Limonoids from Munronia henryi and their anti-tobacco mosaic virus activity

Yan, Ying; Yuan, Chun‐Mao; Di, Ying‐Tong; Huang, Tao; Fan, Yi-Min; Ma, Yuan; Zhang, Jianxin; Hao, Xiao‐Jiang

doi:10.1016/j.fitote.2015.09.016

Cited by 29 publications

(23 citation statements)

References 24 publications

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“…Citrus produces diverse secondary metabolites, including limonoids. Limonoids possess extensive biological and pharmacological activities [1], such as antioxidant [2] and insect antifeedant [3,4] as well as antibacterial [5,6], anticancer [7][8][9], antiviral [10,11], and anti-inflammatory [12] activities. The production of limonoids varies in different citrus species, organs and tissues, and developmental stages [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

The MYB transcription factor CiMYB42 regulates limonoids biosynthesis in citrus

Pan

Liu

et al. 2020

BMC Plant Biol

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Background: Limonoids are major bioactive compounds that are produced by the triterpenoid metabolic pathway. The detailed biochemical process of limonoid biosynthesis and the mechanism of its molecular regulation remain elusive. The identification of transcription factors that regulate limonoid biosynthetic pathways is very important for understanding the underlying regulatory mechanisms. This information could also provide tools for manipulating biosynthesis genes to modulate limonoid production. Results: In this study, the CiMYB42 transcription factor was isolated to identify its role in limonoid biosynthesis. Multiple alignment analysis and phylogenetic analysis demonstrated that CiMYB42 is a typical R2R3MYB transcription factor that shares high similarity of its amino acid sequence with AtMYB42. Limonoids contents were higher in Citrus sinensis and Citrus grandis than in other species. Limonoid accumulation during leaf development also showed diverse trends in different genotypes. The expression of CiMYB42 was significantly related to the limonoid content and the expression of CiOSC in some citrus accessions. The overexpression of CiMYB42 in sweet orange resulted in significant accumulation of limonin, whereas the downregulation of CiMYB42 by RNAi resulted in a dwarf phenotype and less nomilin accumulation. Furthermore, the results of a yeast one-hybrid assay and EMSA indicated that CiMYB42 binds exclusively to the TTGTTG sequence (type II MYB core) in the promoter of CiOSC. Together, these results suggest that CiMYB42 positively regulates limonoid biosynthesis by regulating the expression of CiOSC by binding to the TTGTTG sequence (type II MYB core) of its promoter. Conclusions: CiMYB42 is an important transcription activator involved in limonoid biosynthesis that regulates the expression of CiOSC by binding to the TTGTTG sequence (type II MYB core).

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Section: Introductionmentioning

confidence: 99%

The MYB transcription factor CiMYB42 regulates limonoids biosynthesis in citrus

Pan

Liu

et al. 2020

BMC Plant Biol

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“…The 1 H NMR spectrum (Table 1) exhibited a β ‐substituted furan ring group ( δ H 7.32, 7.18, 6.20, each 1H, br s), six tertiary methyl groups ( δ H 0.77, 1.17, 1.59, 1.62, 1.87, 2.14, each 3H, s), a methoxy group ( δ H 3.66, 3H, s), and a terminal double bond group ( δ H 5.06, 5.03, each 1H, s), which strongly suggested that 1 was a peieurianin‐type limonoid. The 13 C NMR (Table 1) and HSQC data (Figure S5.1.3) of 1 were very similar to those of munronoid A ( 23 ), [ 18 ] a rings A, B‐ seco limonoid with the conjugated Δ 8,30 and Δ 14,15 double bonds. The planar structure of 1 was established by detailed 2D NMR analysis (Figure 2A), in which the methoxy group was located at C‐3 ( δ C 170.7) instead of C‐7 ( δ C 175.0) by the HMBC correlations of H 3 ‐1′ ( δ H 3.66) and H‐1 ( δ H 5.62) to C‐3.…”

