Natural Product Research

Formerly Natural Product Letters

ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20

Diarylheptanoids from the fresh pericarps of

Juglans sigillata

Jingjing Liang, Xiaogang Peng, Jia Zhou, Ming Zhou & Hanli Ruan

To cite this article: Jingjing Liang, Xiaogang Peng, Jia Zhou, Ming Zhou & Hanli Ruan (2017):
Diarylheptanoids from the fresh pericarps of Juglans sigillata, Natural Product Research, DOI:
10.1080/14786419.2017.1419235

To link to this article: https://doi.org/10.1080/14786419.2017.1419235

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Published online: 28 Dec 2017.

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 Natural Product Research, 2017
https://doi.org/10.1080/14786419.2017.1419235

Diarylheptanoids from the fresh pericarps of Juglans sigillata

Jingjing Liang, Xiaogang Peng, Jia Zhou, Ming Zhou and Hanli Ruan
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji
Medical College of Huazhong University of Science and Technology, Wuhan, People’s Republic of China
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ABSTRACT ARTICLE HISTORY

One new diarylheptanoid (3S)-3′, 4″-epoxy-1-(4′-hydroxylphenyl)- Received 12 October 2017
7-(3″-hydroxylphenyl) heptane-3-hydroxy (1), together with eleven Accepted 10 December 2017
known ones (2–12), was isolated from the fresh pericarps of Juglans
KEYWORDS
sigillata. Their structures were elucidated on the basis of extensive Juglans sigillata;
spectroscopic methods, including HR-ESI-MS, 1D and 2D-NMR. All Juglandaceae; fresh
isolates were evaluated for their cytotoxic activities in vitro against pericarps; diarylheptanoids
the growth of human cancer cells lines HT-29 and MCF-7 by MTT assay.

1. Introduction
The genus Juglans (Juglandaceae) comprises about 20 species and is widely distributed in
the temperate and subtropical areas of the world (Liu, Zhao, et al. 2010). The roots, stems
and leaves of this genus had been used as a folk medicine for the treatment of cancer, gas-
tritis, diarrhoea and leucorrhoea (Yao et al. 2015). The fresh pericarps of some species, such
as Juglans mandshurica and Juglans regia, commonly named as ‘qinglongyi’, have been medic-
inally used for thousands of years in China, Japan and Korea, owing to their anti-tumour,
anti-inflammatory, antinociceptive and antioxidant effects (Liu, Zhao, et al. 2010). Some
types of chemical constituents have been reported from different parts of Juglans plants,
such as naphthoquinones (Yu et al. 2011; Zhou et al. 2015), naphthalenyl glucosides

CONTACT  Hanli Ruan  ruanhl@mails.tjmu.edu.cn

 Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2017.1419235.
© 2017 Informa UK Limited, trading as Taylor & Francis Group
 2   J. LIANG ET AL.

R4 R5 O

6' 1' 1 3 5
2 4 R4 H
5' 2' 6
3' 5'' 6''
4' 7
R1 O 4'' R1 O
1''
3''
2''
R2 R3 R2 R3

1 * R1 = OH 8 R1 = OH R2 = OH R3 = H R4 = H
R 2 = OH R3 = H R4 = H R5 = OH
2 R 1 = OH R 2 = OCH 3 R3 = OH R4 = OH R5 = H 9 R1 = OH R2 = OCH 3 R 3 = OH R 4 = H
3 R 1 = OCH3 R2 = OCH 3 R3 = OH R 4 = OH R5 = H 10 R1 = OCH 3 R 2 = OCH3 R 3 = OH R 4 = H
4 R 1 = OH R 2 = OCH 3 11 R1 = OH R2 = OCH 3 R3 = H R4 = H
R3 = H R 4 = OH R 5 = H
12 R1 = OH R2 = OCH 3 R 3 = H R 4 = OH
HO
H OH
R OCH 3
H 3CO
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HO
HO OH
OH
5R=H
6 R = OCH3 7

Figure 1. Structures of compounds 1–12.

