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4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydrofuran-2r-yl)-(3ar,10at,10bt)-decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one | 27495-40-5

物质功能分类

生物化工 - 中草药成分

分子结构分类

有机化合物 - 生物碱及其衍生物 - 百部生物碱

中文名称

——

中文别名

——

英文名称

4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydrofuran-2r-yl)-(3ar,10at,10bt)-decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one

英文别名

protostemonine；4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydro-furan-2r-yl)-(3ar,10at,10bt)-decahydro-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one；4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydro-[2r]furyl)-(3ar,10at,10bt)-decahydro-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one；4-Methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydro-[2r]furyl)-(3ar,10at,10bt)-decahydro-furo[3,2-c]pyrrolo[1,2-a]azepin-2-yliden]-5H-furan-2-on；Protostemonin；Prostemonin；4-methoxy-3-methyl-5-[(1S,2R,3S,6R,11S)-3-methyl-11-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.02,6]tridecan-4-ylidene]furan-2-one

4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydrofuran-2r-yl)-(3ar,10at,10bt)-decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one化学式

CAS

27495-40-5；145841-08-3

化学式

C₂₃H₃₁NO₆

mdl

——

分子量

417.502

InChiKey

JDGNFRYDHRYXNL-COFPNGGOSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

172℃
沸点：

594.1±50.0 °C(Predicted)
密度：

1.27

计算性质

辛醇/水分配系数(LogP)：

3
重原子数：

30
可旋转键数：

2
环数：

5.0
sp3杂化的碳原子比例：

0.74
拓扑面积：

74.3
氢给体数：

0
氢受体数：

7

SDS

SDS：b9840d0e34b7cb8f5bec766a6aa31b65

查看

制备方法与用途

概述

百部是临床治疗咳嗽的常用有效中药，又名“嗽药”，擅长润肺止咳，可用于新久咳嗽，如急、慢性支气管炎、百日咳及肺结核等疾病的治疗。与吗啡、可待因相比，它没有成瘾性和呼吸抑制作用；与右美沙芬不同，它不会导致幻觉或精神不正常症状，具有广阔的开发前景。

制备

蔓生百部粉碎为粗粉（8.5 kg），使用8倍体积分数90%乙醇加热回流提取3次，每次1小时。合并提取液并过滤，滤液减压浓缩至稠浸膏。将浓缩液加入等量1%盐酸溶解，离心分离上清液。用浓氨水调pH值至10，以氯仿萃取3次。减压回收氯仿后得百部粗提取物（75 g）。另取蔓生百部粗提取物10 g，用4%盐酸200 mL溶解并过滤。滤液用氨水调节pH至8~8.5，以氯仿萃取直至无碘化铋钾反应，减压回收氯仿和滤液后干燥，得总生物碱部分6.0 g。

从上述百部总生物碱中，通过Sephedex LH-20柱色谱用甲醇洗脱，去除色素部分。收集含生物碱馏分并减压浓缩得到化合物Ⅰ（650 mg），经结构鉴定为原百部碱（protostemonine）。

生物活性

Protostemonine 是一种具有抗炎活性的生物碱，主要从 Stemona sessilifolia 根中分离得到。它对哮喘及革兰氏阴性菌引起的急性肺损伤表现出显著的抗炎作用。

化学性质

原百部碱为白色结晶粉末，可溶于甲醇、乙醇和DMSO等有机溶剂。

用途

原百部碱具有抗炎、抗菌、抗过敏及镇咳的作用。

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(1S,3aR,7S,9aS,9bR)-1-methyl-7-((2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)decahydro-3-oxa-6a-azacyclopenta[e]azulen-2-one	27498-90-4	C₁₇H₂₅NO₄	307.39

反应信息

作为反应物：

描述：

4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydrofuran-2r-yl)-(3ar,10at,10bt)-decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one 在 silver(l) oxide 作用下，以丙酮为溶剂，以25 mg的产率得到bisdehydroprotostemonine

参考文献：

名称：

Alkaloids of Stemona japonica

摘要：

DOI：

10.1016/s0031-9422(00)89559-x

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文献信息

Kondo; Satomi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1947, vol. 67, p. 182,183

