全 文 ： 药学学报 Acta Pharmaceutica Sinica 2015, 50 (4): 475−479 · 475 ·





Chemical constituents from stems and
leaves of Micromelum integerrimum
LIU Yan1, 2†, WANG Zhi-yao1, 2, 3†, HE Wen-jun2, TAN Ning-hua2*, YIN Zhi-qi1*
(1. Department of Natural Medicinal Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical
University, Nanjing 210009, China; 2. State Key Laboratory of Phytochemistry and Plant Resources in West China,
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
3. Key Laboratory of Natural Products, Henan Academy of Sciences, Zhengzhou 450002, China)
Abstract: A new benzene derivative microintegerrin C (1) and a new norsesquiterpenoid microintegerrin D
(2), along with six known compounds (3−8), were isolated and identified from stems and leaves of Micromelum
integerrimum by various chromatographies such as silica gel, Sephadex LH-20, RP-18 column chromatography
and HPLC. Their structures were mainly identified based on the spectral data analysis such as 1D-, 2D-NMR
and HR-EI-MS. All known compounds were isolated from this plant for the first time.
Key words: Micromelum integerrimum; Rutaceae; benzene derivative; norsesquiterpenoid; microintegerrins
C-D
CLC number: R284 Document code: A Article ID: 0513-4870 (2015) 04-0475-05
小芸木茎和叶中化学成分研究
刘 燕 1, 2†, 王志尧 1, 2, 3†, 贺文军 2, 谭宁华 2*, 殷志琦 1*
(1. 中国药科大学天然药物化学教研室, 天然药物活性组分与药效国家重点实验室, 江苏 南京 210009;
2. 中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室, 云南 昆明 650201;
3. 河南省科学院天然产物重点实验室, 河南 郑州 450002)

摘要: 通过硅胶、凝胶、RP-18和 HPLC等一系列色谱方法对小芸木茎和叶中化学成分进行研究, 得到 8个
化合物, 包括两个新化合物 (1、2) 和 6个已知化合物 (3～8)。通过一维、二维核磁共振以及高分辨质谱等波谱数
据对这些化合物进行结构鉴定, 其中化合物 microintegerrin C (1) 为一个新的苯环衍生物, 化合物 microintegerrin
D (2) 为一个新的降倍半萜, 化合物 3～8为首次从该植物中分离得到。
关键词: 小芸木; 芸香科; 苯环衍生物; 降倍半萜; microintegerrins C-D

Micromelum integerrimum (Buch.-Ham. ex DC.)
Wight & Arn. ex M. Roem. (Rutaceae) is distributed

Received 2014-10-30; Accepted 2014-12-05.
Project supported by the National Natural Science Foundation of China
(31470428, 21202147, 81001379); National New Drug Innovation
Major Project of China (2011ZX09307-002-02); Natural Science
Foundation of Yunnan Province (2012GA003).
†These authors contributed equally.
*Corresponding author
Tel / Fax: 86-25-83271447, E-mail: chyzq2005@126.com;
Tel / Fax: 86-871-65223800, E-mail: nhtan@mail.kib.ac.cn
mainly in China[1]. The leaves and barks have been
used for the treatment of cold and trauma, and the roots
for stomach pain[1]. Previous chemical investigations
on this genus afforded a number of structurally inter-
esting coumarins, alkaloids and other compounds[2−7].
Although coumarins, alkaloids and phenylpropanoids
have also been isolated from M. integerrimum, some
coumarins showed cytotoxicity[3−5, 8]. As part of our
continuous investigation on the chemical and biological
constituents of M. integerrimum, chemical investigation
· 476 · 药学学报 Acta Pharmaceutica Sinica 2015, 50 (4): 475−479


on the stems and leaves of M. integerrimum leads to the
isolation of two new compounds (1, 2) and six known
compounds (3−8).

