Published by De Gruyter

Volume 74 Issue 7-8

Issue of Zeitschrift für Naturforschung C

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Contents
Journal Overview

Publicly Available July 8, 2019

Frontmatter

Page range: i-iii

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Research Articles

May 14, 2019

Ishige sinicola extract stimulates osteoblast proliferation and differentiation via the bone morphogenetic protein 2/runt-related gene 2 signalling pathway

Mihyang Kim, Jeong Hyeon Kang, Geun Hye Oh, Mi Hwa Park

Page range: 167-174

Abstract

Osteoporosis is one of the most common bone diseases, occurring due to an imbalance between bone formation and bone resorption. The aim of this study was to investigate the effects of Ishige sinicola , a brown alga, on osteoblast differentiation through the activation of the bone morphogenetic protein 2 (BMP-2)/runt-related transcription factor 2 (Runx2) signalling pathway in MC3T3-E1 cells. A cell proliferation assay, alkaline phosphatase (ALP) activity assay, alizarin red staining, and expression analysis of osteoblastic genes were carried out to assess MC3T3-E1 cell proliferation and osteoblastic differentiation. We found that I. sinicola extract (ISE) increased cell proliferation in a dose-dependent manner. Ishige sinicola extract markedly promoted ALP activity and mineralization. Alizarin red S staining demonstrated that ISE treatment tended to increase extracellular matrix calcium accumulation. Moreover, ISE up-regulated the osteoprotegerin/receptor activator of nuclear factor κB ligand ratio. Ishige sinicola extract also increased the protein expression levels of type 1 collagen, ALP, osteocalcin, osterix, BMP-2, and Runx2. Therefore, ISE showed potential in stimulating osteoblastic bone formation, and it might be useful for the prevention and treatment of osteoporosis.

March 20, 2019

Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)

Armelle Tontsa Tsamo, Julio Issah Mawouma Pagna, Pamela Kemda Nangmo, Pierre Mkounga, Hartmut Laatsch, Augustin Ephrem Nkengfack

Page range: 175-182

Abstract

Three new limonoids, designated as rubescins F ( 1 ), G ( 2 ), and H ( 3 ), together with two known compounds of this type, TS1 ( 4 ) and trichirubine A ( 5 ), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F ( 1 ) is the first limonoid from Trichilia spp. with an oxetane ring between C-7 and C-14, which seems to be formed by the isomerization of TS1 ( 4 ). The γ-hydroxybutenolide rubescin G ( 2 ) is a potential precursor of trichirubine A ( 5 ), whereas rubescin H ( 3 ) is the first example of a triterpenoid with a single bond between C-7/C-14, forming a cyclopropane ring. The absolute configuration of these limonoids was derived from biosynthetic considerations and ab initio calculations of NMR and optical rotation dispersion data.

June 11, 2019

Impact of water-soluble zwitterionic Zn(II) phthalocyanines against pathogenic bacteria

Vanya Mantareva, Cem Gol, Vesselin Kussovski, Mahmut Durmuş, Ivan Angelov

Page range: 183-191

Abstract

The photodynamic impact of water-soluble zwitterionic zinc phthalocyanines (ZnPc1–4) was studied on pathogenic bacterial strains after specific light exposure (LED 665 nm). The structural differences between the studied ZnPc1–4 are in the positions and the numbers of substitution groups as well as in the bridging atoms (sulfur or oxygen) between substituents and macrocycle. The three peripherally substituted compounds (ZnPc1–3) are tetra-2-( N -propanesulfonic acid)oxypyridine (ZnPc1), tetra-2-( N -propanesulfonic acid)mercaptopyridine (ZnPc2), and octa-substituted 2-( N -propanesulfonic acid)mercaptopyridine (ZnPc3). The nonperipherally substituted compound is tetra-2-( N -propanesulfonic acid)mercaptopyridine (ZnPc4). The uptake and localization capability are studied on Gram (+) Enterococcus faecalis and Gram (−) Pseudomonas aeruginosa as suspensions and as 48 h biofilms. Relatively high accumulations of ZnPc1–4 show bacteria in suspensions with different cell density. The compounds have complete penetration in E. faecalis biofilms but with nonhomogenous distribution in P. aeruginosa biomass. The cytotoxicity test (Balb/c 3T3 Neutral Red Uptake) with ZnPc1–4 suggests the lack of dark toxicity on normal cells. However, only ZnPc3 has a minimal photocytotoxic effect toward Balb/c 3T3 cells and a comparable high potential in the photoinactivation of pathogenic bacterial species.

