Two new compounds from the fruit of Ailanthus altissima

Article abstract of DOI:10.1080/14786419.2018.1437434

A new phenolic derivative, 4-hydroxyphenol-1-O-[6-O-(E)-feruloyl-β-d-glucopyranosyl]-(1→6)-β-d-glucopyranoside (1), and a new terpenylated coumarin, named altissimacoumarin H (2) were identified from the fruit of Ailanthus altissima (Mill.) Swingle (Simaroubaceae), together with ten known compounds (3–12), including two coumarins and eight phenylpropanoids. Their structures were determined on the basis of chemical method and spectroscopic data. Antiviral effect against Tobacco mosaic virus (TMV) of all the compounds obtained were evaluated using leaf-disc method.

Full text of DOI:10.1080/14786419.2018.1437434

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Two new compounds from the fruit of Ailanthus
altissima
Jian-Cheng Ni, Jian-Ting Shi, Qing-Wei Tan & Qi-Jian Chen
To cite this article: Jian-Cheng Ni, Jian-Ting Shi, Qing-Wei Tan & Qi-Jian Chen (2018):
Two new compounds from the fruit of Ailanthus altissima, Natural Product Research, DOI:
10.1080/14786419.2018.1437434
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Natural Product research, 2018
https://doi.org/10.1080/14786419.2018.1437434
Two new compounds from the fruit of Ailanthus altissima
Jian-Cheng Nia, Jian-Ting Shia, Qing-Wei Tana,b and Qi-Jian Chena,b
aKey laboratory of Bio-Pesticide and chemistry-Biology, Ministry of education, Fujian agriculture and Forestry
university, Fuzhou, china; bKey laboratory of Plant Virology of Fujian Province, Institute of Plant Virology,
Fujian agriculture and Forestry university, Fuzhou, china
ABSTRACT
ARTICLE HISTORY
received 5 december 2017
accepted 2 February 2018
A new phenolic derivative, 4-hydroxyphenol-1-O-[6-O-(E)-feruloyl-
β-d-glucopyranosyl]-(1→6)-β-d-glucopyranoside (1), and
a new
terpenylated coumarin, named altissimacoumarin H (2) were identified
from the fruit of Ailanthus altissima (Mill.) Swingle (Simaroubaceae),
together with ten known compounds (3–12), including two coumarins
and eight phenylpropanoids. Their structures were determined on
the basis of chemical method and spectroscopic data. Antiviral effect
against Tobacco mosaic virus (TMV) of all the compounds obtained
were evaluated using leaf-disc method.
KEYWORDS
Ailanthus altissima;
simaroubaceae;
phenylpropanoid; coumarin;
Tobacco mosaic virus (tMV)
1. Introduction
Ailanthus altissima (Mill.) Swingle (Simaroubaceae), a fast-growing deciduous tree commonly
known as tree of heaven, is native to China and introduced into Europe around the end of
eighteenth century (De Feo et al. 2003). In traditional Chinese medicine, the root barks of
A. altissima have been used for treatment of diarrhoea, ascariasis, bleeding, spermatorrhoea
and gastrointestinal diseases, and its samara has been used for antibacterial (Zhao et al.
2005; Kundu and Laskar 2010; Yang, Yuan et al. 2014). The extracts of different parts of
A. altissima were reported exhibiting important and diverse biological activities and medic-
inal properties such as antiproliferative, central nervous depressant, antimicrobial, acaricidal,
insecticidal, herbicidal, and antioxidant activities (Zhao et al. 2005; Gu et al. 2014; Popa
et al. 2015; Khan et al. 2016). Phytochemical studies have revealed the presence of quassinoid,
alkaloid, triterpenoid, coumarin, lignan, flavonoid, as well as phenolic derivatives, etc. in this
plant (Tamura et al. 2003; Tan et al. 2012; Hong et al. 2013; Kim et al. 2015). We have recently
CONTACT Qing-Wei tan
tanqingwei@fafu.edu.cn; Qi-Jian chen
fafuchenqijian@163.com
supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2018.1437434.
© 2018 Informa uK limited, trading as taylor & Francis Group

