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PubMed2025

Transcriptome and metabolome profiling of the medicinal plant Dictamnus dasycarpus reveal key genes involved in quinoline alkaloids biosynthesis and limonoids biosynthesis.

BACKGROUND: As a member of Rutaceae family, Dictamnus dasycarpus Turcz. represents a prominent medicinal plant and economically valuable crop in traditional Chinese medicine, and is renowned for its therapeutic efficacy in treating dermatological conditions. The pharmacological activity of this species primarily stems from quinoline alkaloids and limonoids, which predominantly accumulate in the taproots. These bioactive compounds serve as critical determinants of both medicinal quality and crop yield. Nevertheless, the molecular mechanisms governing their dynamic accumulation patterns in D. dasycarpus taproots remain uncertain, and the fundamental biochemical basis underlying this process has yet to be elucidated. RESULTS: Metabolomic and transcriptomic analyses were carried out to investigate metabolites and gene expression during the development of D. dasycarpus taproots. The differentially accumulated secondary metabolites (DAMs) mainly included quinoline alkaloids and limonoids, and the accumulation of total alkaloids and total limonoids primarily occurred during 2- and 4-year-old. The differentially expressed genes (DEGs) are related to Glycolysis/Gluconeogenesis, Phenylalanine, tyrosine and tryptophan biosynthesis, Tryptophan metabolism, Terpenoid backbone biosynthesis, Sesquiterpenoid and triterpenoid biosynthesis, which had a close relationship with the accumulation of quinoline alkaloids and limonoids. Furthermore, we identified that some CYP450s, acetyltransferase, isomerase, 2-ODDs and others may play an important role in the process of producing quinoline alkaloids and limonoids. CONCLUSION: These results elucidated the molecular mechanisms and metabolic changes underlying the dynamic accumulation process occurring in the taproots of D. dasycarpus. These findings provide a theoretical basis for the planting and harvesting of D. dasycarpus.

Limonins↗
PubMed2004

Dietary flavonoids and cancer risk: evidence from human population studies.

High dietary intake of fruits and vegetables is consistently associated with a reduced risk of common human cancers, including cancers of the lung, breast, prostate, and colon. It is unknown which bioactive compound or compounds in plant foods provide the chemoprotective effects. One class of compounds currently under investigation is flavonoids, a large group of compounds with similar structure, consisting of two phenolic benzene rings linked to a heterocyclic pyran or pyrone. Although there are numerous in vitro and animal model data suggesting that flavonoids influence important cellular and molecular mechanisms related to carcinogenesis, such as cell cycle control and apoptosis, there are limited data from human population studies. This article reviews data from four cohort studies and six case-control studies, which have examined associations of flavonoid intake with cancer risk. There is consistent evidence from these studies that flavonoids, especially quercetin, may reduce the risk of lung cancer. Further research using new dietary databases for food flavonoid content is needed to confirm these findings before specific public health recommendations about flavonoids can be formulated.

Antioxidants↗
PubMed2005

Cyanidin 3-glucoside and peonidin 3-glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo.

Dietary polyphenols, including anthocyanins, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, anticancer effects of peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the inhibitory effect of cyanidin 3-glucoside for tumor cell growth. Therefore, in this study, we have isolated and identified the two bioactive compounds, peonidin 3-glucoside and cyanidin 3-glucoside, from Oryza sativa L. indica, to treat various cancer cells. The results showed that, among analyzed cell lines, HS578T was the most sensitive to peonidin 3-glucoside and cyanidin 3-glucoside. Treatment with peonidin 3-glucoside or cyanidin 3-glucoside resulted in a strong inhibitory effect on cell growth via G2/M arrest. Regarding cell cyclerelated proteins, peonidin 3-glucoside treatment resulted in down-regulation of protein levels of cyclin-dependent kinase (CDK)-1, CDK-2, cyclin B1, and cyclin E, whereas cyanidin 3-glucoside could decrease the protein levels of CDK-1, CDK-2, cyclin B1, and cyclin D1. In addition, cyanidin 3-glucoside or peonidin 3-glucoside also induced caspase-3 activation, chromatin condensation, and cell death. Furthermore, anthocyanins from O. sativa L. indica were evidenced by their inhibition on the growth of Lewis lung carcinoma cells in vivo.

