
浏览全部资源
扫码关注微信
云南中医药大学 中药学院, 云南省傣医药与彝医药重点实验室, 昆明 650500
陈彦伍,在读硕士,从事天然药物提取分离及应用研究,Tel:0871-65939285,E-mail:2743730483@qq.com
何红平,博士,研究员,从事药物化学研究,Tel:0871-65939285,E-mail:95431111@qq.com
网络出版日期:2020-03-16,
纸质出版日期:2020-07-05
移动端阅览
陈彦伍,董发武,秦天丽等.大叶山楝枝叶中的萜类成分[J].中国实验方剂学杂志,2020,26(13):168-173.
CHEN Yan-wu,DONG Fa-wu,QIN Tian-li,et al.Terpenoids from Stems and Leaves of Aphanamixis grandifolia[J].Chinese Journal of Experimental Traditional Medical Formulae,2020,26(13):168-173.
陈彦伍,董发武,秦天丽等.大叶山楝枝叶中的萜类成分[J].中国实验方剂学杂志,2020,26(13):168-173. DOI: 10.13422/j.cnki.syfjx.20201311.
CHEN Yan-wu,DONG Fa-wu,QIN Tian-li,et al.Terpenoids from Stems and Leaves of Aphanamixis grandifolia[J].Chinese Journal of Experimental Traditional Medical Formulae,2020,26(13):168-173. DOI: 10.13422/j.cnki.syfjx.20201311.
目的
2
大叶山楝
Aphanamixis grandifolia
为楝科山楝属植物,具有舒筋活络、通痹及祛风除湿等功效,该文旨在研究大叶山楝枝叶中的萜类成分,揭示其发挥药效的物质基础。
方法
2
取大叶山楝干燥枝叶22 kg,采用90%乙醇加热回流提取3次,减压回收溶剂成浸膏。浸膏加适量的水混匀后,依次用石油醚、乙酸乙酯进行萃取。石油醚和乙酸乙酯层萃取物分别经大孔树脂柱色谱,硅胶柱色谱,LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱和ODS柱色谱进行分离纯化,并通过质谱、核磁共振技术(
1
H和
13
C-NMR)和相关文献数据等对所得化合物进行结构鉴定。
结果
2
从大叶山楝枝叶中分离并鉴定了12个萜类化合物,分别为16
α
-hydroxy-oxo-24-methyllanosta-7,9(11),24(31)-triene-21-oic acid(
1
),23(
E
)-cycloart-en-25-ethoxy-3-ol(
2
),23(
Z
)-9,19-cycloart-ene-3
β
,25-diol(
3
),23(
E
)-cycloart-23-en-3
β
,25-diol(
4
),labda-8,13-(
E
)-dien-15-ol(
5
),labda-7,13-(
E
)-dien-15-ol(
6
),vulgarol(
7
),(
S
,
E
)-6-[6-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl)-2-methylhepta-1,6-dien-1-yl]-4-methyl-5,6-dihydro-2H-pyran-one(
8
),nemoralisin(
9
),nemoralisin C(
10
),1
S
,4
R
,5
S
,6
R
,7
S
,10
S
-1(5),6(7)-diepoxy-4-guaiol(
11
),1
S
,4
S
,5
S
,10
R
-4,10-guaianediol(
12
)。
结论
2
分离得到的化合物类型涉及三萜,二萜和倍半萜,其中8个化合物(
1
~
3
,
5
~
8
,
12
)为首次从该种植物中分离得到,也是首次从该属中分离得到。
Objective
2
Aphanamixis grandifolia
,a perennial herb of genus
Aphanamixis
(Meliaceae),has effects in soothing activating collaterals,dredging paisy,expelling wind-evil and removing wetness. This paper aimed to investigate terpenoids from the stems and leaves of
A. grandifolia
and reveal the effective substances.
Method
2
Totally 22 kg leaves and twigs of
A. grandifolia
were extracted with 90% EtOH for three times by heating reflux. These extracts were decompressed and concentrated,and then dissolved in water. The solvent was successively extracted with petroleum ether and ethyl acetate. The chemical constituents from petroleum ether and ethyl acetate fractions were isolated by macroporous,silica gel,Sephadex LH-20 and ODS columns,and their chemical structures were determined through MS,NMR analysis(
1
H and
13
C-NMR)and spectroscopic data from literatures,respectively.
