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Isoswertisin flavones and otherconstituents from PeperomiaobtusifoliaJonas da S. Mota a , Ana C. Leite a , Massuo J. Kato b , MariaClaudia M. Young c , Vanderlan da S. Bolzani a & Maysa Furlan aa Instituto de Química, Universidade Estadual Paulista , CP 355,CEP 14801-970, Araraquara, SP, Brazilb Instituto de Química, Universidade de São Paulo , CP 26077,05599-970 São Paulo, SP, Brazilc Seção de Fisiologia e Bioquímica de Plantas, Instituto deBotânica , CP 4005, CEP 01061-970, São Paulo, SP, BrazilPublished online: 13 Jan 2011.

To cite this article: Jonas da S. Mota , Ana C. Leite , Massuo J. Kato , Maria Claudia M. Young ,Vanderlan da S. Bolzani & Maysa Furlan (2011) Isoswertisin flavones and other constituents fromPeperomia obtusifolia , Natural Product Research: Formerly Natural Product Letters, 25:1, 1-7, DOI:10.1080/14786410903244954

To link to this article: http://dx.doi.org/10.1080/14786410903244954

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Natural Product ResearchVol. 25, No. 1, January 2011, 1–7

Isoswertisin flavones and other constituents from

Peperomia obtusifolia

Jonas da S. Motaa, Ana C. Leitea, Massuo J. Katob, Maria Claudia M. Youngc,Vanderlan da S. Bolzania and Maysa Furlana*

aInstituto de Quımica, Universidade Estadual Paulista, CP 355, CEP 14801-970,Araraquara, SP, Brazil; bInstituto de Quımica, Universidade de Sao Paulo, CP 26077,05599-970 Sao Paulo, SP, Brazil; cSecao de Fisiologia e Bioquımica de Plantas,Instituto de Botanica, CP 4005, CEP 01061-970, Sao Paulo, SP, Brazil

(Received 5 June 2009; final version received 2 September 2009)

A phytochemical investigation of the leaves and stems of Peperomiaobtusifolia (Piperaceae) yielded a new flavone C-diglycoside isoswertisin-40-methyl-ether-200�-L-rhamnoside (1), along with four known compounds:isoswertisin-200�-L-rhamnoside (2), (þ)-diayangambin (3), 2-episesalatin (4)and corchoionoside C (5). The structures of the two flavone C-diglycosides(1, 2) were elucidated on the basis of 1D and 2D NMR spectroscopy andMS spectrometric data. These flavones were evaluated by bioautographicassay against Cladosporium cladosporioides and C. sphaerospermum andshowed weak antifungal activity.

Keywords: Piperaceae; Peperomia obtusifolia; flavones

1. Introduction

The genus Peperomia is the second largest in the Piperaceae family that comprisesmore than 600 species widely distributed in southeast Brazil (Mabberley, 1993;Wankeet al., 2007). The chemistry of the Piperaceae is based on the occurrence ofphenylpropanoids (Orjala, Erdelmeir, Wright, Rali, Sticher, 1993), lignans, neo-lignans (Benevides, Sartorelli, & Kato, 1999; Monache & Compagnone, 1996; Parmaret al., 1997), aliphatic and aromatic amides (Alecio, Bolzani, Young, Kato, & Furlan,1998; Navickiene et al., 2000; Silva et al., 2002), alkaloids (Dodson, Dyer, Searey,Wright, & Letourneau, 2000), polyketides (Cheng et al., 2003), chromenes (Baldoquiet al., 1999; Lago et al., 2004; Morandim et al., 2005; Moreira, Guimaraes, & Kaplan,1998) and benzoic acid derivatives (Bergamo, Kato, Bolzani, & Furlan, 2005).Compared with the genus Piper, few phytochemical studies of Peperomia have beencarried out. Two major classes of aromatic compounds have been isolated fromdifferent species of Peperomia which include secolignans (Bayma, Arruda, Muller,Arruda, & Canto, 2000; Govindachari, Krishna-Kumari, & Partho, 1998;Monache &Compagnone, 1996) and prenylated phenolic compounds of polyketide origin (Mbah,Tchuendem, Tane, & Sterner, 2002; Seeram, Jacobs, McLean, & Reynolds, 1998;

