Non-Polar Chemical Constituents of Atemoya and Evaluation of the Cytotoxic and Antimicrobial Activity

This study aimed to identify the chemical composition of essential oil from fruits (EOAF) and the hexanic crude extract from aerial parts (At-Hex) of atemoya (Annona cherimola x Annona squamosa), a hybrid belonging to the Annonaceae family. Cytotoxic and antimicrobial activity was also evaluated. OEAF was obtained by hydrodistillation using a Clevenger apparatus, and their composition was analyzed by gas chromatography-mass spectrometry (GC-MS) analyses. Cytotoxicity was tested against human tumor cell lines HCT-116 (colon carcinoma), SF-295 (glioblastoma), OVCAR-8 (ovarian carcinoma) and HL60 (leukemia) using 3-(4,5-dimethyl-2-thiazolyl)-2,5- diphenyl-2H-tetrazolium bromide (MTT) assay, while antimicrobial activity was conducted by bioauthography method against eleven microorganisms strains. Twenty-four compounds were identified in the EOAF and twenty-nine in At-Hex. The monoterpenes linalool (25.70%), α-pinene (10.38%), β-pinene (9.12%), transocimene (7.43%), and the sesquiterpene bicyclogermacrene (12.58%) were the major constituents of EOAF, whereas the sesquiterpene spathulenol (13.91%) was the main compound of At-Hex. At-Hex showed a high cytotoxicity against SF-295 (glioblastoma). These findings show an important chemotaxonomic contribution for the Annonaceae family, mainly for the Annona genus. Atemoya proved to be a promising source of substances with potential cytotoxic activity.     

Positioning Bacillus subtilis as terpenoid cell factory

Increasing demands for bioactive compounds have motivated researchers to employ micro-organisms to produce complex natural products. Currently, Bacillus subtilis has been attracting lots of attention to be developed into terpenoids cell factories due to its generally recognized safe status and high isoprene precursor biosynthesis capacity by endogenous methylerythritol phosphate (MEP) pathway. In this review, we describe the up-to-date knowledge of each enzyme in MEP pathway and the subsequent steps of isomerization and condensation of C5 isoprene precursors. In addition, several representative terpene synthases expressed in B. subtilis and the engineering steps to improve corresponding terpenoids production are systematically discussed. Furthermore, the current available genetic tools are mentioned as along with promising strategies to improve terpenoids in B. subtilis, hoping to inspire future directions in metabolic engineering of B. subtilis for further terpenoid cell factory development.     

Bioassay‐Guided Fractionation,Chemical Compositions and Antibacterial Activity of Extracts from Rhizomes of Globba schomburgkii Hook.f.

Bioassay‐guided fractionation was conducted on dichloromethane extract from the rhizomes of Globba schomburgkii Hook.f., which have previously been reported as the part with the highest antibacterial activity. 10 fractions and 20 sub‐fractions were obtained and evaluated for their potency against various strains of bacteria. The most active sub‐fractions were 8 times more effective against Staphylococcus aureus and Micrococcus luteus than the original crude extract. Moreover, two pure compounds, namely petasol and (E)‐15,16‐dinorlabda‐8(17),11‐dien‐13‐one, were successfully isolated and characterized for the first time from this plant species. Untargeted compound analysis of all fractions and sub‐fractions was performed by gas chromatography hyphenated with mass spectrometry, leading to positive identification of 167 compounds according to comparison with the mass spectrum and retention index database, 137 of which have never been reported for G. schomburgkii. The correlation between antibacterial activity and composition of each fraction suggests that the bioactive compounds could be 4,8‐β‐epoxycaryophyllene, methyl isocostate, (E)‐labda‐8(17),12‐diene‐15,16‐dial, α‐kessyl acetate, zederone, clovanediol, ledene oxide‐(I), alantolactone, or 8α,11‐elemadiol.     

Bioherbicide Potential of Eucalyptus saligna Leaf Litter Essential Oil

We aimed to evaluate the bioherbicide potential of Eucalyptus saligna leaf litter essential oil, its fractions and major compounds. Six essential oil fractions were obtained by preparative thin‐layer chromatography and analyzed by gas chromatography/mass spectrometry. Effects of the oil, its fractions and major compounds (1,8‐cineole and/or α‐pinene) diluted in aqueous solution were assessed on germination and seedling growth. Recipient species were Lactuca sativa (model), Amaranthus viridis (weed), Eragrostis plana (weed), and Paspalum notatum (forage). The essential oil was more phytotoxic on A. viridis and L. sativa, followed by E. plana, and caused no effects on P. notatum. Amaranthus viridis was inhibited by all treatments, mainly the essential oil, α‐pinene and fraction 6, whereas E. plana was more affected by the oil fractions. Results revealed the species‐specific phytotoxic effects of E. saligna essential oil, indicating its potential use for controlling A. viridis and E. plana. Phytotoxic effects of essential oils or their components should not be generalized, as effects may change according to recipient species.     

