Chemical Constituents from the Leaves of Manglietia phuthoensis and Their Effects on Osteoblastic MC3T3-E1 Cells

Abstract

Osteoporosis is characterized by a reduced bone mass, which results in increased bone fragility and fracture risk. Many osteoporotic patients have already lost a substantial amount of bone; therefore, a method of increasing bone mass by stimulating new bone formation is required. Bone is composed of mineralized organic matrix and bone cells. Osteoblasts are the active mature bone cells that synthesize the organic matrix and regulate its mineralization. Accelerated osteoblast growth and protein synthesis are the key factors for efficient bone repair. 1) Hormones, which regulate the calcium balance in the body, are used for the treatment of osteoporosis. The main action mechanism of these agents is the inhibition of bone resorption. However, a substance that inhibits bone resorption while stimulating bone formation would be more suitable for the treatment of bone diseases. There are several reports demonstrating improvement in clinical association with the use of traditional medicines in the treatment of fractures.2) Despite encouraging preliminary reports, basic sciences and clinical reports justifying the clinical application of specific traditional medicines are still not well established.Many plant-derived substances have been used as drugs for the treatment of various diseases since ancient times, and traditional oriental therapies are rich in phytotherapeutic regimens. These medications have fewer side effects and are more suitable for long-term use as compared to chemically synthesized medications. Plants belonging to the family Magnoliaceae are well known as rich sources of phenyl derivatives type neolignan and biphenyl ethers, which showed antimicrobial, muscle-relaxant, antifungal and cytotoxic activities.3-5) Manglietia phuthoensis DANDY (Magnolia phuthoensis DANDY), belonging to Magnoliaceae family, are woody trees distributed in northern Vietnam. In Vietnamese traditional medicine, the plant is used as an anti-inflammatory agent.6) Up to date, no study on phytochemistry and bioactivities of this plant has been reported.We report herein on the isolation and structural elucidation of two new phenyl glycosides, mangliesides A and B (1, 2), a new ionol glycoside, manglieside C (3), two new lignan glycosides, mangliesides D and E (4, 5), and two known compounds as 3-methoxymagnolol (6) and obovatol (7) from the leaves of M. phuthoensis. In an attempt to find pure lead compounds from plant origins to prevent bone loss without serious adverse side effects, we examined the effect of isolated compounds on the function of osteoblastic MC3T3-E1 cells, which has been well-characterized as an in vitro model for osteoblast differentiation. 7) Results and DiscussionsManglieside A (1) was isolated as a white amorphous powder, its molecular formula was suggested as C 15 A and B (1, 2), a new ionol glycoside, manglieside C (3), two new lignan glycosides, mangliesides D and E (4, 5), were isolated from the leaves of Manglietia phuthoensis, along with two known lignans, 3-methoxymagnolol (6) and obovatol (7). Their struc...

Chemical Constituents from the Stems of Ecdysanthera rosea

“…Its molecular formula C 25 H 32 O 11 was deduced by the positive HR-ESIMS m/z 531.1841 [M + Na] + . The NMR of 2 were very similar to the known compound manglieside D [13]. By comparison of the NMR data in literatures, the same structure segments of a 1,3,5-trisubstituted aromatic ring, a disubstituted E -configuration double bond and a sugar unit were confirmed [18, 19].…”

“…The present chemical investigation led to the isolation of three new compounds ( 1–3 ) (Fig. 1), and five known compounds: manglieside D ( 4 ) [13] erythro-guaiacylglycerol- β - O -4′-coniferyl alcohol ( 5 ) [14], (+)-(7 S ,8 R )-guaiacylglycerol ( 6 ) [15], isocopoletin ( 7 ) [16], evofolin-B ( 8 ) [17] from this plant. In addition, preliminary test showed that compound 1 was a moderate antibacterial constituent against Providensia smartii with MIC value of 12.5 μg/mL, but a weak antibacterial constituent against Enterococcus faecalis and Staphylococcus aureus with MIC value of 50 μg/mL and 50 μg/mL respectively.…”

Makomotines A to D from Makomotake, Zizania latifolia infected with Ustilago esculenta

“…The presence of a disaccharides including a -glucopyranosyl group was suggested by the characteristic chemical shifts and coupling constants of its 1 H NMR spectrum: -glucopyranosyl groupC 102.8 (C1), 74.9 (C2), 77.9 (C3), 71.6 (C4), 77.1 (C5), 68.7 (C6); H 4.80 (d, J=8.5 Hz, H1), 3.44 (dd, J=8.5, 8.5 Hz, H2), 3.40 (dd, J=8.5, 9.7 Hz, H3), 3.30 (m, H4), 3.51 (m, H5), 3.57 (dd, J=11.0, 7.3 Hz, H6a), 3 . These chemical shifts of each carbon and protons in the sugar part are very similar to those of manglieside B isolated from the leaves of Manglietia phuthoensis, 5 which possesses 6-O--D-apiofuranosyl--D-glucosyl moiety as the sugar part. The HMBC correlations confirmed the structure (in apiose; H1/C2, H1/C4, H2/C5, H4/C1, H4/C2, H4/C3, H5/C2, H5/C3, H5/C4: in Glc; H2/C3, H3/C2, H3/C4, H4/C3, H5/C3; between apiose and Glc; H1/C6).…”

“…Its molecular formula, C21H29NO10, which was determined by HRESIMS at m/z 478.1709 [M+Na] + (calcd for C21H29NO10Na, 478.1689), indicated the presence of eight degrees of unsaturation in the molecule. The 1 H and 13 C NMR data of the sugar part of 2 are very similar to those of 1 and manglieside B, 5 suggesting that this compound also possessed the same disaccharide as 1 ( Table 1). The aglycon, tryptophol moiety, was determined by HMBC and COSY correlations ( Figure 2); H1/C2, H1/C2, H1/C3, H1/C3a, H2/C1, H2/C3, H2/C1, H2/C3, H2/C3a, H2/C7a, H4/C3, H4/C3a, H4/C6, H4/C7a, H5/C3a, H5/C4, H5/C6, H5/C7, H5/C7a, H6/C3a, H6/C4, H6/C7, H6/C7a, H7/C2, H7/C3a, H7/C4, H7/C5 and H1/H2, H1/H2, H4/H5, H5/H6, H6/H7.…”

Chemistry and Neurotrophic Activities of (–)-Talaumidin and Its Derivatives

“…activity (Piao et al, 2008), superoxide anion scavenging activities (Sasaki et al, 2013), growth and differentiation of osteoblastic MC3T3-E1 (Kiem et al, 2008), anti-HIV-1 activities (Zhang et al, 2007;Warashima et al, 2008), downregulate cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS), and interleukin-1b (IL-1b) gene expressions in a dose-dependent manner in LPS-elicited mouse macrophages (Ma et al, 2007), inhibited NO production (Kim et al, 2014), anti-inflammatory activity (Wu et al, 2005), antimicrobial activities (Ding et al, 2014), antiproliferative activities against human cancer cell lines (Kim et al, 2011), and neurite-outgrowth promoting activity on PC12 cells (Kuroyanagi et al, 2008). On the other hands, biological activity of 1 has been documented as antiplasmodial activity (Abrantes et al, 2008) except for our reports, to date.…”