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Monosubstituted Benzene Derivatives from Fruits of Ficus hirta and Their Antifungal Activity against Phytopathogen Penicillium italicum Chunpeng Wan, Jianxin Han, Chuying Chen, Liangliang Yao, Jinyin Chen, and Tao Yuan J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.6b02176 • Publication Date (Web): 05 Jul 2016 Downloaded from http://pubs.acs.org on July 8, 2016

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Journal of Agricultural and Food Chemistry

Monosubstituted Benzene Derivatives from Fruits of Ficus hirta and Their Antifungal Activity against Phytopathogen Penicillium italicum Chunpeng Wan,†,ǁ Jianxin Han,‡,ǁ Chuying Chen,† Liangliang Yao,§ Jinyin Chen,†,* and Tao Yuan ‡,* †

Jiangxi Key Laboratory for Postharvest Technology and Nondestructive Testing of

Fruits & Vegetables, Collaborative Innovation Center of Post-harvest Key Technology and Quality Safety of Fruits and Vegetables in Jiangxi Province, Jiangxi Agricultural University, Nanchang 330045, China ‡

The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Chinese

Academy of Sciences; State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China §

The Affiliated Hospital of Jiangxi University of Traditional Chinese Medicine,

Nanchang 330006, China

1

ACS Paragon Plus Environment


1

ABSTRACT:

2

Ficus hirta, a widely consumed food by Hakka people, has been reported to show

3

potent antifungal activity against phytopathogen Penicillium italicum. However,

4

there is no report of chemical constituents responsible for the antifungal activity. In

5

the current study, nine monosubstituted benzene derivatives including three new

6

ones (1−3) were isolated from the fruits of F. hirta. The structures of these isolates

7

were elucidated based on the analysis of spectroscopic data (MS and NMR). All of

8

the isolates were evaluated for antifungal activities against P. italicum. At equivalent

9

concentration, compound 1 exhibited stronger antifungal activity than that of ethanol

10

extract of F. hirta fruits.

11 12

KEYWORDS: Ficus hirta; Monosubstituted benzene; Antifungal; Phytopathogen;

13

Penicillium italicum

14

2


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INTRODUCTION

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Postharvest disease is a major factor that causes the decay of fruits and vegetables

17

during storage.1 Around 10%−20% fresh fruits and vegetables were decayed by

18

postharvest disease in the developed country per year.2 Many postharvest diseases

19

are mainly caused by phytopathogenic fungi which usually infect the host through

20

wounds sustained during harvest, handling and processing.3 For citrus fruits, blue

21

and green molds are the two major postharvest diseases caused by Penicillium

22

italicum, Penicillium digitatum, respectively.4 Currently, synthetic fungicides (eg.

23

thiabendazole and imazalil) are usually used for fresh-keeping purpose in many

24

fruits and vegetables. However, many researches showed that synthetic fungicides

25

were harmful to human health and environment.5 Therefore, search for naturally

26

occurring fungicides has attracted more attentions.

27

Ficus hirta Vahl. (Wuzhimaotao) belongs to the family Moraceae, which are

28

largely distributed in tropical and sub-tropical regions.6 The roots of F. hirta have

29

been used as a soup herb by Hakka people for a long time, while its fruits are used in

30

Chinese folk medicine to treat dieresis, hepatitis, tumor, difficult labor and puerperal

31

pain.7 Previous phytochemical investigation of F. hirta was focused on its roots,

32

flavonoids and coumarins are the major constituents.7-9 Our previous study found

33

that the ethanol extracts of fruits of F. hirta showed potent antifungal activity

34

against P. italicum and P. digitatum.4 However, there is no report of chemical

35

constituents responsible for the antifungal activity. Therefore, we conducted a

36

phytochemical investigation of an ethanol extract of F. hirta fruits to find out the

3



37

antifungal constituents, which led to the isolation and identification of nine

38

monosubstituted benzene derivatives including three new ones (1−3) (Figure 1). All

39

of the isolates were evaluated their antifungal activities against P. italicum. Herein,

40

the isolation, structure elucidation, and anti-fungal evaluation of these compounds

41

are reported.