May 17, 2019

Influence of amide versus ester linkages on the anticancer properties of the new flavone–biotin conjugates

Monika Stompor, Marta Świtalska, Agata Bajek, Joanna Wietrzyk

Page range: 193-200

Abstract

Novel biotinylated C-6 substituted flavones were synthesised by a one-step method that connects biotin to 6-hydroxyflavone and 6-aminoflavone by esterification and amidation of hydroxyl and amino groups, respectively. The obtained compounds, 6- O -biotinylflavone and 6-biotinylamidoflavone, are the bifunctional molecules composed of a flavone moiety as a fluorescent reporter and biotin as a cancer-targeting unit. Antiproliferative activity was evaluated using SRB assays in MCF-7, MCF-10A, HepG2, MDA-MB-231, 4T1, and Balb/3T3 cell lines. In vitro evaluation revealed that compounds with biotin moiety displayed better cell selectivity between the cancer and normal cells than the parental substrates. These results indicate that anticancer effect is not related to the position of biotin moiety, but it is related to the presence of ester or amide bond. 6- O -Biotinylflavone was more active than 6-hydroxyflavone against human breast (MDA-MB-231) and liver (HepG2) cancer cells with IC 50 (concentration of tested agent that inhibits proliferation of the cell population by 50%) values equal to 78.5 ± 18.8 μM and 133.2 ± 14.2 μM, respectively. Non biotinylated 6-aminoflavone was more active than 6-biotinylamidoflavone against all tested cell lines, with IC 50 values between 34.3 ± 9.1 μM (4T1) and 173.86 ± 24.3 μM (MCF-7).

June 13, 2019

Metabolomic discrimination of the edible mushrooms Kuehneromyces mutabilis and Hypholoma capnoides (Strophariaceae, Agaricales) by NMR spectroscopy

Aino-Liisa Alanne, Jouni Issakainen, Kati Pihlaja, Johanna Jokioja, Jari Sinkkonen

Page range: 201-210

Abstract

Two edible, cultivable mushroom species of the family Strophariaceae, Kuehneromyces mutabilis (sheathed woodtuft) and Hypholoma capnoides (conifer tuft), were studied using proton nuclear magnetic resonance metabolomic approach. The variation in the metabolites of the two species and their metabolic behaviour regarding caps and stipes and different collection sites were analysed by multivariate analysis methods. Altogether 169 cap and stipe samples of the mushrooms were investigated. The clearest difference between the species was in the sugar composition, which was more diverse in H. capnoides . When mushroom samples collected from different locations were compared, more variance was found in H. capnoides , whereas K. mutabilis appeared more homogeneous as a species. As far as the caps and stipes were concerned, in both species the amount of α-α-trehalose was clearly higher in the stipes, and the caps contained a larger proportion of the amino acids and organic acids.

March 27, 2019

Components of rice husk biochar in promoting the growth, sporulation and iturin A production of Bacillus sp. strain IA

Shohei Ebe, Tatsuya Ohike, Masahiro Okanami, Takashi Ano

Page range: 211-217

Abstract

In a previously study, the Bacillus sp. strain IA was successfully isolated with high sensitivity to rice husk biochar (RHB). Moreover, RHB promoted an antibiotic iturin A production by strain IA. In order to develop the biocontrol agent, we attempted to reveal the functions of the RHB in promoting the production of iturin A by strain IA. The promotion effects of growth, sporulation and iturin A production of strain IA by the RHB were explained as follows. First, the manganese ion, released from RHB, promoted the sporulation and iturin A production of strain IA. Second, the silicon dioxide contained in RHB adsorbed the metabolic inhibitor(s) and promoted the iturin A production of strain IA. Finally, the combination of manganese ion and silicon dioxide promoted the growth, sporulation and iturin A production of the Bacillus sp. strain IA. To culture strain IA in the medium combining manganese ion and silicon dioxide, the total cells, spore cells and iturin A production increased 15 times, 10,000 times and 18 times higher than the control medium, respectively.

About this journal

Objective

A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal and a community resource for the emerging field of natural and natural-like products.

The journal publishes original research on the isolation (including structure elucidation), bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and their biological activity and innovative developed computational methods for predicting the structure and/or function of natural products.

A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) welcomes research papers in fields on the chemistry-biology boundary which address scientific ideas and approaches to generate and understand natural compounds on a molecular level and/or use them to stimulate and manipulate biological processes.

Topics

Bio-chemical synthesis and bioactivities of natural products
Isolation (including structure elucidation)
Biochemistry
Biotechnology
Pharmacology
Chemistry
Biology

Article formats

Original research articles, research notes, letters and review articles

Please have a look at the call for papers for two upcoming Special Issues:

Special Issue on CAZymes

Special Issue on Chitin Structures and Pathways as Targets for Biopesticides and Drugs