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Article(id=1222467101344911467, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222467099071603148, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2019-0234, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1554307200000, receivedDateStr=2019-04-04, revisedDate=1555516800000, revisedDateStr=2019-04-18, acceptedDate=null, acceptedDateStr=null, onlineDate=1769388469301, onlineDateStr=2026-01-26, pubDate=1562860800000, pubDateStr=2019-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1769388469301, onlineIssueDateStr=2026-01-26, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1769388469301, creator=13701087609, updateTime=1769388469301, updator=13701087609, issue=Issue{id=1222467099071603148, tenantId=1146029695717560320, journalId=1189982191388893191, year='2019', volume='54', issue='7', pageStart='1145', pageEnd='1332', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1769388468759, creator=13701087609, updateTime=1769389451859, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1222471222554775860, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222467099071603148, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1222471222554775861, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222467099071603148, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1257, endPage=1259, ext={EN=ArticleExt(id=1222467101865005171, articleId=1222467101344911467, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new cadalene sesquiterpene glycoside from Dendrobium nobile, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Using column chromatographic and preparative HPLC technologies, we isolated a new sesquiterpene glycoside from the stem of Dendrobium nobile. With spectroscopic techniques including NMR and MS, the new compound was identified as cadalene-12-O-β-D-glucopyranoside. This type of compound was dehydrogenated from cadinane sesquiterpene to achieve a naphthalene ring, and it is rare from a natural resource.

, correspAuthors=Shi-ji XIAO, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2019 Acta Pharmaceutica Sinica. All rights reserved., copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=Ting WU, Mao-sheng ZHANG, Jian-yong ZHANG, Xiao-fei LI, De-lin XU, Shi-ji XIAO), CN=ArticleExt(id=1222467102317990014, articleId=1222467101344911467, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=金钗石斛中一个新的卡达烯型倍半萜葡萄糖苷, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

通过各种色谱分离方法从贵州道地药材金钗石斛茎的醇提物非生物碱部分分离得到1个新的卡达烯型倍半萜葡萄糖苷，其结构经质谱和核磁共振等波谱技术鉴定，命名为卡达烯-12-O-β-D-葡萄糖苷。该类化合物骨架生源上由杜松烷型倍半萜高度去氢形成萘环得到卡达烯型倍半萜，此类化合物的糖苷在天然产物中较少见。

, correspAuthors=肖世基, authorNote=null, correspAuthorsNote=
*肖世基, Tel:86-851-28642513, Fax:86-851-28609343, E-mail:
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Position δH δC
1 132.6
2 7.90 (1H, d, J = 8.5 Hz) 125.9
3 7.33 (1H, br. d, J = 8.5 Hz) 128.4
4 136.3
5 7.96 (1H, br. s) 123.8
6 133.6
7 138.7
8 7.17 (1H, d, J = 7.2 Hz) 124.1
9 7.25 (1H, d, J = 7.2 Hz) 126.6
10 133.3
11 3.83 (1H, overlapped) 35.0
12 3.60 (1H, overlapped) 76.1
4.18 (1H, dd, dd, J = 9.7, 4.7 Hz)
13 1.41 (3H, d, J = 6.6 Hz) 19.2
14 2.51 (3H, s) 19.7
15 2.59 (3H, s) 22.2
1' 4.31 (1H, d, J = 7.8 Hz) 104.4
2' 3.20-3.40 (1H, overlapped) 75.2
3' 3.20-3.40 (1H, overlapped) 78.2
4' 3.20-3.40 (1H, overlapped) 71.7
5' 3.20-3.40 (1H, overlapped) 78.1
6' 3.60 (1H, m) 62.8
3.80-3.85 (1H, overlapped)
), ArticleFig(id=1222467106126418317, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222467101344911467, language=CN, label=Table 1, caption=

NMR data of cadalene-12-O-β-D-glucopyranoside (CD3OD, 400/100 MHz)