(Liu, Zhao, et al. 2010; Zhou et al. 2015), tetralones and their derivatives (Machida et al. 2005;
Liu, Li, et al. 2010; Zhou et al. 2015), terpenoids (Zhang et al. 2012; Yao et al. 2016), diaryl-
heptanoids (Li et al. 2003, 2013; Jin et al. 2015; Yao et al. 2015), galloylglucosides (Si, Qin,
et al. 2011; Si et al. 2016), flavonoids (Si, Qin, et al. 2011; Si, Zhang, et al. 2011) and lignans
(Park et al. 2017).
Juglans sigillata Dode, is indigenous in valleys and on mountain slopes of Guizhou,
Sichuan, Tibet, Yunnan provinces of south-west China (Si, Zhang, et al. 2011). To date, many
investigations on the chemical constituents and biological activities of J. mandshurica and
J. regia have been reported. However, few studies have been performed on J. sigillata. Liu
et al. isolated three new α-tetralone galloylglucosides from J. sigillata (Liu, Zhao, et al. 2010).
Si et al. made some investigations on different parts of J. sigillata and obtained several gal-
loylglucosides, and some of them showed significant antioxidant effects (Si, Qin, et al. 2011,
Si et al. 2016). In order to search for more new bioactive constituents, a detailed investigation
on the chemical constituents of J. sigillata was carried out. As a result, one new (1) and eleven
(2–12) known diarylheptanoids were isolated from the green pericarps of J. sigillata. This
paper mainly describes the isolation, structural elucidation and cytotoxic activities of all
isolated compounds.

2.  Results and discussion

Compound 1 was obtained as light brown amorphous powder. Its molecular formula was
determined as C19H22O4 by the HR-ESI-MS (m/z 337.1411 [M + Na]+, calcd for C19H22O4Na
337.1416). The IR spectrum revealed absorptions at 3443, 1598, 1513, 1441 and 1266 cm−1,
assignable to hydroxyl, aromatic ring and ether functions. The 1H-NMR spectrum of 1 exhib-
ited two sets of 1,2,4-trisubstituted benzene ring systems [δH 6.98 (1H, d, J = 7.9 Hz, H-5″),
6.81(1H, d, J = 2.0 Hz, H-2″), 6.78 (1H, dd, J = 7.9, 2.0 Hz, H-6″)] and [δH 6.71 (1H, d, J = 8.0 Hz,
H-5′), 6.55 (1H, dd, J = 8.0, 2.1 Hz, H-6′), 5.73 (1H, dd, J = 2.1 Hz, H-2′)]. The chemical shift of
H-2′ (δH 5.73) appeared abnormally upfield from the ones of other aromatic protons, and
 NATURAL PRODUCT RESEARCH   3

the shielding effect is characteristic of diphenyl ether-type diarylheptanoids that have an

ether linkage between C-3′ and C-4″ (Tanaka et al. 1998). The 13C-NMR spectrum showed 19
carbon signals shared by 12 aromatic carbons and 7 aliphatic carbons, hinting that 1 was a
cyclic diarylheptanoid derivative. The 1H-1H COSY spectrum implied one contiguous struc-
tural sequence with connectivities from H-1 to H-7 on the aliphatic chain, corresponding to
a CH2-1-CH2-2-CH-3-CH2-4-CH2-5-CH2-6-CH2-7 moiety. Taking 1H-NMR, 13C-NMR and molec-
ular formula into consideration, there were three hydroxyls in 1 totally. One hydroxyl group
was located at C-4′, as confirmed by the HMBC correlations of H-6′, H-5′, H-2′ with C-4′.
Another hydroxyl group was positioned at C-3″, based on the cross peaks of H-5″ with C-3″
and H-2″ with C-3″ and C-4″. And the last one was attached to C-3 due to the HMBC corre-
lations of H-1, H-2, H-4 and H-5 with C-3. In addition, correlations of H-1 with C-1′, C-2′, C-6′
and H-7 with C-1″, C-2″, C-6″ established that the C-1 moiety connected with C-1′, C-7 moiety
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linked to C-1″, respectively. With the analysis above, the planar structure of 1 was assigned
to be 3′, 4″-epoxy-1-(4′-hydroxylphenyl)-7-(3″-hydroxylphenyl) heptane-3-hydroxy.
The absolute configuration of 1 was determined to be 3S by comparison of the specific
D  + 53.2°, (c 0.20, EtOH) of 1 with that of (+)-(S)-acerogenin B ([𝛼]D  +84.1°, (c 0.20,
rotation ([𝛼]25 22

