全 文 ： 2009 年 1 月 第 7 卷 第 1 期 Chin J Nat Med Jan. 2009 Vol. 7 No. 1 19

Chinese Journal of Natural Medicines 7 (2009) 0019−0020
doi: 10.3724/SP.J.1009.2009.00019
Chinese
Journal of
Natural
Medicines







•Original Papers•
A New Phenylpropanoid from Alpinia galanga
ZHU Xiao-Lu, YANG Ming-Hua, LUO Jian-Guang, HUANG Xue-Feng, KONG Ling-Yi*
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
Available online 20 Jan 2009
【ABSTRACT】 AIM: To study the chemical constituents from the rhizome of Alpinia galanga METHODS: Silica gel and Sephadex
LH-20 column chromatographies were used to isolate the chemical constituents, and spectroscopic techniques were employed to eluci-
date their structures. RESULTS: A new phenylpropanoid was isolated from the rhizome of Alpinia galanga. Its structure was estab-
lished as 4, 4[(2E, 2E)-bis(prop-2-ene)-1,1-oxy]-diphenyl-7,7-diacetata. CONCLUSION: The compound is a new phenylpropanoid.
【KEY WORDS】 Alpinia galanga; Zingiberaceae; Phenylpropanoid
【CLC Number】 R284.1 【Document code】 A 【Article ID】1672-3651(2009)01-0019-02

1 Introduction
The Zingiberaceae plant Alpinia galanga (L.) Willd. is
widely cultivated in Southeast Asia. The rhizomes of this
plant, also called greater galangal, are extensively used as a
substitute of spice or ginger for flavoring food, and a stom-
achic[1] in traditional Chinese medicine as well. Recent re-
searches have indicated that the galangal had exhibited some
interesting activities such as antitumor[2], antibacterial[3] and
anti-ulcer[4]. However there is little information available in
the literature about the components of greater galangal. Dur-
ing our research for the chemical constituents, a new phenyl-
propanoid was isolated from the galangal. In this paper, we
describe the isolation and identification of this new com-
pound.
2 Results and Discussion
Compound 1 was obtained as a colorless powder, Its
UV(MeOH, λmax, nm, logε) showed the absorptions at
203(4.2), 255(3.9). The HR-ESI-MS spectrum showed a
quasi-molecular ion peak at m/z 389.136 6 [M+Na]+, indicat-
ing that its molecular formula was C22H22O5 (calcd for
C22H22O5Na, m/z 389.1359). The IR spectrum exhibited ab-
sorption bands of carbonyl group at 1 759 cm−1 and aromatic
group at 1 601 cm−1, 1 507 cm−1. In 1H NMR (500 MHz,

【Received on】 2008-11-14
【Foundation Item】 This project was supported by the Scaling
Project for Innovation Scholars, Natural Science Foundation of Ji-
angsu Province (BK2008039)
【 *Corresponding author 】 Kong Ling-Yi: Professor, Tel:
+86-25-85391289. E-mail: lykong@jlonline.com
CDCl3) spectrum, one series ortho coupled doublets at δ 7.04
(4H, d, J = 8.7 Hz) and δ 7.40 (4H, d, J = 8.4 Hz) showed the
presence of two para-subtituted benzene rings. The signals at
δ 6.62 (2H, d, J = 15.9 Hz) and δ 6.27 (2H, td, J = 6.0, 15.9
Hz) could be assigned to two pairs of olefinic protons, of
which the downfield chemical shift confirmed that they were
linked to the aromatic ring. The protons at δ 4.20 (4H, dd, J =
1.5, 6.0 Hz) suggested that there were two methylene groups
attached to the olefinic groups, and its downfield chemical
shift revealed that the methylene groups might have oxygen
atoms on the other side. Meanwhile, the methyl group at δ
2.30 (6H, s) along with the carbon signals at δ 169.3 and δ
21.1 indicated the presence of acetyl groups. In a comparison
of the data with 4-[(E)-3-hy- droxyprop-1-enyl]-phenyl ace-
tate[5], compound 1 should be a completely symmetric struc-
ture with 4-[(E)-3-hydroxyprop-1-enyl]- phenyl acetate as its
symmetric unit. The 13C NMR (125 MHz, CDCl3) spectral
data contained a carbon signal of methylene at δ 70.7. Com-
pared with δ 61.9 in the symmetric unit, this downfield
chemical shift suggested that the two units were connected
through primary hydroxyl. In summary, compound 1 was
established as 4, 4[(2E, 2E)-bis(prop-2-ene)-1,1-oxy]- di-
phenyl-7,7-diacetata. For the 1H NMR and 13C NMR data,
see Table 1.
3 Experimental
3.1 General
Melting points were determined on BUCHI B-545 melt-
ing point apparatus. IR spectra were measured on a Bruker
Tensor-27 spectrophotometer and UV on a Shimadzu
UV-2501 PC spectrophotometer. ESI-MS and HR-ESI-MS
experiments were performed on an Agilent 1100 Series
ZHU Xiao-Lu, et al. /Chinese Journal of Natural Medicines 2009, 7(1): 19−20
20 Chin J Nat Med Jan. 2009 Vol. 7 No. 1 2009 年 1 月 第 7 卷 第 1 期

