1.Isolation and structure determination of coumarine from extract of Eupatorium chinese L
Pharmaceutical Journal 2003;326(6):12-13
Eupatorium chinese L. is an indegenous plant using in the folk medicine of Vietnam. From the ethanol extract and petroleum – ether extract of aerial parts of this plant a coumarin was isolated. It’s structure was identified by MS, 1H-NMR, 13C-NMR and 13C-DEPT methods
Coumarins
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Drugs, Chinese Herbal
;
Medicine
2.Acetylcholinesterase Inhibitors from Angelica polymorpha Stem.
Yongsoo KWON ; Hyun Pyo KIM ; Myong Jo KIM ; Wanjoo CHUN
Natural Product Sciences 2017;23(2):97-102
Fourteen compounds were isolated from the stem of Angelica polymorpha. On the basis of spectral data, these compounds were identified as isoimperatorin (1), phellopterin (2), bergapten (3), xanthyletin (4), cnidilin (5), geijerine (6), (−)-3'-acetyl hamaudol (7), 7-demethylsuberosine (8), dehydrogeijerin (9), (−)-hamaudol (10), (+)-visamminol (11), divaricatol (12), scopoletin (13), and decursidate (14), respectively. Among them, compounds 4 - 6, 8, 9, 13, and 14 were isolated for the first time from A. polymorpha. Dehydrogeijerin (6) and geijerin (9) were isolated for the first time from genus Angelica. All isolates tested for inhibitory activity against acetylcholinesterae. Compounds 1 to 13 showed acetylcholinesterase inhibitory activity with IC₅₀ values ranging from 1.4 to 37.5 µM.
Acetylcholinesterase*
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Angelica*
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Cholinesterase Inhibitors*
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Chromones
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Coumarins
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Scopoletin
3.Chemical Constituents from Leaves of Pileostegia viburnoides Hook.f.et Thoms.
Xiao Jun LI ; Zu Zhen LIU ; Kwan Woo KIM ; Xiang WANG ; Zhi LI ; Youn Chul KIM ; Chang Soo YOOK ; Xiang Qian LIU
Natural Product Sciences 2016;22(3):154-161
Phytochemical investigation on the leaves of Pileostegia viburnoides Hook.f.et Thoms led to the isolation of twenty-five compounds, and their structures were identified as n-dotriacontane (1), taraxeryl acetate (2), friedelin (3), epifriedelinol (4), canophyllal (5), stigmast-4-en-3-one (6), stigmasterol (7), (24R)-5A-stigmastane-3,6-dione (8), ursolic acid (9), pomolic acid (10), umbelliferone (11), 4-epifriedelin (12), n-octatriacontanol (13), β-amyrin (14), α-amyrin (15), taraxerol (16), nonadecanol (17), friedelane (18), arachic acid (19), protocatechuic acid (20), n-pentatriacontanol (21), hexadecanoic acid (22), vincosamide (23), daucosterol (24), and skimming (25), respectively. To our best knowledge, compounds 1, 2, 12, 13, 17 - 19 and 21-23 were new within Saxifragaceae family. Compounds 15, 16, and 20 were produced from this genus for the first time. Compounds 4, 14 and 25 were first obtained from species P. viburnoides and compounds 3, 5 - 11, and 24 were achieved from the leaves of P. viburnoides for the first time. Furthermore, the anti-neuroinflammatory activity of these isolates was evaluated.
Coumarins
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Humans
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Palmitic Acid
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Saxifragaceae
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Stigmasterol
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Triterpenes
4.A new 3, 4-epoxyfurocoumarin from Heracleum moellendorffii Roots.
