CN1194982C - 一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途 - Google Patents

一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途 Download PDF

Info

Publication number
CN1194982C
CN1194982C CNB021521956A CN02152195A CN1194982C CN 1194982 C CN1194982 C CN 1194982C CN B021521956 A CNB021521956 A CN B021521956A CN 02152195 A CN02152195 A CN 02152195A CN 1194982 C CN1194982 C CN 1194982C
Authority
CN
China
Prior art keywords
compound
acanthaceae
glycosides
brankursine
column chromatography
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CNB021521956A
Other languages
English (en)
Other versions
CN1424318A (zh
Inventor
吴军
张偲
龙丽娟
李庆欣
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
South China Sea Institute of Oceanology of CAS
Original Assignee
South China Sea Institute of Oceanology of CAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by South China Sea Institute of Oceanology of CAS filed Critical South China Sea Institute of Oceanology of CAS
Priority to CNB021521956A priority Critical patent/CN1194982C/zh
Publication of CN1424318A publication Critical patent/CN1424318A/zh
Application granted granted Critical
Publication of CN1194982C publication Critical patent/CN1194982C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Landscapes

  • Saccharide Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

本发明涉及从爵床科(Acanthaceae)老鼠簕属植物老鼠簕Acanthus ilicifolius和小花老鼠簕Acanthus ebracteatus中分离得到的新苯乙醇苷(phenylethanoid glycoside)化合物-老鼠簕苷A(ilicifolioside A)的结构和用途。新化合物外观呈淡黄色粉末，分子式为C31H40O16，化学名为β-乙氧基-β-(3′，4′-二羟基苯基)-乙基-O-α-L-吡喃鼠李糖基-(1→3)-4-O-咖啡酰基-β-D-吡喃葡萄糖苷[β-ethoxy-β-(3′，4′-dihydroxyphenyl)-ethyl-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside]，命名为老鼠簕苷A(ilicifolioside A)。结构式如右：该化合物有抗神经细胞、肝细胞病理性细胞凋亡作用。