Section: Resultsmentioning

confidence: 55%

“…[ 11 ] At present, there are only a few reports on the research of M. unifoliolata , but a large number of limonoids with significant anti‐inflammatory, antimicrobial, and anti‐TMV biological activities have been isolated from its genus. [ 12‐19 ] In order to understand the main and active ingredients of M. unifoliolata , the systematic extraction and separation of dichloromethane extract, the main anti‐inflammatory active portion of the whole plants (IC 50 = 17.9 ± 4.6 μmol/L), were carried out in our current research. This resulted in isolation of twenty‐two new limonoids ( 1 — 22 ), including rings A, B‐ seco , ring A‐ seco , and ring‐intact types.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Diverse Ring‐seco Limonoids from Munronia unifoliolata and Their Biological Activities

Sun

Cui

et al. 2021

Chin. J. Chem.

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Comprehensive Summary Twenty‐two new limonoids, mufolinoids A—V (1—22), including six rings A, B‐seco limonoids (1—6), twelve ring A‐seco limonoids (7—18), four ring‐intact limonoids (19—22), together with thirteen known compounds (23—35) were isolated from Munronia unifoliolata. Their structures including absolute configurations were elucidated by combination of NMR, HR‐MS, single‐crystal X‐ray diffraction and calculations of ECD and NMR technologies. Compounds 24, 25, 33, 34 could be significantly reversed the multidrug resistance of MCF‐7/doxorubicin (DOX) cells, and the reversal fold (RF) was much higher than that of positive drug Verapamil. Compounds 24, 28, and 29 exhibited significant anti‐inflammatory activity with the IC50 values in the range of 17.7—39.4 μmol/L. Furthermore, compound 29 could markedly inhibit the release of IL‐1β by inhibiting the initiation and assembly of NLRP3 inflammasome, which demonstrates the great potential of limonoids as an anti‐inflammatory agent.

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“…In ethanolic extracts obtained from M. henryi, in addition to previously characterized limonoids, other novel limonoids, a diterpenoid and a phytosterol, were identified and a strong antiviral activity was also observed (Yan et al, 2015). Chromones: Chromones (three novel compounds) were isolated from plants (C. fistula and N. tabacum).…”

Section: Natural Productsmentioning

confidence: 99%

Chemical Outbreak for Tobacco Mosaic Virus Control

Luvisi¹,

Panattoni²,

Materazzi³

et al. 2017

IJAB

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Tobacco mosaic virus (TMV) represents a paradigm in virology, and its control may open the way to effective treatment against phytoviruses. However, the use of chemicals to eliminate the virus from infected plants is very difficult. In this state of the art survey we include trials on a) natural compounds derived from organisms, b) synthetic compounds and c) plant or microorganism extracts, from 2006 to 2015. Plants have been the main source of natural products for anti-TMV tests in the last ten years, and Nicotiana tabacum was the main focus of research, particularly between 2014-2015. Since 2012, there has been a great increase in publications (+45%) and identified compounds (+241%). Between 2012-2015, an average of 31 papers were published and 140 compounds were tested each year, compared to 9 papers and 26 compounds in 2006-2011. Unfortunately, there is little information on the action mechanisms of newly discovered or modified compounds. Cross references to the basic structure of compounds is provided in this review. This chemical outbreak this massive interest in chemical solutions to TMV could be due to the increasing availability of instruments for the analysis of organic compounds. Alternatively Another explanation could be that the chemistry advances in synthesis, which have provided countless drugs with potential benefits for TMV control, have overwhelmed overloaded the plant pathology screening needed to discriminate between compounds and to provide useful agrochemicals for farmers.

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Limonoids from Munronia henryi and their anti-tobacco mosaic virus activity

Cited by 29 publications

References 24 publications

The MYB transcription factor CiMYB42 regulates limonoids biosynthesis in citrus

The MYB transcription factor CiMYB42 regulates limonoids biosynthesis in citrus

Diverse Ring‐seco Limonoids from Munronia unifoliolata and Their Biological Activities

Chemical Outbreak for Tobacco Mosaic Virus Control

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