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1.山东中医药高等专科学校中药系,山东 烟台 264199
2.山东省高等学校中药生产与质量控制新技术研发中心,山东 烟台 264199
3.黄河流域道地药材产业高质量发展协同创新中心,山东 烟台 264199
4.临沂大学医学院,山东 临沂 276000
5.中山大学实验动物中心,广东 广州 510006
薛俊娟(1979年生),女;研究方向:天然药物化学;E-mail:jjxuejjxue159@163.com
廖琼(1985年生),女;研究方向:天然药物化学;E-mail:liaoq9@mail.sysu.edu.cn
收稿日期:2024-12-06,
录用日期:2024-12-30,
网络出版日期:2025-01-21,
纸质出版日期:2025-05-25
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薛俊娟,李波,王雷清等.桉属植物细叶桉Eucalyptus tereticornis的化学成分[J].中山大学学报(自然科学版)(中英文),2025,64(03):36-46.
XUE Junjuan,LI Bo,WANG Leiqing,et al.Chemical constituents from Eucalyptus tereticornis of genus Eucalyptus[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,2025,64(03):36-46.
薛俊娟,李波,王雷清等.桉属植物细叶桉Eucalyptus tereticornis的化学成分[J].中山大学学报(自然科学版)(中英文),2025,64(03):36-46. DOI: 10.13471/j.cnki.acta.snus.ZR20240343.
XUE Junjuan,LI Bo,WANG Leiqing,et al.Chemical constituents from Eucalyptus tereticornis of genus Eucalyptus[J].Acta Scientiarum Naturalium Universitatis Sunyatseni,2025,64(03):36-46. DOI: 10.13471/j.cnki.acta.snus.ZR20240343.
为研究桉属植物细叶桉(
Eucalyptus tereticornis
)的化学成分,探究所得化合物的潜在生理活性,本研究通过硅胶柱层析、凝胶柱层析和半制备型高效液相色谱等多种分离手段对其乙醇提取物的石油醚和乙酸乙酯萃取部位进行分离纯化,共得到21个化合物。通过核磁共振波谱、质谱和比旋光法并结合文献数据对比分析对化合物进行结构解析,分别鉴定为10个木脂素类化合物:ehletianol C(
1
)、dihydrobuddlenol B(
2
)、二氢去氢双松柏醇(
3
)、波棱素(
4
)、vitrifol A(
5
)、(-)-丁香树脂酚(
6
)、(-)-南烛木树脂酚(
7
)、异落叶松脂素(
8
)、
erythro
-1-(3,4-dimethoxyphenyl)-2-
O
-(2-methoxy-4-omegahydroxypropylphenyl)propane-1,3-diol(
9
)和
threo
-guaiacylglycerol-
β
-
O
-4′-dihydroconiferyl alcohol(
10
);3个间苯三酚类化合物:multifidol glucoside(
11
)、lysidiside A(
12
)和2,4,6-trihydroxy-1-butyrophenone-2-
O
-
β
-D-glucopyranoside(
13
);3个黄酮类化合物:(
S
)-柚皮素7-
O
-葡萄糖苷(
14
)、(-)-2,3-
trans
-dihydro
keampferol-3-
O
-
α
-L-rhamnoside(
15
)和根皮素(
16
);5个芳苷类化合物:garcimangosone D(
17
)、脱氧土大黄苷(
18
)、glochierioside F(
19
)、citrusin C(
20
)和苄基-
β
-D-葡萄糖苷(
21
)。化合物
1
~
21
均为首次从细叶桉中分离得到,化合物
1
、
2
、
4
、
5
、
19
和
20
为首次从桉属中分离得到。利用DPPH法探究所得化合物的体外抗氧化活性,结果显示化合物
1
、
4
、
6
、
7
、
9
、
10
、
12
、
13
、
15
和
16
的抗氧化活性IC
50
为13.42~65.97 μg/mL,均弱于阳性对照维生素C,其中化合物
3
、
6
和
10
活性相对较强,与维生素C接近。
To study the chemical constituents of the
Eucalyptus tereticornis
and explore their potential biological activity, a total of 21 compounds were obtained from the petroleum ether and ethyl acetate part of the ethanol extract of
Eucalyptus tereticornis
by silica gel column chromatography, Sephadex LH-20 column chromatography, and semi-preparative high performance liquid chromatography (HPLC). By the analysis of NMR,ESI-MS, and specific rotation values combined with comparative analysis with literature data, the structures of compounds were identified as ten lignans: Ehletianol C(
1
), dihydrobuddlenol B(
2
), dehydrodiconiferyl alcohol(
3
), herpetin (
4
), vitrifol A(
5
), (-)-syringaresinol (
6
), (-)-lyoniresinol (
7
), (-)-isolariciresinol (
8
),
erythro
-1-(3,4-dimethoxyphenyl)-2-
O
-(2-methoxy-4-omegahydroxypropylphenyl)propane-1,3-diol (
9
), and
threo
-guaiacylglycerol-
β
-
O
-4′-dihydroconiferyl alcohol (
10
); three phloroglucinols: multifidol glucoside (
11
), lysidiside A (
12
), and 2,4,6-trihydroxy-1-butyrophenone-2-
O
-
β
-D-glucopyranoside (
13
); three flavones: (
S
)-naringenin 7-
O
-glycoside (
14
), (-)-2,3-
trans
-dihydrokeampferol-3-
O
-
α
-L-rhamnoside(
15
), and phloretin (
16
); and five aryl
C
-glycosides: garcimangosone D(
17
), deoxyrhaponticin (
18
), glochierioside F(
19
), citrusin C(
20
), and benzyl
β
-D-glucopyranoside (
21
). All the compounds were separated from
Eucalyptus tereticornis
for the first time, and compounds
1
,
2
,
4
,
5
,
19
, and
20
were separated from the genus
Eucalyptus
for the first time. The
in vitro
antioxidant activity of compounds was evaluated by using DPPH method. The
results indicated that compounds
1
,
4
,
6
,
7
,
9
,
10
,
12
,
13
,
15
, and
16
exhibited certain activity, with IC
50
values ranging from 13.42-65.97 μg/mL, weaker than vitamin C. Among them, compounds
3
,
6
, and
10
showed significant antioxidant activity, comparable to vitamin C.
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