A new caffeoylgluconic acid derivative from the nearly ripe fruits of Evodia rutaecarpa

Article abstract of DOI:10.1080/14786419.2015.1024116

A new caffeoylgluconic acid derivative, trans-caffeoyl-6-O-d-gluconic acid methyl ester (1), together with two known compounds named trans-caffeoyl-6-O-d-glucono-γ-lactone (2) and trans-caffeoyl-6-O-d-gluconic acid (3), was isolated from the nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth. These compounds were isolated by various separation methods associated with the UPLC-Q-TOF-MS technique. Their structures were elucidated on the basis of extensive spectroscopic methods.

Full text of DOI:10.1080/14786419.2015.1024116

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A new caffeoylgluconic acid derivative
from the nearly ripe fruits of Evodia
rutaecarpa
Ying Heab, Jie Liab, Hong-Hua Wuab, Xin Chaiab, Jing Yangab, Yue-
Fei Wangab, Peng Zhangab, Yan Zhuab & Xiu-Mei Gaoab
a Tianjin State Key Laboratory of Modern Chinese Medicine,
Tianjin University of Traditional Chinese Medicine, Tianjin 300193,
P.R. China
b Tianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin
University of Traditional Chinese Medicine, Tianjin 300193, P.R.
Click for updates
China
Published online: 24 Mar 2015.
To cite this article: Ying He, Jie Li, Hong-Hua Wu, Xin Chai, Jing Yang, Yue-Fei Wang, Peng Zhang,
Yan Zhu & Xiu-Mei Gao (2015) A new caffeoylgluconic acid derivative from the nearly ripe fruits of
Evodia rutaecarpa, Natural Product Research: Formerly Natural Product Letters, 29:13, 1243-1248,
DOI: 10.1080/14786419.2015.1024116
To link to this article: http://dx.doi.org/10.1080/14786419.2015.1024116
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Natural Product Research, 2015
Vol. 29, No. 13, 1243–1248, http://dx.doi.org/10.1080/14786419.2015.1024116
A new caffeoylgluconic acid derivative from the nearly ripe fruits
of Evodia rutaecarpa
Ying Heab, Jie Liab, Hong-Hua Wuab, Xin Chaiab*, Jing Yangab*, Yue-Fei Wangab,
Peng Zhangab, Yan Zhuab and Xiu-Mei Gaoab
aTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese
Medicine, Tianjin 300193, P.R. China; bTianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin
University of Traditional Chinese Medicine, Tianjin 300193, P.R. China
(Received 16 December 2014; final version received 25 February 2015)
A new caffeoylgluconic acid derivative, trans-caffeoyl-6-O-D-gluconic acid methyl
ester (1), together with two known compounds named trans-caffeoyl-6-O-D-glucono-
g-lactone (2) and trans-caffeoyl-6-O-D-gluconic acid (3), was isolated from the nearly
ripe fruits of Evodia rutaecarpa (Juss.) Benth.. These compounds were isolated by
various separation methods associated with the UPLC-Q-TOF-MS technique. Their
structures were elucidated on the basis of extensive spectroscopic methods.
Keywords: Evodia rutaecarpa; UPLC-Q-TOF-MS; caffeoylgluconic acid derivatives
1. Introduction
The nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth., known as ‘WuZhuYu’ in Traditional
Chinese Medicine, have been used to treat headache, cold pain in the stomach duct and
abdomen, stomachache, colic, dysmenorrhoea, vomiting and diarrhoea (Chinese Pharmacopoeia
Commission 2010). Various compounds, including indole alkaloids (Zuo et al. 2000, 2003;
Wang et al. 2010), quinolone alkaloids (Tang et al. 1996; Huang et al. 2012), limonin (Zhang
et al. 2005; Yang et al. 2008), flavonoids (Pan et al. 2004) and others (Zhao & Yang 2008; Wang
et al. 2011; Cai et al. 2012), have been isolated and identified from E. rutaecarpa. However,
most of the previous studies focused on fat-soluble substances, instead of water-soluble
substances. A new indoloquinazoline alkaloidal glucoside, rutaecarpine-10-O-b-D-glucopyrano-
side, from this plant has been reported (Zhang et al. 2013). In our subsequent investigation, a
number of phenolic acids, including caffeoylgluconic acid derivatives, feruloylgluconic acid
derivatives and chlorogenic acid and its isomers, were identified from the H2O extract of
‘WuZhuYu’ by using the UPLC-Q-TOF-MS technique. To the best of our knowledge, only two
new acylgluconic acid compounds, trans-feruloylgluconic acid and trans-caffeoylgluconic acid,
*Corresponding authors. Email: chaixinphd@aliyun.com; yangjingfei_2006@163.com
The first two authors contributed equally to this article.
