Biochemical Systematics and Ecology 48 (2013) 186188

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Biochemical Systematics and Ecology

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Phytochemical and chemotaxomic study on Polygonum perfoliatum L

Jinxiu Lei, Nan Yao, Kui-Wu Wang*
School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310035, PR China

a r t i c l e i n f o
Article history: Received 18 September 2012 Accepted 7 December 2012 Available online Keywords: Polygonum perfoliatum L. Polygonaceae Flavonoid Lignan Chemotaxomy

1. Subject and source The genus Polygonum belonging to the family Polygonaceae, comprises about 300 species mainly distributed in north temperate regions. In China, 120 species are found, especially in the southwest area, and most of them (80 species) are recorded to use in traditional Chinese medicine, concerning anti-inammatory, promoting blood circulation, dysentery, diuretic and haemorrhage (Gong et al., 2002). Polygonum perfoliatum L. (Polygonaceae) is an annual vine indigenous to temperate regions of Bhutan, China, India, Indonesia, Japan, Korea, Nepal, the Philippines, Russia and Vietnam (Wu and Raven, 2003). This plant has been used as a traditional herb to treat fever, chill, joint pain, oedema, rheumatoid arthritis and bacterial infection in Chinese folk medicine for more than 300 years (Lou et al., 1988). The tubers of P. perfoliatum L. were collected in September 2008 in Jinfoshan, Chongqing, China, and identied by Prof. Changxi Zhang (Jinhua Medical College, Jinhua, Peoples Republic of China.). A voucher specimen (No. zjgsu 20080032) has been deposited at the School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou, P. R. China. 2. Previous work In past studies, a large number of structurally interesting anthraquinones, coumarins, avonoids, lignans, napthaquinone, polyphenols, sesquiterpenes and triterpenes with various biological activities, such as anti-tumour, antioxidant, antiinammatory, anti-HIV, immunosuppressive and insecticidal activities, were discovered from the genus Polygonum (Kim et al., 1994; Sun and Sneden, 1999; Matsuda et al., 2001; Datta et al., 2002; Peng et al., 2003; Wang et al., 2005; Silvia et al., 2006; Li et al., 2007; Yu et al., 2008).

* Corresponding author. 86 571 88071024 7576. E-mail address: wkw220@yahoo.com.cn (K.-W. Wang). 0305-1978/$ see front matter Crown Copyright 2012 Published by Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.bse.2012.12.006

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3. Present study The shade-dried tubers (10 kg) of P. perfoliatum L. were powdered and reuxed with 95% EtOH (3 20 L). After concentration in vacuum, the residual was dissolved in water, and extracted with petroleum ether, EtOAc, and n-butanol successively. The EtOAc extract (56 g) was submitted to silica gel column chromatography (CC), eluted with petroleum ether/ EtOAc (100:00:100). 10 main fractions (Fr. 1Fr. 10) were obtained by check with TLC and combined. b-Sitosterol (120 mg) and stigmasterol (65 mg) were obtained from Fr. 1 and Fr. 2, respectively, and determined by the standard compounds using TLC. Fr. 4 was rechromatographed to afford compounds 30 , 5-dihydroxy-3,40 ,50 ,7-tetramethoxyavone (17 mg) (Datta et al., 2000) and picraquassioside C (51 mg) (Yoshikawa et al., 1995). 8-oxo-pinoresinol (Wang et al., 2012) (43 mg) and catechin (15 mg) (Chen et al., 1999) were obtained from Fr. 5 using the Sephadex LH-20 column chromatography and compound quercetin (38 mg) (Huang et al., 2001) was obtained from Fr. 6 by rechromatographed with silica gel CC. The n-butanol extract (140 g) was submitted to D101 column chromatography, eluted with 25%, 50%, 75% and 95% ethanol to get four fractions (Fr. 1 4). Fr. 2 and Fr. 3 then subjected to silica gel, reversed phase gel (RP-18) and Sephadex LH-20 column chromatography repeatedly, yield compounds quercetin-3-O-b-D-glucuronide (22 mg) (Nawwar et al., 1984) and rutin (35 mg) (Zhou et al.,

