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Article(id=1210147810863870067, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147807885923054, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2021-1633, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1636905600000, receivedDateStr=2021-11-15, revisedDate=1640620800000, revisedDateStr=2021-12-28, acceptedDate=null, acceptedDateStr=null, onlineDate=1766451321568, onlineDateStr=2025-12-23, pubDate=1652284800000, pubDateStr=2022-05-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1766451321568, onlineIssueDateStr=2025-12-23, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1766451321568, creator=13701087609, updateTime=1766451321568, updator=13701087609, issue=Issue{id=1210147807885923054, tenantId=1146029695717560320, journalId=1189982191388893191, year='2022', volume='57', issue='5', pageStart='1219', pageEnd='1540', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1766451320859, creator=13701087609, updateTime=1766451433476, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1210148280286179842, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147807885923054, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1210148280286179843, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210147807885923054, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1444, endPage=1447, ext={EN=ArticleExt(id=1210147811425906809, articleId=1210147810863870067, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new tirucallane-type triterpene from the gum resin of Boswellia carterii, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Two compounds were isolated from 95% ethanol extract of the gum resin of Boswellia carterii by silica gel column chromatography (CC) and high-performance liquid chromatography (HPLC). Their structures were identified with IR, UV, NMR and HR-ESI-MS spectroscopic data as 7α-hydroxy-3, 11-dioxo- tirucalla-8, 24-dien-21-oic acid (1) and 21β-hydroxy-3-acetyl-11-keto-β-boswellic acid (2). In addition, their absolute configurations were also identified by ECD calculations. Among them, compound 1 is a new compound and the absolute configuration of compound 2 is confirmed by ECD calculation for the first time.

, correspAuthors=Long-ru SUN, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2022 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=Ya-mei FENG, Qiang ZHANG, Li-min YIN, Long-ru SUN), CN=ArticleExt(id=1210147814240284868, articleId=1210147810863870067, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=乳香中一个新的甘遂烷型三萜, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

为研究乳香的化学成分, 本文采用硅胶柱色谱和高效液相色谱从乳香95%乙醇浸膏中分离得到2个化合物, 通过IR、UV、NMR和HR-ESI-MS等方法对其进行结构解析, 并借助ECD计算确定其绝对构型, 分别是: 7α-羟基-3, 11-二羰基-甘遂-8, 24-二烯-21-酸(1) 和21β-羟基-3-乙酰基-11-羰基-β-乳香酸(2), 其中化合物1是新化合物, 化合物2为首次采用ECD计算确定其绝对构型的已知化合物。

, correspAuthors=孙隆儒, authorNote=null, correspAuthorsNote=
*孙隆儒, Tel: 86-531-88382012, Fax: 86-531-88382548, E-mail:
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No. δH, J in Hz δC
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1b 2.58 m
2a 2.43 m 35.1
2b 2.65 m
3 211.0
4 47.6
5 2.36 m 45.4
6a 1.28 m 30.5
6b 1.72 m
7 4.30 br s 65.1
8 160.9
9 140.2
10 38.6
11 202.6
12a 2.23 d (18.4) 50.1
12b 2.55 d (18.4)
13 47.6
14 52.0
15a 1.47 m 30.1
15b 2.48 m
16a 1.47 m 27.3
16b 2.08 m
17 2.24 m 48.2
18 1.00 s 18.1
19 1.12 s 18.6
20 2.33 m 45.4
21 180.1
22a 1.56 m 33.5
22b 1.56 m
23 1.97 m 26.9
24 5.11 t (7.2) 124.7
25 133.1
26 1.68 s 25.8
27 1.60 s 17.7
28 1.13 s 28.1
29 1.06 s 21.1
30 1.07 s 25.9
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1H NMR (400 MHz in CD3OD) and 13C NMR (100 MHz in CD3OD) spectroscopic data of compound 1

