全 文 ： 180 Chin J Nat Med May 2011 Vol. 9 No. 3 2011 年 5 月 第 9 卷 第 3 期

Chinese Journal of Natural Medicines 2011, 9(3): 0180−0184
doi: 10.3724/SP.J.1009.2011.00180
Chinese
Journal of
Natural
Medicines







Chemical Constituents of Pittosporum glabratum
NIE Tian-Tian, ZHAO Huan-Xin, BAI Hong*
Key Laboratory of Rare and Uncommon Diseases, Institute of Materia Medica, Shandong Academy of Medical Sciences, Jinan 250062,
China
Available online May 2011
[ABSTRACT] AIM: To investigate the chemical constituents of Pittosporum glabratum Lindl.. METHODS: The compounds were
isolated and purified by repeated column chromatography and preparative HPLC. The structures were elucidated on the basis of spec-
troscopic analyses and physical evidence. RESULTS: Seven compounds were isolated and identified as 6α-hydroxygeniposide (1),
10-O-caffeoyl deacetyl daphylloside (2), (+)-lyoniresinol-3α-O-β-D-glucopyranoside (3), (+)-lyoniresinol-3α-O-(6-3,5-dimethoxy-
4-hydroxybenzoyl)-β-D-glucopyranoside (4), fernandoside [(+)-lyoniresinol-3α-O-(6-3-methoxy-4-hydroxybenzoyl)-β-D-glucopy-
ranoside] (5), (−)-4-epi-lyoniresinol-3α-O-β-D-glucopyranoside (6) and liriodendrin [(+)-syringaresinol-4,4-bis-O-β-D-glucopy-
ranoside] (7). CONCLUSION: Compounds 1-6 were found in the genus Pittosporum for the first time and 7 was isolated from the
plant Pittosporum glabratum for the first time.
[KEY WORDS] Pittosporum glabratum; Chemical constituent; Iridoid glycoside; Lignan glycoside
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2011)03-0180-05

1 Introduction
Pittosporum glabratum Lindl. (Pittosporaceae) is widely
distributed in Sichuan, Yunnan and Guangdong Provinces in
China. The roots of this plant have been used as a folk medi-
cine for the treatment of rheumatic arthritis, insomnia and
hypertension [1]. Only a few chemical or biological studies on
P. glabratum have been reported [2-3]. The potential medicinal
importance and our interest in the biologically active com-
pounds from folk medicines prompted us to investigate the
chemical constituents of P. glabratum, which resulted in the
isolation of two iridoid glycosides (1 and 2) and five lignan
glycosides (3-7). The structures of these compounds were
identified as 6α-hydroxygeniposide (1), 10-O-caffeoyl dea-
cetyl daphylloside (2) (+)-lyoniresinol-3α-O-β-D-glucopy-
ranoside (3), (+)-lyoniresinol-3α-O-(6-3, 5-dimethoxy-4-hy-
droxybenzoyl)-β-D-glucopyranoside (4), fernandoside [(+)-
lyoniresinol-3α-O-(6-3-methoxy-4-hydroxybenzoyl)-β-D-
glucopyranoside] (5), (−)-4-epi-lyoniresinol-3α-O-β-D-glu-
copyranoside (6) and liriodendrin [(+)-syringaresinol-4,4-
bis-O-β-D-glucopyranoside] (7), respectively. Compounds