EtOH)) (Morikawa et al. 2003) and (-)-(R)-rhoiptelol ([𝛼]D  −58.5°, (c 0.30, CHCl3)) (Jiang et al.
15

2001). The CD behaviours ((c 0.0025, MeOH) : Δε (nm) = −103 (206),+57 (227),+17 (282)) of
1 were opposite to that of (-)-(R)rhoiptelol (CD (c 0.0016, MeOH) Δε(nm):+4.42 (218), −3.24
(241), −1.15 (283)) (Jiang et al. 2001), which also indicated the S configuration of C-3 in 1.
Taken together, compound 1 was identified as (3S)-3′, 4″-epoxy-1-(4′-hydroxylphe-
nyl)-7-(3″-hydroxylphenyl) heptane-3-hydroxy, named jugsigin A.
Compared with the corresponding literature data, the known compounds 2–12 were iden-
tified as (11R)-3,11,17-trihydroxy-2-methoxy-1,16-oxo-7,13-diphenyl-11-heptanol (2) (Yao
et al. 2015), rhoiptelol (3) (Jiang et al. 2001), 3′,4″-epoxy-1-(4′-hydroxylphenyl)-7-(3″-methox-
ylphenyl)-heptane-3-hydroxy (4) (Li et al. 2003), 4-(5-hydroxy-7-(4-hydroxyphenyl) hep-
tyl)-2-methoxyphenol (5) (Li et al. 2004), 3-hydroxy-1,7-bis (4-hydroxy-3-methoxyphenyl)
heptane (6) (Jirásek et al. 2014), juglaninB (7) (Liu et al. 2008), pterocarine (8) (Wu et al. 2012),
myricatomentogenin (9) (Liu et al. 2005; Zhang et al. 2012), juglanin A (10) (Liu et al. 2008),
galeon (11) (Zhou et al. 2010) and 3′,4″-epoxy-1-(4′-hydroxylphenyl)-7-(3″-methoxyl-phenyl)-
heptane-2-hydro-3-one (12) (Li et al. 2003), respectively. To the best of our knowledge, com-
pounds 2–12 are reported here for the first time from this plant. The cytotoxicities of compounds
1–12 in vitro against MCF-7 and HT-29 cancer cell lines were tested using a MTT assay, and
only 7 showed weak antiproliferation activity to HT-29 with IC50 81.34 μM (Table S1).

3. Experimental
3.1.  General experimental procedures
Optical rotations were measured on a Perkin-Elmer 341 polarimeter. UV spectra were meas-
ured on a Varian Cary 50 Scan UV/Vis spectrophotometer. IR spectra were recorded on a
Bruker VERTEX 70 FT-IR microscopic spectroscopy. NMR spectra were recorded on a
Bruker-AM-400 spectrometer. HR-ESI-MS was performed on a Thermo Scientific LTQ-Orbitrap
XL mass spectrometer. MPLC was performed using an EZ Purifier III chromatography system
(Lisui Chemical Engineering Co., Ltd., Shanghai, China). Column chromatography was per-
formed with silica gel (200–300 or 300–400 mesh; Qingdao Marine Chemical Inc., Qingdao,
 4   J. LIANG ET AL.

