全 文 ：
Chinese Journal of Natural Medicines 2010, 8(5): 0321−0325
doi: 10.3724/SP.J.1009.2010.00321
Chinese
Journal of
Natural
Medicines






·Original Papers·
Sesquiterpenes from Chinese Red Alga
Laurencia okamurai
MAO Shui-Chun1, 2, GUO Yue-Wei2*
1Department of Pharmacy, School of Pharmaceutical Sciences, Nanchang University, Nanchang 330006;
2Institute of Materia Medica, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, China
Available online Sep. 2010
[ABSTRACT] AIM: To study chemical constituents of red alga Laurencia okamurai Yamada to search new bioactive substances.
METHODS: The Et2O extract of Laurencia okamurai was subjected to repeated column chromatography on Sephadex LH-20 and
silica gel to afford nine pure compounds (1-9), whose structures were elucidated on the basis of spectroscopic analysis and by com-
parison with the data reported in the literature. RESULTS: Nine sesquiterpenes were isolated and identified as laurokamurene C (1),
debromoaplysinol (2), aplysinol acetate (3), debromoisolaurinterol (4), isolaurinterol (5), filiformin (6), α-isobromocuparene (7), cu-
parene-type ether (8) and deoxyprepacifenol (9), respectively. CONCLUSIONS: Compound 1, a new sesquiterpene, represents the
third example with a novel rearranged laurane-type skeleton, exceptionally prone to decompose at room temperature. Compound 3 was
shown for the first time to be true natural product. In antifungal bioassay, compounds 2-9 were found to be inactive against the fungus
Cladosporium cucumerinum.
[KEY WORDS] Red algae; Laurencia okamurai; Sesquiterpenes; Structural identification
[CLC Number] R93 [Document code] A [Article ID] 1672-3651(2010)05-0321-05

1 Introduction
Red algae of the genus Laurencia (Rhodomelaceae)
are extremely mely widespread, found in all oceans and seas
as well as almost all latitudes, mostly in tropical and sub-
tropical regions [1]. Laurencia is one of the most intensively
and chemically investigated of all marine genera [2]. Over the
four decades since Irie’s pioneering investigations on Laur-
encia [3], an astonishing variety of structurally unusual sec-
ondary metabolites have been isolated from the red algal
genus Laurencia. The vast majority of Laurencia metabolites
are predominantly diterpenes, triterpenes, C15-acetogenins
and sesquiter-penes, which, mostly halogenated with bromine,
chlorine and a few even iodine and they comprise a class of
metabolites characteristic of Laurencia. Moreover, some
halogenated metabolites have been reported to possess di-

In the course of our systematic investigations toward the
isolation of bioactive metabolites from Chinese marine or-
ganisms, we carried out a chemical study on the seaweed
Laurencia okamurai Yamada, collected off the coast of Nanji
Island, Zhejiang Province, China, which resulted in the dis-
covery of four cuparane-derived, a laurane and two rear-
ranged laurane (laurokamurenes A and B) sesquiterpenes
[Received on] 24-May-2010
[Research Funding] This project was supported by the National
Science & Technology Major Project (No. 2009ZX09301-001),
Natural Science Foundation of China (Nos. 40976048，30730108 and
20721003), STCSM International Cooperation Project between
SIMM/China and ICB/Italy (No. 10540702900) and partly founded by
the NSFC-TRF International Cooperation Project (No. 20911140471).
[*Corresponding author] GUO Yue-Wei: Prof., Tel: 86-21-
50805813, E-mail: ywguo@mail.shcnc.ac.cn
verse biological activities such as antibacterial [4], ichtyotoxic [5],
antioxidant [6], antimalarial [7], insecticidal [8] and cyto- toxic
[9] activities.
[10-11].
Our further study has led to the isolation of nine additional
sesquiterpenes (1-9, Fig. 1). They were identified as a novel
rearranged laurane sesquiterpenoid, laurokamurene C (1),
along with eight known sesquiterpenes, including five lau-
rane- (2-6), two cuparane- (7 and 8), and one chamigrane- (9)
type sesquiterpenes, among them, compounds 2-9 were found
to be inactive against the fungus Cladosporium cucumeri-
num.
2 Results and Discussion
The known sesquiterpenes were readily identified as de-
bromoaplysinol (2) [12], aplysinol acetate (3) [13], debromoi-
solaurinterol (4) [12], isolaurinterol (5) [14], filiformin (6) [15],
α-isobromocuparene (7) [16], cuparene-type ether (8) [17] and
deoxyprepacifenol (9) [18], by comparing their spectroscopic
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322 Chin J Nat Med Sep. 2010 Vol. 8 No. 5