q 2015 Taylor & Francis

1244
Y. He et al.
have been obtained from E. rutaecarpa (Zhao & Yang 2008) so far. In this paper, we described
the isolation and structural elucidation of a new caffeoylgluconic acid derivative, trans-caffeoyl-
6-O-D-gluconic acid methyl ester (1), and two known compounds named trans-caffeoyl-6-O-D-
glucono-g-lactone (2) (Wu et al. 2005) and trans-caffeoyl-6-O-D-gluconic acid (3) (Zhao &
Yang 2008) (Figure 1) from the H2O extract of E. rutaecarpa. Their structures were confirmed
by NMR spectroscopic and mass spectrometric (HR-ESI-MS) techniques. This was the first
report of trans-caffeoyl-6-O-D-glucono-g-lactone (2) isolated from the genus Evodia.
2. Results and discussion
20
Compound 1 was a yellowish amorphous powder with negative optical rotation ½aꢀD 2 2.7
(c ¼ 0.36, MeOH). The molecular formula was C16H20O10, deduced from HR-ESI-MS with a
quasi-molecular ion peak at m/z 373.1136 [M þ H]þ. The UV spectrum showed lmax (MeOH) at
217, 245, 303 and 329 nm. The IR spectrum indicated the presence of hydroxyl groups at
3263 cm21, carbonyl groups at 1703 and 1743 cm21, an olefinic bond at 1632 cm21 and
aromatic double bonds at 1599, 1516 and 1445 cm21. The 1H NMR spectrum revealed signals of
three aromatic protons at d 7.06 (1H, br s), 7.00 (1H, d, J ¼ 7.2 Hz) and 6.78 (1H, d, J ¼ 7.2 Hz),
a methoxyl group at d 3.65 (3H, s), complex sugar-like signals from d 3.51 to 4.33 and two trans-
olefinic protons at d 7.51 (1H, d, J ¼ 15.6 Hz) and 6.27 (1H, d, J ¼ 15.6 Hz), both displaying
HMBC correlations with a carbonyl ester at dC 167.2. The 13C NMR data of 1 also supported the
presence of a caffeoyl moiety and sugar-like carbon signals. The signal patterns at d 126.0,
115.2, 146.1, 148.8, 116.3, 121.7, 145.4, 114.7 and 167.2 showed the existence of the caffeoyl
moiety (Pauli et al. 1999) in compound 1. The signal patterns at d 173.5, 73.2, 71.0, 72.1, 69.1
and 66.6 indicated that the sugar was a monosaccharic acid (Horton et al. 1983). Comparison of
the 13C NMR spectral data of 1 with those of D-gluconyl (Ramos & Gil 2004), D-galactonyl
(Ramos et al. 1997a) and L-mannonyl (Ramos et al. 1997b) ester suggested that the
monosaccharic acid moiety of 1 was a D-gluconyl group. Furthermore, D-gluconic acid and
caffeic acid were detected after acid catalysed hydrolysis of compound 1 and compared with
authentic samples on TLC. The 1H and 13C NMR spectra of 1 were similar to those of 3, trans-
caffeoyl-6-O-D-gluconic acid, except for additional signals due to a methoxyl group. The
HMBC correlation of H-60 with C-9 proved that the caffeoyl moiety was linked to C-60. The
position of the methoxyl group linked to gluconic acid was deduced by the HMBC correlation
observed between the methyl protons (d 3.65) and C-10 (d 173.5). Therefore, the structure of
compound 1 was assigned as trans-caffeoyl-6-O-D-gluconic acid methyl ester, which was a new
compound.