[Received on] 30-Nov.-2010
[*Corresponding author] BAI Hong: Associate Prof., Tel:
86-531-82919971, E-mail: baihong@gmail.com
These authors have no any conflict of interest to declare.
1-6 were found in the genus for the first time and 7 was iso-
lated from the plant Pittosporum glabratum for the first time.
2 Experimental
2.1 General
The 1H and 13C NMR spectra were recorded on
INOVA-600 NMR spectrometer with TMS as the internal
standard. Specific rotation was measured on High-precision
digital automatic polarimeter (Kerncher, German). The
ESIMS was taken on an Agilent Trap VL mass analyzer.
Preparative HPLC was performed on Agilent 1100 apparatus.
Column chromatography was carried out using silica gel
(200-300 mesh, Qingdao Marine Chemical Factory, Qingdao,
China), Sephadex LH-20 (Amersham Biosciences, Sweden),
Diaion HP-20 (20-60 mesh, Mitsubishi Chemical Holdings
Co., Kyoto, Japan) or ODS (50 µm, YMC Co., Ltd., Kyoto,
Japan).
2.2 Plant material
The roots of Pittosporum glabratum Lindl. were col-
lected from Sichuan Province, China, in September 2009, and
identified by one of the authors B. H. A voucher specimen
(No. 200909) has been deposited at the Department of Natu-
ral Products Chemistry, Institute of Materia Medica, Shan-
dong Academy of Medical Sciences, Jinan, China.
2.3 Extraction and isolation
The air-dried roots of P. glabratum (12 Kg) were
NIE Tian-tian, et al. /Chinese Journal of Natural Medicines 2011, 9(3): 180−184
2011 年 5 月 第 9 卷 第 3 期 Chin J Nat Med May 2011 Vol. 9 No. 3 181


Fig. 1 Compounds 1-7 isolated from P. glabratum Lindl.