Sang Yeol PARK ; Nara LEE ; SunKyoung LEE ; Myong Jo KIM ; Wanjoo CHUN ; Hyun Pyo KIM ; Hee Jung YANG ; Ho Sun LEE ; Yongsoo KWON
Natural Product Sciences 2017;23(3):213-216
Activity-guided isolation of Heracleum moellendorffii roots led to four coumarin derivatives as acetylcholinesterase inhibitors. The structures of these isolates were characterized by spectroscopic method to be angelicin (1), isobergapten (2), pimpinellin (3), and (3S, 4R)-3, 4-epoxypimpinellin (4). All the isolated compounds 1, 2, 3, and 4 showed moderate inhibition activities against acetylcholinesterase with the IC₅₀ values of 10.2, 18.1, 21.5 and 22.9 µM, respectively. (3S, 4R)-3, 4-Epoxypimpinellin (4) was newly isolated from the plant source.
Acetylcholinesterase
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Cholinesterase Inhibitors
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Coumarins
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Heracleum*
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Methods
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Plants
5.L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid.
Xiu-hong LIU ; Ji-cai FAN ; Yang LIU ; Zhi-cai SHANG
Journal of Zhejiang University. Science. B 2008;9(12):990-995
The effect of L-proline as a promoter on the condensation reaction of salicylaldehyde or its derivatives with ethyl acetoacetate in neutral ionic liquid [emim]BF4 was studied. All reactions were carried out under mild reaction conditions and achieved high yields. Moreover, the ionic liquid containing L-proline could be recycled and reused for several times without noticeably decreasing in productivity. The results show that the L-proline-[emim]BF4 system has a potential in contribution to the development of environmentally friendly and inexpensive processes in organic syntheses.
Coumarins
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chemical synthesis
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Ionic Liquids
;
chemistry
;
Proline
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chemistry
6.One new coumarin from seeds of Herpetospermum pedunculosum.
Dan HUANG ; Ying-Xiong MA ; Lin WEI ; Yan SUN ; Qing-Hong ZENG ; Xiao-Zhong LAN ; Zhi-Hua LIAO ; Min CHEN
China Journal of Chinese Materia Medica 2021;46(10):2514-2518
This paper aims to investigate the chemical constituents of the seeds of Herpetospermum pedunculosum. One new coumarin and two known lignans were isolated from the ethanolic extract of the seeds of H. pedunculosum with thin layer chromatography(TLC), silica gel column chromatography, Sephedax LH-20 chromatography, Semi-preparative high performance liquid chromatography and recrystallization, etc. Their structures were elucidated as herpetolide H(1), phyllanglaucin B(2), and buddlenol E(3) by analysis of their physicochemical properties and spectral data. Among them, compound 1 was a new compound, and compounds 2 and 3 were isolated from this genus for the first time. In vitro anti-inflammatory activity test showed that herpetolide H had certain NO inhibitory activity for LPS-induced RAW 264.7 cells, with its IC_(50) value of(46.57±3.28) μmol·L~(-1).
Chromatography, High Pressure Liquid
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Coumarins/pharmacology*
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Cucurbitaceae
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Lignans
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Seeds
7.Advances in Phytochemistry and Modern Pharmacology of Saposhnikovia Divaricata (Turcz.) Schischk.
Jun-Wen GAO ; Yang ZHAN ; Yun-He WANG ; Shu-Jie ZHAO ; Zhong-Ming HAN
Chinese journal of integrative medicine 2023;29(11):1033-1044
Saposhnikovia divaricata (Turcz.) Schischk (S. divaricata, Fangfeng) is a herb in the Apiaceae family, and its root has been used since the Western Han Dynasty (202 B.C.). Chromones and coumarins are the pharmacologically active substances in S. divaricata. Modern phytochemical and pharmacological studies have demonstrated their antipyretic, analgesic, anti-inflammatory, antioxidant, anti-tumor, and anticoagulant activities. Technological and analytical strategy theory advancements have yielded novel results; however, most investigations have been limited to the main active substances-chromones and coumarins. Hence, we reviewed studies related to the chemical composition and pharmacological activity of S. divaricata, analyzed the developing trends and challenges, and proposed that research should focus on components' synergistic effects. We also suggested that, the structure-effect relationship should be prioritized in advanced research.
Drugs, Chinese Herbal/pharmacology*
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Coumarins/pharmacology*
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Apiaceae/chemistry*
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Chromones
8.Phenylpropanoids from Zanthoxylum species and their pharmacological activities: a review.