Figure 1. The structures of compounds 1–3.

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20
Compound 2 was a yellowish amorphous powder with ½aꢀD þ 31.58 (c ¼ 0.38, MeOH). Its
molecular formula of C15H16O9 was determined from HR-ESI-MS data at m/z 341.0870
[M þ H]þ. The UV spectra showed maximum absorptions at 218, 242, 303 and 330 nm,
suggesting the presence of conjugated groups. The IR spectrum showed absorptions for hydroxyl
groups (3394 cm21), an olefinic bond (1632 cm21) and a,b-unsaturated ester bond (1689, 1280–
1
1180 cm21), as well as aromatic double bonds (1601, 1522 and 1446 cm21). The H NMR
spectrum showed a trans-caffeoyl moiety due to an ABX system at d 7.06 (1H, d, J ¼ 2.4 Hz),
7.01 (1H, dd, J ¼ 2.4, 8.4 Hz) and 6.78 (1H, d, J ¼ 8.4 Hz); two trans-olefinic protons at d 7.53
(1H, d, J ¼ 15.6 Hz) and 6.29 (1H, d, J ¼ 15.6 Hz), both displaying HMBC correlations with a
1
carbonyl ester at dC 167.0. H and 13C NMR signals in the aliphatic region constructed a
gluconic acid skeleton due to resonances at d 4.13 (1H, d, J ¼ 4.2 Hz), 4.21 (1H, m), 4.49 (1H,
dd, J ¼ 4.8, 6.6 Hz), 4.08 (1H, m), 4.32 (1H, dd, J ¼ 3.0, 11.4 Hz) and 4.20 (1H, dd, J ¼ 6.0,
11.4 Hz) and d 175.9, 73.5, 73.0, 80.4, 67.1 and 66.1. The HMBC correlation of H-60 with C-9
proved that the caffeoyl moiety was linked to C-60. The downfield-shifted H-40 and the HMBC
connectivities of H-20 to H-40 with C-10 proved that the gluconic acid cyclised to a g-lactone.
Based on the above results, the structure of compound 2 was elucidated as trans-caffeoyl-6-O-D-
glucono-g-lactone, which has been isolated from Vittaria anguste-elongata (Wu et al. 2005).
3. Experimental
3.1. General experimental procedures
UV spectra were measured on a WFZ UV-2102PCS UV-visible photometer (UNICO, Dayton,
NJ, USA). IR spectra were recorded on a Spectrum 65 spectrometer (Perkin-Elmer, Waltham,
MA, USA). NMR spectra were recorded on Bruker AVIII 400 and 600 MHz spectrometers
(Bruker, Zurich, Switzerland). The HR-ESI-MS data were recorded on a Synapt G2 mass
spectrometer (Waters, Milford, MA, USA). Preparative HPLC was performed using an Agilent
1260 system, composed of a quaternary pump, a DAD detector and a ZORBAX SB-C18 PrepHT
column (Agilent, Santa Clara, CA, USA). UPLC was carried out using an ACQUITY UPLC
instrument equipped with a quaternary pump, a UV detector and an ACQUITY UHPLC BEH
C18 column (Waters). Silica gel (200–300 mesh, Qingdao Haiyang Chemical Co., Ltd,
Qingdao, China), ODS silica gel (120 A, 50 mm, YMC, Kyoto, Japan), Sephadex LH-20 gel (GE
Healthcare Bio-Sciences AB, Uppsala, Sweden) and D101 macroporous resin (Tianjin Haiguang
Chemical Co., Ltd, Tianjin, China) were used for column chromatography. Precoated plates with
GF254 silica gel (Qingdao Haiyang Chemical Co., Ltd) were used for TLC analysis.
3.2. Plant material
The dried fruits of E. rutaecarpa were obtained from Anguo county, Hebei province of P.R.