*Corresponding author. Email: maysaf@iq.unesp.br

ISSN 1478–6419 print/ISSN 1029–2349 online

� 2011 Taylor & Francis

DOI: 10.1080/14786410903244954

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Tanaka, Asai, & Linuma, 1998). Some biological activities of Peperomia compoundshave been reported, e.g. antiparasitic (Mahiou, Roblot, Hocquemiller, & Cave, 1996),cytotoxic (Dodson et al., 2000; Li et al., 2006; Wu et al., 2005, 2006) and antifungalactivities (Roussis, Ampofo, & Wiemer, 1990; Salazar, Paredes, Lluncor, Young, &Kato, 2005). Peperomia obtusifolia is a well-known popular foliage plant and growsfrom Mexico to the northern parts of South America. A previous phytochemicalinvestigation of the aerial parts of P. obtusifolia showed the presence of five phenoliccompounds bearing a methyl, an isoprenyl and a geranyl group on a benzene ring core(Tanaka et al., 1998). Recently, we reported the trypanocidal activity of phenolicderivatives isolated from this species (Mota et al., 2009).

In this work, we describe the isolation and structural elucidation of two flavoneC-diglycosides (1 and 2) from the leaves of P. obtusifolia. The antifungal activityof these compounds was evaluated by a bioautographic thin layer chromatographic(TLC) assay against Cladosporium cladosporioides and C. sphaerospermum.In addition, two lignans (3 and 4) and one (6S)-hydroxy-3-oxo-�-ionol glycoside(5) were isolated from the leaves and stems of P. obtusifolia.

2. Results and discussion

Compound 1 was obtained as yellow oil. The IR (KBr) absorptions displayed ahydroxyl band at 3411 cm�1 and UV absorptions appeared at 272 and 326 nm. Themolecular formula, C29H34O14, was obtained on the basis of the [MþH]þ ion at m/z607 on the HRESI-MS and supported by hydrogen and carbon counting on 1D and2D NMR spectra.

The 1HNMR spectral data of 1 (Table 1) showed two doublet signals at � 7.01 and8.18 (J 9.0Hz) assigned to H-30, H-50 and H-20, H-60, respectively, and a singlet at� 6.91 typical of H-3, which suggested that 1was a flavone. Long-range correlations inthe HMBC contour map from the glucosyl anomeric hydrogen H-100 (� 4.80, d,J¼ 10Hz) with carbon signals at � 105.7 (C-8) and 163.1 (C-7) indicated the sugarattachment at the C-8 position of the aglycone moiety. From these data, the sugarsubstituent at C-8 gave a pattern of 13C NMR signals similar to those in isoswertisin(8-C-glycosyl-7-O-methylapigenin) (Scharbert, Holzmann, & Hofmann, 2004). TheESI-MS analysis as well as the detection of a 15 carbon-linked sugar proton indicatedthe presence of a second sugar unit in the molecule. The methyl signal at � 0.42 (d, J6.0Hz) and the HMBC correlation between C-200 (� 75.2) and the doublet at � 4.95,assigned to the anomeric proton H-1000, revealed this second sugar to be arhamnopyranosyl and indicated a C-1000!C-200 linked disaccharide. The value of thecoupling constant of H-1000 (J 1.5Hz) determined that this sugar moiety was present asan �-anomer. The assignments of the signals of the sugarmoiety were confirmed by 1DTOCSY NMR, with the irradiation of H-100 (� 4.80, d, J¼ 10Hz) that showedcorrelation with the signals of H-200 (� 3.99, dd, J¼ 8.5, 10.0Hz), H-300 (� 3.44, m), H-500