42 43

MATERIALS AND METHODS

44

Materials. The fruits of F. hirta were purchased from Zhangshu medicinal

45

market on May 2014, Jiangxi Province, China, and identified by Prof. Shouran Zhou

46

(Jiangxi University of Traditional Chinese Medicine). A voucher specimen

47

(FH-201406) has been deposited in the Jiangxi Key Laboratory for Postharvest

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Technology and Nondestructive Testing of Fruits & Vegetables, Jiangxi Agricultural

49

University (Jiangxi, China). The fruits of F. hirta were dried at 50 OC for 4 h and

50

finely powdered in a knife mill.

51

Extraction and Isolation of Compounds 1−3. The dried fruits of F. hirta (4.9

52

kg) were ground and extracted by ultrasonic-assisted method with 95% ethanol (3 ×

53

25.0 L) at room temperature for 90 min. The dried ethanol extract (FH, 345.1 g) was

54

subjected to D101 macro rein column (8 × 40 cm) chromatography eluted with

55

water (10.0 L), 30% ethanol (8.0 L), 50% ethanol (8.0 L) and 95% ethanol (8.0 L),

56

respectively, collected each solvent gradient together, to yield four fractions

57

(FH1−FH4).

58

The 30% ethanol eluted fraction (FH2, 113.6 g) was subjected to C18 silica gel

59

column (4 × 46 cm) chromatography eluted with gradient MeOH/H2O (from 15/85

60

to 25/75, v/v; each 800 mL), collected 100 mL for each flask, to yield five combined

61

subfractions FH2a‒FH2e. 4


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Fraction FH2c was chromatographed on Sephadex LH-20 (2.5 × 110 cm) eluted

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with MeOH, collected 3 mL for each tube, to give six combined subfractions

64

(FH2c1‒FH2c6). Subfraction FH2c2 was subjected on Sephadex LH-20 (2.5 × 110

65

cm) eluted with MeOH, collected 3 mL for each tube, to give five combined

66

subfractions (FH2c2a‒FH2c2e). Subfraction FH2c2d was subjected the silica gel

67

column (2.5 × 45 cm) chromatography eluted with gradient CH3Cl-MeOH (from

68

100:1 to 1:1, v/v), collected 15 mL for each tube, to get seven combined subfractions

69

(FH2c2d1‒FH2c2d7). Subfraction FH2c2d5 was subjected on Sephadex LH-20 (1.8

70

× 110 cm) eluted with MeOH, collected 3 mL for each tube, to give three

71

sub-fractions

72

semi-preparation HPLC, eluting with MeOH-H2O (0-35 min: 30:70 to 34:66; 35-36

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min: 34:66 to 100:0; 36-37 min: 100:0; 37-38 min: 100:0 to 30:70; 38-45 min:

74

30:70; v/v, 3 mL/min), yielded compound 1 (6.4 mg, tR = 17.6 min). FH2c2d7 was

75

purified by semi-preparation HPLC, eluting with MeOH-H2O (0-20 min: 30:70 to

76

34:66; 20-21 min: 34:66 to 100:0; 21-22min: 100:0; 22-23 min: 100:0 to 30:70;

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23-30 min: 30:70; v/v, 3 mL/min), yielded compound 3 (8.7 mg, tR = 17.8 min).

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Fraction FH2c2e was subjected the silica gel column (2.5 × 45 cm) chromatography

79

eluted with gradient CH3Cl-MeOH (from 100:1 to 1:1, v/v), collected 15 mL for each

80

tube, to get seven combined subfractions (FH2c2e1‒FH2c2e7). Subfraction FH2c2e4

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was purified by semi-preparation HPLC, eluting with MeOH-H2O (0-25 min: 20:80

82

to 66:34; 25-26 min: 66:34 to 100:0; 26-27 min: 100:0; 27-28 min: 100:0 to 30:70;

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28-35 min: 30:70; v/v, 3 mL/min), yielded compound 2 (5.0 mg, tR = 26.6 min).

(FH2c2d5a‒FH2c2d5c).

Purification

of

FH2c2d5b

with

84

Antifungal Assay. The antifungal activity of FH extracts and isolates against P.