Results and discussion
Two new compounds, a benzene derivative (1) and
a norsesquiterpenoid (2), together with six known
compounds (3−8) were isolated and determined as
microintegerrin C (1), microintegerrin D (2), 2-methoxy-
4-(2-propenyl)-phenyl-β-D-glucoside (3)[9], erigesideⅡ
(4)[10], acantrifoside E (5)[11], benzyl-β-D-glucoside
(6)[12], 5,7-dihydroxyl-3,8,4-trimethoxylflavone (7)[13]
and kaempferol 3-O-β-D-glucoside (8)[14] (Figure 1),
based on the spectral data analysis such as 1D-, 2D-
NMR and HR-EI-MS.
Compound 1 was isolated as yellow oil. The
molecular formula of C20H26O9 was determined on
the basis of its HR-EI-MS molecular ion peak (m/z
410.156 7 [M]+), in combination with an analysis of the
13C NMR spectrum (DEPT), corresponding to eight
degrees of unsaturation. The IR spectrum showed
absorption bands of hydroxyl (3 405 cm−1) and carbonyl
groups (1 680 cm−1). The 13C NMR spectrum (Table
1) displayed 20 carbon signals: two CH3 (δC 18.5, 14.5),
three CH2 (δC 74.6, 62.8, 62.5), eleven CH (δC 134.4,
130.6, 130.6, 129.7, 129.7, 122.3, 103.3, 78.2, 78.1,
75.2, 71.7) and four C (δC 170.0, 168.1, 139.6, 131.6).
The 1H NMR, COSY and HMBC spectra (Table 1,
Figure 2) displayed the following moiety signals: one
mono-substituted benzoyl [δC 168.1, 134.4, 131.6, 130.6,
130.6, 129.7, 129.7; δH 8.01 (2H, dd, J = 7.8, 1.2 Hz),
7.60 (1H, m), 7.48 (2H, t, J = 7.8 Hz)], one glucosyl [δC
103.3, 78.2, 78.1, 75.2, 71.7, 62.8; δH 4.28 (1H, d, J =
7.8 Hz), 3.86 (1H, dd, J = 12.0, 1.8 Hz), 3.66 (1H, dd,
J = 12.0, 5.4 Hz), 3.35 (1H, t, J = 9.0 Hz), 3.25 (3H,
overlapped)], one acetyl [δC 170.0, 18.5; δH 2.21 (3H,
s)], and one [-OCH2C(CH3)=CHCH2O-] unit [δC 139.6,
122.3, 74.6, 62.5, 14.5; δH 5.83 (1H, dt, J = 7.2, 1.2 Hz),
4.90 (2H, d, J = 7.2 Hz), 4.31 (1H, d, J = 12.6 Hz), 4.11
(1H, d, J = 12.6 Hz), 1.84 (3H, s)]. The β-configuration
of the glucose was determined from the coupling
constant (7.8 Hz) of the anomeric proton signal in the
1H NMR spectrum[15]. Further analysis of the HMBC
spectrum (Figure 2) revealed the following connections:
the correlation of H-6/C-7 indicated that the acetyl
was linked to C-6 of the β-D-glucopyranosyl unit;
the correlation of H-1/C-1 indicated that the β-D-
glucopyranosyl moiety was linked to C-1; the correlation
of H-4/C-7 indicated that the [-OCH2C(CH3)=CHCH2O-]
unit was linked to C-7. Thus, the structure of 1 is
elucidated and named as microintegerrin C (Figure 1).
Compound 2 was obtained as yellow oil. The
HR-EI-MS revealed an ion peak at m/z 412.207 0 [M]+,
corresponding to the molecular formula C21H32O8
(Calcd. 412.209 7). Comparison of the 1D- and 2D-


Figure 1 Structures of compounds 1−8
LIU Yan, et al: Chemical constituents from the stems and leaves of Micromelum integerrimum · 477 ·



