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Small-molecule compounds with rich sources have diverse structures and activities. The active ingredients in traditional Chinese medicine(TCM) provide new sources for the discovery of new antitumor drugs. Aconitum plants as Chinese medicinal plants have the effects of dispelling wind, removing dampness, warming meridian, and relieving pain. They are mainly used to treat inflammation, pain, rheumatism, and tumors, improve heart function, and dilate blood vessels in clinical practice. Diterpenoid alkaloids are the main active components of Aconitum plants, including C20-, C19-, C18-diterpenoid alkaloids and bis-diterpenoid alkaloids. Stu-dies have demonstrated that diterpenoid alkaloids can effectively treat lung cancer, liver cancer, breast cancer, colon cancer and other cancers. Diterpenoid alkaloids are considered as the most promising natural compounds against cancers. In this review, we summarized the chemical structures and antitumor activities of C20-, C19-, C18-diterpenoid alkaloids and bis-diterpenoid alkaloids extracted from plants of Aconitum, aiming to provide reference for further development of diterpenoid alkaloids from Aconitum as antitumor drugs.
Subject(s)
Humans , Aconitum/chemistry , Molecular Structure , Alkaloids/analysis , Diterpenes/chemistry , Antineoplastic Agents/chemistry , Plant Roots/chemistryABSTRACT
Aconiti Lateralis Radix Praeparata (Fuzi in Chinese) is a commonly used Chinese materia medica in clinic, with the effects in rescuing from collapse by restoring yang, eliminating cold to stop pain, warming yang and transforming qi. C19 diterpenoid alkaloids from Fuzi can be divided into three types: diester type, monoester type and amine alcohol type, which can lead to neurotoxicity and cardiotoxicity while exerting anti-inflammatory, analgesic, anti-tumor and other pharmacodynamic effects. In this paper, the chemical structure, pharmacology and toxicological effects of C19 diterpene alkaloids of Fuzi were systematically combed, in order to provide a theoretical basis for safer and more effective use of Fuzi in clinic.
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Objective: To study the chemical constituents in the aerial parts of Aconitum carmichaelii. Methods: The air-dried arial parts of A. carmichaelii were powdered and extracted with methanol by percolation extraction. After the removal of solvent under reduced pressure, the crude extract was dissolved in 1.5% HCl solution, and then extracted by ethyl acetate to obtain the total crude extract. The compounds were isolated and purified by column chromatography and identified by spectral analyses (MS, 13C-NMR, and 1H-NMR). Results: Fifteen compounds were isolated from A. carmichaelii and characterized as indol-3-carboxylic acid (1), corchoionol C (2), β-sitosterol-3-O-β-D-glucoside-6’-palmitate (3), (+)-pinoresinol (4), (+)-N-formylnorglaucine (5), oxoglaucidaline (6), glaucine (7), (+)-cataline (8), kaempferol-7-O-α-L-rhamnofuranoside (9), kaempferol-3-O-β-(2″-acetyl)-galactopyranoside (10), megastigmane (11), kaempferol-7-O-α-L-arabinoside (12), kaempferol-3-O-β-D-xylopyranoside (13), kaempferol-3-O-β-D- glucopyranoside (14), and quercetin-3-O-β-D-galactopyranoside (15). Conclusion: All compounds are isolated from aerial parts of A. carmichaelii for the first time, and compounds 1-3,5-6,8-15 are isolated from this plant for the first time.
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OBJECTIVE： To study the diterpenoid alkaloids in Aconitum carmichaeli from Guizhou province， and to provide reference for the further enrichment of chemical constituents of plants from the genus Aconitum and the development and utilization of A. carmichaeli from Guizhou province. METHODS： The root tuber of A. carmichaeli from Guizhou province was collected. The total alkaloids of A. carmichaeli roots were extracted by acid extraction and alkali precipitation method. The diterpenoid alkaloids were obtained by isolating and purifying total alkaloids extract with silica gel column chromatography. The structures of the isolated compounds were elucidated on the basis of NMR and MS analysis. RESULTS & CONCLUSIONS： Fifteen diterpenoid alkaloids， including 12-epi-15-O-acetyl-17-benzoyl-16-hydroxy-16，17-dihydronapelline（Ⅰ），songorine（Ⅱ），songoramine（Ⅲ），10-aconifine（Ⅳ），hypaconitine（Ⅴ），deoxyaconitine（Ⅵ），aconitine（Ⅶ），mesaconitine（Ⅷ），14-benzoyltalasamine（Ⅸ），talatisamine（Ⅹ），neoline（ⅩⅠ），6-epi-chasmanine（ⅩⅡ），isotalatizidine（ⅩⅢ），sachaconitine（ⅩⅣ）and kalakoline（ⅩⅤ） were identified form A. carmichaeli roots from Guizhou Province. Compounds Ⅸ and ⅩⅡ were isolated from this specie for the first time.