extracted with 75% EtOH three times. Evaporation of the
aqueous alcohol solution under reduced pressure gave the
EtOH extract (1 065 g). The extract was suspended in H2O
and extracted successively with EtOAc and BuOH. The
BuOH extract (198 g) was subjected to Diaion HP-20 column
and eluted with 0%, 30%, 60% and 90% EtOH to obtain four
fractions. The 30% EtOH eluate (39 g) was separated by
silica gel column chromatography (CC) with CHCl3-MeOH
gradient to give 10 fractions (Fr.A−Fr.J). Further isolation of
Fr.G (5.7 g) and Fr.E (3.1 g) was achieved by repeated silica
gel, Sephadex LH-20, ODS CC and preparative HPLC to
give compounds 1 (42 mg), 2 (100 mg), 3 (118 mg), 4 (71
mg), 5 (35 mg), 6 (3 mg) and 7 (30 mg).
3 Structural Identification
Compound 1 Yellow powder, C17H24O11, [α]D20 +17.7°
(c 1.58, MeOH). Positive ESI-MS m/z: 427 [M + Na]+; nega-
tive ESI-MS m/z 403 [M − H]−. 1H NMR (600 MHz, CD3OD)
δ: 5.05 (1H, d, J = 9.0 Hz, H-1), 7.64 (1H, br s, H-3), 3.01
(1H, dd, J = 7.6, 6.6 Hz , H-5), 4.78 (1H, m, H-6), 6.08 (1H,
br s, H-7), 2.56 (1H, dd, J = 9.0, 7.6 Hz, H-9), 4.45 (1H, d, J
= 15.6 Hz, Ha-10), 4.20 (1H, d, J = 15.6 Hz, Hb-10), 3.74
(3H, s, 11-OCH3), 4.71 (1H, d, J = 8.0 Hz, Glc-H-1), 3.23
(1H, t, J = 8.0 Hz, Glc-H-2), 3.37 (1H, t, J = 8.0 Hz,
Glc-H-3), 3.26 (2H, overlapped, Glc-H-4, Glc-H-5), 3.84 (1H,
br d, J = 12.0 Hz, Glc-Ha-6), 3.61 (1H, dd, J = 12.0 Hz, 5.4
Hz, Glc-Hb-6). 13C NMR (150 MHz, CD3OD) δ: 101.5 (C-1),
155.4 (C-3), 108.2 (C-4), 42.7 (C-5), 75.4 (C-6), 129.7 (C-7),
151.5 (C-8), 45.8(C-9), 61.7 (C-10), 169.4 (C-11), 51.8
(11-OCH3), 100.4 (Glc-C-1), 74.9 (Glc-C-2), 78.5 (Glc-C-3),
71.6 (Glc-C-4), 77.8 (Glc-C-5), 62.8 (Glc-C-6). Compound 1
was identified as 6α-hydroxygeniposide by comparison of the
physical and spectral data with the reported data [4-5].
Compound 2 Yellow powder, C26H30O14, [α]D20 −10° (c
1.58, MeOH). Positive ESI-MS m/z 589 [M + Na]+; negative
ESI-MS m/z: 565 [M − H]−. 1H NMR (600 MHz, CD3OD) δ:
5.10 (1H, d, J = 9.0 Hz, H-1), 7.66 (1H, br s, H-3), 3.06 (1H,
dd, J = 7.5, 6.6 Hz, H-5), 4.81 (1H, m, H-6), 6.05 (1H, br s,
H-7), 2.67 (1H, dd, J = 9.0, 7.5 Hz, H-9), 5.10 (1H, d, J
=16.8 Hz, Ha-10), 4.88 (1H, overlapped, Hb-10), 3.74 (3H, s,
11-OCH3), 7.06 (1H, d, 1.8, H-2), 6.78 (1H, d, J = 8.0 Hz,
H-5), 6.96 (1H, d, J = 8.0, 1.8 Hz, H-6), 7.59 (1H, d, J =
15.6 Hz, H-7), 6.31 (1H, d, J = 15.6 Hz, H-8), 4.73 (1H, d, J
= 7.8 Hz, Glc-H-1), 3.26-3.29 (3H, overlapped, Glc-H-2,
Glc-H-3, Glc-H-4), 3.39 (1H, m, Glc-H-5), 3.86 (1H, br d, J
= 12.0 Hz, Glc-Ha-6), 3.64 (1H, dd, J = 12.0 Hz, 5.4 Hz,
Glc-Hb-6). 13C NMR (150 MHz, CD3OD) δ: 101.1 (C-1),
155.1 (C-3), 107.8 (C-4), 42.1 (C-5), 75.1 (C-6), 131.4 (C-7),
145.9 (C-8), 46.0 (C-9), 63.3 (C-10), 169.0 (C-11), 51.6
(11-OCH3), 127.3 (C-1), 114.9 (C-2), 146.5 (C-3), 149.5
(C-4), 116.2 (C-5), 122.8 (C-6), 147.1 (C-7), 114.4 (C-8),
168.5 (C-9), 100.4 (Glc-C-1), 74.6 (Glc-C-2), 78.2 (Glc-C-3),
71.2 (Glc-C-4), 77.6 (Glc-C-5), 62.6 (Glc-C-6). Compound 2
was identified as 10-O-caffeoyl deacetyl daphylloside by
comparison of the physical and spectral data with the re-
ported data [6-7].
Compound 3 Yellow powder, C28H38O13, [α]D20 +32.8°
(c 0.8, MeOH). Positive ESI-MS m/z 605 [M + Na]+;
negative ESI-MS m/z: 581 [M − H]−. 1H NMR (600 MHz,
CD3OD) and 13C NMR (150 MHz, CD3OD), see the Table 1.
Compound 3 was identified as (+)-lyoniresinol-3α-O-β-D-
glucopyranoside by comparison of the physical and spectral
data with the reported data [8].
Compound 4 Yellow powder, C37H46O17, [α]D20

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182 Chin J Nat Med May 2011 Vol. 9 No. 3 2011 年 5 月 第 9 卷 第 3 期