Figure 2 Key HMBC correlations of compounds 1 and 2

Table 1 1H, 13C NMR data of 1 and 2 at 600 and 150 MHz, in
CD3OD, respectively (J in Hz)
No.
1 2
δH δC δH δC
1 4.31 (1H, d, 12.6) 74.6 (t) 36.7 (s)
4.11 (1H, d, 12.6)
2 139.6 (s) 1.87 (2H, t, 6.7) 38.3 (t)
3 5.83 (1H, dt, 7.2, 1.2) 122.3 (d) 2.50 (2H, t, 6.7) 35.3 (t)
4 4.90 (2H, d, 7.2) 62.5 (t) 201.9 (s)
5 1.84 (3H, s) 14.5 (q) 130.8 (s)
6 163.8 (s)
7 6.41 (1H, d, 16.2) 129.8 (d)
8 5.61 (1H, dd, 16.2, 7.4) 139.4 (d)
9 4.60 (1H, m) 75.3 (d)
10 1.35 (3H, d, 6.5) 22.3 (q)
11 1.19 (3H, s) 27.9 (q)
12 1.20 (3H, s) 27.8 (q)
13 1.80 (3H, s) 13.9 (q)
1 131.6 (s) 4.38 (1H, d, 7.8) 101.5 (d)
2 8.01 (1H, dd, 7.8, 1.2) 130.6 (d) 3.25 (1H, overlapped) 75.1 (d)
3 7.48 (1H, t, 7.8) 129.7 (d) 3.25 (1H, overlapped) 78.3 (d)
4 7.60 (1H, m) 134.4 (d) 3.25 (1H, overlapped) 71.8 (d)
5 7.48 (1H, t, 7.8) 129.7 (d) 3.25 (1H, overlapped) 78.3 (d)
6 8.01 (1H, dd, 7.8, 1.2) 130.6 (d) 3.89 (1H, dd, 11.9, 2.1) 63.0 (t)
3.66 (1H, dd, 11.9, 6.1)
7 168.1 (s) 170.0 (s)
8 2.21 (3H, s) 18.5 (q)
1 4.28 (1H, d, 7.8) 103.3 (d)
2 3.25 (1H, overlapped) 75.2 (d)
3 3.35 (1H, t, 9.0) 78.2 (d)
4 3.25 (1H, overlapped) 71.7 (d)
5 3.25 (1H, overlapped) 78.1 (d)
6 3.86 (1H, dd, 12.0, 1.8) 62.8 (t)
3.66 (1H, dd, 12.0, 5.4)
7 170.0 (s)
8 2.21 (3H, s) 18.5 (q)

NMR data of 2 with those of 4-oxo-β-ionol β-D-
glucopyranoside[15] suggested their structures were
closely related, except for an additional acetyl group
[δC 170.0, 18.5; δH 2.21 (3H, s)]. In the HMBC
spectrum (Figure 2), the correlation of H-6a/C-7
indicated the acetyl was connected with C-6 of the
β-D-glucopyranose. Therefore, compound 2 was
elucidated and named as microintegerrin D (Figure 1).

Experimental
General experiment procedures Optical rotations
were measured with a Horiba SEPA-300 polarimeter.
UV spectra were recorded using a Shimadzu UV-2401A
spectrophometer. CD spectra were recorded on a Chi-
rascan Circular Dichroism spectrometer. IR spectra
were obtained on a Tensor 27 spectrometer with KBr
pellets. 1D and 2D NMR spectra were performed on
the Bruker AV-400 (1H: 400 MHz, 13C: 100 MHz),
Bruker AVANCE III-500 (1H: 500 MHz, 13C: 125 MHz)
or AV-600 (1H: 600 MHz, 13C: 150 MHz) spectrometer
with TMS as the internal standard. Mass spectra were
measured on a VG Auto Spec-3000 or API-Qstar-Pulsar
instrument. Column chromatography was performed
using silica gel (100−200 and 200−300 mesh, Qingdao
marine Chemical Inc., China), Sephadex LH-20 (Amer-
sham Biosciences, Sweden), MCI (CHP-20P, Mitsubi-
shi, Japan) or Lichroprep RP-18 (40−63 mm, Merck,
Darmstadt, Germany). Fractions were monitored by
TLC (GF254, Qingdao Marine Chemical Inc., China).
Spots were first visualized under UV light (254 and 365
nm), followed by spraying with 5% H2SO4 in EtOH
and then heating. Analytical or semi-preparative HPLC
was performed on Agilent 1100 with Eclipse XDB-C18
(Agilnent, 9.4 mm × 250 mm). Preparative HPLC was
performed on an Agilent 1100 apparatus with a diode-
array detector and a Sun FireTM Pre C18 OBDTM (Waters,
19 mm × 250 mm, 5 μm) column.
Plant material The stems and leaves of M.
integerrimum were collected in Xishuangbanna, Yunnan
Province, China, in September 2011, and authenticated
by Prof. Hua Peng, Kunming Institute of Botany, Chinese
Academy of Sciences, where a voucher specimen
(KUN No. 0182256) was deposited.
· 478 · 药学学报 Acta Pharmaceutica Sinica 2015, 50 (4): 475−479


