The conversion of exogenous p-hydroxybenzaldehyde to p-hydroxy-methyl-phenol-beta-D-glucoside (gastrodin) was studied by using cell suspension culture of Datura tatula L. The chemical structure of this synthesized gastrodin was identified based on the spectral analysis and chemical evidence. The conversion procedure of p-hydroxybenzaldehyde into gastrodin by D. tatula L. cell suspension cultures was established. The synthesized gastrodin (II) was isolated from the ferment liquor and identified by spectral analysis. At the same time, the p-hydroxybenzyl alcohol (I) converted through biotransformation of p-hydroxybenzaldehyde by cell suspension cultures of D. tatula L. was also isolated and identified. The efficiency of glucosylation of p-hydroxybenzaldehyde was remarkably enhanced by adding salicylic acid (0.1 mg/L) and keeping the lower pressure (0.001MPa) in 25L airlift loop bioreactor. The biotransformation of exogenous p-hydroxybenzaldehyde to gastrodin by cell suspension culture of D. tatula L. is a promising approach.
Benzaldehydes ; metabolism ; Benzyl Alcohols ; chemistry ; Bioreactors ; Biotransformation ; Datura ; metabolism ; Glucosides ; biosynthesis ; chemistry ; Salicylic Acid ; pharmacology ; Suspensions

Marine fungi are important members of the marine microbiome, which have been paid growing attention by scientists in recent years. The secondary metabolites of marine fungi have been reported to contain rich and diverse compounds with novel structures (Chen et al., 2019). Aspergillus terreus, the higher level marine fungus of the Aspergillus genus (family of Trichocomaceae, order of Eurotiales, class of Eurotiomycetes, phylum of Ascomycota), is widely distributed in both sea and land. In our previous study, the coral-derived A. terreus strain C23-3 exhibited potential in producing other biologically active (with antioxidant, acetylcholinesterase inhibition, and anti-inflammatory activity) compounds like arylbutyrolactones, territrems, and isoflavones, and high sensitivity to the chemical regulation of secondary metabolism (Yang et al., 2019, 2020; Nie et al., 2020; Ma et al., 2021). Moreover, we have isolated two different benzaldehydes, including a benzaldehyde with a novel structure, from A. terreus C23-3 which was derived from Pectinia paeonia of Xuwen, Zhanjiang City, Guangdong Province, China.
Acetylcholinesterase/metabolism* ; Animals ; Anthozoa/microbiology* ; Anti-Inflammatory Agents/pharmacology* ; Aspergillus/chemistry* ; Benzaldehydes/pharmacology* ; Mice ; RAW 264.7 Cells ; Signal Transduction

OBJECTIVETo investigate the chemical constituents of red alga Corallina pilulifera.

METHODCompounds were isolated by normal phase silica gel and Sephadex LH - 20 gel column chromatography, reverse phase HPLC and recrystallization. Their structures were elucidated by spectroscopic methods including MS, 1H-NMR, 13C-NMR, HSQC, HMBC. Cytotoxicity of the compounds was screened by using standard MTT method.

RESULTSeven compounds were isolated from red alga C. pilulifera, their structures were identified as (E) -phytol epoxide (1), phytenal (2), phytol (3), dehydrovomifoliol (4), loliolide (5), 3beta-hydroxy-5alpha, 6alpha-epoxy-7-megastigmene-9-one (6), 4-hydroxybenzaldehyde (7).

CONCLUSIONAll of the compounds were obtained from this species for the first time. These compounds were inactive (IC50 > 10 microg x mL(-1)) in the MTT assay.

Benzaldehydes ; chemistry ; isolation & purification ; pharmacology ; Benzofurans ; chemistry ; isolation & purification ; pharmacology ; Cell Line, Tumor ; drug effects ; Humans ; Phytol ; chemistry ; isolation & purification ; pharmacology ; Rhodophyta ; chemistry

OBJECTIVETo study the effects of mineral cations on the growth of Salvia niltiorrhiza adventitious roots and the accumulation of tanshinone II A and protocatechuic aldehyde.

METHODThe adventitious roots were cultured under different concentrations of metal cations and the contents of tanshinone II A and protocatechuic aldehyde were determined by HPLC.

RESULTFe2 + and Mn2+ in MS medium are suitable for adventitious root growth, but Cu2+ and Mg2+ in high concentration could improve root proliferation, and Zn2+ has no obvious effect on root growth. As for tanshinone II A and protocatechuic aldehyde biosynthesis, Cu2+ and Zn2+ would inhibit the biosynthesis of protocatechuic aldehyde, furthermore, proper Fe2+ and Mg2+ concentration could advance the biosynthesis of protocatechuic aldehyde, whereas, Mn2+ in high concentration could accelerate the biosynthesis of protocatechuic aldehyde. Cu2+, Zn2+, Mg2+ in low concentration and Fe2+ and Mn2+ in high concentration would all advance the biosynthesis of tanshinone II A.