Animals↗
PubMed2002

The phospholipids sphingosine-1-phosphate and lysophosphatidic acid prevent apoptosis in osteoblastic cells via a signaling pathway involving G(i) proteins and phosphatidylinositol-3 kinase.

The naturally occurring phospholipids lysophosphatidic acid (LPA) and sphingosine-1-phosphate (S1P) have recently emerged as bioactive compounds that exert mitogenic effects in many cell types, including osteoblasts. In the current study, we examined the ability of each of these compounds to influence osteoblast survival. Using terminal deoxynucleotidyl transferase-mediated deoxyuridine 5'-triphosphate nick-end labeling and DNA fragmentation assays, we found that both LPA and S1P dose-dependently inhibited (by at least 50% and 40%, respectively) the apoptosis induced by serum withdrawal in cultures of primary calvarial rat osteoblasts and SaOS-2 cells. The antiapoptotic effects were inhibited by pertussis toxin, wortmannin, and LY294002, implicating G(i) proteins and phosphatidylinositol-3 kinase (PI-3 kinase) in the signaling pathway that mediates phospholipid-induced osteoblast survival. Specific inhibitors of p42/44 MAPK signaling did not block LPA- or S1P-induced osteoblast survival. LPA and S1P induced PI-3 kinase-dependent activation of p70 S6 kinase, but rapamycin, a specific inhibitor of p70 S6 kinase activation, did not prevent phospholipid-induced osteoblast survival. LPA and S1P also inhibited apoptosis in Swiss 3T3 fibroblastic cells in a G(i) protein-dependent fashion. In fibroblastic cells, however, the antiapoptotic effects of S1P were sensitive to inhibition of both PI-3 kinase and p42/44 MAPK signaling, whereas those of LPA were partially abrogated by inhibitors of p42/44 MAPK signaling but not by PI-3 kinase inhibitors. These data demonstrate that LPA and S1P potently promote osteoblast survival in vitro, and that cell-type specificity exists in the antiapoptotic signaling pathways activated by phospholipids.

Animals↗
PubMed2001

Pharmacognosy in the 21st century.

The term pharmacognosy as a constituent scientific discipline of pharmacy has been in use for nearly 200 years, and it refers to studies on natural product drugs. During the last half of the 20th century, pharmacognosy evolved from being a descriptive botanical subject to one having a more chemical and biological focus. At the beginning of the 21st century, pharmacognosy teaching in academic pharmacy institutions has been given new relevance, as a result of the explosive growth in the use of herbal remedies (phytomedicines) in modern pharmacy practice, particularly in western Europe and North America. In turn, pharmacognosy research areas are continuing to expand, and now include aspects of cell and molecular biology in relation to natural products, ethnobotany and phytotherapy, in addition to the more traditional analytical method development and phytochemistry. Examples are provided in this review of promising bioactive compounds obtained in two multidisciplinary natural product drug discovery projects, aimed at the elucidation of new plant-derived cancer chemotherapeutic agents and novel cancer chemopreventives, respectively. The systematic study of herbal remedies offers pharmacognosy groups an attractive new area of research, ranging from investigating the biologically active principles of phytomedicines and their mode of action and potential drug interactions, to quality control, and involvement in clinical trials.

Animals↗
PubMed2002

RNA-acting antibiotics: in-vitro selection of RNA aptamers for the design of new bioactive molecules less susceptible to bacterial resistance.

During the last few years, antibiotic multiresistance has been increasing, not only in hospitals, but also, more worryingly, in general medicine. Different ways are being explored to bypass this problem. RNA-acting antibiotics such as aminosides (aminoglycosides) bind to bacterial RNA causing premature termination of proteins and mistranslation in bacteria. It is now possible to study the interactions of such antibiotics with their target by in-vitro selection of RNA molecules that recognize these antibiotics (RNA aptamers, SELEX method). The knowledge of the antibiotic-RNA interactions represents a promising way for the rational design of new bioactive compounds less susceptible to bacterial resistance.

Aminoglycosides↗
PubMed2004

Quantitative analysis of phagolysosome fusion in intact cells: inhibition by mycobacterial lipoarabinomannan and rescue by an 1alpha,25-dihydroxyvitamin D3-phosphoinositide 3-kinase pathway.