Extraction and isolation Air-dried stems and
leaves of M. integerrimum (29.0 kg) were extracted
with methanol at 70 ℃ under reflux for four times. The
extract was concentrated in vacuum to give a residue
(4.5 kg), which was suspended in water, and then parti-
tioned successively with petroleum ether, EtOAc, and
n-BuOH. The EtOAc extract (530.0 g) and n-BuOH
extract (600.0 g) were subjected separately to silica
gel (100−200 mesh) column, and eluted with CHCl3−
MeOH gradient (1∶0, 30∶1, 15∶1, 9∶1, 8∶2, 7∶3,
1∶1, 0∶1, v/v) to give 26 fractions (Fr. A1 to Fr. A26)
and 19 fractions (Fr. B1 to Fr. B19) separately,
monitored by TLC. Fr. A18 (21.0 g) was further
separated to obtain 2 (20.6 mg), 3 (64.8 mg) and 6 (49.4
mg) by MPLC and preparative HPLC with the eluent
of MeOH/H2O and CH3CN/H2O. Fr. A24 (10.0 g)
was subjected to silica gel column (200−300 mesh)
and eluted with a CH3Cl/MeOH gradient to afford 6
fractions (Fr. A24-1 to Fr. A24-6). Fr. A24-3 and Fr.
A24-6 were chromatographed through sephadex LH-20
eluted with MeOH and semi-preparative HPLC with
the eluent of CH3CN/H2O to yield 1 (5.9 mg) and 8
(16.0 mg). Fr. B3 (30.0 g) was further purified by
means of MPLC on RP-18 eluting with MeOH/H2O,
followed by semi-preparative HPLC with the eluent of
CH3CN/H2O to give the pure 7 (696.1 mg). Fr. B7
was further chromatographed through MCI column
with the eluent of MeOH/H2O, semi-preparative and
preparative HPLC with the eluent of CH3CN/H2O to
yield 4 (0.6 mg) and 5 (183.6 mg).
Microintegerrin C (1) Yellow oil; C20H26O9;
[α]17.9 D −22.4 (c 0.16, MeOH); positive ESI-MS m/z : 449
[M+K]+; HR-EI-MS: m/z 410.156 7 [M]+ (Cacld. For
C20H26O9: 410.157 7); IR (KBr): 3 405, 2 924, 1 680,
1 452, 1 430, 1 384, 1 278, 1 205, 1 137, 1 074, 1 027,
839, 802 and 720 cm−1; UV (MeOH) λmax (log ε): 201
(4.2), 226 (4.0), and 273 (3.4) nm; CD (MeOH): 218
(Δε −0.01) nm; 1H and 13C NMR spectral data, see
Table 1.
Microintegerrin D (2) Yellow oil; C21H32O8;
[α]23.3 D −30.8 (c 0.21, MeOH); EI-MS m/z: 412 [M]+;
HR-EI-MS m/z 412.207 0 [M]+ (Calcd. for C21H32O8:
412.209 7); IR (KBr): 3 383, 2 969, 2 934, 1 677, 1 514,
1 429, 1 383, 1 204, 1 187, 1 138, 1 076, 1 037, 840,
802 and 723 cm−1; UV (MeOH) λmax (log ε): 203 (3.9),
261 (3.5) nm; CD (MeOH): 265 (Δε −0.50) nm; 1H and
13C NMR spectral data, see Table 1.
2-Methoxy-4-(2-propenyl)-phenyl-β-D-glucopyra-
noside (3) White solid; C16H22O7; positive ESI-MS
m/z 349 [M+Na]+; 1H NMR (CD3OD, 600 MHz) δ: 7.08