CONCLUSIONThe mineral cations have obvious effects on the secondary metabolites biosynthesis in adventitious root culture of S. niltiorrhiza.

Benzaldehydes ; metabolism ; Catechols ; metabolism ; Copper ; pharmacology ; Diterpenes, Abietane ; Iron ; pharmacology ; Magnesium ; pharmacology ; Manganese ; pharmacology ; Phenanthrenes ; metabolism ; Plant Roots ; growth & development ; metabolism ; Plants, Medicinal ; growth & development ; metabolism ; Salvia miltiorrhiza ; growth & development ; metabolism ; Tissue Culture Techniques ; Zinc ; pharmacology

OBJECTIVETo investigate the chemical constituents from the tuber of the planted Cremastra appendiculata.

METHODThe compounds were isolated by column chromatography over silica gel, Sephadex LH-20 and RP-HPLC, and their structures were elucidated on the basis of spectroscopic analysis.

RESULTEight compounds were isolated, and identified as cirrhopetalanthrin (I), 7-hydroxy-4-methoxyphenanthrene-2-O-beta-D-glucoside (II), 4-(2-hydroxyethyl)-2-methoxyphenyl-1-O-beta-D-glucopyranoside (III), tyrosol 8-O-beta-D-gluco-pyranoside (IV), vanilloloside (V), p-hydroxybenzaldehyde (VI), sucrose (VII), adenosine (VIII).

CONCLUSIONThese compounds are isolated from this plant for the first time. All compounds were evaluated against human colon cancer (HCT-8), human hepatoma (Bel7402), human stomach cancer(BGC-823), human lung adenocarcinoma (A549), human breast cancer (MCF-7), and human ovarian cancer (A2780) cell lines, and cirrhopetalanthrin (I) showed non-selective moderate cytotoxicity with IC50 values of 8.4-13.3 micromol x L(-1), and other compounds were inactive.

Adenosine ; chemistry ; isolation & purification ; pharmacology ; Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; Benzaldehydes ; chemistry ; isolation & purification ; pharmacology ; Cell Line, Tumor ; drug effects ; Humans ; Inhibitory Concentration 50 ; Orchidaceae ; chemistry ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Sucrose ; chemistry ; isolation & purification ; pharmacology

OBJECTIVETo study the predominant calcium-antagonist components of Danshen injection.

METHODThe effects of danshensu, protocatechualdehyde and Danshen injection on calcium concentration in cytoplasm of erythrocytes were examined in vitro by the fluorescent Ca+ -chelator fura-2.

RESULTEither DS182 or PCAD can decrease in dose-dependent cytosolic free calcium concentration in human erythrocytes. They had additive effect when mixed, which was similar to Danshen injection.

CONCLUSIONDS182 and PCAD may be predominant calcium-antagonist components of Danshen injection.

Adult ; Benzaldehydes ; isolation & purification ; pharmacology ; Calcium ; metabolism ; Catechols ; isolation & purification ; pharmacology ; Cytoplasm ; metabolism ; Drug Synergism ; Drugs, Chinese Herbal ; isolation & purification ; pharmacology ; Erythrocytes ; metabolism ; Female ; Humans ; Injections ; Lactates ; isolation & purification ; pharmacology ; Male ; Middle Aged ; Plants, Medicinal ; chemistry ; Salvia miltiorrhiza ; chemistry

OBJECTIVETo study the culture of adventitious root of Salvia miltiorrhiza in vitro systemically.

METHODEffects of sucrose concentrations, medium pH, inoculum size and plant growth regulators on adventitious root growth and secondary metabolites production in S. miltiorrhiza were investigated.

RESULTWith the increase of initial sucrose concentration, adventitious root growth rates increased and tanshinone II A content decreased, while content of protocatechuic aldehyde showed a broken line change and its highest production was obtained under 30 g x L(-1) sucrose in the medium. As for the effect of medium pH, medium pH of 6.5, 5.5 (or 6.0) and 5.8 was favorable for adventitious root growth, tanshinone II A and protocatechuic aldehyde synthesis respectively. Furthermore, adventitious root growth, rate was greatly increased when inoculum size was 2.5%. MS medium added with 0.5 mg x L(-1) KT was much favorable for tanshinone II A and protocatechuic aldehyde accumulation.

CONCLUSIONParameters including sucrose concentrations, medium pH, inoculum size and plant growth regulators have distinct effects on the in vitro culture of adventitious root growth and secondary metabolites synthesis of S. miltiorrhiza.