2
J.-C. NI ET AL.
reported the characterization of four novel chemical constituents, including two phenylpro-
pionamides, one piperidine and a phenolic derivative from this medical plant (Ni et al. 2017).
As a continuation of this study, 12 phenylpropanoid and coumarin derivatives, including
two new compounds (1–2), were identified from the MeOH extract of the samara of A.
altissima. We herein describe the isolation and structural elucidation of the new compounds.
And all of the compounds obtained were screened for their antiviral activity against the
replication of Tobacco mosaic virus (TMV). However, no significant inhibitory effects were
observed.
2. Results and discussion
Repeated column chromatography of the CHCl3 and n-BuOH partitions from the MeOH
extract of dried A. altissima fruit afforded 12 compounds, including two new ones (1 and
2, Figure 1). Compound 1 was isolated as white amorphous powder. It was assigned with
a molecular formula of C28H34O15 by HR-ESI-MS, which showed a sodiated molecular ion
peak at m/z = 633.1831 [M + Na]+ (calcd for C28H34O15Na, 633.1790). The IR spectrum (Figure
S1) exhibited absorption bands due to the presence of hydroxyl (3416 cm−1), conjugated
ester carbonyl (1693 cm−1), double bond (1631 cm−1), and aromatic ring (1600, 1510, and
1452 cm−1). The 1H NMR spectrum of 1 showed signals for an AA′BB′ [δH 6.91 (2H, d, J = 8.9 Hz)
and 6.65 (2H, d, J = 8.9 Hz)] and an ABX spin system [δH 7.30 (1H, d, J = 1.9 Hz), 7.09 (1H, dd,
J = 8.2, 1.9 Hz), and 6.78 (1H, d, J = 8.2 Hz)], which indicated the presence of a 1,4-disubsti-
tuted and a 1,3,4-trisubstituted benzene ring, respectively. In addition, signals for two
trans-olefinic [δH 7.53 (1H, d, J = 15.9 Hz) and 6.46 (1H, d, J = 15.9 Hz)], a methoxyl [δH 3.82
(3H, s)], and two anomeric protons [δH 4.61 (1H, d, J = 7.5 Hz) and 4.30 (1H, d, J = 7.7 Hz)]
were observed in the 1H NMR spectrum. According to the 13C NMR, DEPT, and HSQC spec-
trum, compound 1 contained 28 carbons, including one carbonyl (δC 166.7), two olefinic
(δC 145.3 and 114.2), one methoxyl (δC 55.7), twelve saccharide-type carbons (δC 103.5, 76.4,
Figure 1. chemical structures of 1–12.