(� 3.25, m), H-600a (� 3.75, br d, J¼ 12.5Hz) and H-600b (� 3.58, dd, J¼ 4.5, 12.5Hz).The irradiation of the hydrogens in the methyl group of the rhamnose (� 0.42, d,

J¼ 6.0Hz) showed correlation with the signals at � 3.01 (H-3000), 2.87 (H-4000)and 1.95 (H-5000). In addition, HRESI-MS showed two fragment peaks at m/z 299[M � rha � glcþH]þ and m/z 461 [M � rhaþH]þ, which are in agreement with theproposed structure.

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The 1H NMR spectrum of 1 showed the presence of two singlets at � 3.86(H3CO-40) and � 3.88 (H3CO-7), related to two methoxyl groups. Its corresponding13C NMR spectral assignments at � 55.6 (H3CO-40) and 56.7 (H3CO-7) weredetermined with HMQC data. The position of these groups was established throughNOESY and HMBC experiments. NOESY showed correlations between the signal at� 3.86 with the doublet at � 7.01 (H-30 and H-50). In the HMBC correlation map,a cross-peak correlation of this methoxyl signal with the signal of C-40 (� 162.5) wasobserved. The signal at � 3.88 showed correlations with the signal at � 6.51 (H-6) inboth NOESY data and HMBC spectra with C-7 (� 163.1). Based on these data, it wasdetermined that the methoxyl groups were attached on C-40 and C-7 and thus, thestructure of the new flavone C-diglycoside (1) was determined as isoswertisin-40-methyl-ether-200 �-L-rhamnoside. This proposal was confirmed by a comparisonwith the previously reported data for correlated flavones (Cheng et al., 2000; Lin, Kuo,

Table 1. 1H (500MHz) and 13C (125MHz) NMR spectral data for compounds 1 and 2

isolated from P. obtusifolia in DMSO-d6.

1a

2a

Position �H (J in Hz) �c �H (J in Hz) �c

2 164.6 (s) 164.4 (s)3 6.91 (s) 103.1 (d) 6.82 (s) 102.3 (d)4 182.4 (s) 182.2 (s)5 161.6 (s) 161.4 (s)6 6.51 (s) 94.4 (d) 6.49 (s) 95.2 (d)7 163.1 (s) 163.0 (s)8 105.7 (s) 105.6 (s)9 155.0 (s) 154.9 (s)10 104.7 (s) 104.6 (s)10 123.1 (s) 121.3 (s)20,60 8.18 (d) (9.0) 129.0 (d) 8.04 (d) (9.0) 129.0 (d)30,50 7.01 (d) (9.0) 114.6 (d) 6.89 (d) (9.0) 115.9 (d)40 162.5 (s) 163.0 (s)100 4.80 (d) (10.0) 71.4 (d) 4.80 (d) (10.0) 71.4 (d)200 3.99 (dd)

(8.5, 10.0)75.2 (d) 4.00 (dd) (8.5, 10.0) 75.2 (d)

300 3.44 (m) 79.8 (d) 3.38 (m) 79.8 (d)400 3.44 (m) 70.5 (d) 3.38 (m) 70.5 (d)500 3.25 (m) 81.9 (d) 3.22 (m) 81.8 (d)600 Ha 3.75 (br d) (12.5) Hb 3.58 (dd)

(4.5, 12.5)61.0 (t) Ha 3.75 (br d)

(12.5)Hb 3.54 (dd)(4.5, 12.5)

61.0 (t)

Hb 3.58 (dd)(4.5, 12.5)

Hb 3.54 (dd)(4.5, 12.5)

10 00 4.95 (d) (1.5) 100.2 (d) 4.95 (d) (1.0) 100.1 (d)20 00 3.56 (s) 70.3 (d) 3.56 (s) 70.3 (d)30 00 3.01 (dd)

