Comparison of physicochemical properties and aqueous solubility of xanthone prepared via oil-in-water emulsion and complex coacervation techniques

Ho, Li Yoke; Lim, Yau Yan; Tan, Chin Ping; Siow, Lee Fong

doi:10.1080/10942912.2018.1446022

Cited by 7 publications

(3 citation statements)

References 40 publications

(73 reference statements)

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“…One possible explanation is that TDO can rapidly introduce a second oxidation at the 5-carbon position of 4-hydroxymesotrione, causing this intermediate to be undetectable. After the second oxidation of mesotrione, oxy-mesotrione is generated aqueous solubility of these metabolites, 32,[37][38][39] xanthone and acridone derivatives are immobilized in tissues where these metabolites are formed (Fig. 2).…”

Section: Discussionmentioning

confidence: 99%

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Ectopic expression of a rice triketone dioxygenase gene confers mesotrione tolerance in soybean

Dai

Georgelis

Bedair

et al. 2022

Pest Management Science

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BACKGROUND: Herbicide-resistant weeds pose a challenge to agriculture and food production. New herbicide tolerance traits in crops will provide farmers with more options to effectively manage weeds. Mesotrione, a selective pre-and post-emergent triketone herbicide used in corn production, controls broadleaf and some annual grass weeds via hydroxyphenylpyruvate dioxygenase (HPPD) inhibition. Recently, the rice HIS1 gene, responsible for native tolerance to the selective triketone herbicide benzobicyclon, was identified. Expression of HIS1 also confers a modest level of mesotrione resistance in rice. Here we report the use of the HIS1 gene to develop a mesotrione tolerance trait in soybean.RESULTS: Conventional soybean is highly sensitive to mesotrione. Ectopic expression of a codon-optimized version of the rice HIS1 gene (TDO) in soybean confers a commercial level of mesotrione tolerance. In TDO transgenic soybean plants, mesotrione is rapidly and locally oxidized into noninhibitory metabolites in leaf tissues directly exposed to the herbicide. These metabolites are further converted into compounds similar to known classes of plant secondary metabolites. This rapid metabolism prevents movement of mesotrione from treated leaves into vulnerable emerging leaves. Minimizing the accumulation of the herbicide in vulnerable emerging leaves protects the function of HPPD and carotenoid biosynthesis more generally while providing tolerance to mesotrione.CONCLUSIONS: Mesotrione has a favorable environmental and toxicological profile. The TDO-mediated soybean mesotrione tolerance trait described here provides farmers with a new option to effectively manage difficult-to-control weeds using familiar herbicide chemistry. This trait can also be adapted to other mesotrione-sensitive crops (e.g. cotton) for effective weed management.

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Section: Discussionmentioning

confidence: 99%

“…Xanthone‐OH and acridone‐OH are conjugated with glucosyl and malonyl groups (Figs 5(A),(B) and S6). Most likely due to the poor aqueous solubility of these metabolites, 32,37–39 xanthone and acridone derivatives are immobilized in tissues where these metabolites are formed (Fig. 2).…”

Section: Discussionmentioning

confidence: 99%

Ectopic expression of a rice triketone dioxygenase gene confers mesotrione tolerance in soybean

Dai

Georgelis

Bedair

et al. 2022

Pest Management Science

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“…Many natural and synthetic compounds with anticancer potential are not active enough in terms of bioavailability and full exploitation of their biological properties. Xanthones, presenting examples of such compounds, are polyphenolic heterocyclic compounds that can be isolated from mangosteen rind or semi/fully synthesized [ 1 ]. α-Mangostin (αM), the main representative of the xanthones family, exhibits anticancer activity through various molecular mechanisms, the most important of which are the induction of mitochondria-mediated apoptosis and the inhibition of proliferation, migration, invasion, and angiogenesis [ 2 , 3 , 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of α-Mangostin and Vadimezan Conjugates with Glucoheptoamidated and Biotinylated 3rd Generation Poly(amidoamine) Dendrimer, and Conjugation Effect on Their Anticancer and Anti-Nematode Activities