(1H, d, J = 7.8 Hz, H-6), 6.83 (1H, d, J = 1.8 Hz, H-3),
6.72 (1H, dd, J = 7.8, 1.8 Hz, H-5), 5.95 (1H, m, H-8),
5.06 (1H, dd, J = 16.8, 1.8 Hz, H-9b), 5.03 (1H, dd, J =
9.6, 1.8 Hz, H-9a), 4.86 (1H, d, J = 7.8 Hz, H-1), 3.87
(1H, d, J = 10.8 Hz, H-6a), 3.84 (3H, s, 2-OCH3), 3.69
(1H, m, H-6b), 3.31−3.50 (6H, m, H-2-5, 7); 13C NMR
(CD3OD, 150 MHz) δ: 150.8 (C, C-2), 146.4 (C, C-1),
139.2 (CH, C-8), 136.5 (C, C-4), 122.2 (CH, C-5),
118.2 (CH, C-6), 116.0 (CH2, C-9), 114.1 (CH, C-3),
103.1 (CH, C-1), 78.3 (CH, C-3), 77.9 (CH, C-5), 75.0
(CH, C-2), 71.4 (CH, C-4), 62.6 (CH2, C-6), 56.8
(3-OCH3), 40.9 (CH2, C-7).
ErigesideⅡ (4) Needle (CH3CN-H2O); C17H24O8;
positive ESI-MS m/z 379 [M+Na]+, 735 [2M+Na]+;
1H NMR (CDCl3, 500 MHz) δ: 6.41 (2H, s, H-3, 5),
5.89 (1H, m, H-8), 5.08 (2H, m, H-9), 4.53 (1H, d, J =
7.7 Hz, H-1), 3.81 (6H, s, OCH3 × 2), 3.25−3.74 (6H, m,
H-2-6); 13C NMR (CDCl3, 100 MHz) δ: 152.4 (C, C-2,
6), 137.5 (C, C-1), 136.7 (CH, C-8), 130.4 (C, C-4),
116.3 (CH2, C-9), 105.7 (CH, C-3, 5), 103.0 (CH, C-1),
76.2 (CH, C-3), 76.1 (CH, C-5), 74.1 (CH, C-2) , 69.5
(CH, C-4), 61.6 (CH2, C-6), 56.2 (CH3, OCH3×2), 40.4
(CH2, C-7).
Acantrifoside E (5) White powder; C17H24O8;
positive ESI-MS m/z 379 [M+Na]+, 735 [2M+Na]+;
1H NMR (DMSO-d6, 500 MHz) δ: 6.66 (2H, s, H-3, 5),
6.31 (1H, d, J = 16.1 Hz, H-7), 6.23 (1H, m, H-8), 4.87
(1H, d, J = 7.1 Hz, H-1), 3.74 (6H, s, 2-OCH3, 6-OCH3),
3.00−3.56 (6H, m, H-2-6), 1.81 (3H, d, J = 6.2 Hz,
H-9); 13C NMR (DMSO-d6, 100 MHz) δ: 152.7 (C, C-2,
6), 133.5 (C, C-1), 133.2 (C, C-4), 130.7 (CH, C-7),
125.0 (CH, C-8), 104.0 (CH, C-3, 5), 102.6 (CH, C-1),
77.2 (CH, C-3), 76.5 (CH, C-5), 74.2 (CH, C-2), 69.9
(CH, H-4), 60.9 (CH2, C-6), 56.3 (CH3, 3, 5-OCH3),
18.2 (CH3, C-9).
Benzyl β-D-glucopyranoside (6) White solid;
C13H18O6; positive ESI-MS m/z 293 [M+Na]+, 563
[2M+Na]+; 1H NMR (CD3OD, 400 MHz) δ: 7.44 (2H,
d, J = 7.2 Hz, H-2, 6), 7.35 (2H, t, J = 7.2 Hz, H-3, 5),
7.29 (1H, t, J = 7.2 Hz, H-4), 4.95 (1H, d, J = 12.0 Hz,
H-7b), 4.69 (1H, d, J = 12.0 Hz, H-7a), 4.38 (1H, d, J =
7.7 Hz, H-1), 3.92 (1H, d, J = 11.9 Hz, H-6a), 3.72 (1H,
dd, J = 11.9, 5.3 Hz, H-6b), 3.26−3.38 (4H, m, H-2-5);
13C NMR (CD3OD, 100 MHz) δ: 139.1 (C, C-1), 129.3
(CH, C-3, 5), 129.2 (CH, C-2, 6), 128.7 (CH, C-4),
103.3 (CH, C-1), 78.1 (CH, C-3) , 78.0 (CH, C-5),
75.1 (CH, C-2), 71.7 (CH2, C-7), 71.7 (CH, C-4), 62.8
(CH2, C-6).
LIU Yan, et al: Chemical constituents from the stems and leaves of Micromelum integerrimum · 479 ·


