Structural characteristics-guided investigation of Ailanthus altissima (Mill.) Swingle resulted in the isolation and identification of seven undescribed potential Michael reaction acceptors (1–7). ...Ailanlactone A (1) possesses an unusual 1,7-epoxy-11,12-seco quassinoid core. Ailanterpene B (6) was a rare guaianolide-type sesquiterpene with a 5/6/6/6-fused skeleton. Their structures were determined through extensive analysis of physiochemical and spectroscopic data, quantum chemical calculations, and single crystal X-ray crystallographic technology using Cu Kα radiation. The cytotoxic activities of isolates on HepG2 and Hep3B cells were evaluated in vitro. Encouragingly, ailanaltiolide K (4) showed significant cytotoxicity against Hep3B cells with IC50 values of 1.41 ± 0.21 μM, whose covalent binding mode was uncovered in silico.
Structural characteristics-guided investigation of Ailanthus altissima (Mill.) Swingle resulted in the isolation of seven undescribed potential Michael reaction acceptors. Their structures were determined by NMR data, ECD calculations and X-ray diffraction. The cytotoxic activities against HepG2 and Hep3B cells of isolates were determined. Display omitted
•Seven potential Michael reaction acceptors were isolated from Ailanthus altissima.•A modified tactic that combineing GSH-containing HPLC with NMR technology was presented.•The structures were determined by NMR data, ECD calculations and X-ray diffraction.•Compound 4 exhibited potential inhibitory activity in Hep3B cells.
Seven undescribed terpenylated coumarins, named altissimacoumarin I–O, together with seven known compounds, altissimacoumarin C, altissimacoumarin E, altissimacoumarin G, altissimacoumarin H, ...puberulin, 7-(3-Methyl-2-butenyloxy)-6-methoxycoumarin and artelin were isolated from the root bark of Ailanthus altissima (Mill.) Swingle. Their structures were elucidated by comprehensive spectra data analysis, NMR calculation, DP4+ analysis and ACD/Structure Elucidator software simulation. The absolute configurations of altissimacoumarins K, L, M and N were determined by modified Mosher's method. All isolates were tested for their cytotoxic effect against two hepatoma carcinoma cell lines (HepG2, Hep3B). Altissimacoumarin C exhibited moderate cytotoxic effect against Hep3B cells, with IC50 of 45.21 μM.
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•Seven previously undescribed terpenylated coumarins were isolated and identified.•NMR calculation, DP4+ analysis and ACD/Structure Elucidator were used for structure validation.•The absolute configurations of some isolates were determined by Mosher's method and NOESY experiment.•Structure revision of altissimacoumarin E is proposed.
Eleven compounds including seven triterpenoids (1–6, 8), one steroid compound (7), two β-carbolines (9–10) and an indole (11) were isolated from the leaves of Ailanthus altissima (Mill.) Swingle. The ...structures of these compounds were elucidated by extensive spectroscopic methods and comparison with literature data. Among them, six compounds (1, 2, 3, 6, 7, and 11) were isolated from Simaroubaceae for the first time. A compounds-families network was constructed and the chemotaxonomic significance of these compounds was discussed.
•Eleven compounds (1–11) were isolated from the dried leaves of Ailanthus altissima (Mill.) Swingle.•Six compounds (1, 2, 3, 6, 7, and 11) are firstly reported in Simaroubaceae family.•The chemotaxonomic significance of the isolated compounds was discussed.
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•Four new steroids from the leaves of Ailanthus altissima (Mill.) Swingle.•The structures of steroids were determined by comprehensive spectral analysis and comparison of the ...experimental and calculated ECD spectra. Among them, the relative configurations of 2 were confirmed by acetonide analysis.•All compounds were evaluated for their cytotoxic activity against two hepatoma carcinoma cell lines (HepG2, Hep3B) in vitro. Compound 1 exhibits stronger cytotoxicity against HepG2 cell.
Four new steroids, chouchunsteride A-D (1–4), together with four known steroids (5–8), were isolated from the leaves of Ailanthus altissima (Mill.) Swingle. Their structures were elucidated based on spectroscopic data analysis, while the relative and absolute configurations were determined via acetonide analysis and quantum chemical ECD calculations. All isolated steroids were evaluated for their cytotoxic activity against two hepatoma carcinoma cell lines (HepG2, Hep3B). Among them, 1 exhibited the most potent cytotoxicity against HepG2 cells with an IC50 value of 4.03 μM.
•Predicted potential suitable areas for three species on CMIP6.•Distribution shifts of the three species were analyzed.•The most important climatic variables for each species were assessed.•The ...overlapping ecological niches of the three species were evaluated.