Table 1 1H (600 MHz) and 13C NMR (150 MHz) data for compounds 3-6 in CD3OD
3 4 5 6
Aglycone δΗ δC δH δC δH δC δΗ
1 2.71 (dd, 14.7, 4.2) 2.61 (dd, 14.7, 11.4) 32.7
2.66 (dd, 15.0, 4.8)
2.58 (dd, 15.0, 12.0) 33.7
2.67 (dd, 15.0, 4.2)
2.58 (dd, 15.0, 11.4) 32.5
2.95 (dd, 16.8, 5.4)
2.70 (dd, 16.8, 12.0)
2 1.70 (m) 39.4 1.63 (m) 40.9 1.64 (m) 39.6 1.98 (m)
2a 3.66 (dd, 11.4, 5.4) 3.54 (dd, 11.4, 6.6) 65.0
3.60 (dd, 11.1, 4.8)
3.50 (dd, 11.1, 6.6) 66.2
3.61 (dd, 11.1, 4.2)
3.52 (dd, 11.1, 6.6) 65.0
3.58 (dd, 10.8, 4.8)
3.54 (dd, 10.8, 6.6)
3 2.08 (m) 45.5 2.10 (m) 46.4 2.10 (m) 45.2 2.13 (m)
3a 3.89 (dd, 9.9, 5.4) 3.44 (dd, 9.9, 3.6) 70.2
3.87-3.89 (m)
3.46 (dd, 10.2, 4.2) 71.7
3.84-3.86 (m)
3.44 (dd, 9.6, 3.6) 70.5
3.87-3.89 (m)
3.47 (dd, 9.8, 6.0)
4 4.41 (d, 6.6) 41.6 4.35 (d, 6.0) 42.8 4.35 (d, 6.0) 41.6 4.60 (br d, 4.2)
5 147.4 147.6 147.4
6 137.7 138.9 137.7
7 146.4 148.9 146.4
8 6.57 (s) 106.6 6.53 (s) 107.8 6.54 (s) 106.6 6.57 (s)
9 129.0 130.2 129.0
10 125.2 126.2 125.0
5-OCH3 3.34 (s) 58.9 3.33 (s) 60.2 3.31 (s) 59.0 3.22 (s)
7-OCH3 3.85 (s) 55.4 3.83 (s) 56.6 3.83 (s) 55.2 3.85 (s)
1 138.2 139.3 138.0
2 6.42 (s) 105.6 6.40 (s) 106.9 6.41 (s) 105.6 6.42 (s)
3 147.8 148.9 147.7
4 133.2 134.5 133.2
5 147.8 148.9 147.7
6 6.42 (s) 105.6 6.40 (s) 106.9 6.41 (s) 105.6 6.42 (s)
3-OCH3 3.74 (s) 55.6 3.72 (s) 56.8 3.72 (s) 55.6 3.74 (s)
5-OCH3 3.74 (s) 55.6 3.72 (s) 56.8 3.72 (s) 55.6 3.74 (s)
β-D-glc
1″ 4.27 (d, 7.8 ) 103.6 4.32 (d,7.8) 104.8 4.31 (d ,7.8) 103.6 4.31 (d, 7.8)
2″ 3.22 (dd, 9.6, 7.8) 73.9 3.28a 75.2 3.27 (t, 7.8) 73.9 3.26a
3″ 3.37 (t, 9.6) 77.0 3.40 (t, 8.4) 78.1 3.40a 76.9 3.38 (t, 8.4)
4″ 3.23 (dd, 10.8, 9.6) 70.4 3.40 (t, 8.4) 72.0 3.40a 70.7 3.27a
5″ 3.24 (ddd, 10.8, 5.4, 2.4) 76.7 3.56 (m) 75.5 3.50 (m) 74.3 3.29a
6″ 3.83 (dd, 12.0, 2.4) 3.65 (dd, 12.0, 5.4) 61.6
4.62 (dd, 11.4, 1.8)
4.35a 65.2
4.59 (br d, 12.9)
4.32 (dd, 12.9, 6.0) 63.8
3.84 (dd, 11.4, 2.0)
3.64 (dd, 11.4, 5.4)
1″′ 121.3 120.9
2″′ 7.30 (s) 108.2 7.50 (br s) 112.3
3″′ 149.0 152.2
4″′ 142.1 147.7
5″′ 149.0 6.79 (d, 8.4) 114.9
6″′ 7.30 (s) 108.2 7.53 (d, 8.4) 124.0
7″′ 168.0 166.9
3″′-OCH3 3.79 (s) 56.8 3.80 (s) 55.4
5″′-OCH3 3.79 (s) 56.8
a: overlapped

