Triterpenoids from the stems of <i>Schisandra grandiflora</i> and their biological activity

Shi, Wei; Liu, Han‐Wei; Guo, Xin; Hou, Lan; Gao, Jin‐Ming

doi:10.1080/10286020.2016.1139578

Cited by 12 publications

(8 citation statements)

References 22 publications

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“…When the antifungal activity of eight urs‐12‐en‐28‐oic acid derivatives including asiatic acid ( 16 ) isolated from Schisandra grandiflora stem extracts were investigated against phytopathogenic fungi, only asiatic acid ( 16 ) showed an antifungal activity with MIC values ranging from 25 to 100 μg mL −1 against Alternaria spp. and Botrytis cinerea 45 . Based on our results and the literature data, we suggest that the hydroxyl group at C‐23 of compounds 15 – 16 seems to be important for the antifungal activity; 44,45 further investigation on a wider range of triterpenoid derivatives would be needed to clarify this hypothesis.…”

Section: Resultssupporting

confidence: 54%

“…and Botrytis cinerea. 45 Based on our results and the literature data, we suggest that the hydroxyl group at C-23 of compounds 15-16 seems to be important for the antifungal activity; 44,45 further investigation on a wider range of triterpenoid derivatives would be needed to clarify this hypothesis. Furthermore, the accumulation of knowledge on the structure-activity relationship may provide a scientific approach for the design of antifungal agents.…”

Section: Antifungal Activity Based On the Compound Structurementioning

confidence: 65%

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Antifungal properties of natural products from Pterocarya tonkinensis against phytopathogenic fungi

Ngo

Han

Minh

et al. 2020

Pest Management Science

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BACKGROUND In the search for new natural resources showing antifungal activity, we found that the methanol extract of Pterocarya tonkinensis (Fr.) Dode suppressed the disease development caused by fungi. The objectives of this article were (i) to isolate and identify the antifungal substances from the Pterocarya tonkinensis extract based on a bioassay‐guided fractionation and (ii) to investigate their potential as a biocontrol agent with their antifungal activities in vitro and in vivo. RESULTS Eighteen compounds were identified from the methanol extract of Pterocarya tonkinensis, including two new natural products 1 and 2: 1, pterocaryalactone; 2, pterocaryafuranone; 3, (1S, 6R)‐9‐hydroxymegastigm‐7‐en‐3‐one; 4, (S)‐dimethyl malate; 5, α‐linolenic acid; 6–8, α‐tetralones; 9, (R)‐methyl‐2‐hydroxyl‐3‐phenyl‐propanoate; 10, (E)‐4‐hydroxycinnamic acid methyl ester; 11–14, diarylheptanoids, and 15–18, pentacyclic triterpenoids. Based on the results of the in vitro antifungal assay, Magnaporthe oryzae and Phytophthora infestans were the most sensitive to the isolated compounds among the tested phytopathogenic fungi. When ten active compounds were applied onto plants at a concentration of 100 or 500 μg mL−1, compounds 1 and 8 effectively suppressed rice blast disease, and compounds 15 and 16 not only strongly reduced the development of blast on rice but also effectively controlled the development of late blight on tomatoes. CONCLUSION This is the first report to evaluate the in vitro and in vivo antifungal activities of the isolated compounds from a methanol extract of Pterocarya tonkinensis against phytopathogenic fungi, and our results suggest that Pterocarya tonkinensis and its substances can be used as a source to develop natural fungicides. © 2020 Society of Chemical Industry

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Section: Resultssupporting

confidence: 54%

Section: Antifungal Activity Based On the Compound Structurementioning

confidence: 65%

Antifungal properties of natural products from Pterocarya tonkinensis against phytopathogenic fungi

Ngo

Han

Minh

et al. 2020

Pest Management Science

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“…AA and the plants containing AA have been shown effective in microbial infections of animals and plants along with an activity against fungi. AA isolated from stem extract of Schisandra Grandiflora showed cytotoxicity against human cancer cell line (HepG2) and antifungal activity on plant pathogens, Alternaria alternata and Alternaria solani (Shi et al, 2016 ). AA isolated from Combretum laxum showed an in vitro antifungal activity against Candida albicans, Candidakrusei , and Cryptococcus neoformans (Bisoli et al, 2008 ).…”