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No. δH, J in Hz δC
1a 1.62 m 35.3
1b 2.58 m
2a 2.43 m 35.1
2b 2.65 m
3 211.0
4 47.6
5 2.36 m 45.4
6a 1.28 m 30.5
6b 1.72 m
7 4.30 br s 65.1
8 160.9
9 140.2
10 38.6
11 202.6
12a 2.23 d (18.4) 50.1
12b 2.55 d (18.4)
13 47.6
14 52.0
15a 1.47 m 30.1
15b 2.48 m
16a 1.47 m 27.3
16b 2.08 m
17 2.24 m 48.2
18 1.00 s 18.1
19 1.12 s 18.6
20 2.33 m 45.4
21 180.1
22a 1.56 m 33.5
22b 1.56 m
23 1.97 m 26.9
24 5.11 t (7.2) 124.7
25 133.1
26 1.68 s 25.8
27 1.60 s 17.7
28 1.13 s 28.1
29 1.06 s 21.1
30 1.07 s 25.9
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乳香中一个新的甘遂烷型三萜
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冯亚美 1 , 张强 2 , 尹立敏 1 , 孙隆儒 1, *
药学学报 | 研究论文 2022,57(5): 1444-1447
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药学学报 | 研究论文 2022, 57(5): 1444-1447
乳香中一个新的甘遂烷型三萜
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冯亚美1, 张强2, 尹立敏1, 孙隆儒1, *
作者信息
  • 1.山东大学药学院, 山东 济南 250012
  • 2.西北农林科技大学化学与药学院, 陕西 咸阳 712100

通讯作者:

*孙隆儒, Tel: 86-531-88382012, Fax: 86-531-88382548, E-mail:
A new tirucallane-type triterpene from the gum resin of Boswellia carterii
Ya-mei FENG1, Qiang ZHANG2, Li-min YIN1, Long-ru SUN1, *
Affiliations
  • 1. School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China
  • 2. College of Chemistry & Pharmacy, Northwest A&F University, Xianyang 712100, China
出版时间: 2022-05-12 doi: 10.16438/j.0513-4870.2021-1633
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摘要
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为研究乳香的化学成分, 本文采用硅胶柱色谱和高效液相色谱从乳香95%乙醇浸膏中分离得到2个化合物, 通过IR、UV、NMR和HR-ESI-MS等方法对其进行结构解析, 并借助ECD计算确定其绝对构型, 分别是: 7α-羟基-3, 11-二羰基-甘遂-8, 24-二烯-21-酸(1) 和21β-羟基-3-乙酰基-11-羰基-β-乳香酸(2), 其中化合物1是新化合物, 化合物2为首次采用ECD计算确定其绝对构型的已知化合物。

乳香  /  四环三萜  /  7α-羟基-3, 11-二羰基-甘遂-8, 24-二烯-21-酸

Two compounds were isolated from 95% ethanol extract of the gum resin of Boswellia carterii by silica gel column chromatography (CC) and high-performance liquid chromatography (HPLC). Their structures were identified with IR, UV, NMR and HR-ESI-MS spectroscopic data as 7α-hydroxy-3, 11-dioxo- tirucalla-8, 24-dien-21-oic acid (1) and 21β-hydroxy-3-acetyl-11-keto-β-boswellic acid (2). In addition, their absolute configurations were also identified by ECD calculations. Among them, compound 1 is a new compound and the absolute configuration of compound 2 is confirmed by ECD calculation for the first time.