Description

一种苯乙醇苷化合物—老鼠簕苷A的结构及其用途
技术领域
本发明属于苯乙醇苷新化合物，主要是利用现代色谱技术从爵床科(Acanthaceae)老鼠簕属植物老鼠簕Acanthus ilicifolius和小花老鼠簕Acanthus ebracteatus中分离得到一种新的苯乙醇苷(phenylethanoid glycoside)化合物老鼠簕苷A(Ilicifolioside A)。
发明内容
该化合物外观呈淡黄色粉末，分子式为C31H40O16，化学名为β-乙氧基-β-(3′，4′-二羟基苯基)-乙基-O-α-L-吡喃鼠李糖基-(1→3)-4-O-咖啡酰基-β-D-吡喃葡萄糖苷[β-ethoxy-β-(3′，4′-dihydroxyphenyl)-ethyl-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside]。结构式如下：
该化合物结构鉴定：
由ESI-MS可知此化合物的[M+Na]+为691，结合1H NMR和13C NMR谱得知此化合物的分子式为C31H40O16。1H NMR谱上显示该化合物有：2个重叠的鼠李糖甲基峰[δ1.08(6H，d，J＝6.0Hz)]，2个与-CH2相连的甲基峰[δ1.16，1.18(3H each，t，J＝6.8Hz)]；2个β-D-葡萄糖的端基质子[4.37，4.42(1H each，d，J＝8.0Hz)]；2个O-α-L-鼠李糖的端基质子[5.18，5.21(1H each，d，J＝1.7Hz)]；1对呈AB系统的反式烯氢质子[δ6.25，7.57(2H each，d，J＝16.0Hz)]；2组完全重叠的呈ABX系统的芳香质子峰[δ6.75(2H，d，J＝8.0Hz)，δ6.94(2H，dd，J＝8.0，2.0Hz)，δ7.04(2H，d，J＝2.0Hz)]；2组不完全重叠的呈ABX系统的芳香质子峰[δ6.73(1H，d，J＝8.0Hz)，δ6.68(1H，dd，J＝8.0，2.0Hz)，δ6.78(1H，d，J＝2.0Hz)；及δ6.73(1H，d，J＝8.0Hz)，δ6.65(1H，dd，J＝8.0，2.0Hz)，δ6.76(1H，d，J＝2.0Hz)]。以上波谱数据结合HPLC分析可知该化合物为1对苯乙醇二糖苷的差向异构体。其13C NMR谱数据与campneoside I比较(见附图2)可知该化合物甙元的β碳向高场移动了2.2ppm，且多了1个乙氧基。1H-1HCOSY证实了乙氧基的存在，且HMBC显示乙氧基的-OCH2质子[δ3.42(m)]与甙元的β碳有远程相关。故此化合物最终确定为β-乙氧基-β-(3′，4′-二羟基苯基)-乙基-O-α-L-吡喃鼠李糖基-(1→3)-4-O-咖啡酰基-β-D-吡喃葡萄糖苷[β-ethoxy-β-(3′，4′-dihydroxyphenyl)-ethyl-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside]。该化合物的碳氢完整归属见附图2。经CA检索该化合物为新化合物，属于苯乙醇苷(phenylethanoid glycoside)类化合物。
附图3--附图5是该化合物图谱。
该化合物的制备方法：以爵床科(Acanthaceae)老鼠簕属植物地上部分为原料，粉碎后用95％和50％乙醇各提取3次，减压浓缩后得乙醇提取物。乙醇提取物依次用石油醚、乙酸乙酯、正丁醇萃取，减压浓缩得各萃取部位。正丁醇萃取部位经硅胶柱层析、Sephadex LH-20柱层析、ODS柱层析及HPLC制备得老鼠簕苷A。具体步骤提取分离流程见附图1，本化合物制法中所用原料的具体植物来源：为爵床科(Acanthaceae)老鼠簕属植物老鼠簕Acanthus ilicifolius和小花老鼠簕Acanthus ebracteatus。
本发明所述的化合物的用途，是该化合物具有抗神经细胞、肝细胞病理性细胞凋亡作用。

Claims (4)

1、一种苯乙醇苷化合物，其特征在于外观呈淡黄色粉末，分子式为C31H40O16，化学名为β-乙氧基-β-(3′，4′-二羟基苯基)-乙基-O-α-L-吡喃鼠李糖基-(1→3)-4-O-咖啡酰基-β-D-吡喃葡萄糖苷，命名为老鼠簕苷A，结构式如下：
Figure C021521950002C1
2、制造权利要求1中所述化合物的方法，其特征在于该方法是从爵床科老鼠簕属植物中提取分离得到该化合物，具体步骤包括：
以爵床科老鼠簕属植物地上部分为原料，粉碎后用95％和50％乙醇各提取3次，减压浓缩后得乙醇提取物；乙醇提取物依次用石油醚、乙酸乙酯、正丁醇萃取，减压浓缩得各萃取部位；正丁醇萃取部位经硅胶柱层析、SephadexLH-20柱层析、ODS柱层析及HPLC制备得老鼠簕苷A。
3、根据权利要求2中所述的方法，其特征在于所述的植物来源包括爵床科老鼠簕属植物老鼠簕和小花老鼠簕。
4、权利要求1中所述化合物在制备具有抗神经细胞、肝细胞病理性细胞凋亡作用的药物中的用途，其特征在于该化合物具有抗神经细胞、肝细胞病理性细胞凋亡作用。
CNB021521956A 2002-12-11 2002-12-11 一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途 Expired - Fee Related CN1194982C (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CNB021521956A CN1194982C (zh) 2002-12-11 2002-12-11 一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CNB021521956A CN1194982C (zh) 2002-12-11 2002-12-11 一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途

Publications (2)

Publication Number Publication Date
CN1424318A CN1424318A (zh) 2003-06-18
CN1194982C true CN1194982C (zh) 2005-03-30

Family

ID=4752142

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB021521956A Expired - Fee Related CN1194982C (zh) 2002-12-11 2002-12-11 一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途

Country Status (1)