Macrophage cell membranes were labeled with PKH26 and subsequently incubated with latex beads to generate phagosomes surrounded by a red-fluorescent membrane suitable for flow cytometry. Following cell disruption and partial purification of phagosomes, these vesicles were readily distinguished from both cell debris and free beads released from disrupted vacuoles. Flow cytometry analysis of phagosomes stained with specific mAbs and FITC-labeled secondary antibodies showed progressive acquisition of both Rab7 and LAMP-1 consistent with movement along the endocytic pathway. Alternatively, macrophages were preloaded with the lysosomal tracer FITC-dextran before membrane labeling with PKH and incubation with latex beads. Phagosome-lysosome fusion was then quantified on the basis of the colocalization of red and green signals. Using these flow cytometry-based systems, we showed that co-internalization of beads with lysates of Mycobacterium tuberculosis, but not lysates from the nonpathogenic organism Mycobacterium smegmatis, markedly decreased phagosome acquisition of Rab7 and LAMP-1 and vesicle fusion with FITC-dextran-loaded lysosomes. Inhibition of phagolysosome fusion could be attributed, at least in part, to the mycobacterial cell wall glycolipid lipoarabinomannan, and further analysis showed complete rescue of phagosome maturation when cells were pretreated with vitamin D3 before exposure to lipoarabinomannan. Moreover, the ability of vitamin D3 to reverse the phenotype of phagosomes in the presence of the glycolipid was completely abrogated by LY-294002, suggesting that vitamin D3 promotes phagolysosome fusion via a phosphoinositide 3-kinase signaling pathway. These findings establish a robust platform technology based on labeling of phagocyte cell membranes and flow cytometry capable of supporting broad-based screens to identify microbial and other bioactive compounds that influence phagosome biology.

Antigens, CD↗
PubMed2002

Development of a simple HPLC method for determination of paeoniflorin-metabolizing activity of intestinal bacteria in rat feces.

A simple and reproducible HPLC method for the determination of paeoniflorin (PF)-metabolizing activity of intestinal bacteria in rat feces was developed and validated. Orally administered PF, a major active constituent of Paeoniae Radix, is metabolized into a bioactive compound, paeonimetabolin I (PM-I) by intestinal bacteria. Direct determination of the PF-metabolizing rate into PM-I is hard to achieve by HPLC due to the lack of intense chromophore in PM-I. However, when PF was incubated with Lactobacillus brevis, an intestinal bacterium, in the presence of phenylmercaptan, the metabolizing rate of PF into 8-phenylthio-paeonimetabolin I (PT-PM-I) was found to be equivalent to that of PF into PM-I. Thus, the PF-metabolizing activity of intestinal bacteria in rat feces was determined by measuring the rate of biotransformation of PF into PT-PM-I, which was detected by HPLC at 255 nm. This method can be utilized in the biopharmaceutical study of traditional Chinese formulations containing Paeoniae Radix.

Animals↗
PubMed2003

Antiedematogenic activity of two thiazolidine derivatives: N-tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene) rhodanine (GS26) and N-tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2,4-thiazolidinedione (GS28).

The search for new anti-inflammatory drugs has been constant in several research centers. The use of the Bioisostery concept allows the elaboration of new bioactive compounds with different properties through the introduction of substitute groups in one or more positions of a main molecule with known biological activity. Preliminary works accomplished at our laboratory with 2,4-thiazolidinedione isosters demonstrated inhibitory activity on edema formation for N-tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2,4-thiazolidinedione (GS28) and N-tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene) rhodanine (GS26). We verified the antiedematogenic and ulcerogenic activity of these two compounds in Wistar rats. The carrageenan induced paw edema suffered significant (p<0.05) inhibition (28.36% on average) for GS28 (100 mg/kg; v.o.) during the entire time of the experiment. GS26 (50 and 100 mg/kg; v.o.) significantly inhibited (p<0.05) the paw edema dextran induced (22.1 and 27.8%, for the respective doses) after 180 min. The compounds GS26 and GS28 did not show ulcerogenic activity on gastric mucous. The results suggest antiedematogenic action for both compounds without the appearance of gastric lesions.

Animals↗
PubMed2006

Two new sesquiterpene lactones from the leaves of Laurus nobilis.