2022

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α-Mangostin and vadimezan are widely studied potential anticancer agents. Their biological activities may be improved by covalent bonding by amide or ester bonds with the third generation poly(amidoamine) (PAMAM) dendrimer, substituted with α-D-glucoheptono-1,4-lactone and biotin. Thus, conjugates of either ester- (G3gh4B5V) or amide-linked (G32B12gh5V) vadimezan, and equivalents of α-mangostin (G3gh2B5M and G32B12gh5M, respectively), were synthesized, characterized and tested in vitro against cancer cells: U-118 MG glioma, SCC-15 squamous carcinoma, and BJ normal human fibroblasts growth, as well as against C. elegans development. α-Mangostin cytotoxicity, stronger than that of Vadimezan, was increased (by 2.5–9-fold) by conjugation with the PAMAM dendrimer (with the amide-linking being slightly more effective), and the strongest effect was observed with SCC-15 cells. Similar enhancement of toxicity resulting from the drug conjugation was observed with C. elegans. Vadimezan (up to 200 µM), as well as both its dendrimer conjugates, was not toxic against both the studied cells and nematodes. It showed an antiproliferative effect against cancer cells at concentrations ≥100 µM. This effect was significantly enhanced after conjugation of the drug with the dendrimer via the amide, but not the ester bond, with G32B12gh5V inhibiting the proliferation of SCC-15 and U-118 MG cells at concentrations ≥4 and ≥12 μM, respectively, without a visible effect in normal BJ cells. Thus, the drug delivery system based on the PAMAM G3 dendrimer containing amide bonds, partially-blocked amino groups on the surface, larger particle diameter and higher zeta potential can be a useful tool to improve the biological properties of transported drug molecules.

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Natural xanthones as modulators of the Nrf2/ARE signaling pathway and potential gastroprotective agents

Gunter,

Teh,

Jantan

et al. 2024

Phytotherapy Research

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Oxidative stress is implicated in the initiation, pathogenesis, and progression of various gastric inflammatory diseases (GID). The prevalence of these diseases remains a concern along with the increasing risks of adverse effects in current clinical interventions. Hence, new gastroprotective agents capable of inhibiting oxidative stress by modulating cellular defense systems such as the nuclear factor erythroid 2‐related factor 2 (Nrf2)/antioxidant response element (ARE) signaling pathway are critically needed to address these issues. A candidate to solve the present issue is xanthone, a natural compound that reportedly exerts gastroprotective effects via antioxidant, anti‐inflammatory, and cytoprotective mechanisms. Moreover, xanthone derivatives were shown to modulate the Nrf2/ARE signaling pathway to counter oxidative stress in both in vitro and in vivo models. Thirteen natural xanthones have demonstrated the ability to modulate the Nrf2/ARE signaling pathway and have high potential as lead compounds for GID as indicated by their in vivo gastroprotective action–particularly mangiferin (2), α‐mangostin (3), and γ‐mangostin (4). Further studies on these compounds are recommended to validate the Nrf2 modulatory ability in relation to their gastroprotective action.

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Comparison of physicochemical properties and aqueous solubility of xanthone prepared via oil-in-water emulsion and complex coacervation techniques

Cited by 7 publications

References 40 publications

Ectopic expression of a rice triketone dioxygenase gene confers mesotrione tolerance in soybean

Ectopic expression of a rice triketone dioxygenase gene confers mesotrione tolerance in soybean

Synthesis and Properties of α-Mangostin and Vadimezan Conjugates with Glucoheptoamidated and Biotinylated 3rd Generation Poly(amidoamine) Dendrimer, and Conjugation Effect on Their Anticancer and Anti-Nematode Activities

Natural xanthones as modulators of the Nrf2/ARE signaling pathway and potential gastroprotective agents

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