Fig. 1 Structures of compounds 1-9

data with those reported in the literature. Among them, com-
pound 3 was reported as an acetated synthetic product de-
rived from aplysinol [13]. However, this is the first report to
isolate it from a natural source.
Compound 1 was obtained as an unstable colorless oil,
extremely prone to at room temperature decompose to lauro-
kamurene B, a co-occurring rearranged laurane sesquiterpene
(Scheme 1) [10], and it was thus only characterized by 1D
NMR spectroscopy and by HR-EI-MS. The observed
quasi-molecular ion peak [M - H2O]+ at m/z 200.155 4 (calcd.
200.156 5) in the HR-EI-MS spectrum of 1 showed the mo-
lecular formula C15H22O and demonstrated loss of H2O when
compared to laurokamurene B. The NMR data of 1 (Table 1)
exhibited two 2H doublets at δ 7.37 (2H, d, J = 7.8 Hz, H-7,
11) and 7.15 (2H, d, J = 7.8 Hz, H-8, 10) and six aromatic

Scheme 1 Decomposition of laurokamurene C (1) in CDCl3

Table 1 1H and 13C NMR data for compounds 1a and 10b
1 10
Position
δH (J in Hz) δc δH (J in Hz) δc
1 — 090.5 — 086.0
2 — 047.9 — 046.6
3 2.07 (m) 041.3 2.05-1.70 (m) 041.2
4 1.41 (m) 2.33 (m) 028.5
1.50-1.60 (m)
2.05-1.70 (m) 029.9
5 1.67 (ddd, 10.5, 7.2, 3.0) 2.68 (ddd, 10.5, 8.7, 4.5) 036.5
1.50-1.60 (m)
2.44-2.26 (m) 038.0
6 — 136.2 — 136.0
7 7.37 (d, 7.8) 128.2 7.28 (d, 8.1) 128.1
8 7.15 (d, 7.8) 126.8 7.08 (d, 8.1) 126.6
9 — 143.2 — 143.0
10 7.15 (d, 7.8) 126.8 7.08 (d, 8.1) 126.6
11 7.37 (d, 7.8) 128.2 7.28 (d, 8.1) 128.1
12 2.34 (s) 021.0 2.33 (s) 021.0
13 0.86 (s)c 019.3d 0.92 (s)e 017.5f
14 0.43 (s)c 018.9d 0.50 (s)e 016.6f
15 0.92 (d, 6.6) 014.8d 0.93 (d, 5.4) 015.8f
aBruker DRX 400 spectrometer in CDCl3, chemical shifts referred to CHCl3 (δH 7.26) and to CDCl3 (δc 77.0). The assignments were based on
DEPT, 1H and 13C NMR spectra.
bChemical shifts referred to CDCl3 + CCl4 in the literature.
cdef Signals may be interchanged.