NATURAL PRODUCT RESEARCH
3
73.7, 73.6, 70.0, 63.6; δC 101.5, 76.7, 75.6, 73.3, 70.0, 69.0), and twelve aromatic carbons. The
chemical shifts of these saccharidic carbons corresponded to those of two glucopyranose
moieties with a 1,6-linkage (Jiao et al. 2015). Acid hydrolysis revealed only the presence of
D-glucose, and the coupling constants of the anomeric protons confirmed the presence of
two β-d-glucopyranosyl moieties in 1. The HMBC correlations (Figure S10) observed from
H-7‴ to C-2‴, C-6‴, and C-9‴; from H-8‴ to C-1‴; and from the methoxyl protons (δH 3.80,
s) to C-3‴, confirmed the presence of a feruloyl group. And it was connected with C-6″ of
Glc-2 as indicated by HMBC correlation from H2-6″ to C-9‴. The HMBC correlation observed
from the anomeric proton H-1′ to C-1 indicated that Glc-1 was attached at C-1 of a p-hy-
droxyphenoxyl group. These connectivities were further confirmed by NOESY correlations
(Figure S10) between H-1′/H-2 and H-6, and between H-1″/H2-6′. Therefore, the structure
of1wasestablishedas4-hydroxyphenol-1-O-[6-O-(E)-feruloyl-β-d-glucopyranosyl]-(1→6)-β-d-
glucopyranoside.
Compound 2 was obtained as white amorphous powder. Its molecular formula was
deduced to be C21H26O7 by HR-ESI-MS negative ion peak at m/z 425.1347 [M + Cl]− (calcd for
C21H26ClO7, 425.1373). The IR spectrum (Figure S11) exhibited absorption bands due to the
presence of hydroxyl (3423 cm−1), conjugated ester carbonyl (1727 cm−1), and aromatic ring
(1611, 1561, and 1465 cm−1). Compound 2 has the same molecular formula with that of a
terpenylated coumarin (altissimacoumarin G) isolated from the bark of A. altissima, which
was an isofraxindin-type derivative bearing a terahydrofuran ring in the monoterpenyl side-
chain (Hong et al. 2013). And the 13C NMR data of 2 were similar to those of altissimacoumarin
G, except that C-2′ (δC 81.8), C-3′ (δC 78.2), and C-9′ (δC 22.2) in 2 were shifted upfield by 2.9,
1.2, and 1.4 ppm, respectively, which suggested that 2 could be a stereoisomer of altissima-
coumarin G. The 1H NMR spectrum of 2 displayed signals for an AB-spin system [δH 7.60 (1H,
d, J = 9.5 Hz) and 6.34 (1H, d, J = 9.5 Hz)], an aromatic proton singlet [δH 6.67 (1H, s)], and
two methoxyl signals [δH 4.02 (3H, s) and 3.88 (3H, s)]. These data were assigned for an isof-
raxidin skeleton (Hwang et al. 2005) and identical with that in altissimacoumarin G. The
planer structure of 2 was confirmed by 1H-1H COSY and HMBC correlations as shown in Figure
S20. And NOESY experiment was employed to determine its relative configuration. The key
NOESY correlations (Figure S20) observed between Me-9′/Hα-4′, Me-9′/H-5′, and Me-9′/Hα-1′
indicated that Me-9′ and H-5′ were in the same side of the tetrahydrofuran ring, while H-2′
adopted the opposite orientation as indicated from the key NOESY correlation between
H-2′/Hβ-1′. Thus, the structure of 2 was established as 7-[(2,5)-epoxy-3β-hydroxy-3α,7-dime-
thyl-6-octenoxy]-6,8-dimethoxycoumarin, and named altissimacoumarin H.
The known structures (3–12) were identified by a comparison of their spectroscopic data
(Table S2 and S3) with those reported in the literature as esculetin (3) (Wang et al. 2006),
scopoletin (4) (Adfa et al. 2010), methyl chlorogenate (5) (Lee et al. 2010), 5-O-caffeoyl quinic
acid butyl ester (6) (Chai et al. 2004), syringin (7) (Niwa et al. 1988), p-coumaric acid (8) (Ralph
et al. 1994), caffeic acid (9) (Saleem et al. 2004), 3-hydroxy-1-(4-hydroxyphenyl)-1-propanone
(10) (Jacubert et al. 2010), ω-hydroxypropioguaiacone (11) (Achenbach et al. 1988), and
threo-1-(4-hydroxyphenyl)-1-methoxy-2,3-propanediol (12) (Yang, Li et al. 2014). All the iso-
lated compounds were tested for their inhibitory activity (Table S1) against Tobacco mosaic
virus (TMV) replication using leaf-disc method at a concentration of 0.5 mM. However, only
weak to no inhibitory activity were observed.