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2011 年 5 月 第 9 卷 第 3 期 Chin J Nat Med May 2011 Vol. 9 No. 3 183

+27.2° (c 1.58, MeOH). Positive ESI-MS m/z 785 [M + Na]+;
negative ESI-MS m/z: 761 [M − H]−. 1H NMR (600 MHz,
CD3OD) and 13C NMR (150 MHz, CD3OD), see the Table 1.
Compound 4 was identified as (+)-lyoniresinol-3α-O-(6-3,
5-dimethoxy-4-hydroxybenzoyl)-β-D-glucopyranoside by com-
parison of the physical and spectral data with the reported
data [9].
Compound 5 Yellow powder, C36H44O16, [α]D20 +25.6°
(c 1.29, MeOH). Positive ESI-MS m/z 755 [M + Na]+; nega-
tive ESI-MS m/z: 731 [M − H]−. 1H NMR (600 MHz, CD3OD)
and 13C NMR (150 MHz, CD3OD), see the Table 1. Com-
pound 5 was identified as fernandoside [(+)-lyoniresinol-
3α-O-(6-3-methoxy-4-hydroxybenzoyl)-β-D-glucopyranosi-
de] by comparison of the physical and spectral data with the
reported data [10].
Compound 6 Yellow powder, C28H38O13, [α]D20
−147.2° (c 0.36, MeOH). Positive ESI-MS m/z 605 [M + Na]+;
negative ESI-MS m/z: 581 [M − H]−. 1H NMR (600 MHz,
CD3OD) see the Table 1. Compound 6 was identified as (−)-
4-epi-lyoniresinol-3α-O-β-D-glucopyranoside by comparison
of the physical and spectral data with the reported data [11].
Compound 7 White amorphous solid, C34H46O19, [α]D20
−42.2° (c 1.54, MeOH:H2O 40:60). Positive ESI-MS m/z 765
[M + Na]+; negative ESI-MS m/z: 741 [M − H]−. 1H NMR
(600 MHz, C5D5N) δ: 6.92 (4H, s, H-2,6,2,6), 4.94 (2H, d, J
= 3.0 Hz, H-7,7), 3.15 (2H, m, H-8,8), 4.03 (2H, dd, J = 9.0
Hz, 3.0 Hz, Ha-9,9), 4.18 (2H, m, Hb-9,9), 3.79 (12H, s,
3,3,5,5-OCH3), 5.81 (2H, d, J = 6.6 Hz, Glc-H-1, Glc-H-1),
4.30-4.39 (12H, m, Glc-H-2,2′, Glc-H-3,3, Glc-H-4,4,
Glc-H-5,5, Glc-H-6,6). 13C NMR (150 MHz, C5D5N) δ:
135.7 (C-1,1), 105.1 (C-2,2), 154.3 (C-3,5,3,5), 138.5
(C-4,4), 105.1 (C-6,6), 86.5 (C-7,7), 55.1 (C-8,8), 72.6
(C-9,9), 57.0 (3,3,5,5-OCH3), 105.3 (Glc-C-1,1), 76.4
(Glc-C-2,2), 78.7 (Glc-C-3,3), 71.9 (Glc-C-4,4), 79.0
(Glc-C-5,5), 62.9 (Glc-C-6,6). Compound 7 was identified
as liriodendrin [(+)-syringaresinol-4, 4-bis-O-β-D-glucopy-
ranoside] by comparison of the physical and spectral data
with the reported data [12-15].
It is known that P. genus (Pittosporaceae) contains triter-
penes, triterpene saponins, carotenoids and phthalides [16].
In this paper, we reported the isolation of two iridoid
glycosides (1 and 2), four arylnaphthalene lignan glycosides
(3-6) and a syringaresinol glycoside (7). Iridoid glycosides
generally have 6α- and 6β-configurations. A literature survey
revealed that the NMR spectroscopy is a valuable and reli-
able technique for the prediction of 6α- or 6β-configurations
