Constituents from Polygonum cuspidatum.

Xiao, Kai; Liu, Xuan; Xu, Yaming; Bai, Donglu; Zhong, Dexin

doi:10.1248/cpb.50.605

Cited by 81 publications

(44 citation statements)

References 25 publications

(30 reference statements)

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“…There are mainly six classes of compounds in this plant, including anthraquinones (Chu et al 2004;Murakami et al 1968;Zhao et al 2005), stilbenes (Nonomura et al 1963;Vastano et al 2000), flavonoids (Kuznetsova 1979;Xiao et al 2002), procyanidins (Fan et al 2009;Kuznetsova 1979;Molnar 1991) and organic acid (Murakami et al 1968). In our previous work, to reveal the phytochemical differences between the original and the invasive varieties of P. cuspidatum, the chromatographic fingerprints of root samples from China and Switzerland were run using the technique of liquid chromatography simultaneously coupled to ultra-violet detection and electrospray ionization mass spectrometry (HPLC/UV/ESI-MS).…”

Section: Introductionmentioning

confidence: 99%

Allelochemicals of the invasive neophyte Polygonum cuspidatum Sieb. & Zucc. (Polygonaceae)

2010

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Polygonum cuspidatum Sieb. and Zucc., a traditional Chinese medicine is now a wide-spread invasive neophyte in Europe and America. The novel weapon hypothesis states that some invasive weed species owe part of their success as invaders to allelopathy mediated by some allelochemicals. Previous HPLC/UV/ESI-MS analysis showed that the constituents of the roots of P. cuspidatum from China were obviously different from the species collected in Switzerland (present as an invasive neophyte) with respect to piceatannol glucoside, resveratroloside and some proanthocyanidin. This work isolated these special constituents from the invasive plant and studied their allelopathy effect, as well as the related structures by the seedling and growing model of Lepidium sativum (garden cress, Brassicaceae). The results revealed that stilbenes as piceatannol glucoside, resveratroloside and proanthocyanidins as catechin, epicatechin from this plant were comparatively stronger allelochemicals than the reported allelochemical (-)-catechin, which may partly explain the invasive behavior of this plant in Europe.

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Section: Introductionmentioning

confidence: 99%

Allelochemicals of the invasive neophyte Polygonum cuspidatum Sieb. & Zucc. (Polygonaceae)

2010

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“…(Polygonaceae) is a medicinal plant that has been widely used in Chinese and Japanese folk medicine for the treatment of atherosclerosis, hypertension, cough, suppurative dermatitis, and gonorrhea (Nonomura et al 1963;Yi et al 2007). Various aromatic polyketides including anthraquinones, such as emodin, physcion and chrysophanol, and stilbenes, such as resveratrol, piceid and 2,3,5,4Ј-tetrahydroxystilbene-2-O-D-glucoside, have been isolated from this plant (Xiao et al 2002;Hegde et al 2004), suggesting that, besides the typical CHS involved in the biosynthesis of Xavonoids, several functionally divergent PKSs occur in P. cuspidatum.…”

Section: Introductionmentioning

confidence: 99%

A novel type III polyketide synthase encoded by a three-intron gene from Polygonum cuspidatum

Pang

Shen

et al. 2008

Planta

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A type III polyketide synthase cDNA and the corresponding gene (PcPKS2) were cloned from Polygonum cuspidatum Sieb. et Zucc. Sequencing results showed that the ORF of PcPKS2 was interrupted by three introns, which was an unexpected finding because all type III PKS genes studied so far contained only one intron at a conserved site in flowering plants, except for an Antirrhinum majus chalcone synthase gene. Besides the unusual gene structure, PcPKS2 showed some interesting characteristics: (1) the CHS "gatekeepers" Phe215 and Phe265 are uniquely replaced by Leu and Cys, respectively; (2) recombinant PcPKS2 overexpressed in Escherichia coli efficiently afforded 4-coumaroyltriacetic acid lactone (CTAL) as a major product along with bis-noryangonin (BNY) and p-hydroxybenzalacetone at low pH; however, it effectively yielded p-hydroxybenzalacetone as a dominant product along with CTAL and BNY at high pH. Beside p-hydroxybenzalacetone, CTAL and BNY, a trace amount of naringenin chalcone could be detected in assays at different pH. Furthermore, 4-coumaroyl-CoA and feruloyl-CoA were the only cinnamoyl-CoA derivatives accepted as starter substrates. PcPKS2 did not accept isobutyryl-CoA, isovaleryl-CoA or acetyl-CoA as substrate. DNA gel blot analysis indicated that there are two to four PcPKS2 copies in the P. cuspidatum genome. RNA gel blot analysis revealed that PcPKS2 is highly expressed in the rhizomes and in young leaves, but not in the roots of the plant. PcPKS2 transcripts in leaves were induced by pathogen infection, but not by wounding.

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“…14,15) Stilbenes, anthraquinones, and flavoids have been isolated from the genus Pleuropterus. 16) Recently, a new naphthopyrone, pleuropyrone A with antioxidant activity was reported from Pleuropterus ciliinervis.…”

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Inhibition of Chitin Synthases and Antifungal Activities by 2'-Benzoyloxycinnamaldehyde from Pleuropterus ciliinervis and Its Derivatives

Kang

Hwang

Yun

et al. 2007

Biological & Pharmaceutical Bulletin

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In the course of search for potent chitin synthase inhibitors from natural resources, a novel chitin synthases inhibitor, 2-benzoyloxycinnamaldehyde (2-BCA) (I), was isolated from the aerial parts of Pleuropterus ciliinervis NAKAI. 2-BCA inhibited chitin synthase 1 and 2 of Saccharomyces cerevisiae with the IC 50 s of 54.9 and 70.8 m mg/ml, respectively, whereas it exhibited no inhibitory activity for chitin synthase 3 up to 280 m mg/ml. Its derivatives, 2-chloro-(V) and 2(-bromo-cinnamaldehyde (VI), each showed 1.9 and 2.7-fold stronger inhibitory activities than 2-BCA, with the IC 50 s of 37.2 and 26.6 m mg/ml, respectively. Especially, the IC 50 of compound VI against chitin synthase 2 represented 1.7-fold more potent inhibitory activity than polyoxin D, a well-known chitin synthase inhibitor. Furthermore, compounds V and VI showed potent antifungal activities against various fungi including human pathogenic fungi, with a particularly strong inhibitory activity against Cryptococcus neoformans (MIC‫61؍‬ m mg/ml). Although the chemical synthesis of this compound has been reported, the present study is the first report to describe the isolation of 2-BCA from natural resources and chitin synthases inhibitory activities of its derivatives. These results suggested that 2-BCA and its derivatives can potentially serve as useful lead compounds for development of antifungal agents.

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Constituents from Polygonum cuspidatum.

Cited by 81 publications

References 25 publications

Allelochemicals of the invasive neophyte Polygonum cuspidatum Sieb. & Zucc. (Polygonaceae)

Allelochemicals of the invasive neophyte Polygonum cuspidatum Sieb. & Zucc. (Polygonaceae)

A novel type III polyketide synthase encoded by a three-intron gene from Polygonum cuspidatum

Inhibition of Chitin Synthases and Antifungal Activities by 2'-Benzoyloxycinnamaldehyde from Pleuropterus ciliinervis and Its Derivatives

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