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Eight C_(19)-diterpenoid alkaloids( 1-8) were isolated from the ethyl acetate soluble fraction of 95% ethanol extract of the ground roots of Aconitum austroyunnanense through various column chromatographies on silica gel,ODS,Sephadex LH-20 and MCI gel.Their structures were elucidated as 14α-benzoyloxy-13β,15α-dihydroxy-1α,6α,8β,16β,18-pentamethoxy-19-oxoaconitan( 1),N-deethylaconitine( 2),spicatine B( 3),leucanthumsine A( 4),acofamine B( 5),macrorhynine B( 6),aconitilearine( 7),and ambiguine( 8) based on their chemical and physicochemical properties and spectroscopic data. Compound 1 was a new compound and alkaloids 2-8 were isolated from this plant for the first time. Some isolated alkaloids were tested in vitro for cytotoxic potential by employing the MTT method. As a result,alkaloid 1 exhibited weak cytotoxic activity against three tested tumor cell lines( A-549,He La,and Hep G2) with IC_(50) values less than 20 μmol·L~(-1).
Subject(s)
Aconitum , Alkaloids , Diterpenes , Molecular Structure , Plant RootsABSTRACT
Objective To study the chemical constituents in the roots of Aconitum hemsleyanum var. circinatum. Methods The constituents were isolated and purified by silica gel chromatography from the roots of Aconitum hemsleyanum var. circinatum, and the structures were identified by spectral analysis (1H-NMR, 13C-NMR, and MS). Results Seventeen compounds were isolated from Aconitum hemsleyanum var. circinatum and characterized as sachaconitine (1), 8-O-methylsachaconitine (2), liljestrandisine (3), talatisamine (4), chasmannine (5), 8-O-methyltalatisamine (6), 14-O-acetyltalatisamine (7), 8-deacetyl-yunaconitine (8), crassicautine (9), crassicaudine (10), crassicauline A (11), vilmorianine C (12), vilmorianine A (13), yunaconitine (14), transconitine B (15), kongboendine (16), and franchetine (17). Conclusion Seventeen compounds are isolated from Aconitum hemsleyanum var. circinatu. Compounds 2-3, 6-7, 9, and 12-16 are isolated from Aconitum hemsleyanum var. circinatum for the first time.
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Objective: To study the chemical constituents in the roots of Aconitum bulleyanum Diels. Methods: The air-dried roots of A. bulleyanum were powdered and extracted by methanol with percolation. After removing the solvent under reduced pressure, the crude extract was dissolved in 1. 5％ HCl solution, and then basified to pH 9 by NaOH (5％) and extracted by ethyl acetate to ob-tain crude alkaloidal extract after ethyl acetate removal. The alkaloidal extract was isolated and purified by column chromatography, and their structures were identified based on spectral analysis ( 1 H-NMR, 13 C-NMR, MS) . Results:Totally 12 diterpenoid alkaloids were isolated from A. bulleyanum and characterized as foresaconitine (1), crassicauline A (2), chasmanine (3), talatisamine (4), 14-debenzoyl-franchetine (5), pengshenine A (6), crassicautine (7), yunaconitine (8), franchetine (9), liljestrandisine (10), transconitine B (11) and pseudoaconine (12). Conclusion:Compounds 3-7, 10-12 are isolated from this plant for the first time.