85

italicum was evaluated by the disk diffusion method.4 P. italicum was provided by

86

the Jiangxi Key Laboratory for Postharvest Technology and Nondestructive Testing

5



87

of Fruits & Vegetables (Nanchang, China) and preserved on potato dextrose agar

88

(PDA) at 4.0 ± 0.5 °C. The concentration of the fungi spores was determined by the

89

aid of a hematocyte counter and adjusted to 105—106 CFU/mL with sterile distilled

90

water. Petri dishes (diameter, 9.0 cm) were prepared with PDA and surface

91

inoculated with 2.0% of spore suspensions (105—106 CFU/mL) in sterile saline

92

solution. Sterile Oxford cup (diameter, 8 mm) were impregnated with 200 µL of

93

each extracts and isolates. The diameters of inhibition zones (DIZs) around the

94

Oxford cups were evaluated by vernier micrometer after 48 h of culture at 27.0 ± 1.0

95

°C in the darkness. Five replicate trials were conducted against each extracts and

96

isolates. The antifungal results were expressed as the mean value of diameters ±

97

standard deviation. The larger the mean value of diameters is, the stronger antifungal

98

activity is.

99 100

RESULTS AND DISCUSSION

101

The compounds isolated from fruits of F. hirta included three new compounds (1−3)

102

and six known compounds (4−9). Herein, the structure elucidation of the new

103

compounds is presented.

104

Compound 1, was obtained as colorless amorphous solid, [α]25D = -98 (c 0.100,

105

MeOH), displayed a molecular formula of C15H20O8 as determined by HRESIMS at

106

m/z 351.1031 [M+Na]+ (calcd for C15H20O8Na, 351.1056). In the 1H NMR spectrum,

107

five aromatic protons signal at δH 7.36‒7.50 suggested the presence of

108

mono-substituted benzene ring. Combined analysis of 1H and 13C NMR data (Table 1)

109

revealed the presence of a β-pyranoglucose moiety, whose anomeric proton and

110

carbon resonated at δH 4.06 (1H, d, J = 7.6 Hz, H-1′) and δC 100.8 (C-1′), respectively.

111

Except the mono-substituted benzene ring and β-pyranoglucose moiety, an

6


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112

oxygenated methine (δH 5.43, δC 77.3), a methoxyl (δH 3.62, δC 52.4) and an ester

113

carbonyl (δC 170.9), were observed in the 1H and 13C NMR spectra. Further analysis

114

of 2D NMR data allowed the establishment of the structure of Compound 1. From the

115

1

116

Figure 2A) was established. The HMBC correlation (Figure 2A) from H-1′ to C-2

117

assigned the hexose moiety to C-2. The HMBC correlations from H-2 to C-1, C-3,

118

C-4 and C-8, indicated that the OCH-2 was linked to C-3 of benzene ring and ester

119

carbonyl C-1. The methoxyl was attached to C-1 by the HMBC correlation between

120

proton signals of methoxyl (δH 3.62) and C-1. Thus, a planar structure of 1 was

121

established as glucoside methyl mandelate. Acid hydrolysis of 1 afforded D-glucose,

122

which was identified by direct comparison with an authentic sample. By using

123

Hudson’s rules of isorotation,10 the molecular rotation of the aglycone methyl

124

mandelate was readily calculated as a negative value from the measured specific

125

rotations of 1. The absolute configuration of the aglycone was thus assigned to be 2R

126

by comparing its optical rotatory properties to that of reported data. The structure of 1

127

was thus determined as (2R) methyl 2-O-β-D-glucopyranosyl-2-phenyl acetate.

H–1H COSY spectrum, a hexose moiety (C-1′ to C-6′) (drawn with bold bond in

128

Compound 2 was obtained as colorless amorphous solid with a molecular formula

129

of C12H12O6, as determined by the HRESIMS ion at m/z 275.0529 [M+Na]+ (calcd for

130

C12H12O6Na, 275.0532). Five aromatic protons signal at δH 7.98 (2H, d, J = 7.6 Hz),

131

7.71 (1H, t, J = 7.6 Hz), 7.57 (2H, t, J = 7.6 Hz) were observed in the 1H NMR

132

spectra (Table 1), which indicated the presence of mono-substituted benzene ring. In

133

the

134

129.3, supported the presence of mono-substituted benzene ring. Except the NMR

135

signals of mono-substituted benzene ring, an oxygenated methine (δH 5.55, δC 69.9), a

13

C NMR spectrum, the carbon resonances at δC 134.3, 129.8 (2C), 129.4 (2C),

7



136

methylene (δH 2.90, δC 36.9), a methoxyl (δH 3.70, δC 52.9) and three carbonyls (δC

