全 文 ： 2009 年 7 月 第 7 卷 第 4 期 Chin J Nat Med July 2009 Vol. 7 No. 4 287








Chemical Constituents from the Stems of Uvaria
microcarpa

YANG Xiang-Nan, CHEN Hai-Sheng*, JIN Yong-Sheng, LIU Hong, YANG Xiao-Wei
Department of Natural Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
[ABSTRACT] AIM: To study the chemical constituents from the stems of Uvaria microcarpa Champ. ex Benth.
METHODS: Extraction was performed with 95% EtOH; and isolation and purification were carried out on silica gel,
Sephadex-LH20 column and C18 silica gel column; and the structures of the chemical constituents were identified by
physicochemical properties and spectral analysis. RESULTS: Six compounds were isolated and identified as clemochi-
nenoside B (1), (+)-isolariciresinol 3α-O-β-D-glucopyranoside (2), grandiuvarin C (3), uvamalol G (4), enterocarpam-I
(5), and piperolactam D (6). CONCLUSION: Compounds 1 and 2 were isolated from the family Annonaceae for the
first time. Compounds 1~6 were all isolated from this plant for the first time.
[KEY WORDS] Uvaria microcarpa Champ. ex Benth; Chemical constituents
[CLC Number] R284 [Document code] A [Article ID] 1672-3651(2009)04-0287-03
doi: 10.3724/SP. J. 1009.2009.00287
Uvaria microcarpa Champ. ex Benth. belongs to the
genus Uvaria of the family Annonaceae. It’s the tropical
shrub, widely distributed in the provinces of Guangdong,
Guangxi and Hainan[1]. Its roots and leaves are used as a
traditional Chinese folk drug for treating rheumatism, trau-
matic injury and pain in waist. Alkaloids, polyoxygenated
cyclohexenes, flavonoids and acetogenins have been re-
ported to be isolated from this plant.
Chemical constituents of the stems of Uvaria micro-
carpa Champ. ex Benth. were studied in this paper. Six
compounds were identified as: clemochinenoside B (1),
(+)-isolariciresinol 3α-O-β-D-glucopyranoside (2), gran-
diuvarin C (3), uvamalol G (4), enterocarpam-I (5), and
piperolactam D (6). Among them, compounds 1 and 2 were
isolated from the family Annonaceae for the first time and
compounds 1~6 were all isolated from this plant for the first
time.
1 Apparatus and Reagents
Melting points were determined using an RY-2 digital
micromelting point apparatus (uncorrected). NMR spectra
were run on a Bruker DRX-600 spectrometer with TMS as
internal standard. ESI-MS spectra were measured using a
Q-Tof instrument. Column chromatography was performed
with: silica gel (200-300 mesh and thin-layer H; Qingdao

[Received on] 15-Dec-2008
[Foundation Item] This project was supported by the Shanghai
Research Fund for the Construction of Key Projects(No.B906)
[*Corresponding author] CHEN Hai-Sheng: Prof., Tel&Fax:
86-21-81871250, E-mail: haishengc@hotmail.com
Marine Chemical Co. Ltd., Qingdao, China), and Sephadex
LH-20 (Pharmacia Fine Chemical Co. Ltd.). All solvents
used were of analytical grade except EtOH.
2 Plant Material
Uvaria microcarpa Champ. ex Benth. was collected
from Hainan province in May 2007 and identified by Mr.
Zhu Ping (Hainan Tropical Botanic Garden of the Chinese
Academy of Science).
3 Exrtraction and Isolation
The dried stems of Uvaria microcarpa Champ. ex
Benth. (10 Kg) were chopped and percolated with 95%
EtOH (5 L× 4) at room temperature, and then evaporated in
vaccum. The extract (530 g) was further suspended in water
and portioned successively with petroleum ether, ethyl ace-
tate and n-butanol. The ethyl acetate layer (80 g) was sub-
jected to column chromatography over silica gel (200-300
mesh) eluted with CHCl2-MeOH (100:1 to 10:1) to afford 9
fractions (1~9). Fraction 4 was chromatographed on a silica
gel column with the gradient petroleum ether-EtOAc (10:1,
7:1, 5:1, 1:1, EtOAc), and Sephadex LH-20 (CHCl3-MeOH
1:1, MeOH) successively to yield compounds 5 (33 mg)
and 6 (73 mg). Fraction 7 afforded compounds 1 (23 mg), 2
(18 mg), 3 (74 mg) and 4 (29 mg) using column chroma-
tography over silica gel (200-300 mesh) eluted with
CHCl3-MeOH (20:1 to 1:1).
4 Identification
Compound 1 White powder, ESI-MS m/z: 654 [M]+,
YANG Xiang-Nan, et al. /Chinese Journal of Natural Medicines 2009, 7(4): 287−289
288 Chin J Nat Med July 2009 Vol. 7 No.4 2009 年 7 月 第 7 卷 第 4 期