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Objective: To study the chemical constituents in the roots of Aconitum iochanicum Ulbr.Methods: The air-dried roots of A.iochanicum were powdered and extracted by methanol with a percolation method.After removing the solvent under reduced pressure, the crude extract was dissolved in1.5% HCl solution, and then extracted by ecetic ether.The acidic solution was basified to pH 9.0 by NaOH (5%) and extracted with ethyl acetate to obtain crude alkaloidal extract after the removal of ethyl acetate.The compounds were isolated and purified by column chromatography and identified based on spectral analysis (1H-NMR, 13C-NMR and MS).Results: Totally 18 compounds were isolated from A.iochanicum and characterized as 14-O-acetylsachaconitine (1), franchetine (2), crassicaudine (3), indaconoitine (4), 14-benzoyl chasmanine (5), 14-O-acetyltalatisamine (6), talatisamine (7), chasmannine (8), crassicauline A (9), bikhaconine (10), 13,15-dideoxyaconitine (11), crassicautine (12), kongboensine (13), liljestrandisine (14), ludaconitine (15), 8-deacetyl-yunaconitine (16), yunaconitine (17) and ouvrardiantine (18).Conclusion: It''s the first time to study the chemical constituents of A.iochanicum, and 18 diterpenoid alkaloids are isolated.
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Four compounds were isolated from the lateral roots of Aconitum carmichaeli by Al2O3,silica gel and preparative HPLC.Their structures were identified as:(13R,15S,19S)-13,15,19-triol-hetisan (1),fuziline (2),neoline (3) and beiwutine (4),by methods of NMR,MS spectroscopy as well as single crystal X-ray crystallography.Among them,compound 1 was considered as a new diterpenoid alkaloid.
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Objective:To study the chemical constituents in the roots of Aconitum transsectum. Methods:The compounds were i-solated and purified by column chromatography on the columns of silica gel, Al2 O3 and Sephadex LH-20, and their structures were elu-cidated on the basis of spectroscopic evidence ( MS and NMR) . Results:Totally 12 compounds were isolated from A. transsectum, and characterized as yunaconitine (1), indaconitine (2), crassialine A (3), 8-deacetylyunaconitine (4), talatisamine (5), chasma-conitine (6), 14-acetyltalatisamine (7), vilmoraconitine (8), sachaconitine (9), 14-acetylsachaconitine (10), acoforestinine (11) and vilmorrianine C (12). Conclusion:Compounds 8-11 are obtained from A. transsectum for the first time.
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Objective:To study the chemical constituents of Aconitum straminiflorum. Methods:The air-dried roots of A. stra-miniflorum were powdered and extracted three times with 90% ethonal under reflux. After the removal of the solvent under reduced pressure,the crude extract was dissolved in 1. 5% HCl solution(7 L). The acidic solution was basified to pH 9. 0 with ammonia (25%)and extracted with CHCl3 to obtain crude extract of total alkaloids after the removal of CHCl3 . The compounds were isolated and purified by column chromatography and identified based on spectral analysis( MS,1 H-üMR and 13 C-üMR). Results:Totally 7 compounds were isolated from A. straminiflorum,and characterized as aconosine(1),13-deoxyludaconitine(2),dolaconine(3), ezochasmanine(4),talatisamine(5),scopaline(6)and cammaconine(7),respectively. Conclusion:Seven diterpenoid alkaloids are isolated from A. Straminiflorum for the first time.
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AIM@#The aim of this work was to establish a specific and sensitive method to comprehensively investigate and compare chemical constituents of Fuzi-Gancao herb pair (FG), consisting of Aconitum carmichaelii Debeaux (Fuzi, Chinese) and Roast Radix Glycyrrhizae (Glycyrrhiza glabra L., Gancao, in Chinese) and Fuzi alone to explore the underlying interaction mechanism of FG.@*METHOD@#An ultra-fast liquid chromatography-ion trap/time-of-flight mass spectrometry (UFLC/MS-IT-TOF) method using diazepam as internal standard was developed for the identification and semi-quantitative analysis of the phytochemical constituents of Fuzi and FG. Chromatographic separation was achieved on a UFLC column using a gradient program with 40 mmol·L(-1) ammonium acetate and acetonitrile as the mobile phase.@*RESULTS@#Fifty-one of the sixty compounds, including forty-five C19-diterpenoid alkaloids and six C20-diterpenoid alkaloids were tentatively identified in the extracts of Fuzi and FG through accurate mass measurements and fragmentation patterns. Comparing the contents of these alkaloids in these two extracts, it was found that the diester-diterpenoid alkaloids (DDAs) and the alkylolamine-diterpenoid alkaloids (ADAs) were increased, while the monoester-diterpenoid alkaloids (MDAs) were decreased in the extracts of FG.@*CONCLUSION@#This work provided comprehensive information for the quality control of Fuzi preparations, and the further investigation on the compatibility mechanisms of FG.