As a part of our ongoing interest in new bioactive compounds from natural sources, we studied Laurus nobilis (Lauraceae). This plant is widespread in the Mediterranean area and is used for medicinal and economic purposes. Chromatographic separations on active extracts led to the isolation of two new sesquiterpene lactones, 5a,9-dimethyl-3-methylene-3,3a,4,5,5a,6,7,8-octahydro-1-oxacyclopenta[c]azulen-2-one (1) and 3beta-chlorodehydrocostuslactone (2). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high resolution mass spectrometry. The cytotoxic activity was also evaluated against three different tumor cell lines of human origin.

Cell Line, Tumor↗
PubMed2002

[Synthetic studies on sugar-related bioactive substances based on the ring transformation].

The development of two novel ring conversions of sugar derivatives is described. The first is an efficient conversion of 5-enopyranosides and 6-O-acetyl-5-enopyranosides to the corresponding substituted cyclohexanones mediated by a catalytic amount of palladium dichloride. After a survey of various substrates, the reaction was confirmed to be general and useful. Syntheses of bioactive compounds utilizing this method were therefore investigated. Cyclophellitol, which is a potent beta-glucoidase inhibitor, and its diastereoisomer were efficiently synthesized. Furthermore, novel synthesis of all enantiomerically pure diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides was investigated. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate. The second investigation involved novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars. The important intermediate, delta-hydroxyalkoxamate, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al. In contrast to the preparation of beta-lactam skeletons from beta-hydroxyalkoxamates, the cyclization of delta-hydroxyalkoxamates under Mitsunobu conditions resulted in O-alkylation rather than N-alkylation. It is noteworthy that delta-hydroxyalkoxamates derived from D-mannono-1,5-lactones afforded the O-alkylation product in 91% yield. No N-alkylation product was detected in this case. These O-cyclized oximes, in which the inversion of the configuration at C5 was secured, were efficiently converted into L-sugars.

Carbohydrates↗
PubMed2000

[A design and development of novel polymeric prodrugs prepared by mechanochemical solid-state polymerization].

The mechanochemical polymerization of solid-state monomer was first reported in 1959. Nevertheless, relatively little work has been done. We reported the first in-depth study of the mechanochemical polymerization of specially synthesized solid-state monomers, methacryloyl derivatives of bioactive compounds including detailed mechanistic implications. There are many advantages for this reaction. One of the most striking properties observed in the resulting polymers is that these polymeric prodrugs are of very low heterogeneity (narrow molecular weight distribution) which is of great value in pharmaceuticals for highly functionalized polymeric prodrugs. Thus, the present reaction provides a novel and simple methodology for the syntheses of highly functionalized polymeric prodrugs through a totally dry process. The nature of drug release from many kinds of polymeric prodrugs prepared by mechanochemical polymerization was also investigated. The rate of drug release from the polymeric prodrugs can be controlled by the property of comonomer and the structure of spacer between the main chain of polymer and drug. Several applications of polymeric prodrugs (chemoembolization and hybrid polymeric prodrugs) were also described. We have carried out the mechanochemical polymerization in the presence of pharmaceutical aids to exploit the features of this reaction. If one takes the physicochemical property of pharmaceutical aids into consideration, novel composite polymeric prodrugs possessing a variety of rates of drug release can be synthesized simultaneously with mixing.

Chemical Phenomena↗
PubMed2003

[Protein transduction by poly-arginine].

Protein transduction methods have been developed utilizing the delivery of peptides and proteins into eukaryotic cells by the protein transduction domain (PTD). Initially, the PTD domain was developed from the sequences from HIV-1 TAT, HSV VP-22 and antennapedia homeoprotein. Recently, several novel PTDs were developed and has been used as a valuable strategy for transduction of therapeutic protein. We developed a novel, high efficiency PTD (11 arginine) based on the TAT sequence and used 11R for the regulation of intracellular signal cascades. PTD can deliver proteins and other bioactive compounds and therefore serves as a very useful strategy for the development of therapeutic agents.

Amino Acid Sequence↗
PubMed2007

1,1-Diphenyl-2-picrylhydrazyl radical scavenging activity and tyrosinase inhibitory effects of constituents of sugarcane molasses.

