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Shixing Zhou
University of Chinese Academy of Sciences, Beijing 100049, China

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State Key Laboratory of Desert and Oasis Ecololjgy, Xinjiang Institute of Ecology and Geography, Chinese Academy of Sciences, Urumqi, 830011, China

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Review
Published: 16 July 2021 in Toxins
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Phthalic acid esters (PAEs) are a class of lipophilic chemicals widely used as plasticizers and additives to improve various products’ mechanical extensibility and flexibility. At present, synthesized PAEs, which are considered to cause potential hazards to ecosystem functioning and public health, have been easily detected in the atmosphere, water, soil, and sediments; PAEs are also frequently discovered in plant and microorganism sources, suggesting the possibility that they might be biosynthesized in nature. In this review, we summarize that PAEs have not only been identified in the organic solvent extracts, root exudates, and essential oils of a large number of different plant species, but also isolated and purified from various algae, bacteria, and fungi. Dominant PAEs identified from natural sources generally include di-n-butyl phthalate, diethyl phthalate, dimethyl phthalate, di(2-ethylhexyl) phthalate, diisobutyl phthalate, diisooctyl phthalate, etc. Further studies reveal that PAEs can be biosynthesized by at least several algae. PAEs are reported to possess allelopathic, antimicrobial, insecticidal, and other biological activities, which might enhance the competitiveness of plants, algae, and microorganisms to better accommodate biotic and abiotic stress. These findings suggest that PAEs should not be treated solely as a “human-made pollutant” simply because they have been extensively synthesized and utilized; on the other hand, synthesized PAEs entering the ecosystem might disrupt the metabolic process of certain plant, algal, and microbial communities. Therefore, further studies are required to elucidate the relevant mechanisms and ecological consequences.

ACS Style

Ling Huang; Xunzhi Zhu; Shixing Zhou; Zhenrui Cheng; Kai Shi; Chi Zhang; Hua Shao. Phthalic Acid Esters: Natural Sources and Biological Activities. Toxins 2021, 13, 495 .

AMA Style

Ling Huang, Xunzhi Zhu, Shixing Zhou, Zhenrui Cheng, Kai Shi, Chi Zhang, Hua Shao. Phthalic Acid Esters: Natural Sources and Biological Activities. Toxins. 2021; 13 (7):495.

Chicago/Turabian Style

Ling Huang; Xunzhi Zhu; Shixing Zhou; Zhenrui Cheng; Kai Shi; Chi Zhang; Hua Shao. 2021. "Phthalic Acid Esters: Natural Sources and Biological Activities." Toxins 13, no. 7: 495.

Journal article
Published: 05 March 2021 in Plants
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The chemical profile and allelopathic effect of the volatile organic compounds (VOCs) produced by a dominant shrub Serphidium kaschgaricum (Krasch.) Poljak. growing in northwestern China was investigated for the first time. Serphidium kaschgaricu was found to release volatile compounds into the surroundings to affect other plants’ growth, with its VOCs suppressing root elongation of Amaranthus retroflexus L. and Poa annua L. by 65.47% and 60.37% at 10 g/1.5 L treatment, respectively. Meanwhile, volatile oils produced by stems, leaves, flowers and flowering shoots exhibited phytotoxic activity against A. retroflexus and P. annua. At 0.5 mg/mL, stem, leaf and flower oils significantly reduced seedling growth of the receiver plants, and 1.5 mg/mL oils nearly completely prohibited seed germination of both species. GC/MS analysis revealed that among the total 37 identified compounds in the oils, 19 of them were common, with eucalyptol (43.00%, 36.66%, 19.52%, and 38.68% in stem, leaf, flower and flowering shoot oils, respectively) and camphor (21.55%, 24.91%, 21.64%, and 23.35%, respectively) consistently being the dominant constituents in all oils. Eucalyptol, camphor and their mixture exhibited much weaker phytotoxicity compared with the volatile oils, implying that less abundant compounds in the volatile oil might contribute significantly to the oils’ activity. Our results suggested that S. kaschgaricum was capable of synthesizing and releasing allelopathic volatile compounds into the surroundings to affect neighboring plants’ growth, which might improve its competitiveness thus facilitate the establishment of dominance.

ACS Style

Shixing Zhou; Toshmatov Zokir; Yu Mei; Lijing Lei; Kai Shi; Ting Zou; Chi Zhang; Hua Shao. Allelopathic Effect of Serphidium kaschgaricum (Krasch.) Poljak. Volatiles on Selected Species. Plants 2021, 10, 495 .