Result
2
Twelve compounds were obtained and identified as 16
α
-hydroxy-3-oxo-24-methyllanosta-7,9(11),24(31)-triene-21-oic acid (
1
),23(
E
)-cycloart-en-25-ethoxy-3-ol(
2
),23(
Z
)-9,19-cycloart-ene-3
β
,25-diol(
3
),23(
E
)-cycloart-en-3
β
,25-diol(
4
),labda-8,13-(
E
)-dien-15-ol(
5
),labda-7,13-(
E
)-dien-15-ol(
6
),vulgarol(
7
),(
S
,
E
)-6-[6-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl]-2-methylhepta-1,6-dien-1-yl]
-4-methyl-5,6-dihydro-2H-pyran-one(
8
),nemoralisin(
9
),nemoralisin C(
10
),1
S
,4
R
,5
S
,6
R
,7
S
,10
S
-1(5),6(7)-diepoxy-4-guaiol(
11
) and 1
S
,4
S,
5
S
,10
R
-4,10-guaianediol(
12
),respectively.
Conclusion
2
The structures involves triterpenoids,diterpenoids and sesquiterpennoids,and eight of them (
1
-
3
,
5
-
8
and
12)
are obtained from
A. grandifolia
for the first time. Those compounds are also isolated from the geneus
Aphanamixis
for the first time.
中国科学院《中国科植物志》编辑委员会 . 中国植物志:第43卷 [M]. 北京 : 科学出版社 , 1997 .
WANG G W , JIN H Z , ZHANG W D . Constituents from Aphanamixis species and their biological activities [J]. Phytochem Rev , 2013 , 12 : 915 - 942 .
周健 , 黎玉华 , 周颖 , 等 . 变叶树参化学成分的分离与鉴定 [J]. 中国实验方剂学杂志 , 2019 , 10 ( 8 ): 1 - 5 .
汪镇朝 , 张海燕 , 邓锦松 , 等 . 迷迭香的化学成分及其药理作用研究进展 [J]. 中国实验方剂学杂志 , 2019 , 25 ( 23 ): 211 - 218 .
KAWANGISH H , HANG L . A lanostane-type teiterpene from a mushroom Daedaiea dickins [J]. Phytochemistry , 1997 , 46 ( 5 ): 959 - 961 .
LAI K H , LU M C , DU Y C , et al . Cytotoxic lanostanoids from Poria cocos [J]. J Nat Prod , 2016 , 79 ( 11 ): 2805 - 2813 .
PEI Y G , WU Q X , SHIA Y P . Triterpenoids and other constituents from Euphorbia humifusae [J]. J Chin Chem Soc-Taip , 2007 , 54 : 1565 - 1572 .
MARINA D G , ANTONIO F , PIETRO M , et al . Cycloartane triterpenes from Juncus effusus [J]. Phytochemistry , 1994 , 35 ( 4 ): 1017 - 1022 .
LIU Q , CHEN C J , SHI X . Chemical constituents from Aphanamixis grandifolia [J]. Chem Pharm Bull (Tokyo) , 2010 , 58 ( 11 ): 1431 - 1435 .
LAGO J H , BROCHINI C B , ROQUE N F , et al . Terpenes from leaves of Guarea macrophylla (Meliaceae) [J]. Phytochemistry , 2000 , 55 ( 7 ): 727 - 731 .
NOVAES L T , GONCALVES K A , TRIVELLA D B B , et al . Formal total synthesis of actinoranone synthesis approaches and cytotoxic studies [J]. J Org Chem , 2018 , 83 ( 9 ): 5160 - 5176 .
AL-MUSAYEIB N M , ABBAS F A , AHMAD M S , et al . Labdane diterpenes from Otostegia fruticosa [J]. Phytochemistry , 2000 , 54 ( 8 ): 771 - 775 .
YIN J P , GU M LI Y , et al . Total synthesis of aphadilactones A-D [J]. J Org Chem , 2014 , 79 ( 13 ): 6294 - 6301 .
HE X F , WANG X N , YUE J M , et al . Chemical constituents of Polyalthia nemoralis [J]. Helv Chim Acta , 2007 , 90 ( 4 ): 783 - 791 .
ZHANG Y , WANG J S , WEI D D , et al . Bioactive terpenoids from the fruits of Aphanamixis grandifolia [J]. J Nat Prod , 2013 , 76 ( 6 ): 1191 - 1195 .
LIU J , YANG S P , NI G . Triterpenoids from Aglaia odorata var. microphyllina [J]. J Asian Nat Prod Res , 2012 , 14 ( 10 ): 929 - 939 .
WANG X Y , TANG G H , YUAN C M , et al . Two new tirucallane triterpenoids from Aphanamixis grandifolia [J]. Nat Prod Bioprospect , 2012 , 2 ( 5 ): 222 - 226 .
ZHANG G W , MA X Q , ZENG L M , et al . Two new bioactive sesquiterpenes from the soft coral Sinularia sp .[J]. Nat Prod Res , 2006 , 20 ( 7 ): 659 - 664 .
0
浏览量
14
下载量
1
CSCD
关联资源
相关文章
相关作者
相关机构
京公网安备11010802024621