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1.
Yan Qin Ying-Jie He Yun-Li Zhao Zhong-Shun Zhou Zhao-Jie Wang Yan-Yan Zhu Xiao-Dong Luo 《Journal of separation science》2023,46(17):2200843
Monoterpene indole alkaloids exhibit structural diversity in herbal resources and have been developed as promising drugs owing to their significant biological activities. Confidential identification and quantification of monoterpene indole alkaloids is the key to quality control of target plants in industrial production but has rarely been reported. In this study, quantitative performance of three data acquisition modes of ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry including full scan, auto-MS2 and target-MS2, was evaluated and compared for specificity, sensitivity, linearity, precision, accuracy, and matrix effect using five monoterpene indole alkaloids (scholaricine, 19-epi-scholaricine, vallesamine, picrinine, and picralinal). Method validations indicated that target-MS2 mode showed predominant performance for simultaneous annotation and quantification of analytes, and was then applied to determine monoterpene indole alkaloids in Alstonia scholaris (leaves, barks) after extraction procedures optimization using Box-Behnken design of response surface methodology. The variations of A. scholaris monoterpene indole alkaloids in different plant parts, harvest periods, and post-handling processes, were subsequently investigated. The results indicated that target-MS2 mode could improve the quantitative capability of ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry for structure-complex monoterpene indole alkaloids in herbal matrices. Alstonia scholaris, monoterpene indole alkaloids, quadrupole time of flight mass spectrometry, qualitative and quantitative analysis, ultra-high-performance liquid chromatography 相似文献
2.
Rolf Kyburz Emanuel Schpp Manfred Hesse I. Ralph C. Bick 《Helvetica chimica acta》1979,62(8):2539-2546
Sorelline and Hobartine, Two New Indole Alkaloids from Aristotelia peduncularis (LABILL .) HOOK . F. From Aristotelia peduncularis (LABILL .) HOOK . F. two new indole alkaloids, sorelline ( 1 ) and hobartine ( 2 ), have been isolated. Their structures were elucidated on the basis of spectroscopic data (the formulae represent their relative configurations). The alkaloids 1 and 2 have closely related structures with a monosubstituted indole moiety and an unrearranged monoterpene unit in the aliphatic part. 相似文献
3.
《Tetrahedron letters》1988,29(42):5395-5396
Elegansamine (1) isolated from Gelsemium elegans (Thailand) was proved to be a new type of alkaloid composed by the carbon-carbon linkage of a monoterpenoid indole alkaloid and a monoterpene unit having the iridoid skeleton. 相似文献
4.
Total Synthesis of (+)‐Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization
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Ze‐Xin Zhang Si‐Cong Chen Prof. Dr. Lei Jiao 《Angewandte Chemie (International ed. in English)》2016,55(28):8090-8094
A new method for one‐step construction of the tetracyclic core structure of the indole alkaloid (+)‐minfiensine was developed utilizing a palladium‐catalyzed asymmetric indole dearomatization/iminium cyclization cascade. An efficient total synthesis of (+)‐minfiensine was realized using this strategy. The present method enables access to the common core structure of a series of monoterpene indole alkaloids, such as vincorine, echitamine, and aspidosphylline A. 相似文献
5.
Lutz-F. Tietze 《Angewandte Chemie (International ed. in English)》1983,22(11):828-841
The monoterpene glycoside secologanin is a key intermediate in the biosynthesis of most indole, cinchona, ipecacuanha, and pyrroloquinoline alkaloids, as well as of simple monoterpene alkaloids. More than a thousand alkaloids are formed from secologanin in vivo; this represents almost a quarter of this large group of natural products. It is also the parent compound of the secoiridoids. Many of the compounds derived from secologanin display a high degree of biological activity and are employed as pharmaceuticals, e.g., the dimeric indole alkaloid leurocristine (vincristine) which is used very successfully in the treatment of acute leukemia. A knowledge of the biosynthesis and biological reactions of secologanin provides a sound basis for the biosynthesis-orientated classification of numerous natural products and the taxonomy of many plants. Secologanin and structurally related substances can be synthesized in a few steps by stereocontrolled photochemical and thermal cycloadditions. Its biomimetic reaction with amines and amino acids yields other natural products and compounds of pharmacological interest. 相似文献
6.
Two new oxindole alkaloids, rankiniridine (1) and humanteniridine (2), having a nitrogen-carbon linkage between a humantenine-type monoterpenoid indole alkaloid and a monoterpene unit with an iridoid skeleton, were isolated from Gelsemium rankinii and Gelsemium elegans, respectively. 相似文献
7.
Markus Dobler James C. Anderson Mathias Juch Hans-Jürg Borschberg 《Helvetica chimica acta》1995,78(2):292-300
Synthetic (+)-makomakine ( 6 ) was transformed in six steps into (+)-17R,18R)-17,18-dihydrohobartine-17,18-diol ((+)- 5 ) with an overall yield of 38% (Scheme 2). This compound was shown to be identical with natural hobartinol, a monoterpene indole alkaloid from Aristotelia australasica, originally believed to be the (17S)-epimer 1 . At the same time, the synthesis of (+)- 5 delineates the hitherto unknown absolute configuration of this metabolite. 相似文献
8.
Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine,and (−)‐Strychnogucine B from (−)‐Strychnine
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Dr. Senzhi Zhao Christiana N. Teijaro Heng Chen Dr. Gopal Sirasani Dr. Shivaiah Vaddypally Prof. Dr. Michael J. Zdilla Prof. Dr. Graham E. Dobereiner Prof. Dr. Rodrigo B. Andrade 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(33):11593-11596
The first chemical syntheses of complex, bis‐Strychnos alkaloids (?)‐sungucine ( 1 ), (?)‐isosungucine ( 2 ), and (?)‐strychnogucine B ( 3 ) from (?)‐strychnine ( 4 ) is reported. Key steps included (1) the Polonovski–Potier activation of strychnine N‐oxide; (2) a biomimetic Mannich coupling to forge the signature C23?C5′ bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3CN‐mediated reduction to fashion the ethylidene moieties in 1 – 3 . DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners. 相似文献
9.
Strictosidine (1), a well-known monoterpene indole alkaloid glycoside[1,2], is the precursor and building stone of nearly 2200 indole and related alkaloids and was first isolated by G. N. Smith from Rhazya[3]. It is constructed in vivo from secologanin (2) and tryptamine (3) by plant species[1], as well as in vitro in the presence of the enzyme strictosidine synthase, or under biomimetic conditions in aqueous solution at pH 4.5 (Scheme 1). In the coupling reaction, a new chiral center is formed with complete stereoselectivity in the presence of the enzyme, or together with vincoside (4) in a 1:1 ratio in the absence of the enzyme. Here we describe the preparation of the analog of strictosidine and vincoside from geniposide via the biomimetic conditions. 7 and 8 can be used as the starting material to synthesize other analogs of indole and related alkaloids. 相似文献
10.
Jucimar J. de Souza Leda Mathias Raimundo Braz‐Filho Ivo J. Curcino Vieira 《Helvetica chimica acta》2010,93(3):422-429
Two new monoterpene indole alkaloids named ibogamine‐7,8‐dione ( 1 ) and 12‐methoxyvoachalotine ( 2 ), and eight known ones, coronaridine ( 3 ), coronaridine hydroxyindolenine ( 4 ), 5‐oxocoronaridine ( 5 ), 3‐oxocoronaridine hydroxyindolenine ( 6 ), 3‐oxocoronaridine ( 7 ), vobasine ( 8 ), ibogamine ( 9 ), and olivacine ( 10 ), were isolated from a CH2Cl2 extract of the root bark from Tabernaemontana hystrix. The structures of the compounds were elucidated on the basis of spectroscopic data analyses, mainly 1H‐ and 13C‐NMR, including 2D experiments (1H,1H‐COSY, HMBC, and HMQC). 相似文献
11.
Yingchao Dou Cyrille Kouklovsky Vincent Gandon Guillaume Vincent 《Angewandte Chemie (International ed. in English)》2020,59(4):1527-1531
The first total synthesis of the caged monoterpene indole alkaloid cymoside is reported. This natural product displays a unique hexacyclic‐fused skeleton whose biosynthesis implies an early oxidative cyclization of strictosidine. Our approach to the furo[3,2‐b]indoline framework relied on an unprecedented biomimetic sequence which started by the diastereoselective oxidation of the indole ring into a hydroxyindolenine which triggered the addition of an enol ether and was followed by the trapping of an oxocarbenium intermediate. 相似文献
12.
A full account of the development of the base-mediated intramolecular Diels-Alder cycloadditions of tryptamine-derived Zincke aldehydes is described. This important complexity-generating transformation provides the tetracyclic core of many indole monoterpene alkaloids in only three steps from commercially available starting materials and played a key role in short syntheses of norfluorocurarine (five steps), dehydrodesacetylretuline (six steps), valparicine (seven steps), and strychnine (six steps). Reasonable mechanistic possibilities for this reaction, a surprisingly facile dimerization of the products, and an unexpected cycloreversion to regenerate Zincke aldehydes under specific conditions are also discussed. 相似文献
13.
Bachmann BO 《Chemistry & biology》2007,14(8):875-876
In this issue of Chemistry & Biology, Bernhardt and coworkers [1] assay the functional plasticity of strictosidine synthase, a gateway enzyme in the biosynthetic pathways of monoterpene indole alklaloids, and the downstream operability of the products of strictosidine synthase variants in the larger context of the plant biosynthetic pathways. 相似文献
14.