AMA Style

Shixing Zhou, Toshmatov Zokir, Yu Mei, Lijing Lei, Kai Shi, Ting Zou, Chi Zhang, Hua Shao. Allelopathic Effect of Serphidium kaschgaricum (Krasch.) Poljak. Volatiles on Selected Species. Plants. 2021; 10 (3):495.

Chicago/Turabian Style

Shixing Zhou; Toshmatov Zokir; Yu Mei; Lijing Lei; Kai Shi; Ting Zou; Chi Zhang; Hua Shao. 2021. "Allelopathic Effect of Serphidium kaschgaricum (Krasch.) Poljak. Volatiles on Selected Species." Plants 10, no. 3: 495.

Journal article
Published: 13 October 2019 in Toxins
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The present investigation studied the chemical composition of the essential oils extracted from Dracocephalum integrifolium Bunge growing in three different localities in northwest China and evaluated the phytotoxic, antimicrobial and insecticidal activities of the essential oils as well as their major constituents, i.e., sabinene and eucalyptol. GC/MS analysis revealed the presence of 21-24 compounds in the essential oils, representing 94.17-97.71% of the entire oils. Monoterpenes were the most abundant substances, accounting for 85.30-93.61% of the oils; among them, sabinene (7.35-14.0%) and eucalyptol (53.56-76.11%) were dominant in all three oils, which occupied 67.56-83.46% of the total oils. In general, phytotoxic bioassays indicated that the IC50 values of the oils and their major constituents were below 2 μL/mL (1.739-1.886 mg/mL) against Amaranthus retroflexus and Poa annua. Disc diffusion method demonstrated that the oils and their major constituents possessed antimicrobial activity against Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli, Saccharomyces cerevisiae, and Candida albicans, with MIC values ranging from 5-40 μL/mL (4.347-37.712 mg/mL). The oils, sabinene and eucalyptol also exhibited significant pesticidal activity, with the mortality rates of Aphis pomi reaching 100% after exposing to 10 μL oil/petri dish (8.694-9.428 mg/petri dish) for 24 h. To the best of our knowledge, this is the first report on the chemical composition, phytotoxic, antimicrobial and insecticidal activity of the essential oils extracted from D. integrifolium; it is noteworthy to mention that this is also the first report on the phytotoxicity of one of the major constituents, sabinene. Our results imply that D. integrifolium oils and sabinene have the potential value of being further exploited as natural pesticides.

ACS Style

Shixing Zhou; Caixia Wei; Chi Zhang; Caixia Han; Nigora Kuchkarova; Hua Shao. Chemical Composition, Phytotoxic, Antimicrobial and Insecticidal Activity of the Essential Oils of Dracocephalum integrifolium. Toxins 2019, 11, 598 .

AMA Style

Shixing Zhou, Caixia Wei, Chi Zhang, Caixia Han, Nigora Kuchkarova, Hua Shao. Chemical Composition, Phytotoxic, Antimicrobial and Insecticidal Activity of the Essential Oils of Dracocephalum integrifolium. Toxins. 2019; 11 (10):598.

Chicago/Turabian Style

Shixing Zhou; Caixia Wei; Chi Zhang; Caixia Han; Nigora Kuchkarova; Hua Shao. 2019. "Chemical Composition, Phytotoxic, Antimicrobial and Insecticidal Activity of the Essential Oils of Dracocephalum integrifolium." Toxins 11, no. 10: 598.