2010 年 9 月 第 8 卷 第 5 期

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carbons at δ 143.2 (C), 136.2 (C), 128.2 (2C, CH) and 126.8
(2C, CH), clearly indicating the presence of a 1, 4-disubsti-
tuted benzene ring, the same as that of laurokamurene B.
Further, the 1H NMR spectrum revealed the presence of three
aliphatic methyls (δ 0.43, s, H3-14; δ 0.86, s, H3-13; δ 0.92,
d, J = 6.6 Hz, H3-15), two methylenes (δ 1.67, ddd, J = 10.5,
7.2, 3.0 Hz, Hα-5; δ 2.68, ddd, J = 10.5, 8.7, 4.5 Hz, Hβ-5;
δ 1.41, m, Hα-4; and δ 2.33, m, Hβ-4), and one methine
(δ 2.07, m, H-3), suggesting the aliphatic portions of mole-
cule to be 1-hydroxyl-2, 2, 3-trimethyl-cyclopentanyl, the
same as that of 10, a synthetic intermediate (compound 10)
derived in the course of total synthesis of laurokamurene B[19].
The 13C NMR and DEPT spectra of 1 further confirmed the
presence of the 1-hydroxyl-2, 2, 3-trimethyl-cyclopen- tanyl
as judged from carbon signals, including two quaternary
carbons at δ 90.5 (C-1) and 47.9 (C-2), one secondary carbon
at δ 41.3 (C-3), two primary carbons at δ 28.5 (C-4) and 36.5
(C-5), and three methyl carbons at δ 19.3 (C-13), 18.9 (C-14)
and 14.8 (C-15). The NMR spectra were completed by signal
attributable to an aromatic methyl group (δH 2.34, s; δC 21.0).
The NMR data of 1 mentioned above were strongly
reminiscent to those of 10. A comparison of the NMR data of
1 and 10 revealed the only difference resided in the configu-
ration of the hydroxyl group at C-1, while the rest of the
structure of 1 is the same as in 10. In the 13C NMR spectra of
1 and 10, the distinct difference, 4.5, was observed for the
signals of C-1 appeared at 90.5 in 1 and 86.0 in 10, while the
much lesser downfield shifts were also observed for the sig-
nals of C-2, C-3, C-4 and C-5 on the cyclopentanyl moiety in
1 (47.9, 41.3, 28.5 and 36.5, respectively) relative to those of
10 (46.6, 41.2, 29.9 and 38.0, respectively). Thus, the abso-
lute configuration of C-1 in 1 was assumed to be opposite to
that of 10 on the basis of the above data. Therefore, the
structure of 1 was elucidated as a new rearranged laurane
sesquiterpene, namely laurokamurene C. Unfortunately, we
could not further confirm the proposed structure as 1 decom-
posed gradually to laurokamurene B via dehydration in
CDCl3 (Scheme 1) during the overnight 13C NMR and
DEPT experiments in CDCl3 before optical rotation, IR, UV
and 2D NMR could be recorded.
Sesquiterpenes with a rearranged laurane-type carbon
skeleton are rare in the nature and were firstly found by the
author from a natural source [10]. To the best of our knowl-
edge, compound 1 represents one of the only three examples
with such a carbon skeleton from a natural source. In addition,
literature checking revealed that the known sesquiterpenes
2-9 exhibited antimicrobial, antifungal, cytotoxic and insecti-
cidal bioactivities [20-22], while they were found in our assay
to be inactive against the fungus Cladosporium cucumerinum.
Further studies should be conducted to screen other bioactivi-
ties, such as cytotoxic and insecticidal properties, of these
compounds.
3 Experimental
3.1 General
NMR spectra were measured on Bruker DRX-400 spec-