Antonia Torres Ávila Pimenta Raimundo Braz‐Filho Piero Giuseppe Delprete Elnatan Bezerra de Souza Edilberto Rocha Silveira Mary Anne Sousa Lima 《Magnetic resonance in chemistry : MRC》2010,48(9):734-737
Two unusual monoterpene indole alkaloids, stachyoside ( 1 ) and nor‐methyl‐23‐oxo‐correantoside ( 2 ), have been isolated from the aerial parts of Psychotria stachyoides. The structural elucidation of both compounds was performed by the aid of HRESIMS, FT‐IR, and 1D‐ and 2D‐NMR techniques including COSY, HSQC, HMBC, and NOESY. Copyright © 2010 John Wiley & Sons, Ltd. 相似文献
15.
Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Total Synthesis of (−)‐17‐nor‐Excelsinidine
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Maxime Jarret Dr. Aurélien Tap Prof. Cyrille Kouklovsky Prof. Erwan Poupon Dr. Laurent Evanno Dr. Guillaume Vincent 《Angewandte Chemie (International ed. in English)》2018,57(38):12294-12298
We report the first total synthesis of (?)‐17‐nor‐excelsinidine, a zwitterionic monoterpene indole alkaloid that displays an unusual N4?C16 connection. Inspired by the postulated biosynthesis, we explored an oxidative coupling approach from the geissoschizine framework to forge the key ammonium–acetate connection. Two strategies allowed us to achieve this goal, namely an intramolecular nucleophilic substitution on a 16‐chlorolactam with the N4 nitrogen atom or a direct I2‐mediated N4?C16 oxidative coupling from the enolate of geissoschizine. 相似文献
16.
Tsugunori Watanabe Dr. Naoki Umezawa Dr. Nobuki Kato Prof. Dr. Tsunehiko Higuchi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(13):4255-4261
Scholarisine A, isolated from the leaves of Alstonia scholaris, is a monoterpene indole alkaloid with an unprecedented cage‐like structure. In this paper, preparation of the distinctive cage‐like core skeleton of scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10‐oxa‐tricyclo[5.3.1.03, 8]undecan‐9‐one structure fused with indolenine. Intramolecular oxidative coupling by using N‐iodosuccinimide gave the carbon framework of scholarisine A in moderate yield, which is the first example of intramolecular oxidative‐coupling reaction between non‐activated enolate and indole. This study lays the foundation for continued investigations towards the total synthesis of scholarisine A. 相似文献
17.
Hans-Peter Ros Rolf Kyburz Nigel W. Preston Rex T. Gallagher I. Ralph C. Bick Manfred Hesse 《Helvetica chimica acta》1979,62(2):481-487
The revised structure 1 is put forward for peduncularine, the main alkaloid of Aristotelia peduncularis (Labill.) HOOK. F. (Elaeocarpaceae), on the basis of its spectroscopic properties and those of its degradation products, the Hofmann base 3 and the hydrogenation product 4 . Structure 1 represents the relative configuration of the alkaloid. Peduncularine belongs to the class of indole alkaloids with a monoterpene unit as the aliphatic portion. To our knowledge it constitutes the first example in which an isopropyl group has become detached from the terpene unit and occurs as a substituent on nitrogen. 相似文献
18.
Summary During LSC of naturally occurring monoterpene hydrocarbon mixtures from essential oils using silica gel as adsorbent alterations in the composition of the mixtures were observed by means of gas chromatography. Impurities (metals) and active sites on dried silica gels were found to be responsible for a series of isomerizations of a number of the constituents. After purification by washing the silica gel with acid and base and after deactivation of the dried silica gel by adding water (5%) the isomerization processes could be avoided. This was tested by means of the monoterpene hydrocarbon mixtures of three essential oils and a number of pure monoterpene hydrocarbons. 相似文献
19.
Dr. Weiwu Ren Dr. Qian Wang Prof. Dr. Jieping Zhu 《Angewandte Chemie (International ed. in English)》2014,53(7):1818-1821
A total synthesis of aspidophylline A, a pentacyclic akuammiline‐type monoterpene indole alkaloid, is described. The synthesis features: 1) rapid access to a fully functionalized dihydrocarbazole through the desymmetrization of readily available 2‐allyl‐2‐(o‐nitrophenyl)cyclohexane‐1,3‐dione; 2) an intramolecular azidoalkoxylation of an enecarbamate to install both the furoindoline ring and the azido functionality; and 3) an intramolecular Michael addition for the construction of the 2‐azabicyclo[3.3.1]nonane ring system. 相似文献
20.
Ke Ma Jun-Song WangJun Luo Ming-Hua YangHe-Quan Yao Hong-Bin SunLing-Yi Kong 《Tetrahedron letters》2014
Two novel dimeric monoterpene indole alkaloids, bistabercarpamines A (1) and B (2) possessing unprecedented bis-vobasinyl-chippiine-type skeleton, were isolated from the leaves of Tabernaemontana corymbosa. The structures were elucidated on the basis of spectroscopic data, and the absolute configurations of these isolates were determined by CD excition chirality method. Bistabercarpamine A (1) exhibited moderate cell growth inhibitory activity against HepG-2 cells with IC50 of 38.14 ± 1.1 μM. 相似文献