, figureFileSmall=null, figureFileBig=null, tableContent=
Position δH δC
1 132.6
2 7.90 (1H, d, J = 8.5 Hz) 125.9
3 7.33 (1H, br. d, J = 8.5 Hz) 128.4
4 136.3
5 7.96 (1H, br. s) 123.8
6 133.6
7 138.7
8 7.17 (1H, d, J = 7.2 Hz) 124.1
9 7.25 (1H, d, J = 7.2 Hz) 126.6
10 133.3
11 3.83 (1H, overlapped) 35.0
12 3.60 (1H, overlapped) 76.1
4.18 (1H, dd, dd, J = 9.7, 4.7 Hz)
13 1.41 (3H, d, J = 6.6 Hz) 19.2
14 2.51 (3H, s) 19.7
15 2.59 (3H, s) 22.2
1' 4.31 (1H, d, J = 7.8 Hz) 104.4
2' 3.20-3.40 (1H, overlapped) 75.2
3' 3.20-3.40 (1H, overlapped) 78.2
4' 3.20-3.40 (1H, overlapped) 71.7
5' 3.20-3.40 (1H, overlapped) 78.1
6' 3.60 (1H, m) 62.8
3.80-3.85 (1H, overlapped)
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金钗石斛中一个新的卡达烯型倍半萜葡萄糖苷
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武婷 1 , 张茂生 1 , 张建永 1 , 李晓飞 2 , 徐德林 3 , 肖世基 1, 2, *
药学学报 | 研究论文 2019,54(7): 1257-1259
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药学学报 | 研究论文 2019, 54(7): 1257-1259
金钗石斛中一个新的卡达烯型倍半萜葡萄糖苷
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武婷1, 张茂生1, 张建永1, 李晓飞2, 徐德林3, 肖世基1, 2, *
作者信息
  • 1.遵义医科大学药学院, 贵州 遵义 563006
  • 2.遵义医科大学贵州省兰科药用植物繁育及高效应用工程研究中心, 贵州 遵义 563006
  • 3.遵义医科大学基础医学院, 贵州 遵义 563006

通讯作者:

*肖世基, Tel:86-851-28642513, Fax:86-851-28609343, E-mail:
A new cadalene sesquiterpene glycoside from Dendrobium nobile
Ting WU1, Mao-sheng ZHANG1, Jian-yong ZHANG1, Xiao-fei LI2, De-lin XU3, Shi-ji XIAO1, 2, *
Affiliations
  • 1. School of Pharmacy, Zunyi Medical University, Zunyi 563006, China
  • 2. Guizhou Provincial Research Center for the Propagation and Efficient Utilization of Medicinal Orchids, Zunyi Medical University, Zunyi 563006, China
  • 3. School of Basic Medical Sciences, Zunyi Medical University, Zunyi 563006, China
出版时间: 2019-07-12 doi: 10.16438/j.0513-4870.2019-0234
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摘要
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通过各种色谱分离方法从贵州道地药材金钗石斛茎的醇提物非生物碱部分分离得到1个新的卡达烯型倍半萜葡萄糖苷，其结构经质谱和核磁共振等波谱技术鉴定，命名为卡达烯-12-O-β-D-葡萄糖苷。该类化合物骨架生源上由杜松烷型倍半萜高度去氢形成萘环得到卡达烯型倍半萜，此类化合物的糖苷在天然产物中较少见。

金钗石斛  /  兰科  /  倍半萜  /  葡萄糖苷  /  卡达烯

Using column chromatographic and preparative HPLC technologies, we isolated a new sesquiterpene glycoside from the stem of Dendrobium nobile. With spectroscopic techniques including NMR and MS, the new compound was identified as cadalene-12-O-β-D-glucopyranoside. This type of compound was dehydrogenated from cadinane sesquiterpene to achieve a naphthalene ring, and it is rare from a natural resource.

