounds 1 –3 inhibited bone morphogenic protein (BMP)-induced alkaline phosphatase activity in mutant BMP receptor-carrying C2C12 cells with IC50 values of 51, 4.6, and 20 μM, respectively.