(3.0, 9.5)70.4 (d) 3.01 (dd)

(3.0, 9.5)70.5 (d)

40 00 2.87 (t) (9.5) 71.5 (d) 2.88 (t) (9.5) 71.5 (d)50 00 1.95 (m) 68.2 (d) 1.94 (m) 68.1 (d)60 0.42 (d) (6.0) 17.7 (q) 0.44 (d) (6.0) 17.7 (q)H3CO-7 3.88 (s) 56.7 (q) 3.88 (s) 56.6 (q)H3CO-40 3.86 (s) 55.6 (q)OH 13.20 (s) 13.20 (s)

Note: aAssignments based on 1H–1H COSY, HMQC and HMBC.

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Chung, Ko, & Teng, 1997; Picerno, Mencherini, Lauro, Barbato, & Aquino, 2003;Scharbert, Holzmann, & Hofmann, 2004). This information rectified the previouslyreported data (Mota et al., 2009) that described 1 as a known compound.

Compound 2 was isolated as a yellow amorphous solid, with the molecularformula C28H32O14 deduced from the [MþH]þ ion at m/z 593 on the HRESI-MS.The analysis of 1D and 2D NMR spectra established that 2 was isoswertisin-200 �-L-rhamnoside. This compound, previously found in Avena sativa (Quabonzi, Bouillant,& Chopin, 1983) and Gnetum africanum (Chopin et al., 1977), has been identifiedthrough UV spectroscopy and mass spectrometry of its permethyl ether derivative(Quabonzi et al., 1983). The 1H and 13C NMR data and the glycoside configurationof 2 are being described here for the first time. Compound 2 differed from 1 by thepresence of a hydroxyl group at C-40 instead of a methoxyl group. The 1H and 13CNMR spectra of 2 showed the signal of only one methoxyl group, corresponding to asinglet at � 3.88 and � 56.6 through HMQC experiment. The attachment position ofthe methoxyl group was substantiated by NOESY experiments in which theirradiation at � 3.88 showed correlation with the signal of H-6 (� 6.49). In addition,the HMBC data showed a cross-peak between the methoxyl signal with C-7 (� 163.0),confirming the placement of the methoxyl group attached at C-7.

The phytochemical investigation of the leaves and stems of P. obtusifolia allowedthe isolation of four other known compounds, including two lignans:(þ) diayangambin (3) and 2-episesalatin (4) and a (6S)-hydroxy-3-oxo-�-ionolglycoside: corchoionoside C (5). These compounds were identified by comparingtheir NMR spectral data with the previously reported data in the literature (Calis,Kuruuzum-Uz, Lorenzetto, & Ruedi, 2002; Kamal-Eldin & Yousif, 1992; Russell &Fenemore, 1973).

The antifungal activity of the flavone C-diglycosides (1 and 2), isolated from theleaves of P. obtusifolia, was evaluated against C. cladosporioides andC. sphaerospermum. These compounds showed Rf values of 0.67 and 0.30, usingEtOAc :MeOH (9 : 1) as eluent. The antifungal activity was considered weak and nofurther investigations were carried out.

3. Experimental

3.1. General1H and 13C NMR spectra were recorded at 500/125 and 200/50MHz, respectively,on Varian Inova-500 and Bruker AC 200 spectrometers. DMSO-d6 (Aldrich) wasused as the solvent and TMS as the internal standard. Chemical shifts were reportedin units � (ppm) and coupling constants (J) in Hertz. IR spectra were measured inKBr pellets on a Perkin–Elmer infrared spectrometer model. UV spectra wererecorded on an Ultrospec 2100 pro UV-visible spectrophotometer using MeOH assolvent. HRESI-MS spectra were recorded on a Bruker Daltonics ultrOTOFQ-ESI-TOF.