5, 7-Dihydroxyl-3, 8, 4-trimethoxylflavone (7)
Yellow needle (CHCl3-MeOH); C18H16O7; positive ESI-
MS m/z 711 [2M+Na]+; 1H NMR (CDCl3, 400 MHz) δ:
12.45 (1H, s, OH), 8.13 (2H, d, J = 8.8 Hz, H-2, 6),
7.06 (2H, d, J = 8.8 Hz, H-3, 5), 6.43 (1H, s, H-6),
4.10 (3H, s, OCH3), 3.92 (3H, s, OCH3), 3.87 (3H, s,
OCH3); 13C NMR (CDCl3, 100 MHz) δ: 178.9 (C, C-4),
161.7 (C, C-4), 157.3 (C, C-7), 155.6 (C, C-5), 155.1
(C, C-3), 148.0 (C, C-9), 138.7 (C, C-2), 130.0 (CH,
C-2, 6), 126.8 (C, C-8), 122.7 (C, C-1), 114.2 (CH,
C-3, 5), 105.5 (C, C-10), 98.5 (CH, C-6), 61.9 (C,
3-OCH3), 60.2 (C, 8-OCH3), 55.4 (C, 4-OCH3),
Kaempferol 3-O-β-D-glucopyranoside (8) Yellow
needle (MeOH); C21H20O11: negative ESI-MS m/z 447
[M−H]+, 895[2M−H]+; 1H NMR (DMSO-d6, 500 MHz)
δ: 12.62 (1H, s, OH), 10.97 (1H, s, OH), 10.26 (1H, s,
OH), 8.04 (2H, d, J = 8.7 Hz, H-2, H-6), 6.88 (2H, d,
J = 8.7 Hz, H-3, H-5), 6.44 (1H, s, H-8), 6.21 (1H, s,
H-6), 5.46 (1H, d, J = 7.5 Hz, H-1), 3.08−3.57 (6H, m,
H-2-6); 13C NMR (DMSO-d6, 150 MHz) δ: 177.5 (C,
C-4), 164.1 (C, C-7), 161.2 (C, C-5), 160.0 (C, C-4),
156.4 (C, C-2), 156.2 (C, C-9), 133.1 (C, C-3), 130.9
(CH, C-2, 6), 120.9 (C, C-1), 115.1 (CH, C-3, 5),
104.0 (C, C-10), 100.8 (CH, C-1), 98.7 (CH, C-6),
93.6 (CH, C-8), 77.5 (CH, C-3), 76.4 (CH, C-5), 74.2
(CH, C-2), 69.9 (CH, C-4), 60.8 (CH2, C-6).
Acknowledgments: The authors thank the analytical group
from the State Key Laboratory of Phytochemistry and Plant
Resources in West China, Kunming Institute of Botany, Chinese
Academy of Sciences, for measuring the IR, UV, CD, NMR, [α]
and mass spectra.
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