Boswellia carterii  /  tirucallane-type triterpene  /  7α-hydroxy-3, 11-dioxo-tirucalla-8, 24-dien-21-oic acid
冯亚美, 张强, 尹立敏, 孙隆儒. 乳香中一个新的甘遂烷型三萜. 药学学报, 2022 , 57 (5) : 1444 -1447 . DOI: 10.16438/j.0513-4870.2021-1633
Ya-mei FENG, Qiang ZHANG, Li-min YIN, Long-ru SUN. A new tirucallane-type triterpene from the gum resin of Boswellia carterii[J]. Acta Pharmaceutica Sinica, 2022 , 57 (5) : 1444 -1447 . DOI: 10.16438/j.0513-4870.2021-1633
正文
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乳香是橄榄科(Burseraceae) 植物卡氏乳香树(Boswellia carterii Birdw.) 和齿叶乳香树(Boswellia serrate.) 的皮部渗出的胶状树脂, 主产于索马里、埃塞俄比亚等地。乳香为传统中药, 临床上常用于治疗风湿和类风湿性关节炎[1, 2]。乳香的化学成分主要是萜类, 包括五环三萜、四环三萜、二萜和单萜类化合物[3, 4]。此外, 还含有挥发油、有机酸和多糖类化合物[5, 6]。其中, 3-乙酰基-11-羰基-β-乳香酸(AKBA) 是乳香中五环三萜类的代表性化合物, 为目前许多学者的研究热点[[7, 8]。本实验借助硅胶柱色谱、制备薄层色谱和高效液相色谱, 对乳香中的化学成分进行分离和结构鉴定, 得到2个化合物(图 1), 分别是: 7α-羟基-3, 11-二羰基-甘遂-8, 24-二烯-21-酸(1) 和21β-羟基-3-乙酰基-11-羰基-β-乳香酸(2), 其中化合物1是新化合物, 化合物2为首次采用ECD计算确定其绝对构型的已知化合物。
结果与讨论
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化合物1, 白色无定形粉末。根据其HR-ESI-MS m/z: 519.289 1 [M+Cl]- (C30H44O5Cl计算值为519.279 9), 确定其分子式是C30H44O5。红外图谱3 200~2 500 cm-1的振动吸收峰表明有羧基, 3 427、1 700和1 657 cm-1振动吸收表明有羟基、羰基和双键的存在。1H NMR谱中7组甲基质子信号(表 1) 分别是: δH 1.00 (3H, s, CH3-18)、1.12 (3H, s, CH3-19)、1.68 (3H, s, CH3-26)、1.60 (3H, s, CH3-27)、1.13 (3H, s, CH3-28)、1.06 (3H, s, CH3-29) 和1.07 (3H, s, CH3-30), 1个双键烯质子信号δH 5.11 (1H, t, J = 7.2 Hz, H-24) 和1个连氧的次甲基质子信号δH 4.30 (1H, brs, H-7), 在化学位移δH 1.2~2.7之间是多个重叠的亚甲基和次甲基质子信号。13C NMR图谱中有30个碳信号, 结合DEPT和HSQC图谱, 其含有7个甲基、8个亚甲基、5个次甲基、7个季碳和3个羰基碳(δC 180.1、δC 202.6和δC 211.0), 故推断其为甘遂烷型四环三萜类化合物。
在HMBC谱中(图 2), δH 1.12 (3H, s, CH3-19) 与C-1、C-10、C-9 (δC 140.2) 和C-5相关; δH 1.07 (3H, s, CH3-30) 与C-8 (δC 160.9)、C-13、C-14和C-15相关; 且H-12与C-11 (δC 202.6) 相关; 由此确定C-8、C-9和C-11为α, β不饱和酮片段。在1H-1H COSY图谱上, H-5与H-6相关, H-6与δH 4.30 (H-7) 相关, 故推测OH连在C-7位置上。NOESY图谱中(图 3) CH3-18与H-20相关, H-5与CH3-28相关; H-2a与CH3-19、CH3-29相关, CH3-19与CH3-30相关, CH3-30与H-12a和H-17相关, 且H-7与CH3-30存在相关信号, 表明7-OH为α构型, 故确定其相对结构为7α-羟基-3, 11-二羰基-甘遂-8, 24-二烯-21-酸。此外, 该化合物的CD谱上, 在250 nm和289 nm显示正Cotton效应(图 4), 而且其实验ECD曲线和计算ECD曲线相吻合, 进一步确定其绝对构型为(5R, 7R, 10S, 13S, 14S, 17S, 20S)-7α-羟基-3, 11-二羰基-甘遂-8, 24-二烯-21-酸。