of iridoid glycosides which have a substituent at C-4: (1) The
chemical shift difference between C-3 and C-4 is lager than
47 for α-epimers, whereas it is smaller than 45 for β-epimers;
(2) The chemical shift of C-1 is larger than 99 for α-epimers,
whereas it is smaller than 97 for β-epimers; (3) The coupling
constant of H-1 and H-9 is equal to or greater than 8 Hz for
α-epimers, whereas it is less than 8 Hz for β-epimers [17-18].
Both 1 and 2 were iridoid glycosides having a substituent at
C-4 and their NMR characteristic was consistent with that of
iridoid glycosides having 6α-configuration. Thus, the hy-
droxyls of C-6 of 1 and 2 were 6α-configuration. Further-
more, the molecular formula of compound 6 was the same as
that of 3. The 1H NMR of 6 was almost superimposable with
that of 3, except that H-2 and H-4 of 6 were shifted down-
field. After careful comparison of 1H data and specific rota-
tion of 6 with those in the literature, the structure of 6 was
established as C-4 epimer of 3.
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光叶海桐根的化学成分
聂田田, 赵焕新, 白 虹*
山东省医学科学院药物研究所 山东省罕少见病重点实验室, 济南 250062
【摘 要】 目的：对光叶海桐根的化学成分进行研究。方法：通过多种柱层析方法和制备高效液相对化合物进行分离纯化,
通过理化常数及波谱数据对其结构进行解析。结果：从光叶海桐根中分离得到 7 个化合物, 分别鉴定是 6α-羟基-京尼平苷(1),
10-O-咖啡酰基-脱乙酰基-交让木苷(2), (+)-南烛木树脂酚-3α-O-β-D-葡萄糖苷(3), (+)-南烛木树脂酚-3α-O-(6-3,5-二甲氧基-4-羟
基-苯甲酰基)-β-D-葡萄糖苷(4), (+)-南烛木树脂酚-3α-O-(6-3-甲氧基-4-羟基-苯甲酰基)-β-D-葡萄糖苷(5), (−)-4-epi-南烛木树脂酚-
3α-O-β-D-葡萄糖苷(6)和(+)-丁香脂素-4,4-O-双-β-D-葡萄糖苷(7)。结论：化合物 1−6 为该属首次分离, 化合物 7 为该种首次分离。
【关键词】 光叶海桐根; 化学成分; 环烯醚萜苷; 木脂素苷

·Information·

37th International Symposium on High
Performance Liquid Phase Separations
and related Techniques

Start Date: 2011-10-9
End Date: 2011-10-13
Country: China
Venue name: Dalian World Expo Center
Organized by: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Chairman: Prof. Zhang Yu-Kui; Prof. Peter Schoenmakers
Contact person: Hou Xiao-Li
E-mail: hplc_dalian@dicp.ac.cn
International call: 86-411-84379520
Fax: 86-411- 84379559
Address:
457 Zhongshan Road 116023, Dalian, China
Useful link: http://www.hplc2011.dicp.ac.cn
General Information:
The HPLC Symposium Series represents the premier conference for liquid phase
separations and related techniques. The HPLC conference has grown over the years to
become the largest meeting in the world dedicated to liquid phase separation science.
This international meeting series is multi-disciplinary in nature and brings together
many of the worlds leading authorities to address the practical and economical issues
and challenges related to all aspects of liquid phase separation science techniques.