1
2 3
4
OMe
O
O
O
HO OH
OH
CH2
O
O
OHOHO
OH
O
H2C MeO
MeO
O
Glc
Glc
A
B 1
23
4
5 6
7
56

1
2
345
6
7
8
1
2
3
4
5
6
9
10
2a
MeO
HO
CH2OH
OH
OMe O
OH
OH
OH
OH
O
3a

1
2
3
4
OO
O
CH3O
O
O
1
1
2
3
4
5
6
1
2
7
5
6
7
2
3
4
5
6
7

1 2 3
1
2
34
1
1
2 3
4
56
75
6
7
2 3
4
56
7
H
H
H
O
C
O
O
O
HO

NH
HO
MeO
O
OMe
OMe

NH
OH
MeO
MeO
O

4 5 6

molecular formula was C29H34O17 by 1H NMR and 13C
NMR. 1H NMR (DMSO-d6, 600MHz) δ: Vanilloyl: 7.34
(1H, d, J = 1.8 Hz, H-2), 6.97 (1H, dd, J = 8.4 Hz, H-5),
6.78 (1H, dd, J = 2.4, 8.4 Hz, H-6), Syringoyl: 7.48 (1H, d,
J = 1.8 Hz, H-6), 7.07 (1H, d, J = 2.4 Hz, H-2); Glc: 5.04
(1H, d, J = 7.8 Hz, H-1), 4.39 (1H, dd, J = 12.0, 4.8 Hz,
H-6a), 3.90 (1H, d, J = 12.0 Hz, H-6b), 3.47 (1H, dd, J =
8.4, 7.8 Hz, H-2), 3.34-3.38 (2H, m, H-3, H-5), 3.18 (1H, m,
H-4), Glc, : 5.33 (1H, d, J = 7.2 Hz, H-1), 4.45 (1H, dd, J =
12.0, 4.8 Hz, H-6a), 3.96 (1H, dd, J = 8.4, 7.8 Hz, H-2),
3.93 (1H, d, J = 12.0 Hz, H-6b), 3.28-3.31 (2H, m, H-3,
H-5), 3.11 (1H, m, H-4); 13C NMR (DMSO-d6, 150MHz) δ:
Vanilloyl: 165.0 (C-7), 149.9 (C-4), 148.3 (C-3), 122.5
(C-6), 122.3 (C-1), 111.9 (C-2), 114.4 (C-5), 55.5 (3-OCH3),
Syringoyl: 164.8 (C-7), 153.1 (C-5), 152.0 (C-3), 137.7
(C-4), 124.5 (C-1), 107.0 (C-2), 106.8 (C-6), 56.5 (3-OCH3),
55.9 (5-OCH3); Glc: 99.0 (C-1), 77.2 (C-3), 73.9 (C-2),
73.0 (C-5), 71.1 (C-4), 64.3 (C-6a), Glc, : 101.0 (C-1), 76.7
(C-3), 73.9 (C-2, C-5), 70.6 (C-4), 64.9 (C-6a). Compound
1 was charac te r ized as c lemochinenos ide B by
comparison of its physical and spectral data with the litera-
ture[2].
Compound 2 White powder, ESI-MS m/z: 545
[M+Na]+, 522 [M]+, molecular formula was C26H34O11 by
1H NMR and 13C NMR. 1H NMR (CD3OD, 600MHz) δ:
6.78 (1H, d, J = 1.8 Hz, H-2), 6.73 (1H, d, J = 7.8 Hz, H-5),
6.64 (1H, s, H-8), 6.62 (1H, dd, J = 6.6, 1.8 Hz, H-6), 6.17
(1H, s, H-5), 4.10 (1H, d, J = 7.8 Hz, H-1), 3.79 (3H, s,
7-OCH3), 3.78 (3H, s, 3-OCH3); 13C NMR (CD3OD,
150MHz) δ: 148.9 (C-3), 147.2 (C-7), 145.8 (C-6), 145.2
(C-4), 138.7 (C-1), 134.4 (C-10), 129.2 (C-9), 123.1 (C-6),
117.4 (C-5), 116.1 (C-5), 114.4 (C-2), 112.4 (C-8), 105.2
(C-1), 78.1 (C-5), 77.9 (C-3), 75.2 (C-2), 71.7 (C-4),
69.6 (C-3a), 65.2 (C-2a), 62.8 (C-6), 56.5 (7-OCH3), 56.4
(3-OCH3), 45.9 (C-3), 39.6 (C-2), 33.9 (C-1). Compound 2
was characterized as (+)-isolariciresinol 3α-O-β-D- glu-
copyranoside by comparison of its physical and spectral