China), ODS (50 µm, YMC Co. Ltd., Tokyo, Japan), Sephadex LH-20 gel (GE Healthcare, Uppsala,
Sweden) and MCI (microporous resin) gel (CHP20P, 75–150 µm; Mitsubishi Chemical
Industries Ltd., Tokyo, Japan). HPLC was performed on Agilent 1260 system and 1100 system.
The reversed-phase HPLC column (C18, 5 µm, 250 × 10 mm i.d.; YMC, Tokyo, Japan) were used
for analytical and semi-preparative purposes. Thin-layer chromatography (TLC) was per-
formed with silica gel 60 GF254 (Yantai Chemical Industry Research Institute). MTT assays
were performed on a BioTek Synergy 2 multimode microplate reader. And 3-(4, 5-Dimethyl-
2-thiazolyl)-2, 5-diphenyl-2-tetrazolium bromide (MTT) were purchased from Aladdin
Industry Corporation, Shanghai, China.

3.2.  Plant material

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The green pericarps of J. sigillata were collected in August 2015 in qiangbi city, yunnan
province, P.R. China. Plant samples were confirmed taxonomically by Prof. Hanli Ruan (Faculty
of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology). A
voucher specimen (voucher number : 20151010) has been deposited in the Herbarium of
Materia Medica, Faculty of Pharmacy, Tongji Medical College of Huazhong University of
Science and Technology, Wuhan, P. R. China.

3.3.  Extraction and isolation

The air-dried and powdered pericarps of J. sigillata (89.0 kg) were extracted three times with
95% EtOH (v/v) at room temperature and the combined extracts were evaporated to dryness
under vacuum to give the crude extract (9.7 kg). The crude extract was suspended in water
and partitioned successively with a serious of solvents to give fractions of petroleum ether
(PE), CH2Cl2 and EtOAc. The CH2Cl2 fraction (298.0 g) was subjected to MCI gel column with
MeOH-H2O (30:70 to 100:0, v/v) to give 5 fractions (A–E). Fraction C (15.4 g) was separated
by silica gel column chromatography with a gradient of PE-EtOAc (1:0 to 1:10, v/v) to afford
seven subfractions (C1-C7). Fraction C5 (3.7 g) was applied to Sphadex LH-20 column eluted
with CH2Cl2-MeOH (1:1, v/v) to obtained four subfractions (C5-1 to C5-4). Fraction C5-2 (1.3 g)
was further loaded over ODS column with MeOH-H2O (35:65 to 100:0, v/v) to give subfrac-
tions C5-2-1 to C5-2-3. C5-2-1 and C5-2-2 were finally purified by semi-preparative HPLC
(MeOH-H2O, 50:50, v/v) to yield compound 1 (5.3 mg), 2 (6.0 mg), 3 (6.1 mg), 4 (4.5 mg), 5
(8.4 mg) and 6 (9.6 mg). Recrystallisation of subfraction C5-3 from 100% MeOH yielded com-
pound 7 (25.0 mg). Fraction C6 (2.6 g) was separated by a series of purification steps using
Sephadex LH-20 column chromatography (CH2Cl2-MeOH, 1:1, v/v), ODS column chromatog-
raphy (MeOH-H2O, 30:70 to 100:0, v/v), followed by semi-preparative HPLC (MeOH-H2O, 55:45,
v/v) to afford compound 8 (28.2 mg), 9 (30.0 mg), 10 (8.1 mg), 11 (7.6 mg) and 12 (3.2 mg).
(3S)-3′, 4″-epoxy-1-(4′-hydroxylphenyl)-7-(3″-hydroxylphenyl) heptane-3-hydroxy (1):
white amorphous powder; [𝛼]25 D  + 53.2°, (c 0.2, EtOH); UV (MeOH): λmax (log ε) = 205 (7.85),
280 (6.83) nm; CD (c 0.0025, MeOH) : Δε (nm) = −103 (206), + 57 (227), + 17 (282); IR (KBr)
νmax = 3442, 3307, 2933, 1598, 1513, 1498, 1266 cm−1; HR-ESI-MS: m/z = 337.1411 [M + Na]+
(calcd for C19H22O4Na: 337.1416); 1H-NMR (CD3OD, 400 MHz) δ 6.98 (1H, d, J = 7.9 Hz, H-5″),
6.81 (1H, d, J = 2.0 Hz, H-2″), 6.78 (1H, dd, J = 7.9, 2.0 Hz, H-6″), 6.71 (1H, d, J = 8.0 Hz, H-5′),
6.55 (1H, dd, J = 8.0, 2.1 Hz, H-6′), 5.73 (1H, d, J = 2.1 Hz, H-2′), 3.15−3.08 (1H, m, H-3), 2.70
(1H, ddd, J = 12.9, 6.4, 4.3 Hz, H-7a), 2.65−2.53 (2H, m, H-1a, H-7b), 2.53−2.43 (1H, m, H-1b),
 NATURAL PRODUCT RESEARCH   5