Benzaldehydes ; metabolism ; Catechols ; metabolism ; Culture Media ; Diterpenes, Abietane ; Hydrogen-Ion Concentration ; Phenanthrenes ; metabolism ; Plant Growth Regulators ; pharmacology ; Plant Roots ; growth & development ; metabolism ; Plants, Medicinal ; growth & development ; metabolism ; Salvia miltiorrhiza ; growth & development ; metabolism ; Sucrose ; Tissue Culture Techniques

OBJECTIVE: The current study aimed to elucidate the effect of vanillin on behavioral changes, oxidative stress, and histopathological changes induced by potassium bromate (KBrO3), an environmental pollutant, in the cerebellum of adult mice. METHODS: The animals were divided into four groups: group 1 served as a control, group 2 received KBrO3, group 3 received KBrO3 and vanillin, and group 4 received only vanillin. We then measured behavioral changes, oxidative stress, and molecular and histological changes in the cerebellum. RESULTS: We observed significant behavioral changes in KBrO3-exposed mice. When investigating redox homeostasis in the cerebellum, we found that mice treated with KBrO3 had increased lipid peroxidation and protein oxidation in the cerebellum. These effects were accompanied by decreased Na+-K+ and Mg2+ ATPase activity and antioxidant enzyme gene expression when compared to the control group. Additionally, there was a significant increase in cytokine gene expression in KBrO3-treated mice. Microscopy revealed that KBrO3 intoxication resulted in numerous degenerative changes in the cerebellum that were substantially ameliorated by vanillin supplementation. Co-administration of vanillin blocked the biochemical and molecular anomalies induced by KBrO3. CONCLUSION Our results demonstrate that vanillin is a potential therapeutic agent for oxidative stress associated with neurodegenerative diseases.
Animals ; Antioxidants ; metabolism ; Behavior, Animal ; drug effects ; Benzaldehydes ; pharmacology ; Bromates ; toxicity ; Cerebellum ; drug effects ; metabolism ; pathology ; Cytokines ; genetics ; metabolism ; Environmental Pollutants ; toxicity ; Gene Expression ; drug effects ; Lipid Peroxidation ; drug effects ; Mice ; Oxidative Stress ; drug effects ; Rotarod Performance Test

OBJECTIVETo study the chemical constituents in fruit of Alpinia oxyphylla and their cytotoxicities on cancer cell lines.

METHODCompounds were isolated and purified by various column chromatographic methods. Their structures were determined by physico-chemical properties and spectral analyses. Compound cytotoxicity was assessed by the sulforhodamine B (SRB) assay.

RESULTEight compounds were obtained from Me2CO-H2O (70%) extract of the fruit of A. oxyphylla and their structures were identified as: (9E)-humulene-2, 3; 6, 7-diepoxide (1), 3(12), 7(13), 9(E)-humulatriene-2, 6-diol (2), (-)-oplopanone (3), yakuchinone A (4), yakuchinone B (5), tectochrysin (6), isovanillin (7), (2E, 4E)-6-hydroxy-2, 6-dimethylhepta-2, 4-dienal (8), and the cytotoxicities of compounds 1, 3-5 on cancer cell lines, A549, HT-29 and SGC-7901, were also investigated.

CONCLUSIONCompounds 1-3, 7, 8 were isolated for the first time from this genus and compounds 1, 3-5 exhibited no cytotoxicity against three cancer cell lines at a concentration of 10 mg x L(-1).

Alpinia ; chemistry ; Benzaldehydes ; chemistry ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Cell Survival ; drug effects ; Diarylheptanoids ; chemistry ; isolation & purification ; pharmacology ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; Flavonoids ; chemistry ; isolation & purification ; pharmacology ; Fruit ; chemistry ; Guaiacol ; analogs & derivatives ; chemistry ; isolation & purification ; pharmacology ; HT29 Cells ; Humans

ATP-binding cassette transporter A1 (ABCA1) promotes cholesterol and phospholipid efflux from cells to lipid-poor apolipoprotein A-I (apoA-I), and plays a key role in the initial steps of the whole process of reverse cholesterol transport (RCT). Upregulation of ABCA1 is beneficial for atherosclerosis (AS) prevention and/or therapy, which indicated that ABCA1 was a target for anti-AS drug development. In the previous study, a high-throughput screening method was established using ABCA1p-LUC HepG2 cell line to find the upregulators of ABCA1. In the present study, compound 2030421B was found using this method, with EC50 of 0.50 microg x mL(-1). The compound was further identified as an upregulator of ABCA1 expression by real-time quantitative reverse transcription-polymerase chain reaction (RT-PCR) and Western blotting analysis. Studies also showed that the 2030421B could induce apoA-I-mediated cholesterol efflux and inhibit lipids uptake into mouse peritoneal macrophages RAW264.7.
ATP Binding Cassette Transporter 1 ; ATP-Binding Cassette Transporters ; genetics ; metabolism ; Animals ; Anticholesteremic Agents ; administration & dosage ; chemistry ; pharmacology ; Apolipoprotein A-I ; metabolism ; Benzaldehydes ; administration & dosage ; chemistry ; pharmacology ; Biological Transport ; Cells, Cultured ; Cholesterol ; secretion ; Dose-Response Relationship, Drug ; Hep G2 Cells ; High-Throughput Screening Assays ; Humans ; Lipid Metabolism ; Lipids ; analysis ; Macrophages, Peritoneal ; cytology ; metabolism ; Mice ; Molecular Structure ; RNA, Messenger ; Up-Regulation ; drug effects