Subject(s)
Aconitum , Chemistry , Chromatography, High Pressure Liquid , Methods , Drug Interactions , Drugs, Chinese Herbal , Chemistry , Glycyrrhiza , Chemistry , Mass Spectrometry , Methods , Molecular StructureABSTRACT
Objective: To study the chemical constituents in Qili Qiangxin Capsule (QQC) and to clear its material basis for efficacy. Methods: A rapid ultra-performance liquid chromatography/orthogonal acceleration time-of-flight mass spectrometry (UPLC/Q-TOF-MS/MS) method was established to identify the diterpenoid alkaloids in the active fraction of QQC. Using target compound screening method, the structures of monitored chemical constituents were identified by retention time, exact relative molecular mass, and cleavage fragments of MS/MS. Results: Twenty diterpenoid alkaloids were identified using XIC Manager, including 6 diester-diterpenoid alkaloids and 14 monoester-diterpenoid alkaloids. Conclusion: This method is simple and rapid for the identification of the constituents in QQC and the results are useful for the quality control of QQC.
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A HPLC-ELSD method was developed and validated for simultaneous determination of five Hetisane-type diterpenoid alkaloids in a Tibetan traditional herbal medicine, “Gebu Dilu” (Herba Delphinii), using a Kromasil C18 column (250 mm ? 4.6 mm, 5μm) with the mobile phase consisting of acetonitrile and 0.1% triethylamine in gradient (detected by evaporative light scattering detector). The linear ranges of five compounds were determined and method validation was evaluated completely. The established method is rapid and accurate with high repeatability, and can be applied for the quality control of Herba Delphinii.
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Aconitum species were used as the major component in the Chinese and Bhutanese herbal medicines. The species posses many phytochemical compounds which possess many of the pharmacological activities. Diterpene alkaloids were the main compound with the pharmacological activities such as analgesic and against inflammation. This alkaloid possesses certain toxic hydrolyzed bases which could be detoxified by the intervention of recent technologies. Apart from this, the plant possess many alkaloids, amide alkaloids, flavonoids, flavonol glycosides, diterpenoid and norditerpenoid compounds which possess medicinal values. The above mentioned compounds of potent importance were isolated and characterized by the chromatographic separation techniques and their structures were usually elucidated by the spectroscopic studies especially with Nuclear Magnetic Resonance techniques. These compounds were the central target of the medicinal chemist as they possess both medicinal and toxic nature. The measures to be taken in such a way that the medicinal compounds of the plant should be isolated and formulated without the toxic nature. This review encompasses the total phytochemical compounds that have been isolated from various species of the plant genus Aconitum.
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OBJECTIVE: To research the content of alkaloids and polysaccharides in different varieties of Aconitum carmichaeli. METHODS: The contents of total alkaloids, diester diterpenoid alkaloids and polysaccharides were measured by acid dye colorimetry, HPLC and sulphuric acid-anthrone colorimetric method respectively. RESULTS: In different varieties, the differences of total alkaloids and diester diterpenoid alkaloids were significant. However, the difference of polysaccharides wasn’t significant. The content of total alkaloids and diester diterpenoid alkaloids in processed A. carmichaeli reduced significantly while the content of polysaccharides increased slightly. CONCLUSION: The results of study could provide a scientific basis for rational breeding of A. carmichaeli.
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AIM: Radix Aconite is unprocessed parent root tuber of Aconitum carmichaeli Debx.containing toxic diterpenoid alkaloids such as mesaconitine,aconitine and hypaconitine.To establish the quality standard for this potent herb. METHODS: The microscopic examination technique,HPLC-UV and LC-MS-MS methods had been used. RESULTS: These methods can be used to analyse the quality of this potent herb. CONCLUSION: This paper proposes microscopic examination technique and physio-chemical methods such as HPLC-UV and LC-MS-MS for the identification and quantitative analysis of the herbs.