data with the literature[3].g
Compound 3 Viscous liquid, ESI-MS m/z: 394 [M]+,
molecular formula was C23H22O6 by 1H NMR and 13C NMR.
1H NMR (DMSO-d6, 600MHz) δ: 7.96 (2H, d, J = 7.2 Hz,
H-2′′, H-6′′), 7.94 (2H, d, J = 7.2 Hz, H-2′, H-6′), 7.49-7.53
(4H, m, H-3′, H-5′, H-3′′, H-5′′), 6.88 (1H, d, J = 12.0 Hz,
H-3), 6.63 (1H, t, J = 11.4 Hz, H-4), 5.86 (1H, m, H-5),
5.02 (2H, d, J = 6.6 Hz, H-6), 4.91 (2H, s, H-1), 4.83 (2H, s,
H-7); 13C NMR (DMSO-d6, 150MHz) δ: 170.2 (C-1′′′),
165.5 (C-7′′), 165.4 (C-7′), 133.4 (C-4′, C-4′′), 132.7 (C-2),
129.5 (C-1′, C-1′′), 129.2 (C-2′, C-6′), 129.1 (C-2′′, C-6′′),
128.7 (C-3′, C-5′, C-3′′, C-5′′), 128.5 (C-5), 127.5 (C-3),
126.5 (C-4), 66.6 (C-1), 60.4 (C-6), 59.1 (C-7), 20.5 (C-2′′′).
Compound 3 was characterized as grandiuvarin C by com-
parison of its physical and spectral data with the litera-
ture[4].
Compound 4 Yellow oil, ESI-MS m/z: 375 [M+Na]+,
molecular formula was C21H20O5 by 1H NMR and 13C NMR.
1H NMR (DMSO-d6, 600MHz) δ: 7.99 (4H, m, H-2′, H-6′,
H-2′′, H-6′′), 7.55 (2H, m, H-4′, H-4′′), 7.45 (4H, m, H-3′,
H-5′, H-3′′, H-5′′), 6.71 (1H, d, J = 11.4 Hz, H-3), 6.64 (1H,
t, J = 11.4 Hz, H-4), 5.77 (1H, m, H-5), 5.02 (2H, d, J = 7.2
Hz, H-6), 4.92 (2H, s, H-1), 4.23 (2H, s, H-7); 13C NMR
(DMSO-d6, 150MHz) δ: 165.6 (C-7′′), 165.5 (C-7′), 138.9
(C-2), 133.4 (C-4′′), 132.3 (C-4′), 129.7 (C-1′′), 129.6
(C-1′), 129.2 (C-2′, C-6′, C-2′′, C-6′′), 128.7 (C-3′′, C-5′′),
128.4 (C-3′, C-5′), 127.2 (C-5), 126.3 (C-3), 123.7 (C-4),
66.2 (C-1), 60.3 (C-6), 57.5 (C-7). Compound 4 was char-
acterized as uvamalol G by comparison of its physical and
spectral data with the literature[5].
Compound 5 Yellow powder, mp: 214-215 °C.
ESI-MS m/z: 325 [M]+, 1H NMR (CD3OD, 600MHz) δ:
10.77 (1H, s, NH), 8.67 (1H, d, J = 8.4 Hz, H-5), 7.50 (1H,
s, H-2), 7.26 (1H, t, J = 8.4, 7.8 Hz, H-6), 6.98 (1H, d, J =
7.8 Hz, H-7), 4.31 (3H, s, 9-OCH3), 4.04 (3H, s, 4-OCH3),
4.00 (3H, s, 8-OCH3). Compound 5 was characterized as
enterocarpam-I by comparison of its physical and spectral
data with the literature[6].
Compound 6 yellow needle, mp: 226-227 °C.
ESI-MS m/z: 295 [M]+, 1H NMR (DMSO-d6, 600MHz) δ:
10.91 (1H, s, NH), 9.11 (1H, m, H-5), 7.89 (1H, m, H-8),
7.52 (2H, m, H-6, H-7), 7.17 (1H, s, H-9), 4.30 (3H, s,
YANG Xiang-Nan, et al. /Chinese Journal of Natural Medicines 2009, 7(4): 287−289
2009 年 7 月 第 7 卷 第 4 期 Chin J Nat Med July 2009 Vol. 7 No. 4 289