Dendrobium nobile  /  Orchidaceae  /  sesquiterpene  /  glycoside  /  cadalene
武婷, 张茂生, 张建永, 李晓飞, 徐德林, 肖世基. 金钗石斛中一个新的卡达烯型倍半萜葡萄糖苷. 药学学报, 2019 , 54 (7) : 1257 -1259 . DOI: 10.16438/j.0513-4870.2019-0234
Ting WU, Mao-sheng ZHANG, Jian-yong ZHANG, Xiao-fei LI, De-lin XU, Shi-ji XIAO. A new cadalene sesquiterpene glycoside from Dendrobium nobile[J]. Acta Pharmaceutica Sinica, 2019 , 54 (7) : 1257 -1259 . DOI: 10.16438/j.0513-4870.2019-0234
正文
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金钗石斛(Dendrobium nobile Lindl.)为兰科石斛属药用植物, 又名吊兰花、扁金钗、小黄草, 是我国传统名贵中药材, 贵州省赤水市的金钗石斛为地理标记产品。金钗石斛主要生长于海拔800~1 700 m的山坡林中树上或路边岩石上, 多为栽培, 分布于西南及台湾、湖北、广东、海南、广西等省份。金钗石斛以茎入药, 甘, 性微寒, 益胃生津, 滋阴清热。用于阴伤津亏、口干烦渴、食少干呕, 病后虚热、目暗不明[1]。研究表明石斛属植物具有增强机体免疫能力、抗氧化、抗肿瘤、抗血小板凝集及降血糖等方面的药理作用[2-4]。石斛属植物含有的化学成分复杂, 不同种所含化学成分不尽相同, 同种不同产地的石斛化学成分含量也有较大差异。金钗石斛主要含生物碱、芳香类和倍半萜类化合物[4-6]。为了进一步阐明黔产金钗石斛化学成分[7, 8], 为贵州道地药材的利用奠定物质基础, 本课题组继续对采自遵义赤水市的金钗石斛化学成分进行了研究, 从其醇提物非生物碱部位中分离得到1个新的卡达烯型倍半萜葡萄糖苷, 通过波谱技术鉴定了它的结构, 命名为卡达烯-12-O-β-D-葡萄糖苷(图 1)。此类化合物为杜松烷骨架上高度去氢而形成了萘环结构, 即卡达烯骨架, 卡达烯糖苷在天然产物中较少见[9-11]。
结果与讨论
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化合物为黄色胶状物, [α]D20-25.7 (c 0.13, MeOH)。HR-ESI-MS给出其准分子离子峰[M+Na]+ m/z: 399.180 2 (C21H28O6Na+, 计算值399.178 4), 确定其分子式为C21H28O6, 不饱和度为8。1H NMR (400 MHz, CD3OD) (表 1)显示有5个芳香氢信号, 包括1组1, 2, 4-三取代芳香氢信号δH 7.90 (1H, d, J = 8.5 Hz)、δH 7.33 (1H, br. d, J = 8.5 Hz)和δH 7.96 (1H, br. s); 1组芳香环上邻位偶合氢信号δH 7.17、7.25 (各1H, d, J = 7.2 Hz); 3个甲基氢信号δH 1.41 (3H, d, J = 6.6 Hz)、δH 2.51 (3H, s)和δH 2.59 (3H, s); 以及δH 3.00~4.40之间若干连氧的氢信号, 推测有1个糖单元结构。13C NMR (100 MHz, CD3OD)谱结合二维谱显示有21个碳信号包括10个芳香区碳信号δC 132.6、125.9、128.4、136.3、123.8、133.6、138.7、124.1、126.6、133.3; 3个甲基碳信号δC 19.2、19.7、22.2; 7个连氧的碳信号δC 76.1、62.8、104.4、75.2、78.2、71.7、78.1;还有1个叔碳信号δC 35.0。通过以上核磁数据推测化合物应该是一个萘环上有甲基的糖苷类化合物[12-14]。通过1H-1H COSY推测有CH3CH-CH2O-片段。通过和文献比较得出其有1个D-葡萄糖单元, 通过糖上端基氢的偶合常数J = 7.8 Hz推测出为β构型[15, 16], 进一步通过水解反应得到确证[17]。HMBC谱中H-15 [δH 2.59 (3H, s)]和C-3、C-4、C-5有相关, H-2和C-4、C-6有相关, 可以确定1个甲基处在萘环的C-4位上; H-14 [δH 2.51 (3H, s)]和C-1、C-9、C-10有相关, H-8和C-10有相关, H-9和C-10有相关, H-2和C-10也有相关, 可以确定另外1个甲基处在萘环的C-10位上; H-13 [δH 1.41 (3H, d, J = 6.6 Hz)]和C-11、C-12、C-7有相关, H-5和C-7有相关, 可以确定CH3CH-CH2O-片段连在C-7位上; H-12 [δH 4.18 (1H, dd, J = 9.7, 4.7 Hz)]和C-1'有相关, H-1' [δH 4.31 (1H, d, J = 7.8 Hz)]和C-12有相关, 可以确定葡萄糖单元连在C-12位上。至此, 化合物的结构得到确证, 命名为卡达烯-12-O-β-D-葡萄糖苷。该化合物苷元为双环倍半萜中的杜松烷型倍半萜骨架, 2个环都去氢之后得到萘环共轭体系, 称为卡达烯类化合物, 此类化合物的糖苷在自然界中较为少见。