China, and authenticated by Prof. Tian-Xiang Li, Tianjin University of Traditional Chinese
Medicine (Tianjin, China). A voucher specimen (No. 10523266) was deposited in the herbarium
of pharmacognosy, Tianjin University of Traditional Chinese Medicine.
3.3. Extraction and isolation
The dried nearly ripe fruits of E. Rutaecarpa (3 kg) were refluxed with H2O twice. The H2O
extract was subjected to D101 macroporous resin column chromatography with 95% EtOH to
remove the impurities, then eluted with 0.1% formic acid–H2O. The eluent was evaporated and
concentrated to yield a crude extract (197 g), 40 g of which were exposed to Sephadex LH-20
column chromatography and eluted with MeOH–H2O (90:10, 100:0) to afford 22 fractions
(Fr.1–Fr.22) and 16 fractions (Fr.23–Fr.38), respectively. Frs9–38 (35 g) were separated by

1246
Y. He et al.
ODS column chromatography, eluted with 10%, 15%, 20%, 30%, 40% and 50% MeOH as
eluants to get 76 fractions. The target compounds were found in Frs12–36 on the basis of UPLC-
MS. Then Frs12–36 were purified by preparative HPLC with MeOH–0.1% formic acid (23%–
30%, 30 min) as mobile phase to give compounds 1–3.
3.3.1. trans-Caffeoyl-6-O-D-gluconic acid methyl ester (1)
20
C16H20O10, yellowish amorphous powder, ½aꢀD 2 2.7 (c ¼ 0.36, MeOH). HR-ESI-MS m/z:
373.1136 [M þ H]þ (calcd for C16H21O10, 373.1135). UV (MeOH) lmax nm (log 1): 217 (4.19),
245 (4.0), 303 (4.11), 329 (4.23). IR (KBr) v cm21: 3263, 1743, 1703, 1632, 1599, 1515, 1445,
1282, 1161. 1H NMR (600 MHz, DMSO-d6): d 7.06 (1H, br s, H-2), 6.78 (1H, d, J ¼ 7.2 Hz, H-
5), 7.00 (1H, d, J ¼ 7.2 Hz, H-6), 7.51 (1H, d, J ¼ 15.6 Hz, H-7), 6.27 (1H, d, J ¼ 15.6 Hz, H-8),
3.65 (3H, s, OCH3), 4.25 (1H, br s, H-20), 3.95 (1H, m, H-30), 3.51 (1H, m, H-40), 3.77 (1H, m, H-
50), 4.04 (1H, m, H-60), 4.33 (1H, d, J ¼ 9.6 Hz, H-60). 13C NMR (150 MHz, DMSO-d6): d 126.0
(C-1), 115.2 (C-2), 146.1 (C-3), 148.8 (C-4), 116.3 (C-5), 121.7 (C-6), 145.4 (C-7), 114.7 (C-8),
167.2 (C-9), 173.5 (C-10), 73.2 (C-20), 71.0 (C-30), 72.1 (C-40), 69.1 (C-50), 66.6 (C-60), 51.9
(OCH3).
3.3.2. trans-Caffeoyl-6-O-D-gluconic-g-lactone (2)
20
C15H16O9, yellowish amorphous powder, ½aꢀD þ 31.58 (c ¼ 0.38, MeOH). HR-ESI-MS m/z:
341.0870 [M þ H]þ (calcd for C15H17O9, 341.0873). UV (MeOH) lmax nm (log 1): 218 (4.22),
242 (4.02), 303 (4.12), 330 (4.23). IR (KBr) v cm21: 3394, 1689, 1632, 1601, 1522, 1446, 1280,
1180. 1H NMR (400 MHz, DMSO-d6): d 7.06 (1H, d, J ¼ 2.4 Hz, H-2), 6.78 (1H, d, J ¼ 8.4 Hz,
H-5), 7.01 (1H, dd, J ¼ 2.4, 8.4 Hz, H-6), 7.53 (1H, d, J ¼ 15.6 Hz, H-7), 6.29 (1H, d,
J ¼ 15.6 Hz, H-8), 4.13 (1H, d, J ¼ 4.2 Hz, H-20), 4.21 (1H, m, H-30), 4.49 (1H, dd, J ¼ 4.8,
6.6 Hz, H-40), 4.08 (1H, m, H-50), 4.32 (1H, dd, J ¼ 3.0, 11.4 Hz, H-60), 4.20 (1H, dd, J ¼ 6.6,
11.4 Hz, H-60). 13C NMR (100 MHz, DMSO-d6): d 126.0 (C-1), 115.3 (C-2), 146.1 (C-3), 148.9
(C-4), 116.2 (C-5), 121.8 (C-6), 145.8 (C-7), 114.3 (C-8), 167.0 (C-9), 175.9 (C-10), 73.5 (C-20),
73.0 (C-30), 80.4 (C-40), 67.1 (C-50), 66.1 (C-60).