化合物2, 白色针状结晶(甲醇), 熔点164~166 ℃, [α]$ {}_{\mathrm{D}}^{20} $: +47.1 (c 0.5, CH3OH)。根据其HR-ESI-MS m/z: 527.337 7 [M-H]- (C32H47O6计算值为527.337 2), 确定其分子式是C32H48O6。1H NMR图谱显示8个甲基质子信号和1个双键烯质子信号δH 5.55 (1H, s, H-12), 2个连氧的次甲基质子信号δH 5.31 (1H, brs, H-3) 和δH 3.41 (1H, m, H-21), 碳谱上对应的碳化学位移分别为73.1和78.3。13C NMR图谱显示有32个碳信号, DEPT和HSQC图谱显示, 该化合物结构中含有8个甲基、7个亚甲基、8个次甲基、6个季碳和3个羰基碳(δC 170.2、δC 179.6和δC 196.6)。将其1H NMR和13C NMR数据与文献[9, 10]数据比较, 结合2D NMR图谱分析, 在HMBC图谱上, δH 0.98 (3H, s, CH3-30) 与C-21 (δC 78.3)、C-19和C-20相关, 表明羟基连在C-21位; 在NOESY图谱上, H-21与H-30存在NOE相关信号, 表明21-OH是β构型, 故确定其为21β-羟基-3-乙酰基-11-羰基-β-乳香酸。此外, 为进一步确定其绝对构型, 测定了该化合物的CD图谱, 其CD谱上250 nm处峰为正Cotton效应, 且实验ECD曲线和计算ECD曲线吻合, 故确定其绝对构型为(3R, 4R, 5R, 8R, 9R, 10S, 14S, 17S, 18R, 19R, 20S, 21R)-21β-羟基-3-乙酰基-11-羰基-β-乳香酸(图 5)。
实验部分
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旋转蒸发仪(日本EYELAN-1000); RY-1G型显微熔点测定仪(天津天光光学仪器有限公司); MCP 200型旋光测定仪(奥地利Anton Paar); Nicolet iN10型显微红外光谱仪(德国Thermo Fisher公司); LTQ-Orbitrap XL型质谱仪(德国Thermo Fisher公司); Bruker Avance AVIII-400核磁共振仪(德国Bruker公司); Agilent 1200型高效液相色谱仪(美国Agilent公司)。柱色谱硅胶(100~200目和200~300目) 和薄层色谱硅胶GF254 (青岛海洋化工厂); 柱色谱所用石油醚(PE)、乙酸乙酯(EtOAc) 和二氯甲烷(CH2Cl2) 等均为分析纯, 购于天津市富宇精细化工有限公司; HPLC中使用的乙腈(CH3CN) 均为色谱级别, 纯净水由杭州娃哈哈公司生产。
乳香于2019年3月购自购于安徽亳州药材市场, 经山东大学温学森教授鉴定为橄榄科植物卡氏乳香树(Boswellia carterii Birdw.) 的皮部渗出的胶状树脂, 保存在山东大学药学院天然药物化学研究所, 样品编号为2019003。
1 提取分离
乳香4.50 kg, 粉碎后用95%乙醇提取4次, 每次2 h, 合并提取液后, 减压回收溶剂得到浸膏3.21 kg。取1.97 kg浸膏加乙酸乙酯溶解后用1% NaOH溶液萃取并调酸, 最后得到乳香总三萜酸类浸膏660.45 g。取浸膏50.00 g, 用200~300目硅胶柱色谱进行分离, 以石油醚-乙酸乙酯(100∶0, 99∶1, 98∶2, 97∶3, 96∶4, 95∶5, 90∶10, 80∶20和50∶50) 为洗脱剂进行分离, 得到25个组分Fr.1~Fr.25。Fr.22采用硅胶柱色谱, 以PE-EtOAc和CH2Cl2-CH3OH梯度洗脱后, 又分成15个亚组分Fr.22-1~Fr.22-15。Fr.22-9经过两次HPLC纯化(流动相依次为90% CH3CN和60% CH3CN, 检测波长247 nm; 流速1.5 mL·min-1; 保留时间分别为15 min和38 min) 得到化合物1 (2.48 mg)。Fr.22-10同样经过两次HPLC纯化(流动相依次为90% CH3CN和60% CH3CN, 检测波长247 nm; 流速1.5 mL·min-1; 保留时间分别为14 min和34 min) 得到化合物2 (2.84 mg)。
2 结构鉴定
化合物1  白色无定形粉末, HR-ESI-MS m/z: 519.289 1 [M+Cl]- (C30H44O5Cl计算值为519.279 9), 483.311 4 [M-H]- (C30H43O5计算值为483.311 0); [α]$ {}_{\mathrm{D}}^{20} $ +26.4 (c 1.0, CH3OH); UV (CH3OH) λmax (log ε): 250 (1.16) nm; ECD (c 1.05×10-3 mol·L-1, CH3OH) λmax (Δε): 250 (+21.12) nm、289 (+10.66) nm; IR (KBr) νmax: 3 427、2 934、1 700、1 657 cm-1; 1H NMR和13C NMR数据见表 1。
化合物2  白色粉末; HR-ESI-MS m/z: 527.337 7 [M-H]- (C32H47O6计算值为527.337 2); 熔点164~166 ℃; [α]$ {}_{\mathrm{D}}^{20} $ +47.1 (c 0.5, CH3OH); UV (CH3OH) λmax (log ε): 247 (1.24) nm; ECD (c 1.05×10-3 mol·L-1, CH3OH) λmax (Δε): 250 (+ 10.72) nm; IR (KBr) νmax: 3 448、2 970、2 927、2 872、1 740、1 670、1 658、1 232 cm-1; 1H NMR (400 MHz, CDCl3) δ: 5.55 (1H, s, H-12), 5.31 (1H, brs, H-3), 3.41 (1H, m, H-21), 2.43 (1H, s, H-9), 2.09 (3H, CH3COO), 1.37 (3H, s, CH3-27), 1.24 (3H, s, CH3-23), 1.20 (3H, s, CH3-26), 1.15 (3H, s, CH3-25), 1.00 (3H, s, CH3-28), 0.98 (3H, s, CH3-30), 0.80 (3H, d, J = 6.4 Hz, CH3-29); 13C NMR (100 MHz, CDCl3) δ: 34.6 (C-1), 23.5 (C-2), 73.1 (C-3), 46.4 (C-4), 50.4 (C-5), 20.4 (C-6), 32.7 (C-7), 45.2 (C-8), 60.4 (C-9), 37.4 (C-10), 196.6 (C-11), 130.7 (C-12), 164.1 (C-13), 44.4 (C-14), 26.7 (C-15), 26.7 (C-16), 39.1 (C-17), 58.5 (C-18), 39.0 (C-19), 37.3 (C-20), 78.3 (C-21), 38.9 (C-22), 23.8 (C-23), 179.6 (C-24), 13.3 (C-25), 18.3 (C-26), 20.6 (C-27), 21.3 (C-28), 17.3 (C-29), 24.9 (C-30), 20.8 (CH3COO), 170.2 (CH3COO)。根据以上数据, 结合参考文献[9], 确定该化合物为21β-羟基-3-乙酰基-11-羰基-β-乳香酸。
作者贡献: 冯亚美主要负责乳香化学成分的提取分离、化合物的结构鉴定和文章的整理。张强主要负责化合物1和化合物2的ECD图谱计算, 确定其绝对构型。尹立敏协助完成化合物结构鉴定。通讯作者孙隆儒对稿件负总责。
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基金
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  • 山东省自然科学基金资助项目(ZR2019MH088)
文献
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参考文献 引证文献
排序方式：
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Banno N , Akihisa T , Yasukawa K et al . Anti-inflammatory activities of the triterpene acids from the resin of Boswellia carteri[J]. J Ethnopharmacol, 2006, 107: 249-253.
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Lv MH , Zhuang XB , Zhang Q et al . Acetyl-11-keto-β-boswellic acid enhances the cisplatin sensitivity of non-small cell lung cancer cells through cell cycle arrest, apoptosis induction, and autophagy suppression via p21-dependent signaling pathway[J]. Cell Biol Toxicol, 2021, 37: 209-228.
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Yu JQ , Geng YL , Wang DJ et al . Terpenes from the gum resin of Boswellia carterii and their NO inhibitory activities[J]. Phytochem Lett, 2018, 28: 59-63.
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Wang C , Dong PP , Zhang LY et al . Regio- and stereo-selective oxidation of β-boswellic acids transformed by filamentous fungi[J]. RSC Adv, 2015, 5: 12717-12725.
2022年第57卷第5期
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doi: 10.16438/j.0513-4870.2021-1633
  • 接收时间：2021-11-15
  • 首发时间：2025-12-23
  • 出版时间：2022-05-12
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  • 收稿日期：2021-11-15
  • 修回日期：2021-12-28
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山东省自然科学基金资助项目(ZR2019MH088)
作者信息
    1.山东大学药学院, 山东 济南 250012
    2.西北农林科技大学化学与药学院, 陕西 咸阳 712100

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*孙隆儒, Tel: 86-531-88382012, Fax: 86-531-88382548, E-mail:
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2种不同金属材料的力学参数
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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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