实验部分
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Finnigan LCQDECA型质谱仪(美国Thermo公司); Agilent DD2400-MR型核磁共振仪, TMS为内标(美国Agilent公司); Bruker BiOTOF Q型质谱仪(德国Bruker公司); UV3600紫外可见近红外分光光度计(日本岛津公司); Varian1000红外光谱仪, KBr压片(美国Varian公司); Sepacore中压制备系统(瑞士BÜCHI公司); LC3000型高效液相色谱仪(中国北京创新通恒公司); C18 5 μ 10 mm×250 mm半制备HPLC柱(日本YMC公司); 20~45 μm ODS填料(日本Fuji Silysia公司); 薄层色谱硅胶GF 254和柱色谱硅胶(100~200, 300~400目) (青岛海洋化工公司); MCI树脂(日本Mitsubishi公司)。
金钗石斛茎于2014年9月采购自遵义赤水市, 由遵义医科大学生药学教研室杨建文教授鉴定为金钗石斛(Dendrobium nobile Lindl.), 样品标本(No.20141011)保存在遵义医科大学天然药物化学实验室。
将烘干的金钗石斛茎(50 kg)打粉后, 用乙醇回流提取3次, 浓缩得乙醇提取物4.8 kg, 将其分散于2.0%的盐酸水溶液中充分震荡, 减压过滤得酸水不溶物。将该酸水不溶物用乙醇充分溶解后拌入100~200目硅胶, 挥干溶剂后装入色谱柱, 先用石油醚洗脱, 接着用1:1石油醚-乙酸乙酯洗脱, 然后再用乙酸乙酯洗脱。减压浓缩得乙酸乙酯部分浸膏500 g, 将该部分浸膏充分溶解拌样, 进行柱色谱分离, 依次用石油醚、石油醚-乙酸乙酯(1:1)、乙酸乙酯、乙酸乙酯-甲醇(1:1)、甲醇洗脱, 浓缩各部分洗脱液合并得到乙酸乙酯部位浸膏共55 g, 该浸膏拌样之后再通过柱色谱分离, 用二氯甲烷-甲醇体系梯度洗脱(20:1、10:1、5:1、3:1、1:1), 得45瓶样品。第13到16瓶合并得到20 g浸膏, 拌样后过ODS柱色谱, 甲醇-水(30%~100%)梯度洗脱, 得5个部分Fr.1~5, Fr.3部分(2.89 g), 经中压硅胶柱色谱分离, 用二氯甲烷-甲醇梯度洗脱得到7个部分(Fr.3.1~7); Fr.3.3经半制备HPLC分离(甲醇-水, 83:17, V/V, 4.0 mL·min-1)得到该新化合物(tR = 12.0 min, 14 mg)。
基金
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  • 国家自然科学基金资助项目(31560102)
  • 贵州省教育厅自然科学研究项目(黔教合KY字[2015]362)
  • 贵州省科技重大专项子项目(黔科合重大专项字[2015]6010-2)
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2019年第54卷第7期
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doi: 10.16438/j.0513-4870.2019-0234
  • 接收时间：2019-04-04
  • 首发时间：2026-01-26
  • 出版时间：2019-07-12
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  • 收稿日期：2019-04-04
  • 修回日期：2019-04-18
基金
国家自然科学基金资助项目(31560102)
贵州省教育厅自然科学研究项目(黔教合KY字[2015]362)
贵州省科技重大专项子项目(黔科合重大专项字[2015]6010-2)
作者信息
    1.遵义医科大学药学院, 贵州 遵义 563006
    2.遵义医科大学贵州省兰科药用植物繁育及高效应用工程研究中心, 贵州 遵义 563006
    3.遵义医科大学基础医学院, 贵州 遵义 563006

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2种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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