O
C
H3C
O
O
O
C
CH3
O
1 14 47 7

Fig. 1 The structure of compound 1

Table 1 1H NMR and 13C NMR data of compound 1 (δ, J in
Hz) in CDCl3
Position δC δH
1, 1′ 70.7 4.20 (4H, dd, J=1.5, 6.0)
2, 2′ 134.6 6.27 (2H, td, J=6.0, 15.9)
3, 3′ 150.2 6.62 (2H, d, J=15.9)
4, 4′ 126.3
5, 5′ 121.7 7.04 (2H, d, J=8.7)
6, 6′ 127.5 7.40 (2H, d, J=8.4)
7, 7′ 131.5
8, 8′ 127.5 7.40 (2H, d, J=8.4)
9, 9′ 121.7 7.04 (2H, d, J=8.7)
7, 7-COCH3 169.3(-C=O)
21.1(-CH3) 2.30 (6H, s)

LC/MSD Trap mass spectrometer and Agilent TOF MSD.
1946D mass spectrometer. NMR spectra were recorded on
Bruker DRX-500 instrument. Absorbents for column chro-
matography were silica gel (200-300 mesh, Qingdao Marine
Chemistry Ltd.) and Sephadex LH-20 (20-100 μm, Phar-
macia). Silica gel GF254 for TLC were made in Qingdao Ma-
rine Chemistry Ltd.
3.2 Plant material
Dried rhizomes of greater galangal (Alpinia galanga (L.)
Willd.) were purchased at a local market in the Anhui Prov-
ince of China, and botanically authenticated by Prof. QIN
Min-Jian. A voucher specimen (No. 971006) is deposited in
the Department of Phytochemistry, China Pharmaceutical
University.
3.3 Extraction and Isolation
The rhizomes (20 kg) were cut into pieces, refluxed with
95% EtOH, then concentrated in vacuo. The solution contin-
ued to be concentrated to afford a residue, which was parti-
tioned between H2O and petroleum ether, CHCl3, succes-
sively. The CHCl3 fraction (237 g) was subjected to silica gel
column chromatography, being eluted with CHCl3-MeOH
(99: 1 → 95: 5). The fraction of 99:1 eluate was chroma-
tographed on silica gel column and then purified by
Sephadex LH-20 column chromatography to afford 1 (3 mg).
4,4-[(2E,2E)-bis(prop-2-ene)-1,1-oxy]-diphenyl-7,7-
diacetata (1) colorless powder. mp 92.5°C; UV(MeOH, λmax,
nm, logε): 203(4.2), 255(3.9); IR (KBr, cm−1): 1 759, 1 601, 1
507; HR-ESI-MS m/z: 389.136 6 [M+Na]+ (calcd for
C22H22O5Na, m/z 389.135 9); 1H and 13C NMR see table 1.
References
[1] Dictionary of Chinese Crude Drugs[M], Shanghai Scientific
Technologic Pulisher, 1977: 125.
[2] Lee CC, Houghton P. Cytotoxicity of plants from Malaysia
and Thailand used traditionally to treat cancer[J]. J Ethno-
pharm, 2005, 100(3): 237-243.
[3] Khattak S, Saeed-ur-Rehman, Shah HU, et al. Biological
effects of indigenous medicinal plants Curcuma longa and
Alpinia galanga[J]. Fitoterapia, 2005, 76(2): 254-257.
[4] Matsuda H, Pongpiriyadacha Y, Morikawa T, et al. Gastro-
protective effects of phenylpropanoids from the rhizomes of
Alpinia galanga in rats: structural requirements and mode of
action[J]. Eur J Pharmacol, 2003, 471(1): 59-67.
[5] Abhimanyu S, Arumugam S. Enantioselective synthesis of
(-)-cytoxazone and (+)-epi-cytoxazone novel cytokine
modulators via Sharpless asymmetric epoxidation and
L-proline catalyzed Mannich reaction[J]. Tetrahedron, 2006,
62(24): 5756-5762.

大高良姜中的一个新苯丙素类化合物
朱小璐, 杨鸣华, 罗建光, 黄雪峰, 孔令义*
中国药科大学天然药化教研室, 南京 210009
【摘 要】 目的：研究大高良姜(Alpinia galanga)的化学成分。方法：运用硅胶柱色谱, Sephadex LH-20 柱色谱等方法分离
和纯化化合物, 根据理化性质和光谱数据鉴定化合物的结构。结果：从大高良姜中分离并鉴定得到 1 个化合物, 鉴定为对二乙酰
基苯丙烯醚。结论：该化合物为新化合物。
【关键词】 大高良姜; 姜科; 苯丙素

【基金项目】 江苏省自然科学基金创新学者攀登项目(BK2008039)