OH OH H H OH OH O H O HO O HO O OH OH COOH

H H OH H

-sitosterol

stigmasterol

quercetin-3-O- -D-glucuronide

OH OH HO O HO O

OH OH HO O OH O rutinose OH catechin O

OH OH

OH OH O

OH

quercetin OH OCH3 H3CO O

rutin

OCH3 H3CO OH H3CO OCH3 HO O OH H3CO picraquassioside C H O O H OH

OCH3 OH O

3', 5-dihydroxy-3, 4', 5', 7-tetramethoxyflavone

OCH3 O H HO H H3CO 8-oxo-pinoresinol

Fig. 1. The structures of all isolates.

H OH H O OH HO OH

3, 4-dihydroxybenzoic acid

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2002). The structures of isolates (Fig. 1) were established by analysis of their NMR and MS data, and by comparison of their spectroscopic data with literature values. 4. Chemotaxomic signicance Among the secondary metabolites isolated from this genus, avonoids have been considered as important chemotaxonomic marker in Polygonum (Isobe and Noda, 1987; Park, 1987; Datta et al., 2002). Glycosylation at C-3 of the quercetin moiety is the most common feature (Park, 1987), which is conrmed by the results of the present study. Homoisoavanones have to date only been isolated from P. perfoliatum (Lpez et al., 2006), Polygonum senegalense (Midiwo et al., 2007) and Polygonum odoratum (Li et al., 2009). The presence of the sesquiterpenes is another important diagnostic marker for the delimitation of the Persicaria section in Polygonum genus (Derita and Zacchino, 2011). In the present study, 3-substituted avonoids were the main secondary metabolites in the species P. perfoliatum L. However, sesquiterpenes were not isolated from this species. When compared the distribution of avoniods (Isobe and Noda, 1987; Park, 1987; Datta et al., 2002) with that of lignans in this genus, we deduced that lignans show more taxonomic importance than avonoids, since avonoids widely distribute in Polygonum genus and lack of structural distinction. Aryltetralin type of lignans have been isolated from Polygonum aviculare (Kim et al., 1994; Konuklugil, 2002), Polygonum cuspidatum (Xiao et al., 2002) and Polygonum capitatum (Zhao et al., 2010), which suggests that the three species could be systematically related. Sesquilignans have only been isolated from Polygonum oriental L (Zheng et al., 1998) and P. perfoliatum, which can be used to differentiate P. oriental and P. perfoliatum from other species of Polygonum. The main structural lignan unit of the sesquilignan from P. perfoliatum is a 2,6-di-(substituted aryl)-cis3,7-dioxabicyclo[3.3.0]octane skeleton. However, tetrahydrofuran-9,90 - monoepoxy lignan is the main part of the sesquilignan from P. oriental L (Zheng et al., 1998). This structural difference could be used to differentiate P. perfoliatum and P. oriental (Zheng et al., 1998) containing sesquilignans. 8-Oxo-pinoresinol is a 2,6-di-(substituted aryl)-cis-3,7-dioxabicyclo[3.3.0]octane lignan peculiar to P. perfoliatum and this kind of lignan has not been reported from other species of Polygonum. Although () pinoresinol (not isolated) is the precursor of many types of lignans and sesquilignans (Whetten and Sederoff, 1995; Dinkova-Kostova et al., 1996; Federolf et al., 2007), the 8-oxygenated 2,6-di-(substituted aryl)-cis-3,7-dioxabicyclo[3.3.0] type of lignan is rare in nature. Thus, lignans and sesquilignans with dioxabicyclo[3.3.0] substructure could be used as important chemotaxonomic markers of the species P. perfoliatum L. Acknowledgements This work was supported by the NSFC of China (No. 31171701). References
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