4
J.-C. NI ET AL.
3. Experimental
3.1. General experimental procedures
IR spectra were obtained with a Nicolet iS50 FT-IR spectrometer (Thermo Scientific, Waltham,
MA, USA). HR-ESI-MS were measured on an Agilent 6520 Q-TOF mass spectrometer (Agilent
1
Technologies, Santa Clara, CA, USA). H and 13C NMR spectra were recorded on a Bruker
AVANCE III 500 spectrometer (Bruker BioSpin, Fällanden, Switzerland). Column chromatog-
raphy was performed using silica gel (200–300 mesh), silica gel H (Qingdao Oceanic Chemical
Co., Qingdao, China), Sephadex LH–20 (25–100 μm, Pharmacia Fine Chemical Co., Ltd.,
Uppsala, Sweden), Lichroprep RP-18 gel (40–63 μm, Merck, Darmstade, Germany), and MCI
gel CHP-20P (75−150 μm, Mitsubishi Chemical Co., Tokyo, Japan). Fractions were monitored
by TLC (H, Qingdao Oceanic Chemical Co., Qingdao, China) and spots were visualized by
sprayed with 5% H2SO4 in EtOH followed by heating. All solvents and chemicals used were
of analytical reagent grade (Sinopharm Chemical Reagent Co., Ltd., Shanghai, China). The
absorbance was measured at 405 nm using a Thermo Scientific Multiskan MK3 microplate
reader (Thermo Fisher Scientific (China) Co. Ltd, Shanghai, China).
3.2. Plant materials
The fruit of A. altissima was collected in Muyang City, Jiangsu Province, China, in October
2013. The plant was identified by associate Professor Chun-Mei Huang, College of Life
Sciences, Fujian Agriculture and Forestry University, Fuzhou, China. A voucher specimen
(sample MF131001) was deposited at the Key Laboratory of Bio-Pesticide and Chemistry-
Biology, Ministry of Education, Fujian Agriculture and Forestry University.
3.3. Extraction, fraction and isolation
The air-dried and pulverized fruit (7.5 kg) of A. altissima was extracted with MeOH (25 L,
3 day) at room temperature for three times. After being concentrated in vacuo, the extract
(390.0 g) was suspended in water and successively partitioned with organic solvents to give
n-hexane (168.0 g), CHCl3 (30.0 g), and n-BuOH-soluble (90.0 g) fractions. The CHCl3-soluble
fraction (30.0 g) was chromatographed using silica gel, Sephadex LH-20, and RP-18 columns
to afford 2 (5.0 mg), 4 (15.0 mg), and 11 (22.0 mg). The n-BuOH-soluble fraction (90.0 g) was
purified by column chromatography over silica gel, MCI, Sephadex LH-20, and RP-18 gels to
yield 1 (23.2 mg), 3 (14.8 mg), 5 (74.9 mg), 6 (21.6 mg), 7 (4.8 mg), 8 (28.0 mg), 9 (26.0 mg),
10 (12.0 mg), and 12 (7.5 mg).
4-Hydroxyphenol-1-O-[6-O-(E)-feruloyl-β-
d
-glucopyranosyl]-(1→6)-β- -glucopyranoside
d
(1): white amorphous powder. IR (KBr) υmax: 3416, 2968, 2899, 1693, 1631, 1600, 1510, 1452,
1271, 1214, 1177, 1065 cm−1; positive HR-ESI-MS m/z: 633.1831 [M + Na]+ (calcd for
C28H34O15Na, 633.1790). 1H NMR (DMSO-d6, 500 MHz): δ 7.53 (1H, d, J = 15.9 Hz, H-7‴), 7.30
(1H, d, J = 1.9 Hz, H-2‴), 7.09 (1H, dd, J = 8.2, 1.9 Hz, H-6‴), 6.91 (2H, d, J = 8.9 Hz, H-2 and
H-6), 6.78 (1H, d, J = 8.2 Hz, H-5‴), 6.65 (2H, d, J = 8.9 Hz, H-3 and H-5), 6.46 (1H, d, J = 15.9 Hz,
H-8‴), 4.61 (1H, d, J = 7.5 Hz, H-1′), 4.40 (1H, dd, J = 11.9, 2.0 Hz, Ha-6″), 4.30 (1H, d, J = 7.7 Hz,
H-1″), 4.14 (1H, dd, J = 11.9, 6.2 Hz, Hb-6″), 3.96 (1H, br d, J = 10.8 Hz, Ha-6′), 3.82 (3H, s, OMe-
3‴), 3.61 (1H, dd, J = 11.7, 7.1 Hz, Hb-6′), 3.53 (1H, m, H-5′), 3.35 (1H, overlap, H-5″), 3.15–3.27
(4H, overlap, H-2′, H-3′, H-3″, and H-4″), 3.11 (1H, t, J = 9.1 Hz, H-4′), 3.03 (1H, t, J = 8.3 Hz,