3-OCH3), 3.99 (3H, s, 4-OCH3). Compound 6 was charac-
terized as piperolactam D by comparison of its physical and
spectral data with the literature [7].
References
[1] Editing Board of Flora of People’s Republic of China, Chi-
nese Academy of Sciences, Flora of Republicae Popularis
Sinicae (Science Press) [M]. 1979:14.
[2] Shi SP, Dong CX, Jiang D, et al. Macrocyclic glucosides
from Clematis mandshurica and Clematis hexapetala[J].
Biochem Sys Ecol, 2007, 35: 57-70.
[3] Achenbach H, Lowel M, Waibel R, et al. New lignan gluco-
sides from Stemmadenia minima[J]. Planta Med, 1992, 58(3):
270-272.
[4] Ankisetty S, ElSohly HN, Li XC, et al. Aromatic constitu-
ents of Uvaria grandiflora[J]. J Nat Prod, 2006, 69(4):
692-694.
[5] Wang S, Chen RY, Yu SS, et al. Uvamalols D-G: Novel
polyoxygenated seco-cyclohexenes from the roots of Uvaria
macrophylla[J]. J Asian Nat Prod Res, 2003, 5(1): 17-23.
[6] Mahmood K, Chan KC, Park MH, et al. Aristolactams of
Orophea enterocarpa[J]. Phytochemistry, 1986, 25(4):
965-967.
[7] Desai SJ, Chaturvedi R, Mulchandani NB. Piperolactam D, a
new aristolactam from India piper species[J]. J Nat Prod,
1990, 53(2): 496-497.

紫玉盘茎的化学成分
杨向楠, 陈海生*, 金永生, 刘 虹, 杨小唯
第二军医大学药学院天然药物化学教研室，上海 200433
【摘 要】 目的：研究紫玉盘茎枝的化学成分。方法：采用 95%乙醇渗漉提取, 硅胶柱, Sephadex LH-20 柱和反相硅
胶柱层析分离纯化,根据理化性质和波谱学方法进行结构鉴定。结果：从该植物中分离鉴定了 6 个化合物, 分别为：
clemochinenoside B (1), (+)-异落叶松树脂醇 3α-O-β-D-葡萄糖苷 (2), grandiuvarin C (3), uvamalol G (4), 因特洛卡内酰胺-I
(5), 胡椒内酰胺 D (6)。结论：化合物 1 和 2 为首次从番荔枝科植物中分离得到, 化合物 1~6 均为首次从该植物中分离得到。
【关键词】 紫玉盘; 化学成分

【基金项目】 上海市重点学科建设项目(No. B906)

·信 息·


《中国天然药物》在中国学术期刊评价报告（RCCSE）中
排名药学核心期刊第 1 位

《中国天然药物》编辑部日前接获由中国科学评价研究中心研制的 “中国学术期刊评价报告” (RCCSE)核心期
刊证书, 在 67 种药学期刊中, 有 11 种核心期刊(A 等), 3 种权威期刊(A+),《中国天然药物》排名药学核心期刊第 1
位。结果表明本刊具有较高的学术质量与影响力。
参与评价的期刊是以专业学者为作者和读者对象, 以刊登研究报告、学术论文、综合评述为主要内容的 6170
种中文学术期刊。从期刊发文和被引用两个方面定量反映期刊的学术质量和影响力, 选取的指标主要有：基金论文
比、总被引频次、影响因子、web 即年下载率、二次文献转载或收录(社会科学期刊被二次文献转载, 自然科学期刊
被国外重要数据库收录)。这些指标都从定量角度反映了期刊的学术质量和影响力。而在定性方面, 以专家评审意见
作为期刊排名微调的依据。
在某一学科领域, 计算出各刊的最终得分, 由高到低分五个等级, 对各刊依次排列, A+取前 5%的期刊为“权威
期刊”, A 取前 5%-20%为“核心期刊”, B+取前 20%-50%, B 取前 50%-80%, C 取 80%-100%。
中国科学评价研究中心是专业进行学术评价的研究机构, “中国学术期刊评价报告” (RCCSE)旨在建立完善及
丰富综合性学术期刊评价体系, 以期为广大读者重点阅读提供参考指南, 为作者选刊投稿提供快速通道, 为各种期
刊竞争发展提供定位信息, 为单位订购期刊提供选择标准, 为政府部门期刊管理提供决策依据。
(本刊编辑部)