1.72 (1H, ddd, J = 13.6, 6.7, 4.8 Hz, H-6a), 1.60−1.48 (1H, m, H-6b), 1.48−1.39 (2H, m, H-2),
1.33−1.18 (2H, m, H-4a, H-5a), 1.14−1.01 (1H, m, H-5b), 1.00−0.87 (1H, m, H-4b). 13C- NMR
(100 MHz, CD3OD) δ 151.0 (C-3″), 149.6 (C-3′), 144.3 (C-4′), 143.2 (C-4″), 142.4 (C-1″), 135.2
(C-1′), 125.2 (C-5″), 123.0 (C-6′), 122.4 (C-6″), 120.2 (C-2″), 116.9 (C-5′), 114.4 (C-2′), 72.8 (C-3),
39.5 (C-4), 37.9 (C-2), 36.3 (C-7), 31.5 (C-6), 29.5 (C-1), 23.7 (C-5).

3.4.  Cytotoxicity assay

Two cancer cell lines (MCF-7 and HT-29) were used for cytotoxic activity assays. MCF-7 and
HT-29 cells were cultured in RPMI-1640 medium (Hyclone), supplemented with 10% fetal
bovine serum (Sijiqing, Hangzhou, People’s Republic of China), 100 U/mL penicillin, and
100 μg/mL streptomycin in a 37 °C incubator (Heal Force HF-90, Hong Kong) supplied with
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5% CO2. Cell viability was determined by the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetra-

zolium bromide (MTT) assay. 90 μL of adherent cells was seeded into the 96-well culture
plates with initial destiny of 1 × 104 cells/mL, and cultured for 24 h to attach to the surface
of the plates completely. Then, cells were treated with various concentrations (12.5, 25, 50,
70, 100 μM) of compound 7 and (50, 100 μM) of compounds (1–6, 8–12) with a volume of
10 μL in triplicate, and Doxorubicin hydrochloride was used as positive control. After 24 h
of treatment, 15 μL MTT (5 mg/mL) was added to each well and the plates were incubated
for 4 h at 37 °C. For the MTT assays, the supernatant was discarded, and DMSO (100 μL/well)
was added. The optical density of the lysate at 490 nm was measured by Enzyme immuno-
assay instrument (BioTek Synergy 2 reader). Results were expressed as a percentage of the
control, and the half-maximal inhibitory concentration values (IC50) were obtained from the
MTT viability curves using GraphPad Prism 5.0.

4. Conclusion
Twelve diarylheptanoids (1–12) were isolated from the green pericarps of J. sigillata.
Compound 1 was new, and 2–12 were isolated from this plant for the first time. The above
results indicate that diarylheptanoids can be regarded as characteristic constituents of this
plant. All isolates were evaluated for their cytotoxic activities in vitro against the growth of
human cancer cells lines HT-29 and MCF-7, only 7 exhibited weak activity against HT-29 with
IC 50 81.34 μM.

Supplementary material
Experimental data of compound 1 are available alongside Figures S1–S10.

Acknowledgements
We are grateful to the staff at the Analytical and Testing Center of Huazhong University of Science and
Technology for collecting the spectroscopic data.

Disclosure statement
No potential conflict of interest was reported by the authors.
 6   J. LIANG ET AL.

Funding
This work was supported by the National Natural Science Foundation of China [grant number
21572073], [grant number 31770380], [grant number 31270394]; the Fundamental Research Funds
for the Central Universities [grant number 2016YXMS150].

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