137

171.1, 169.9, 165.4), were also observed in the 1H and

138

analysis of 2D NMR data allowed the establishment of the structure of 2. The 1H–1H

139

COSY correlation of H-2/H-3, and the HMBC correlations (Figure 2B) from H-2 to

140

C-4, and from H-3 to C-1, indicated the presence of butanedioic acid moiety. The

141

HMBC correlations from H-2, H-2′, H-6′ to C-7′, and from the methoxy protons to

142

the carbonyl C-4 (δC 169.9), implied that a benzoyl group and methoxyl were attached

143

to C-2 and C-4, respectively. The absolute configuration of compound 2 was

144

determined by comparing its specific rotation with that of reported compound,

145

(S)-benzoyl malic acid dimethyl ester (2a) (see Supporting information).11 Thus,

146

compound 2 was assigned as an S configuration based on its specific rotation being a

147

negative value ([α]25D = -29). Finally, the structure of compound 2 was elucidated as

148

(2S) 2-O-benzoyl-butanedioic acid-4-methyl ester.

13

C NMR spectra. Further

149

Compound 3, colorless amorphous solid, had the molecular formula C14H16O7, as

150

determined by HRESIMS at m/z 295.0780 [M-H]- (calcd for C14H15O7, 295.0818).

151

Similar to compound 2, five aromatic protons signal at δH 8.03 (2H, d, J = 8.1 Hz),

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7.67 (1H, t, J = 8.1 Hz), 7.55 (2H, t, J = 8.1 Hz), and corresponding carbon signals at

153

δC 133.6, 129.8 (2C), 129.1 (2C), 130.8, and 165.9, were observed in the 1H and 13C

154

NMR spectra (Table 1), which suggested the presence of a benzoyl moiety in 3. In

155

addition, the carbon signals at δC 176.0, 77.7, 74.2, 66.4, 64.8, 40.5, and 38.6, implied

156

the presence of a quinic acid. Detailed analysis of 2D NMR data (including 1H–1H

157

COSY, HSQC and HMBC) allowed the determination of the structure of compound 3.

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158

The 1H–1H COSY correlations assigned a linkage of C-2 to C-6 (drawn with bold

159

bond in Figure 2C), combination of the HMBC correlations (Figure 2C) from H-2 and

160

H-6 to C-7, supported the presence of quinic acid moiety. The benzoyl moiety was

161

located to C-4 by the HMBC correlation from H-4 to C-7′. Therefore, the structure of

162

compound 3 was elucidated as 4-O-benzoyl-quinic acid.

163

Six know compounds were identified as 4-O-benzoyl-quinic acid methyl ester (4),

164

12-13

165

phenylethyl-O-β-vicianoside

166

1-O-trans-cinnamoyl-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (9)17 on the

167

basis of their NMR and ESIMS data, and comparison of their spectroscopic data with

168

those reported.

3-O-benzoyl-quinic

acid

(5),14

(7),15

2-phenylethyl-O-β-D-glucoside benzyl-β-D-glucopyranoside

(6),15 2-

(8),16

and

169

As described in the experimental part, the ethanol extract of the fruits of F. hirta

170

(FH) was fractionated to four sub-fractions (FH1−FH4) by D101 macro rein column

171

chromatography. The extract and all of the sub-fractions and isolates were evaluated

172

for their antifungal activities against P. italicum. As shown in Figure 3, fractions

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FH2−FH4 showed stronger antifungal activities with concentration-dependent manner

174

than that of FH, while FH1 did not show any activity. Due to the amount of fraction

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FH2 account for around 33% of the total FH extract, the isolation work was focused

176

on the FH2 fraction, which led to the isolation of nine monosubstituted benzene

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derivatives (1−9). The antifungal activities of all the isolates were tested at two

178

concentrations (2.0 and 4.0 mg/mL), due to the the limited available amount of the

179

isolates. The results showed that only compound 1 showed antifungal activity with the

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DIZs of 21.0 ± 0.5 mm and 26.7 ± 0.6 mm at 2.0 and 4.0 mg/mL, respectively, which

9



181

are stronger than that of FH (11.0 ± 0.6 mm at 2.0 mg/mL), and comparable to that of

182

FH2 (25.0 ± 0.7 mm at 2.0 mg/mL).