转录因子调控植物萜类化合物生物合成研究进展

萜类化合物是植物次生代谢物中结构和数量最多的一类化合物, 它们在植物体内以及植物与环境和其它生命体的相互作用中发挥重要作用。转录因子通过调控代谢通路中基因的转录起始来调节次生代谢物质的产量。目前, 研究发现参与萜类合成的转录因子家族主要有6个, 包括AP2/ERF、bHLH、MYB、NAC、WRKY和bZIP。该文主要对其家族的结构特点、调控模式以及研究进展进行综述, 以期进一步丰富萜烯合成的网络调控, 为植物萜类相关的分子育种、优质栽培和病虫害生物防治等提供新的思路与方法。     

Yield,chemical composition,and bioactivity of essential oils from 12 species of Eucalyptus on Aedes aegypti larvae

The insecticidal activity of essential oils from 12 species of Eucalyptus (Myrtaceae) was evaluated on larvae of Aedes aegypti (L.) (Diptera: Culicidae), the most important vector of dengue and yellow fever in the Americas. Oils were obtained by hydrodistillation and their chemical composition was determined by gas chromatography coupled to mass spectrometry; yields ranged from 0.2 to 2.5%. Essential oils were mainly composed of 1,8‐cineole, α‐pinene, α‐phellandrene, β‐phellandrene, γ‐terpinene, 4‐terpineol, α‐terpineol, p‐cymene, and spathulenol. Larvicidal effects were tested on susceptible third or fourth stage Ae. aegypti larvae, determining median lethal concentration (LC₅₀) and median effective concentration (EC₅₀). Essential oils from Eucalyptus dunnii (Maiden), Eucalyptus gunnii (Hook), Eucalyptus tereticornis (Smith), Eucalyptus camaldulensis (Dehn), and Eucalyptus saligna (Smith) showed the best larvicidal activities with LC₅₀ values of 25.2, 21.1, 22.1, 26.8, and 22.2, respectively. No significant differences were observed between LC₅₀ and EC₅₀ values of the same oil. Regression analysis revealed a significant relationship between total essential oil yields and 1,8‐cineole concentration. Significant relationships were also revealed between larval mortality and the concentration of 1,8‐cineole and p‐cymene. This indicated that Eucalyptus species with high oil yields have higher 1,8‐cineole concentrations and lower p‐cymene concentrations and have less effect on Ae. aegypti. Our results suggest the potential of controlled crossing methods to obtain Eucalyptus trees with chemical profiles having enhanced activity against this mosquito.     

Specific biodegradation of polychlorinated biphenyls (PCBs) facilitated by plant terpenoids

The aim of this study was to examine how plant terpenoids, as natural growth substrates or inducers, would affect the biodegradation of PCB congeners. Various PCB degraders that could grow on biphenyl and several terpenoids were tested for their PCB degradation capabilities. Degradation activities of the PCB congeners, 4,4′-dichlorobiphenyl (4,4′-DCBp) and 2,2′-dichlorobiphenyl (2,2′-DCBp), were initially monitored through a resting cell assay technique that could detect their degradation products. The PCB degraders,Pseudomonas sp. P166 andRhodococcus sp. T104, were found to grow on both biphenyl and terpenoids ((S)-(−) limonene,p-cymene and α-terpinene) whereasArthrobacter sp. B1B could not grow on the terpenoids as a sole carbon source. The B1B strain grown on biphenyl exhibited good degradation activity for 4,4′-DCBp and 2,2′-DCBp, while the activity of strains P166 and T104 was about 25% that of the B1B strain, respectively. Concomitant GC analysis, however, demonstrated that strain T104, grown on (S)-(−) limonene,p-cymene and α-terpinene, could degrade 4,4′-DCBp up to 30%, equivalent to 50% of the biphenyl induction level. Moreover, strain T104 grown on (S)-(−) limonene, could also degrade 2,2′-DCBp up to 30%. This indicates that terpenoids, widely distributed in nature, could be utilized as both growth and/or inducer substrate(s) for PCB biodegradation in the environment.     

The essential oil of Artemisia capillaris

Twenty-five terpenoids, 6-phenylacetylenes, 7 phenols, and 15 fatty acids were characterized in this oil. It differs considerably in composition from the oils of A. kurromensis, A. maritima and A. fukudo, which have α- and β-thujone as the major constituents.     

Plant P450s as versatile drivers for evolution of species-specific chemical diversity

The irreversible nature of reactions catalysed by P450s makes these enzymes landmarks in the evolution of plant metabolic pathways. Founding members of P450 families are often associated with general (i.e. primary) metabolic pathways, restricted to single copy or very few representatives, indicative of purifying selection. Recruitment of those and subsequent blooms into multi-member gene families generates genetic raw material for functional diversification, which is an inherent characteristic of specialized (i.e. secondary) metabolism. However, a growing number of highly specialized P450s from not only the CYP71 clan indicate substantial contribution of convergent and divergent evolution to the observed general and specialized metabolite diversity. We will discuss examples of how the genetic and functional diversification of plant P450s drives chemical diversity in light of plant evolution. Even though it is difficult to predict the function or substrate of a P450 based on sequence similarity, grouping with a family or subfamily in phylogenetic trees can indicate association with metabolism of particular classes of compounds. Examples will be given that focus on multi-member gene families of P450s involved in the metabolic routes of four classes of specialized metabolites: cyanogenic glucosides, glucosinolates, mono- to triterpenoids and phenylpropanoids.     

Discrimination Between BI and BII Conformational Substates of B-DNA Based on Sugar-base Interproton Distances

Abstract

Molecular dynamics (MD) simulations of four water-solvated DNA duplexes were used to generate a database of ～27000 dinucleotide conformations. Analyzing this database, we investigated the relationship between so-called BI-BII transitions and short-range interproton distances. Four H-H distances were found particularly sensitive to BI-BII transitions: inter- nucleotide H1′(n)-H68(n+1), H2′(n)-H68(n+1), and H2″(n)-H68(n+1), and intranucleotide H2″(n)-H68(n). Determination of these distances using classical NOESY spectroscopy can thus provide valuable indications on the existence of BII substates, complementing the existing method based on ³¹P chemical shifts and ³¹P-¹H spin-spin coupling constants.