Country Link
CN (1) CN1194982C (zh)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1596901A (zh) * 2003-09-19 2005-03-23 上海药港生物技术有限公司 用于治疗更年期综合征的广防风根提取物制剂及制备方法
CN102304156B (zh) * 2011-06-24 2016-03-16 浙江爱诺药业股份有限公司 一种苯乙醇苷类成份及其制备方法和用途
WO2013156858A1 (en) * 2012-04-20 2013-10-24 Purapharm Company Limited Materials and methods for prevention and treatment of viral infections
CN106265793B (zh) * 2015-06-08 2019-10-29 深圳海王医药科技研究院有限公司 海洋红树植物老鼠簕提取物在制备治疗老年痴呆症药物中的应用
CN105461763B (zh) * 2015-11-18 2018-07-06 浙江大学 一种多酚双糖苷化合物及其制备方法和应用
CN110812375A (zh) * 2019-12-12 2020-02-21 中国海洋大学 一种老鼠簕中苯乙醇苷类提取物及其制备方法与作为抗肝损伤药物的应用
CN112426444A (zh) * 2020-11-03 2021-03-02 福建医科大学 用于治疗类风湿性关节炎的厦门老鼠簕提取物
CN112940055A (zh) * 2021-01-26 2021-06-11 上海中医药大学 从金腺莸中提取的苯乙醇苷类化合物及其制备方法和医药用途

Also Published As

Publication number Publication date
CN1424318A (zh) 2003-06-18

Similar Documents

Publication Publication Date Title
Sashidhara et al. Identification of the antioxidant principles of Polyalthia longifolia var. pendula using TEAC assay
Hu et al. A new C-glycosyl flavone and a new neolignan glycoside from Passiflora edulis Sims peel
Fico et al. Comparative phytochemical and morphological analyses of three Italian Primula species
CN1194982C (zh) 一种苯乙醇苷化合物－老鼠簕苷a的结构及其用途
CN105348192B (zh) 一种翅荚决明中抗病毒活性的异喹啉生物碱类化合物及其制备方法
Vitalini et al. Study on secondary metabolite content of Helleborus niger L. leaves
Nie et al. New triterpenoid saponins from the roots of Gypsophila pacifica Kom.
Avilov et al. Triterpene glycosides from the Far-Eastern sea cucumber Pentamera calcigera. 1. Monosulfated glycosides and cytotoxicity of their unsulfated derivatives
Chokchaisiri et al. Flavonoid glycosides from the aerial parts of Curcuma comosa
Ishimaru et al. Polyacetylene glycosides from Pratia nummularia cultures
Li et al. A new 9, 11-seco sterol, stellettasterol from a marine sponge Stelletta sp
Ji et al. A new polyacetylene glycoside from the rhizomes of Atractylodes lancea
Teng et al. Two new steroidal glycosides from the root of Cynanchum auriculatum
Zolfaghari et al. Furostanol saponins from the bulbs of Welsh onion, Allium fistulosum L.
CN105713002A (zh) 抗生素Versicoloids A和B及其制备方法和在制备抗植物病原菌药物中的应用
Kamel et al. Cardiac glycosides from Cryptostegia grandiflora
CN1226299C (zh) 一种脂肪醇苷化合物－老鼠簕苷c及其用途
Ahmad et al. New salirepin derivatives from Symplocos racemosa
Rumalla et al. A new triterpene glycoside from Centella erecta
Gaidi et al. A new major triterpene saponin from the roots of Cucurbita foetidissima
CN1421453A (zh) 一种脂肪醇苷化合物－老鼠簕苷b的结构及其用途
CN1263768C (zh) 一种蒲公英萜醇的衍生物及制法和用途
CN104151374B (zh) 一种昆仑血菊查耳酮化合物的制备方法及应用
CN1513853A (zh) 柠檬苦素化合物－木果楝内酯及其用途
Huo et al. New neolignan glycosides and a new cerebroside from Symplocos caudata

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C19 Lapse of patent right due to non-payment of the annual fee
CF01 Termination of patent right due to non-payment of annual fee