Journal article
Published: 01 November 2018 in Molecules
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The aim of this study was to identify bioactive compounds from leaves of the invasive plant Xanthium spinosum and assess their phytotoxic activity. Activity-guided fractionation led to the isolation of 6 bioactive compounds: xanthatin (1), 1α,5α-epoxyxanthatin (2), 4-epiisoxanthanol (3), 4-epixanthanol (4), loliolide (5) and dehydrovomifoliol (6). Of them, compounds 2–6 were isolated from the X. spinosum for the first time. The structures of 1–6 were elucidated on the basis of extensive NMR studies and ESI-MS measurements as well as comparison with literature data. All of compounds were evaluated for their phytotoxic activity. Among them, compounds 1–4 exhibited stronger activity on 2 receiver plants compared with the other 2 compounds, with xanthatin (1) being the most potent compound, which suppressed root growth of the dicot plant Amaranthus retroflexus by 32.5%, 39.4%, 84.7% when treated xanthatin (1) at 5, 20, and 100 µg/mL, while for the monocot plant, root growth was inhibited by 14.7%, 28.0%, and 40.0%, respectively. Seedling growth was nearly completely inhibited when the concentration of xanthanolides increased to 500 µg/mL, whereas there was still some seedling growth when loliolide (5) and dehydrovomifoliol (6) were applied at the same concentration. Dehydrovomifoliol (6) did not negatively affect seedling growth of P. annua at all tested concentrations, and root length was still 42.0% of the control when the highest concentration 500 µg/mL was used. This is the first report of the phytotoxicity of 1α,5α-epoxyxanthatin (2), 4-epiisxanthanol (3) and 4-epixanthanol (4). These compounds have the potential to be utilized as natural herbicides, especially 4-epiisoxanthanol (3), which exhibited significant selective activity between the dicot and monocot plants. On the other hand, whether these bioactive substances serve as allelochemicals to facilitate the invasion success of X. spinosum needs to be further studied.

ACS Style

Zhuogeng Yuan; Xiangwei Zheng; Yu Zhao; Ying Liu; Shixing Zhou; Caixia Wei; Yunxia Hu; Hua Shao. Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum. Molecules 2018, 23, 2840 .

AMA Style

Zhuogeng Yuan, Xiangwei Zheng, Yu Zhao, Ying Liu, Shixing Zhou, Caixia Wei, Yunxia Hu, Hua Shao. Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum. Molecules. 2018; 23 (11):2840.

Chicago/Turabian Style

Zhuogeng Yuan; Xiangwei Zheng; Yu Zhao; Ying Liu; Shixing Zhou; Caixia Wei; Yunxia Hu; Hua Shao. 2018. "Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum." Molecules 23, no. 11: 2840.

Full paper
Published: 26 October 2018 in Chemistry & Biodiversity
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To evaluate the potential value of Seriphidium terrae‐albae (Krasch) Poljak essential oil as bioherbicide, its chemical composition as well as phytotoxic activity were investigated. Seventeen compounds were identified via GC‐MS, representing 98.1% of the total oil, and the most abundant constituents were α‐thujone (43.18%), β‐thujone (16.92%), eucalyptol (17.55%) and camphor (13.88%). Phytotoxic assay revealed that the essential oil as well as its major constituents exhibited inhibitory activity on root and shoot growth of receiver plants in a dose‐dependent manner. When the concentration reached 20 μg/mL, root length of Amaranthus retroflexus was reduced to 31.3%, 70.6%, 36.9%, 66.6% of the control, respectively, when treated with α‐thujone, eucalyptol, camphor and the mixture of these compounds; meanwhile, root length of Poa annua was 3.0%, 24.2%, 0%, and 4.4% of the control when the same chemicals were applied. On the other hand, the essential oil showed a much stronger activity. At 1.5 μL/mL, root and shoot length of A. retroflexus and P. annua were reduced to 0.65%, 0.5%, and 1.53%, 1.51% of the control, respectively, and seed germination of A. retroflexus and P. annua were completely inhibited when the oil concentration reached 3 μg/mL and 5 μg/mL, respectively. This is the first report on the chemical composition of the essential oil of S. terrae‐albae, and our results indicated that it has the potential to be further exploited as a bioherbicide. This article is protected by copyright. All rights reserved.

ACS Style

Hua Shao; Yunxia Hu; Caixia Han; Caixia Wei; Shixing Zhou; Chenpeng Zhang; Chi Zhang. Chemical Composition and Phytotoxic Activity of Seriphidium terrae-albae (Krasch .) Poljakov (Compositae) Essential Oil. Chemistry & Biodiversity 2018, 15, e1800348 .

AMA Style

Hua Shao, Yunxia Hu, Caixia Han, Caixia Wei, Shixing Zhou, Chenpeng Zhang, Chi Zhang. Chemical Composition and Phytotoxic Activity of Seriphidium terrae-albae (Krasch .) Poljakov (Compositae) Essential Oil. Chemistry & Biodiversity. 2018; 15 (11):e1800348.

Chicago/Turabian Style

Hua Shao; Yunxia Hu; Caixia Han; Caixia Wei; Shixing Zhou; Chenpeng Zhang; Chi Zhang. 2018. "Chemical Composition and Phytotoxic Activity of Seriphidium terrae-albae (Krasch .) Poljakov (Compositae) Essential Oil." Chemistry & Biodiversity 15, no. 11: e1800348.