Section: Asiatic Acid As Antifungalmentioning

confidence: 99%

Pharmacological Properties, Molecular Mechanisms, and Pharmaceutical Development of Asiatic Acid: A Pentacyclic Triterpenoid of Therapeutic Promise

et al. 2018

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Asiatic acid (AA) is a naturally occurring aglycone of ursane type pentacyclic triterpenoids. It is abundantly present in many edible and medicinal plants including Centella asiatica that is a reputed herb in many traditional medicine formulations for wound healing and neuropsychiatric diseases. AA possesses numerous pharmacological activities such as antioxidant and anti-inflammatory and regulates apoptosis that attributes its therapeutic effects in numerous diseases. AA showed potent antihypertensive, nootropic, neuroprotective, cardioprotective, antimicrobial, and antitumor activities in preclinical studies. In various in vitro and in vivo studies, AA found to affect many enzymes, receptors, growth factors, transcription factors, apoptotic proteins, and cell signaling cascades. This review aims to represent the available reports on therapeutic potential and the underlying pharmacological and molecular mechanisms of AA. The review also also discusses the challenges and prospects on the pharmaceutical development of AA such as pharmacokinetics, physicochemical properties, analysis and structural modifications, and drug delivery. AA showed favorable pharmacokinetics and found bioavailable following oral or interaperitoneal administration. The studies demonstrate the polypharmacological properties, therapeutic potential and molecular mechanisms of AA in numerous diseases. Taken together the evidences from available studies, AA appears one of the important multitargeted polypharmacological agents of natural origin for further pharmaceutical development and clinical application. Provided the favorable pharmacokinetics, safety, and efficacy, AA can be a promising agent or adjuvant along with currently used modern medicines with a pharmacological basis of its use in therapeutics.

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“…Related with the antimicrobial activities, Shi et al . 33 and Lahlou et al . 34 described the potent antimicrobial property of asiatic acid.…”

Section: Discussionmentioning

confidence: 92%

Identification of novel compounds, oleanane- and ursane-type triterpene glycosides, from Trevesia palmata: their biocontrol activity against phytopathogenic fungi

Kim

Han

Ngo

et al. 2018

Sci Rep

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Plants contain a number of bioactive compounds that exhibit antimicrobial activity, which can be recognized as an important source of agrochemicals for plant disease control. As part of our search for new antimicrobial agents from natural sources, we found that a crude methanol extract of Trevesia palmata exhibited a promising antifungal activity against phytopathogenic fungi, such as Magnaporthe oryzae and Botrytis cinerea. Furthermore, based on activity-guided fractionation, we isolated five antifungal compounds from the methanol extract of T. palmata: two new triterpene glycosides (TPGs), TPG1 (hederagenin-3-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside) and TPG5 (3-O-α-L-rhamnopyranosyl asiatic acid), along with three known TPGs (TPG2 [macranthoside A], TPG3 [α-hederin], and TPG4 [ilekudinoside D]). The chemical structures of the TPGs were determined by spectroscopic analyses and by comparison with literature data. An in vitro antifungal bioassay revealed that except for TPG4 (ilekudinoside D; IC50 >256 μg/ml), the other TPGs exhibited strong antifungal activities against the rice blast pathogen M. oryzae with IC50 values ranging from 2–5 μg/ml. In particular, when the plants were treated with compound TPG1 (500 μg/ml), disease control values against rice blast, tomato grey mold, tomato late blight, and wheat leaf rust were 84, 82, 88, and 70%, respectively, compared to the non-treatment control. Considering the in vitro and in vivo antifungal activities of the TPGs and the T. palmata methanol extracts, our results suggest that T. palmata can be a useful source to develop new natural fungicides.

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Triterpenoids from the stems of Schisandra grandiflora and their biological activity

Cited by 12 publications

References 22 publications

Antifungal properties of natural products from Pterocarya tonkinensis against phytopathogenic fungi

Antifungal properties of natural products from Pterocarya tonkinensis against phytopathogenic fungi

Pharmacological Properties, Molecular Mechanisms, and Pharmaceutical Development of Asiatic Acid: A Pentacyclic Triterpenoid of Therapeutic Promise

Identification of novel compounds, oleanane- and ursane-type triterpene glycosides, from Trevesia palmata: their biocontrol activity against phytopathogenic fungi

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