trometer with the residual CHCl3 (δH 7.26; δC 77.0) as an
internal standard. EI-MS and HR-EI-MS spectra were re-
corded on a Finnigan-MAT-95 mass spectrometer. All sol-
vents were of analytical grade (Shanghai Chemical Plant,
Shanghai, China). Commercial Si gel (Qingdao Marine
Chemical Group Co., 200-300 and 400-600 mesh) was used
for column chromatography, and precoated Si gel plates
(Yantai Zifu Chemical Group Co., G60 F-254) were used for
analytical TLC. Sephadex LH-20 (Amersham Biosciences)
was also used for column chromatography.
3.2 Plant Material
The alga L. okamurai was collected by hand along the
coast of Nanji Island in East China Sea, Zhejiang Province,
China, at a depth of 0.5-1 m, in June 1999, and the algal ma-
terial was stored at -20 °C until processed. A voucher speci-
men (No. MA99-01) was deposited at the Shanghai Institute
of Materia Medica, CAS for inspection.
3.3 Extraction and Isolation
The fresh algal material (dry weight, 500 g) of L. oka-
murai was exhaustively extracted with acetone (3 × 1 L). The
acetone extract was concentrated in vacuo to give a residue
(36.1 g), which was partitioned between Et2O and H2O. The
Et2O soluble portion (25.8 g) was chromatographed by Si gel
CC using light petroleum ether with increasing amounts of
Et2O as eluent to give 12 fractions (I-XII) on the basis of
TLC analysis. Fraction IV eluted with petroleum ether/Et2O
(8∶2) was further purified by Si gel CC using a stepped
gradient (petroleum ether/Et2O, 9∶1-8∶2) to yield 3 (8.6
mg), 6 (6.9 mg), 7 (5.7 mg), 8 (15.7 mg) and 9 (3.5 g). Frac-
tion VI eluted with petroleum ether/Et2O (7.5∶2.5) was
further separated on Si gel CC (petroleum ether/Et2O 8∶2 as
eluent) and followed by Sephadex LH-20 CC to afford com-
pound 1 (3.6 mg), 2 (16.6 mg), 4 (7.0 mg) and 5 (10.6 mg).
Laurokamurene C (1): unstable colorless oil; C15H22O;
1H and 13C NMR data, see Table 1; HR-EI-MS m/z 200.155 4
(calcd. for C15H20, [M - H2O]+ 200.156 5).
Debromoaplysinol (2): colorless oil; C15H20O2;
1H NMR (400 MHz, CDCl3) δ: 6.92 (1H, d, J = 6.8 Hz,
H-11), 6.69 (1H, dd, J = 6.8, 1.2 Hz, H-10), 6.59 (1H, d, J =
1.2 Hz, H-8), 3.86 (1H, d, J = 12.0 Hz, Hα-14), 3.73 (1H, d, J
= 12.0 Hz, Hβ-14), 2.30 (3H, s, H3-12), 1.86 (1H, m, H-3),
1.86 (1H, m, Hα-5), 1.64 (1H, m, Hβ-5), 1.64 (1H, m, Hα-4),
1.19 (1H, m, Hβ-4), 1.48 (3H, s, H3-13), 1.11 (3H, d, J = 6.8
Hz, H3-15); EI-MS m/z 232 [M]+.
Aplysinol acetate (3): white needle crystal; C17H21O3Br;
1H NMR (400 MHz, CDCl3) δ: 7.14 (1H, s, H-11), 6.65 (1H,
s, H-8), 4.36 (1H, d, J = 12.0 Hz, Hα-14), 4.14 (1H, d, J =
12.0 Hz, Hβ-14), 2.30 (3H, s, H3-12), 2.02 (3H, s, -OAc),
1.97 (1H, m, H-3), 1.89 (1H, m, Hα-5), 1.70 (1H, m, Hβ-5),
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324 Chin J Nat Med Sep. 2010 Vol. 8 No. 5
1.68 (1H, m, Hα-4), 1.15 (1H, m, Hβ-4), 1.48 (3H, s, H3-13),
1.10 (3H, d, J = 6.0 Hz, H3-15); EI-MS m/z 352 [M]+.
Debromoisolaurinterol (4): white needle crystal;
C15H20O; 1H NMR (400 MHz, CDCl3) δ: 7.12 (1H, d, J = 7.9
Hz, H-11), 6.76 (1H, dd, J = 7.9, 1.2 Hz, H-10), 6.69 (1H, dd,
J = 1.2, 0.9 Hz, H-8), 5.12 (1H, d, J = 2.1 Hz, Ha-14), 4.97
(1H, d, J = 2.1 Hz, Hb-14), 2.87 (1H, m, H-3), 2.33 (3H, s,