Invasive species Tree-of-heaven (Ailanthus altissima (Mill.) Swingle) caused serious damage on ecosystem, economy, and public health in the United States and Europe. Two weevils (Eucryptorrhynchus scrobiculatus (Motschulsky) and E. brandti (Harold)) are considered to be potential enemies for biological control. In this study, we integrated potential distribution, bioclimatic suitability shifts and niche overlap to assess the global invasion risk of A. altissima under climate change and the possibility of E. scrobiculatus and E. brandti as potential natural enemies. Suitable area of A. altissima will be expanded under SSP 585. The future climate conditions do not seem to be suitable for the growth of E. scrobiculatus, but are conducive to E. brandti. We found that the suitable area of A. altissima would spread to the south and north, while two weevils spread mainly to the central and northern parts in the United States. The mean temperature of the coldest quarter (BIO11, 43.3%) was the most important bioclimatic variable in the forecasts for A. altissima and E. brandti. The wettest quarter’s mean temperature (BIO8, 35.7%) had the strongest influence on predictions for E. scrobiculatus. Our findings can provide a theoretical basis for preventing A. altissima from continuing to invade other areas. At the same time, it explained one reason why E. scrobiculatus and E. brandti could not effectively control A. altissima, and evaluated its feasibility as a potential natural enemy under future climatic conditions.
Demand for the exploration of botanical pesticides continues to increase due to the detrimental effects of synthetic chemicals on human health and the environment and the development of resistance by ...pests. Under the guidance of a bioactivity-guided approach and HSQC-based DeepSAT, 16 coumarin derivatives were discovered from the leaves of Ailanthus altissima (Mill.) Swingle, including seven undescribed monoterpenoid coumarins, three undescribed monoterpenoid phenylpropanoids, and two new coumarin derivatives. The structure and configurations of these compounds were established and validated via extensive spectroscopic analysis, acetonide analysis, and quantum chemical calculations. Biologically, 5 exhibited significant antifeedant activity toward the Plutella xylostella. Moreover, tyrosinase being closely related to the growth and development of larva, the inhibitory potentials of 5 against tyrosinase was evaluated in vitro and in silico. The bioactivity evaluation results highlight the prospect of 5 as a novel category of botanical insecticide.
Sixteen compounds were isolated from the root barks of Ailanthus altissima (Mill.) Swingle, including thirteen lignans (1–13), two coumarins (14–15), and one chalcone (16). This is the first report ...on the occurrence of compounds 1–16 in the genus Ailanthus. Their structures were elucidated on the basis of NMR spectroscopic data. The plant distribution network of all isolated compounds was described to illustrate the significance of taxonomy. The presence of these congenetic lignans (1–13) and their biosynthetic relationships may be used for identification of Ailanthus genus.
•Sixteen compounds were found in the root barks of A. Altissima.•Fourteen compounds (1, 3–8, 10–16) were firstly reported in the Simaroubaceae.•The chemotaxonomic significance was discussed by the distribution of compounds.•The plausible biosynthetic relationships of lignans (1–13) was deduced.
Climate, land use and disturbances are well known drivers of invasion. However, their relative influence may change across spatial scales, where climate is expected to be the main filter at broad ...scales; land use is expected to have more influence at intermediate scales, and disturbance, at fine ones. Understanding the underlying processes that drive invasion patterns at different spatial scales is thus crucial to be able to anticipate the future spread of invaders. Here, we quantified the relative importance of climate, land use, and disturbance on the distribution of the invasive trees Ailanthus altissima and Robinia pseudoacacia, across three nested spatial scales, namely global, country (Spain) and riverbank (three riparian riverbanks). To do so, for each species and scale, we built ensemble species distribution models. We also identified their range filling and inferred the most suitable areas in Spain for them to spread. In general, our study confirms that climate acts as an initial coarse filter of species distribution, whilst both climate and land use were important at the country scale; at the riverbank scale human-mediated disturbances gained importance. However, R. pseudoacacia and A. altissima showed differences in their degree of range filling, where A. altissima has a higher potential for range expansion in the near future. Overall, the integration of different scales into invasion studies shows a great potential to enrich our understanding of species-habitat relationships, and to help anticipate their future dynamics.
Phytochemistry investigations on
(Mill.) Swingle, a Simaroubaceae plant that is recognized as a traditional herbal medicine, have afforded various natural products, among which C
quassinoid is the ...most attractive for their significant and diverse pharmacological and biological activities. Our continuous study has led to the isolation of two novel quassinoid glycosides, named chuglycosides J and K, together with fourteen known lignans from the samara of
. The new structures were elucidated based on comprehensive spectra data analysis. All of the compounds were evaluated for their anti-tobacco mosaic virus activity, among which chuglycosides J and K exhibited inhibitory effects against the virus multiplication with half maximal inhibitory concentration (IC
) values of 56.21 ± 1.86 and 137.74 ± 3.57 μM, respectively.
Quassinoids are bitter constituents characteristic of the family Simaroubaceae. A total of 18 C20 quassinoids, including nine new quassinoid glycosides, named chuglycosides A–I (1–6 and 8–10), were ...identified from the samara of Ailanthus altissima (Mill.) Swingle. All of the quassinoids showed potent anti-tobacco mosaic virus (TMV) activity. A preliminary structure–anti-TMV activity relationship of quassinoids was discussed. The effects of three quassinoids, including chaparrinone (12), glaucarubinone (15), and ailanthone (16), on the accumulation of TMV coat protein (CP) were studied by western blot analysis. Ailanthone (16) was further investigated for its influence on TMV spread in the Nicotiana benthamiana plant.
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