NATURAL PRODUCT RESEARCH
5
H-2″). 13C NMR (DMSO-d6,125 MHz): δ 166.7 (C-9‴), 152.1 (C-4), 150.3 (C-1), 149.3 (C-4‴), 148.0
(C-3‴), 145.3 (C-7‴), 125.6 (C-1‴), 123.3 (C-6‴), 117.5 (C-2, 6), 115.5 (C-3, 5), 115.4 (C-5‴), 114.2
(C-8‴), 111.1 (C-2‴), 103.5 (C-1″), 101.5 (C-1′), 76.7 (C-3′), 76.4 (C-3″), 75.6 (C-5′), 73.7 (C-5″),
73.6 (C-2″), 73.3 (C-2′), 70.0 (C-4′, 4″), 69.0 (C-6′), 63.6 (C-6″), 55.7 (OMe-3‴).
Altissimacoumarin H (2): white amorphous powder. IR (KBr) υmax: 3423, 2971, 2933, 1727,
1611, 1561, 1465, 1411, 1349, 1295, 1129, 1038 cm−1; negative HR-ESI-MS m/z: 425.1347
[M + Cl]– (calcd for C21H26ClO7, 425.1373). 1H NMR (CDCl3, 500 MHz): δ 7.60 (1H, d, J = 9.5 Hz,
H-4), 6.67 (1H, s, H-5), 6.34 (1H, d, J = 9.5 Hz, H-3), 5.34 (1H, dt, J = 8.9, 1.5 Hz, H-6′), 4.76 (1H,
td, J = 8.9, 6.7 Hz, H-5′), 4.62 (1H, dd, J = 9.9, 4.7 Hz, Hβ-1′), 4.11 (1H, dd, J = 9.0, 4.7 Hz, H-2′),
4.02 (3H, s, OMe-8), 4.01(1H, t, J = 9.5 Hz, Hα-1′), 3.88 (3H, s, OMe-6), 2.17 (1H, dd, J = 12.4,
6.7 Hz, Hα-4′), 2.00 (1H, dd, J = 12.4, 9.0 Hz, Hβ-4′), 1.74 (3H, d, J = 1.3 Hz, Me-8′), 1.68 (3H, d,
J = 1.3 Hz, Me-10′), 1.40 (3H, s, Me-9′). 13C NMR (CDCl3, 125 MHz): δ 160.4 (C-2), 149.3 (C-6),
144.8 (C-7), 143.5 (C-4), 143.3 (C-8a), 140.5 (C-8), 136.4 (C-7′), 126.4 (C-6′), 115.4 (C-3), 114.4
(C-4a), 103.9 (C-5), 81.8 (C-2′), 78.2 (C-3′), 74.2 (C-5′), 73.2 (C-1′), 62.0 (OMe-8), 56.4 (OMe-6),
47.3 (C-4′), 26.0 (C-8′), 22.2 (C-9′), 18.2 (C-10′).
3.4. Acid hydrolysis
Compound 1 (2 mg) was hydrolyzed in 1 M HCl (dioxane–H2O, 1:1, 2 mL) at 95 °C for 2 h.
After evaporated to dryness, the reaction mixtures were diluted in H2O and extracted with
Et2O (3 × 2 mL). The aqueous layer was neutralized with NaHCO3 and evaporated under
vacuum to furnish a neutral residue, from which D-glucose was identified by TLC over silica
gel (MeCOEt–isoPrOH–Me2CO–H2O 20:10:7:6) by comparison with authentic samples
(D-glucose Rf 0.40) (Phat et al. 2015).
3.5. Anti-TMV assay
Nicotiana tabacum cv. K326 of 5-6-leaf stage, cultivated in insect-free greenhouse, were used
for anti-TMV assay by previously described leaf-disc method (Shen et al. 2008;Tan et al. 2017).
Pure compounds were dissolved in DMSO and diluted with 0.01 M PBS, and the final con-
centration of DMSO in test solution (≤ 2%) showed no adverse effect on plant. Ningnanmycin
and ribavirin were used as agent control. All tests were conducted in triplicates. Data analysis
was conducted using SPSS version 13.0 statistical software.
4. Conclusions
Two novel compounds, 4-hydroxyphenol-1-O-[6-O-(E)-feruloyl-β-d-glucopyranosyl]-(1→6)-
β- -glucopyranoside (1) and altissimacoumarin H (2), together with ten known compounds
d
were identified from methanol extract of Ailanthus altissima fruit. Six of the known com-
pounds (5–7, 10–12) were reported from genus Ailanthus for the first time. All compounds
showed no significant inhibitory activity against TMV replication.
Supplementary materials
IR, HR-ESI-MS, 1D and 2D NMR spectra of 1 and 2; 1H and 13C NMR data of 3–12; Anti-TMV activity and
a detailed description of the extraction, fraction and isolation procedure of 1–12 are provided in the
supplementary material.

6
J.-C. NI ET AL.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was supported by the National Natural Science Foundation of China [grant numbers
31501687 and 31371987].
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