In the course of our work into the use of cane by-products, we have studied the isolation and structural determination of bioactive compounds in sugarcane molasses. In this study, three stereo isomers of syringyl glycerol 3'-O-beta-D-glucopyranoside, three stereo isomers of guaiacyl glycerol 3'-O-beta-D-glucopyranoside, a syringyl glycerol 2'-O-beta-D-glucopyranoside, tachioside and a 2,3-dihydro-3,5-dihydroxy-6-methyl-4-(H)-pyran-4-one (DDMP) were isolated from the 25% methanol eluate by Amberlite XAD-2 column chromatography of sugarcane molasses. The structures of these compounds were determined on the basis of spectroscopic evidence. These isolated compounds were examined for their scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical species, and for their inhibitory activity against mushroom tyrosinase. All of the isolated compounds showed DPPH radical scavenging activity, while DDMP and tachioside showed mushroom tyrosinase inhibitory activity.

Biphenyl Compounds↗
PubMed1997

Effects of medium-chain fatty acids and their acylglycerols on the transport of penicillin V across Caco-2 cell monolayers.

The transport-enhancing effects of medium-chain fatty acids (caproic, caprylic, and capric acids) and their acylglycerols (mono-, di-, and triacylglycerols) were investigated by using Caco-2 cell monolayers as a model of the human intestinal epithelium. Penicillin V was used as a model for a hydrophilic bioactive compound. Among the fatty acids and acylglycerols tested, 1,2-dicaproin, monocaprin, monocaprylin, and capric acid sodium salt effectively enhanced the transport rate, whereas other substances enhanced the rate only slightly or not at all. With each of these four substances, the rate of enhancement was proportional to the concentration at low concentrations, but leveled off at high concentrations. The transport-enhancing effects were well correlated with the reduction in surface tension and with a physico-chemical parameter, denoted by the surface energy-lowering coefficient, characterizing the surface activity of a substance.

Caco-2 Cells↗
PubMed2002

CYP92B1, A cytochrome P450, expressed in petunia flower buds, that catalyzes monooxidation of long-chain fatty acids.

In higher plants, long-chain fatty acid hydroperoxides are intermediates in the synthesis of a diverse group of bioactive compounds. We used the reverse trascriptase-polymerase chain reaction to isolate a gene responsible for the oxidization of fatty acids from Petunia hybrida. A P450 cDNA not isolated earlier, CYP92B1, contained an open reading frame predicted to encode a polypeptide consisting of 510 amino acid residues. The transcript of the cyp92B1 gene was expressed at a high level in the early stage of flower development. CYP92B1 cDNA was expressed in a yeast, Saccharomyces cerevisiae, and recombinant yeast microsomes containing CYP92B1, a hemoprotein, metabolized lauric acid, linoleic acid, and linolenic acid.

5' Flanking Region↗
PubMed2003

Systematic strategy for the synthesis of cyanobacterin and its stereoisomers. 1. Asymmetric total synthesis of dechloro-cyanobacterin and its enantiomer.

The stereocontrolled total synthesis of the non-chlorinated analog of cyanobacterin, a potent photosynthesis inhibitor, was achieved by 12 steps in a 10.0% overall yield. Its enantiomer was also synthesized from the same starting material. This synthetic strategy is expected to be applicable to prepare cyanobacterin and all its stereoisomers, together with other similar bioactive compounds.

4-Butyrolactone↗
PubMed2005

Vialinin A, a novel 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenger from an edible mushroom in China.

While screening for bioactive compounds from edible mushrooms, a new potent antioxidant, vialinin A (1), together with a known compound, ganbajunin B (2), and a mixture of ganbajunins D (3) and E (4), were isolated from the dry fruiting bodies of Thelephora vialis. The structure of 1, 5',6'-bis(phenylacetoxy)-1,1':4',1''-terphenyl-2',3',4,4''-tetraol, was elucidated by spectroscopic and chemical methods. This compound had strong 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical-scavenging activity with an EC(50) value of 14.0 microM, nearly equal to that of butylated hydroxytoluene (BHT; EC(50) = 10.0 microM). A radical scavenging experiment using 1 and DPPH radicals indicated that 1 donated two hydrogen atoms to two molecules of the DPPH radical under hydrophobic conditions.

Agaricales↗