3.3.3. trans-Caffeoyl-6-O-D-gluconic acid (3)
C15H18O10, yellowish amorphous powder. HR-ESI-MS m/z: 359.0978 [M þ H]þ (calcd for
C15H19O10, 359.0978). UV (MeOH) lmax nm (log 1): 218 (4.48), 244 (4.30), 301 (4.43), 329
(4.53). IR (KBr) v cm21: 3395, 1689, 1632, 1603, 1518, 1445. 1H NMR (400 MHz, DMSO-d6):
d 7.05 (1H, br s, H-2), 6.76 (1H, d, J ¼ 8.0 Hz, H-5), 6.98 (1H, d, J ¼ 8.0 Hz, H-6), 7.50 (1H, d,
J ¼ 16.0 Hz, H-7), 6.26 (1H, d, J ¼ 16.0 Hz, H-8), 3.57 (1H, m, H-20), 3.95 (1H, m, H-30), 3.77
(1H, m, H-40), 4.00 (1H, m, H-50), 4.01 (1H, m, H-60), 4.33 (1H, d, J ¼ 10.8 Hz, H-60). 13C NMR
(100 MHz, DMSO-d6): d 125.5 (C-1), 114.2 (C-2), 148.3 (C-3), 144.9 (C-4), 115.8 (C-5), 121.2
(C-6), 145.6 (C-7), 114.7 (C-8), 166.7 (C-9), 175.2 (C-10), 72.7 (C-20), 68.6 (C-30), 71.9 (C-40),
70.2 (C-50), 66.3 (C-60).
3.4. Acid hydrolysis of compounds 1–3
Compounds 1–3 (each 2 mg) were dissolved in 1 M HCl (50 mL), and then heated in a H2O bath
at 808C for 1 h. After cooling to room temperature, each reaction mixture was extracted by
EtOAc three times (Zhang et al. 2013). The extract of EtOAc was evaporated under vacuum to
obtain a residue, which was dissolved in MeOH and then analysed by silica gel GF254 TLC
(CHCl3/MeOH ¼ 4:1, Rf ¼ 0.31). Caffeic acid was identified in the above residue in
comparison with an authentic sample. The aqueous layer was neutralised with Ag2CO3,

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centrifuged and evaporated to dryness, which was dissolved in MeOH–H2O (2:1, v/v) and
analysed by silica gel TLC (MeOH/H2O/HAc ¼ 6:4:1, Rf ¼ 0.50) together with authentic D-
gluconic acid. TLC detection was obtained by soaking into the solution of the lead
tetraacetate/2,7-dichlorofluorescein followed by heating, which appeared as yellow elliptic
spots.
4. Conclusion
So far, few caffeoylgluconic acid compounds have been reported from E. rutaecarpa. In this
study, three caffeoylgluconic acid derivatives were isolated from the nearly ripe fruits of
E. rutaecarpa by using the UPLC-Q-TOF-MS technique as guidance to find target compounds.
Our study indicated that the UPLC-Q-TOF-MS analytical system in combination with
traditional separation methods is more rapid and reliable to obtain new/target compounds.
Moreover, the biological activity of acylgluconic acid compounds is worth to be investigated in
the future.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was financially supported by the National Science and Technology Major Projects for ‘Major
New Drugs Innovation and Development’ [grant number 2015ZX09J15102-004-004], [grant number
2012ZX09304007].
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