Hai-Mei YUAN ; Lu QIU ; Yu SONG ; Liang ZOU ; Long-Fei YANG ; Qiang FU
China Journal of Chinese Materia Medica 2021;46(22):5760-5772
Phenylpropanoids are one of the major chemical constituents in Zanthoxylum species. They include simple phenylpropanoids, coumarins, and lignans and possess anti-tumor, anti-inflammatory, anti-platelet aggregation, anti-bacterial, anti-viral, insecticidal, and antifeedant activities. This review summarizes the chemical constituents and pharmacological activities from the Zanthoxylum plants in hopes of providing reference for the research and application of phenylpropanoids from this genus.
Anti-Inflammatory Agents/pharmacology*
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Coumarins/pharmacology*
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Lignans
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Plant Extracts
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Zanthoxylum
9.Expression of β-glucosidase An-bgl3 from Aspergillus niger for conversion of scopolin.
Kunpeng YU ; Cheng PENG ; Yanling LIN ; Lijun LI ; Hui NI ; Qingbiao LI
Chinese Journal of Biotechnology 2023;39(3):1232-1246
Scopoletin is a coumarin compound with various biological activities including detumescence and analgesic, insecticidal, antibacterial and acaricidal effects. However, interference with scopolin and other components often leads to difficulties in purification of scopoletin with low extraction rates from plant resource. In this paper, heterologous expression of the gene encoding β-glucosidase An-bgl3 derived from Aspergillus niger were carried out. The expression product was purified and characterized with further structure-activity relationship between it and β-glucosidase analyzed. Subsequently, its ability for transforming scopolin from plant extract was studied. The results showed that the specific activity of the purified β-glucosidase An-bgl3 was 15.22 IU/mg, the apparent molecular weight was about 120 kDa. The optimum reaction temperature and pH were 55 ℃ and 4.0, respectively. Moreover, 10 mmol/L metal ions Fe2+ and Mn2+ increased the enzyme activity by 1.74-fold and 1.20-fold, respectively. A 10 mmol/L solution containing Tween-20, Tween-80 and Triton X-100 all inhibited the enzyme activity by 30%. The enzyme showed affinity towards scopolin and tolerated 10% methanol and 10% ethanol solution, respectively. The enzyme specifically hydrolyzed scopolin into scopoletin from the extract of Erycibe obtusifolia Benth with a 47.8% increase of scopoletin. This demonstrated that the β-glucosidase An-bgl3 from A. niger shows specificity on scopolin with good activities, thus providing an alternative method for increasing the extraction efficiency of scopoletin from plant material.
Aspergillus niger/genetics*
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beta-Glucosidase/chemistry*
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Scopoletin
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Polysorbates
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Coumarins
10.Chemical constituents of Lobelia chinensis.
Jinglan HAN ; Fengling ZHANG ; Zhihong LI ; Guanhua DU ; Hailin QIN
China Journal of Chinese Materia Medica 2009;34(17):2200-2202
OBJECTIVETo study the chemical constituents from Lobelia chinensis.
METHODThe constituents were extracted with 95% EtOH, partitioned with different solvents, and isolated and purified by silica gel column chromatography and crystallization, their structures were elucidated by physico-chemical properties and spectroscopic data.
RESULTSeven compounds were isolated from the titled plant. They were identified as 5-hydroxy-4'-methoxyflavone-7-O-rutinoside (1), n-butyl-O-beta-D-fructopyranoside (2), 5,7-dimethoxycoumarin (3), cirsiumaldehyde (4), diosmetin (5), 5-hydroxymethyl-2-furancarboxaldehyde (6), and 6-hydroxy-7-methoxycoumarin (7).
CONCLUSIONCompounds 2-4, 6, and 7 were obtained from the titled plant for the first time.
Coumarins ; analysis ; Furans ; analysis ; Lobelia ; chemistry ; Plant Extracts ; chemistry ; isolation & purification