作者：Kondo、Satomi

DOI：——

日期：——
Alkaloids of Stemona japonica

作者：Ye Yang、Qin Guo-Wei、Xu Ren-Sheng

DOI：10.1016/s0031-9422(00)89559-x

日期：1994.11

同类化合物

金刚大碱百部碱新对叶百部碱对叶百部碱 (7aR,8R,8aS,11S,11aS,11bR,11cR)-8-乙基十二氢-11-甲基-呋喃并[2,3-h]吡咯并[3,2,1-jk][1]苯并氮杂卓-10(2H)-酮 <3'S-<3'α,9'α(S*),9'aα>>-1',2',3',5',6',7',8'-octahydro-4-methyl-5-oxospiropyrrolo<1,2-a>azepin>-3'-carboxylic acid, hydrobromide salt <3'S-<3'α(S*),9'α(S*),9'aα>>-3'-(2,5-dihydro-4-methyl-5-oxo-2-furanyl)-1',2',3',5',6',7',8'-octahydro-4-methylspiropyrrolo<1,2-a>azepin>-5-one stemoamide (2S,4R,3'S,8'R,9a'S,2’’S,4’’S)-8'-methoxy-4-methyl-3’-(4-methyl-5-oxotetrahydrofuran-2-yl)octahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5(4H)-one tuberostemospiroline 2-oxostenine (3aR,10aR,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione (3aR,9aS,9bR)-3a,6,8,9,9a,9b-Hexahydro-1H-3-oxa-6a-aza-cyclopenta[e]azulene-2,7-dione (2S,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-1',2',3',7',8',9a'-hexahydro-5H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(6'H)-dione diethyl (2S,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-5,5'-dioxo-1',2',3',5',6',7,'8',9a'-octahydro-5H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin-4-yl}phosphonate (2S,4R,3'S,8'R,9a'S,2’’S)-8'-methoxy-4-methyl-3’-(4-methylene-5-oxotetrahydrofuran-2-yl)hexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione (2S,4R,3'S,8'R,9a'S,2’’R)-8'-methoxy-4-methyl-3’-(4-methylene-5-oxotetrahydrofuran-2-yl)hexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione (1R,2S,10R,12R,16R)-14,14-dimethyl-11,13,15-trioxa-6-azatetracyclo[8.6.0.02,6.012,16]hexadec-8-en-5-one 13-desmethyl-5-oxostenine (3aR,10aS)-1-methyl-3a,4,5,6,10,10a-hexahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(9H)-dione (1R,9R,10R,11S,14S,15S,16R)-14-methyl-10-prop-2-enyl-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadecane-5,13-dione 8-des-ethyl-(8S)-allyl-(-)-tuberostemonine didehydrotuberostemonine (-)-4-thiostenine (-)-4-oxostenine (3aR,10aS,10bS)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione (+)-9a-epi-stemoamide (2S,4R,3'S,8'R,9a'S)-3'-hydroxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione isoprotostemonine (1S,2S,3R,4R,6R)-3-hydroxy-4-methoxy-5-oxa-10-azatricyclo[8.3.0.02,6]tridecan-11-one (1S,3aR,7S,9aS,9bR)-1-methyl-7-((2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)decahydro-3-oxa-6a-azacyclopenta[e]azulen-2-one 4-methoxy-3-methyl-5-[(2Z,3aR)-1t-methyl-8t-((2S)-4c-methyl-5-oxo-tetrahydrofuran-2r-yl)-(3ar,10at,10bt)-decahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-5H-furan-2-one 8-epi-stemoamide sessilifoliamide A (2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione (2R,3'S,8'R,9a'S)-8'-methoxy-4-methylene-3'-[(2S)-4-methylene-5-oxotetrahydrofuran-2-yl]hexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione (2R,3'S,8'R,9a'S)-3'-hydroxymethyl-5,5'-dioxo-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-(4H,6'H)-carbaldehyde (2R,3'S,8'R,9a'S,2''R)-8'-methoxy-4-methylene-3'-[(2S)-4-methylene-5-oxotetrahydrofuran-2-yl]hexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione (2R,3'S,8'R,9a'S)-3'-hydroxymethyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione protostemonine (3S,9R,10R,11S,15R)-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-10-prop-2-enyl-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadec-6-en-13-one Tuberostemonin (1R,4S,10R,11R,12R,15S,16S)-11-ethyl-15-hydroxy-15-methyl-4-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-13-oxa-5-azatetracyclo[8.6.0.01,5.012,16]hexadecan-14-one (1R,3S,9R,10R,11S,14S,15S,16R)-3-[(2S)-4,4-dimethyl-5-oxooxolan-2-yl]-14-methyl-10-prop-2-enyl-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadecan-13-one (3S,9R,10R,11S,14S,15S,16R)-10-ethyl-14-methyl-3-[(2S,4R)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadecan-13-one (1S,2R,3S)-3-methyl-11-[(2S)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.02,6]tridecan-4-one (9R,10R,11S,14S,15S,16R)-10-ethyl-14-methyl-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadecan-13-one (10S,11S,14R,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadeca-1(16),2-dien-13-one