Anti-TMV and Insecticidal Potential of Four Iridoid Glycosides from Gardenia Jasminoides Fruit

Li, Ling; Zou, Jiyong; Xia, Qing; Cui, Hongmin; You, Shengyong; Liu, Yuxiu; Wang, Qingmin

doi:10.1007/s40242-018-8197-8

Cited by 9 publications

(7 citation statements)

References 14 publications

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“…The natural products crocin-1 and crocin-2 showed significantly higher anti-TMV activity than the commercial ribavirin and were the most active anti-TMV compounds currently isolated from the fruits of G. fructus . The difference in structure between crocin-1 and crocin-2 is the different glycosyl groups linked to aglycon crocetin, but their anti-TMV activity levels are similar.…”

Section: Resultsmentioning

confidence: 99%

“…As one of the most significant and widely employed herbal drugs in traditional Chinese medicine, Gardeniae fructus has been confirmed to be a significant chemotherapeutic agent for the acceleration of ligament cell proliferation and collagen synthesis, protections of liver and gallbladder cells from infringement, and treatment of cardiovascular and cerebrovascular diseases. − In our previous work, the iridoid glycosides derived from the fruits of G. fructus and genipin derivatives have been proven to have restrained anti-TMV potential. − As a continuous exploit on G. fructus, the carotenoid substances, crocin-1 and crocin-2 from the fruits of G.…”

Section: Introductionmentioning

confidence: 99%

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Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

Zou

et al. 2021

J. Agric. Food Chem.

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The development of antiviral agents with an original structure and noticeable effect is always in great need. Natural products are important lead compounds in the development of new pesticides. Crocin-1 and crocin-2 were effectively isolated from Gardeniae fructus and found to have higher anti-tobacco mosaic virus (TMV) activity levels than ribavirin. A series of the crocetin diester derivatives were synthesized with separated crocetin-1 as material and evaluated for their anti-TMV activities. They could be dissolved in common organic solvents as dichloromethane, ethyl acetate, tetrahydrofuran, and methanol. Compounds 5, 9, 13, 14, and 15 displayed higher activities in vivo than ribavirin. Compound 14 with significantly higher antiviral activities than lead compounds (crocin-1 and crocin-2) emerged as a new antiviral candidate.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

Zou

et al. 2021

J. Agric. Food Chem.

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“…6 Cerbinal was reported to show antifungal activity against Bipolaris sorokiniana, Helminthosporium, Pyricularia, Colletotrichum lagenarium, and Puccinia species. 7 In our previous work, the iridoid glycosides from the gardenia jasminoides fruit 8 and genipin glycoside derivatives 9 were found to have good anti-TMV and insecticidal potential. As a continuation of our work, cerbinal was synthesized and evaluated for its biological activities.…”

Section: ■ Introductionmentioning

confidence: 95%

Natural Product Cerbinal and Its Analogues Cyclopenta[c]pyridines: Synthesis and Discovery as Novel Pest Control Agents

Zou

You

et al. 2019

J. Agric. Food Chem.

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Owing to the changing needs of agriculture, the exploration of new pest control agents remains as critical as ever. The analogues 3a–3v of the natural product cerbinal were synthesized from genipin by an efficient and practical method under additive-free conditions. The antiviral and insecticidal effects of cerbinal and these cyclopenta[c]pyridines (3a–3v) were evaluated systematically. Most of the synthesized compounds exhibited higher anti-TMV activities than the lead compound cerbinal. Compound 3s (2-(4-methoxyphenyl)) had the most promising inhibitory activities against TMV (inactivation effect 49.0 ± 0.8%, curative effect 41.2 ± 4.3%, and protection effect 51.5 ± 2.7% at 500 μg/mL). Among the synthesized compounds, only 3v (2-(2-chloro-4-(trifluoromethoxy)phenyl)) reached the activity level of cerbinal against Plutella xylostella. This suggested that the cyclopenta[c]pyridines obtained by modifications of cerbinal at position 2 are very significant for the anti-TMV activity, and yet were exceptionally less active for the insecticidal activities.

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“…It is a common TCM and food used alone or in formulations for the treatment of various diseases, including jaundice, diarrhea, liver disease, and gastroenteritis (Chen et al., 2016; Debnath et al., 2011; Yokoyama & Nagino, 2014) and is additionally used as a natural colorant in food (Li et al., 2020; Yamada et al., 1996). The major bioactive constituents are iridoids (Li et al., 2018), carotenoids (Ni et al., 2017), flavonoids, and organic acids (Kim et al., 2006). Among them, the iridoids, such as geniposide, are the major bioactive constituents and their contents in FG are high.…”

Section: Introductionmentioning

confidence: 99%

Effects of medicine food Fructus Gardeniae on liver and kidney functions after oral administration to rats for 12 weeks

Gao

et al. 2021

J Food Biochem

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Fructus Gardeniae (FG) is medicine food widely used for the treatment and prevention of various diseases. However, in recent years, research has suggested that high doses of FG can cause hepatotoxicity and nephrotoxicity. To assess this potential toxicity in more depth, this study investigated the effects of decocted FG and two of its bioactive constituents (geniposide and genipin) on liver and kidney function in rats. Rats were intragastrically administered FG (330 mg/kg body weight), geniposide (50 mg/kg body weight), or genipin (50 mg/kg body weight) for 12 weeks. Changes in body weight, liver and kidney indices, biochemical indices, and inflammatory factors were monitored. In addition, pathological sections were assessed and the expression of caspase‐3, NF‐κBp65, COX‐2, and iNOS was detected by immunohistochemistry and Western blot. It was found that the levels of aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase, creatinine, and urea nitrogen increased following administration of FG, geniposide, and genipin. Furthermore, the activities of superoxide dismutase and reduced glutathione decreased following treatment, while malondialdehyde levels increased. Pathological and immunohistochemical evaluations further confirmed that FG and its constituents may cause damage to the liver and kidneys. The mechanism study revealed that the protein level of inflammatory pathway increased and further promoted apoptosis, suggesting that it should not be taken orally for extended periods of time. Practical applications Chinese medicine and food safety have always been public health concerns. Fructus Gardeniae (FG) is a plant with a dual‐purpose as it is used as both a medicine and food. Medicinally, it has the effects of heat‐clearing and detoxification. However, its adverse effects and related mechanisms are not clear, and this has potential safety implications. In this study, rats were treated with FG for 12 weeks and found that the long‐term administration of FG or high dosing can lead to damage to liver and kidney function. Therefore, close attention must be paid to the dosage of FG in order to achieve a therapeutic effect and avoid adverse reactions. Thus, this study lays a foundation for the safety evaluation and clinical application of FG.

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Anti-TMV and Insecticidal Potential of Four Iridoid Glycosides from Gardenia Jasminoides Fruit

Cited by 9 publications

References 14 publications

Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

Natural Product Cerbinal and Its Analogues Cyclopenta[c]pyridines: Synthesis and Discovery as Novel Pest Control Agents

Effects of medicine food Fructus Gardeniae on liver and kidney functions after oral administration to rats for 12 weeks

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