H3-12), 2.26 (1H, m, Hα-5), 1.63 (1H, m, Hβ-5), 2.06 (1H, m,
Hα-4), 1.43 (1H, m, Hβ-4), 1.49 (3H, s, H3-13), 1.23 (3H, d,
J = 7.0 Hz, H3-15); EI-MS m/z 216 [M]+.
Isolaurinterol (5): white needle crystal; C15H19OBr;
1H NMR (400 MHz, CDCl3) δ：7.45 (1H, s, H-11), 6.73 (1H,
s, H-8), 5.10 (1H, d, J = 2.1 Hz, Ha-14), 4.94 (1H, d, J = 2.1
Hz, Hb-14), 2.84 (1H, m, H-3), 2.31 (3H, s, H3-12), 2.21 (1H,
ddd, J = 14.7, 7.2, 6.6 Hz, Hα-5), 1.61 (1H, ddd, J = 14.7, 9.9,
7.2 Hz, Hβ-5), 2.06 (1H, m, Hα-4), 1.39 (1H, m, Hβ-4), 1.46
(3H, s, H3-13), 1.21 (3H, d, J = 6.0 Hz, H3-15). EI-MS m/z
294 [M]+.
Filiformin (6): white needle crystal; C15H19OBr;
1H NMR (400 MHz, CDCl3) δ：7.14 (1H, s, H-11), 6.55 (1H,
s, H-8), 2.25 (3H, s, H3-12), 1.85 (1H, q, J = 6.8 Hz, H-2),
1.65 (2H, m, H2-4), 1.75 (1H, m, Hα-5), 1.61 (1H, m, Hβ-5),
1.38 (3H, s, H3-13), 1.32 (3H, s, H3-15), 0.73 (3H, d, J = 6.8
Hz, H3-14); 13C NMR (100 MHz, CDCl3) δ：152.3 (C-7),
136.4 (C-9), 130.1 (C-6), 128.4 (C-11), 117.4 (C-8), 85.3
(C-3), 46.4 (C-2), 44.9 (C-1), 42.2 (C-5), 37.3 (C-4), 23.0
(C-13), 22.5 (C-15), 20.4 (C-12), 7.4 (C-14); EI-MS m/z 294
[M]+.
α-Isobromocuparene (7): colorless oil; C15H21Br;
1H NMR (400 MHz, CDCl3) δ： 7.27 (1H, dd, J = 8.0, 0.4 Hz,
H-7, 11), 7.13 (1H, dd, J = 8.0, 0.4 Hz, H-8, 10), 4.46 (1H, t,
J = 9.2 Hz, H-3), 2.33 (3H, s, H3-12), 2.21 (1H, s, Hα-5), 1.60
(1H, s, Hβ-5), 2.70 (1H, m, Hα-4), 2.51 (1H, m, Hβ-4), 1.28
(3H, s, H3-13), 1.10 (3H, s, H3-14), 0.65 (3H, s, H3-15);
EI-MS m/z 278 [M]+.
Cuparene-type ether (8): colorless oil; C15H20O; 1H
NMR (400 MHz, CDCl3) δ 7.00 (1H, d, J = 7.7 Hz, H-11),
6.63 (1H, dd, J = 7.7, 1.7 Hz, H-10), 6.54 (1H, d, J = 1.7 Hz,
H-8), 4.14 (1H, d, J = 5.2 Hz, H-3), 2.26 (3H, s, H3-12), 2.04
(1H, m, Hα-5), 1.92 (1H, m, Hβ-5), 1.98 (1H, m, Hα-4),, 1.92
(1H, m, Hβ-4), 1.27 (3H, s, H3-13), 1.00 (3H, s, H3-14), 0.93
(3H, s, H3-15); EI-MS m/z 216 [M]+.
Deoxyprepacifenol (9): colorless oil; C15H21OBr2Cl; 1H
NMR (400 MHz, CDCl3) δ：6.24 (1H, d, J = 2.1 Hz, H-9),
4.68 (1H, dd, J = 9.6, 3.3 Hz, H-2), 2.95 (1H, d, J = 2.1 Hz,
H-8), 2.12-2.33 (6H, m, H2-1, 4, 5), 1.70 (3H, s, H3-15), 1.63
(3H, s, H3-14), 1.20, 1.18 (6H, each s, H3-12, 13). EI-MS m/z
410 [M]+.
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中国东海冈村凹顶藻 Laurencia okamurai中的倍半萜类成分
毛水春1, 2, 郭跃伟2*
1南昌大学医学院药学系天然药物化学实验室, 南昌 330006;
2中国科学院上海生命科学研究院药物研究所国家新药研究重点实验室, 上海 201203
【摘 要】 目的：对采自中国东海的红藻冈村凹顶藻 Laurencia okamurai 的化学成分进行研究, 从中寻找具有生物活性的次
生代谢产物。方法：运用硅胶柱层析和凝胶柱层析对冈村凹顶藻的乙醚提取物进行分离纯化; 根据其理化性质, 结合现代波谱分
析技术(MS, NMR 等)并与文献报道的化合物数据相比较, 对分离得到的化合物进行结构鉴定。结果：从冈村凹顶藻中分离并鉴
定了 9 个倍半萜类化合物, 分别为 laurokamurene C (1), debromoaplysinol (2), aplysinol acetate (3), debromoisolaurinterol (4), iso-
laurinterol (5), filiformin (6), α-isobromocuparene (7), cuparene-type ether (8) 和 deoxyprepacifenol (9)。结论：化合物 1 为新化合物,
是天然界中发现的第三个重排的月桂烷型倍半萜, 3 系首次从天然界分离得到, 化合物 2-9 对真菌 Cladosporium cucumerinum 均
无明显的抑制活性。
【关键词】 红藻; 冈村凹顶藻; 倍半萜; 结构解析

【基金项目】 国家科技重大专项 (No. 2009ZX09301-001), 国家自然科学基金项目 (Nos. 40976048; 30730108; 20721003), 上海
市科委中-意非政府间国际合作项目 (No. 10540702900), 部分内容受国家自然科学基金中-泰政府间国际合作项目 (No.
20911140471)资助

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2010 年 9 月 第 8 卷 第 5 期 Chin J Nat Med Sep. 2010 Vol. 8 No. 5 325