183

In summary, nine monosubstituted benzene derivatives including three new ones

184

(1−3) were isolated from the antifungal activity fraction of the ethanol extract of the

185

fruits of F. hirta. New compound 1 showed stronger antifungal activity against P.

186

italicum than that of ethanol extract at the same concentration, suggested that

187

compound 1 may be a potential naturally occurring fungicide.

188 189

ASSOCIATED CONTENT

190

Supporting Information

191

The Supporting information is available free of charge on the ACS Publications

192

website at DOI:

193

Original NMR and mass spectra of compounds 1−9; general experimental

194

procedures; extraction and isolation of known compounds 4−9, absolute

195

configurations of compound 2 and 2a.

196 197

AUTHOR INFORMATION

198

ǁ

199

Corresponding Authors

200

*(J.C.) Phone/Fax: +86 791-8381-3492. E-mail: [email protected].

201

*(T.Y.) Phone/Fax: +86 991-369-0335. E-mail: [email protected].

Equal contribution.

202 203

ACKNOWLEDGMENTS

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The authors gratefully acknowledge the financial support of this study by the

205

National Natural Science Foundation of China (31460533 and 31500286),

206

Recruitment Program of Global Experts (Tao Yuan) and National Science &

207

Technology of Supporting Programs (2012BAD38B03).

208

REFERENCES

209

1.

210 211

Janisiewicz, W. J.; Korsten, L. Biological control of postharvest diseases of fruits. Annu. Rev. Phytopath. 2002, 40, 411−441.

2.

Ippolito, A.; Nigro, F. Impact of preharvest application of biological control

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agents on postharvest diseases of fresh fruits and vegetables. Crop Prot. 2000,

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19, 715−723.

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3.

Sivakumar, D.; Bautista-Baños, S. A review on the use of essential oils for

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postharvest decay control and maintenance of fruit quality during storage. Crop

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Prot. 2014, 64, 27−37.

217

4.

Chen, C.; Wan, C.; Peng, X.; Chen, Y.; Chen, M.; Chen, J. Optimization of

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antifungal extracts from Ficus hirta fruits using response surface methodology

219

and antifungal activity tests. Molecules. 2015, 20, 19647−19659.

220

5.

Oliva, A.; Meepagala, K. M.; Wedge, D. E.; Harries, D.; Hale, A. L.; Aliotta, G.;

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Duke, S. O. Natural fungicides from Ruta graveolens L. leaves, including a new

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quinolone alkaloid. J. Agric. Food Chem. 2003, 51, 890−896.

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6.

224 225

Flora Compilation Committee of Chinese Academy of Science. Flora of China. Science Press, Beijing, China, 1998; vol. 23. no 1., pp. 67, 160.

7.

Ya, J.; Zhang, X. Q.; Wang, Y.; Zhang, Q. W.; Chen, J. X.; Ye, W. C. Two new

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phenolic compounds from the roots of Ficus hirta. Nat. Prod. Res. 2010, 24,

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621−625. 11



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8.

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Li, C.; Bu, P. B.; Qiu, D. K.; Sun, Y. F. Chemical constituents from roots of Ficus hirta. China J. Chin. Mater. Med. 2006, 31, 131−133.

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Ya, J.; Zhang, X. Q.; Wang, G. C. Flavonoids from the roots of Ficus hirta Vahl. Asia. Chem. Lett. 2009, 13, 21−26.

10. Hudson, C.S. The significance of certain numerical relations in the sugar group. J. Am. Chem. Soc. 1909, 31, 66−86.

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11. Yoshihara, T.; Sakamura, S. Benzoic acid derivatives conjugated with

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dicarboxylic acids from alfalfa (Medicago sativa). Agric. Biol. Chem. 1977, 41,

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2427−2429.

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12. Mercier, D.; Cléophax, J.; Hildesheim, J.; Sépulchre, A. M.; Géro, S. D. Selective

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reactivity

of

the

hydroxyls

of

methyl

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agents. Tetrahedron Lett. 1969, 10, 2497−2500.

quinate

towards

acylating

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13. Armesto, N.; Ferrero, M.; Fernández, S.; Gotor, V. Novel enzymatic synthesis of

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4-O-cinnamoyl quinic and shikimic acid derivatives. J. Org. Chem. 2003, 68,

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5784−5787.