3.2. Plant material

Leaves and stems of P. obtusifolia A. Dieter were collected at the greenhouse of theInstituto de Quımica-UNESP, Brazil, and identified by Dr Ines Cordeiro, Instituto

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de Botanica (IBt), Sao Paulo, SP, Brazil. A voucher specimen (Kato-70) has been

deposited at the Herbario do Estado ‘Maria Eneyda P. Kaufmann Fidalgo (SP)’ –

IBt, Sao Paulo, SP, Brazil.

3.3. Extraction and isolation

Compounds 1–4 were isolated from the leaves of P. obtusifolia as reported previously

(Mota et al., 2009).Air-dried and powdered stems (64.2 g) of P. obtusifolia were extracted with EtOH

four times. The ethanolic extract (5.7 g) was dissolved in MeOH :H2O (4 : 1) and

successively partitioned using solvents of increasing polarity (hexane, EtOAc and

n-BuOH). The EtOAc fraction (2.3 g) was subjected to low-pressure chromatography

with C18 silica gel, using a gradient MeOH/H2O (5–100% MeOH) to give 19

fractions (C-1–C-19). Fraction C-5 (27.5mg) was fractionated by preparative HPLC

under gradient elution (MeOH :H2O 40 : 60 with 0.5% AcOH), using a Phenomenex

LUNA phenyl–hexyl column (250.0� 21.2mm2, 10 mm, flow rate of 2.0mL min�1,

�¼ 254 nm) to give 5 (5.1mg).

Isoswertisin-40-methyl-ether-200a-L-rhamnoside (1): Yellow oil; [�]27D ¼�4.5 (c 0.01,

MeOH); IR �max (cm�1) 1434, 1508, 1600, 1653, 2927, 3412 (KBr); UV �max (nm)

(MeOH) (log "): 272 (5.2), 326 (5.3); HRESI-MS m/z (rel. int.): 607.2199 [MþH]+

(Calcd for C29H34O14: 606.5868).1H and 13C NMR (500 and 125MHz, DMSO-d6):

Table 1.

Isoswertisin-200a-L-rhamnoside (2): Amorphous solid; IR �max (cm�1) (KBr) 1446,

1500, 1600, 1655, 2923, 3409; UV �max (nm) (MeOH) (log "): 266 (5.2), 326 (5.3);

ESI-MS m/z (rel. int.): 591.1697 [M�H]� (Calcd for C28H32O14: 592.5599).1H and

13C NMR (500 and 125MHz, DMSO-d6): Table 1. UV and mass spectrometry data

of 2 were previously reported (Quabonzi et al., 1983).

3.4. Bioassay

The microorganisms used in the antifungal assays, C. cladosporioides (Fresen) de

Vries SPC 140 and C. sphaerospermum (Perzig) SPC 491, have been maintained at

the Instituto de Botanica, Sao Paulo, Brazil. Initially, the pure compound solutions

were applied to precoated silica gel TLC plates, developed with EtOAc :MeOH

(9 : 1), and dried for the complete removal of solvents. The chromatograms were

sprayed with a spore suspension of C. cladosporioides or C. sphaerospermum in

glucose and salt solution (5� 107 spores mL�1) in TLC plates with 200 mg of pure

compounds and incubated for 48 h in darkness in a moistened chamber at 25�C,

following the previously reported procedure (Della Greca, Mangoni, Molinaro,

Monaco, & Previtera, 1998; Lopez, Ming, & Towers, 2002; Mors, Nascimento,

Pereira, & Pereira, 2000). After the incubation period, fungi grew all over the plates,

except for spots where antifungal compounds were present, which remained white.

Nystatin and miconazole were used as positive controls, whereas ampicillin and

chloramphenicol were used as negative controls.

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Acknowledgements

The authors thank the financial support provided by FAPESP within the BIOTA/FAPESP –The Biodiversity Virtual Institute Program (www.biotasp.org.br). M.J. Kato, Vanderlan daS. Bolzani and M. Furlan are grateful to CNPq for research fellowships.

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