Aphanamixoid A, a Potent Defensive Limonoid, with a New Carbon Skeleton from <i>Aphanamixis polystachya</i>

Cai, Jiangping; Yu, Zhongbo; Luo, Shi‐Hong; Chen, Duo-Zhi; Tang, Gui‐Hua; Yuan, Chun‐Mao; Di, Ying‐Tong; Li, Shenghong; Hao, Xiao‐Jiang; He, Hong‐Ping

doi:10.1021/ol3008149

Cited by 60 publications

(24 citation statements)

References 33 publications

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“…Recently, unprecedented quassinoids and limonoid derivatives with notable biological properties have been discovered and evaluated by our group141516. As part of our continuous effort to search for bioactive natural products17181920, two new 16-nor limonoids, harperspinoids A and B ( 1 and 2 ), with a unique 7/5/5/6/5 ring system, as well as a known one, Harperforin G ( 3 ), were isolated from the aerial parts of the title plant (Fig. 1).…”

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confidence: 99%

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

Yan

Cao

et al. 2016

Sci Rep

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Two new 16-nor limonoids, harperspinoids A and B (1 and 2), with a unique 7/5/5/6/5 ring system, have been isolated from the plant Harrisonia perforate together with a known one, Harperforin G (3). Their structures were elucidated by NMR spectroscopy, X-ray diffraction analysis and computational modelling. Compound 1 exists as polymorphic crystals. Conformations of 1 in solution were further discussed based on the computational results. These compounds exhibited notable inhibitory activity against the 11β-HSD1 enzyme. Compound 3 had potencies for the inhibition of human 11β-HSD1 with high selectivity against 11β-HSD2 (IC50 0.58 μM, SI > 174). Molecular docking and quantitative structure-activity relationship studies revealed a mixed regulatory mechanism.

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confidence: 99%

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

Yan

Cao

et al. 2016

Sci Rep

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“…The two new limonoids 1 and 2 displayed promising antifeedant activity against Spodoptera exigua with EC 50 values of 25.1 and 17.3 μg/cm 2 , respectively, which were less active than that of the positive control (EC 50 = 3.7 μg/cm 2 ), a commericial neem oil containing 1 % azadirachtin, while slightly more active than aphanamixoid A (EC 50 = 25.8 μg/cm 2 ), a potential natural product with antifeedant activity [28]. Furthermore, both compounds 1 and 2 , together with the known lignan, phyllanthusmin C, showed moderate cytotoxicity against the ECA109 cell line, with the IC 50 values of 11.5, 8.5, and 7.8 μM, respectively, compared to the positive control, 17-AAG (IC 50 = 1.1 μM).…”

Section: Resultsmentioning

confidence: 99%

Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

Zhao

Wang

Zhu

et al. 2014

Nat. Prod. Bioprospect.

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Two new highly oxygenated limonoids, flexuosoids A (1) and B (2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D–F (3–5), were isolated from the roots of Phyllanthus flexuosus, in addition to three known lignans, phyllanthusmin C, arabelline, and (+)-diasyringaresinol. Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1 and 2, two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1, C-2, C-3, C-7, C-11, C-17, and C-30, represent the second example of limonoids in the Euphorbiaceae family. Most of the isolates were tested for their antifeedant, anti-herpes simplex virus 1, and cytotoxic activities. The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm (Spodoptera exigua) with EC50 values of 25.1 and 17.3 μg/cm2, respectively. In addition, both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, along with the known lignan glycoside, phyllanthusmin C, with the IC50 values of 11.5 (1), 8.5 (2), and 7.8 (phyllanthusmin C) μM, respectively.Graphical AbstractTwo new highly oxygenated limonoids, flexuosoids A (1) and B (2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D–F (3–5), were isolated from the roots of Phyllanthus flexuosus, along with three known lignans. Flexuosoids A (1) and B (2) showed promising antifeedant activity against the beet army worm (Spodoptera exigua) with EC50 values of 25.1 and 17.3 μg/cm2, respectively. In addition, both of them and the known lignan glycoside, phyllanthusmin C, displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, with the IC50 values of 11.5, 8.5, and 7.8 μM, respectively.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-014-0026-2) contains supplementary material, which is available to authorized users.

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“…Limonoids have a broad range of bioactivities including insecticidal, antibacterial, antifungal, antimalarial, and antiviral, but are best-known as insect antifeedants, e.g., azadirachtin from the neem tree (Fang et al, 2011;Tan and Luo, 2011). Recently, aphanamixoid A, a novel skeleton limonoid that may be derived from an analogy of aphanamixoid B via 3,3-rearrangement ( Figure 6), was found to be a potent antifeedant against Helicoverpa armigera (Cai et al, 2012). For the first time, the Hao laboratory reported that some limonoids are potent activators of plant-induced SAR.…”

Section: Limonoids Activate Plant Sar and Inhibit Tmvmentioning

confidence: 99%

Natural product sciences: an integrative approach to the innovations of plant natural products

Shen

Hao

2020

Sci. China Life Sci.

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The study on plant natural products not only helps us understand that their structural diversity is the inevitable result of plant species diversity, but also helps us understand certain rules and unity of the inevitable connection between the two. The diversity and complexity of chemical structures of many natural products are beyond imagination before we elucidated their structures. The question that follows is what is the biological significance of these natural products. Intrigued by the relationship between plant resources, natural products and biological functions, the Hao laboratory has taken an integrative approach that employs tools and knowledge from multi-disciplines, including natural product chemistry, chemical ecology and chemical biology, to unveil the effects of plant natural products on plant resistance to diseases, and environmental acclimations. Collaborating with cell biologists, the research has resulted in discovery of new mechanisms of cellular signaling and lead compounds.

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Aphanamixoid A, a Potent Defensive Limonoid, with a New Carbon Skeleton from Aphanamixis polystachya

Cited by 60 publications

References 33 publications

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

Natural product sciences: an integrative approach to the innovations of plant natural products

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