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14. Kondo, T.; Toyama-Kato, Y.; Yoshida, K. Essential structure of co-pigment for

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blue sepal-color development of hydrangea. Tetrahedron Lett. 2005, 46,

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6645−6649.

246 247 248 249

15. Yang, Y. N.; Feng, Z. M.; Jiang, J. S.; Zhang, P. C. Chemical constituents of roots Rhodiola crenulata. J. Chin. Pharm. Sci. 2013, 48, 410−413. 16. Wen, B.; Li, B.; Shen, Y. H. Chemical constituents from the aerial parts of Psammosilene tunicoides. Nat. Prod. Res. Dev. 2014, 26, 675−678.

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17. Latza, S.; Ganßer, D.; Berger, R. G. Carbohydrate esters of cinnamic acid from

251

fruits of Physalis peruviana, Psidium guajava and Vaccinium vitis-idaea.

252

Phytochemistry. 1996, 43, 481−485.

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253

Figure captions

254 255

Figure 1. The chemical structures of the compounds 1–9 isolated from the fruits

256

of F. hirta.

257

Figure 2. Key 1H−1H COSY (▬) and selected HMBC correlations (H→C) of 1

258

(A), 2 (B) and 3 (C).

259 260

Figure 3. Antifungal activities of FH extracts and compound 1. Each value is

261

mean ± standard derivation of five replicates.

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Tables Table 1. 1H and 13C NMR Data of 1− −3 (in DMSO-d6)a 1

2

3

No. 1 2

δH (mult, J, Hz)

δC

δH (mult, J, Hz)

δC

δH (mult, J, Hz)

δC

5.43 (brs)

170.9 77.3

5.55 (t, 5.8)

171.1 69.9

2.06 (dd, 13.4, 3.3)

74.2 38.6

136.4

2.90 (2H, brs)

36.9

4.18 (brs)

66.4

169.9

4.86 (dd, 7.2, 2.8)

77.7

1.86 (dd, 13.4, 7.1) 3 4

7.48 (d, 7.7)

127.9

5

7.39 (t, 7.7)

128.9

4.06 (m)

64.8

6

7.37 (t, 7.7)

129.0

1.93 (2H, m)

40.5

7

7.39 (t, 7.7)

128.9

8

7.49 (d, 7.7)

127.9

OMe

3.62 (3H, s)

52.4

1′

4.06 (d, 7.6)

100.8

2′

3.05 (m)

73.7

7.98 (d, 7.6)

129.8

8.03 (d, 8.1)

129.8

3′

3.04 (m)

77.2

7.57 (t, 7.6)

129.4

7.55 (t, 8.1)

129.1

4′

3.04 (m)

70.5

7.71 (t, 7.6)

134.3

7.67 (t, 8.1)

133.6

5′

3.01 (m)

77.6

7.57 (t, 7.6)

129.4

7.55 (t, 8.1)

129.1

6′

3.66 (dd, 10.8, 6.5)

61.6

7.98 (d, 7.6)

129.8

8.03 (d, 8.1)

129.8

176.0 3.70 (3H, s)

52.9 129.3

130.8

3.44 (dd, 10.8, 5.8) 165.4

7′ a

1

13

Recorded at 600 or 150 MHz for H and C.

14


165.9

Page 15 of 18


Figure graphics

Figure 1

15



4

HO

8 O

2 O

1' OH

HO OH

3'

O 1

3

Page 16 of 18

O

HO 5 O

1'

O 5' 7' O 4 2 COOCH3 HOOC 3 1

A

1'

5'

B

Figure 2

16


7' O 4

7 COOH

6 1 3 OH

3' C

OH 2


Diameter of antifungal circles (mm)

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70 60

0.5 mg/mL

1.0 mg/mL

2.0 mg/mL

5.0 mg/mL

10.0 mg/mL

4.0 mg/mL

50 40 30 20 10 0 FH

FH-2

FH-3 Samples

FH-4

Figure 3

17


Compound 1


TOC

Monosubstituted Benzene Derivatives from Fruits of Ficus hirta and Their Antifungal Activity against Phytopathogen Penicillium italicum Chunpeng Wan, Jianxin Han, Chuying Chen, Liangliang Yao, Jinyin Chen, and Tao Yuan O O O

O

HO OH

HO OH 1

Fruits of Ficus hirta

Penicillium italicum

18


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Monosubstituted Benzene Derivatives from Fruits ... - ACS Publications

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