Two New Indole Alkaloids from Evodia rutaecarpa

The tyuit of Evodia rutaecarpa (Juss.) Benth is a Chinese traditional drug (Wu-Chu-Yu).The components of Wu-Chu-Yu have been studied by several groups, including indolealkaloids,quinolone alkaloids. limonoids and other kinds]. Further chemical investigationofthis drug led us to isolate two new indole alkaloids 1 and 2. This is the first time toisolate indolinone alkaloids from this plant.Wuchuyuamide I (l ), was isolated as colorless needles, m,p. 261 -262<> C (CHCI,MeOH), [Q].=# 0(c 0…     

Evodiagenine and dievodiamine, two new indole alkaloids from Evodia rutaecarpa

<正>Two new indole alkaloids,evodiagenine 1 and dievodiamine 2 were isolated from the fruits of Evodia rutaecarpa(Juss.) Benth. The structure of compounds 1 and 2 were elucidated by comprehensive spectroscopic analysis and compound 1 was confirmed by X-ray crystallographic analysis.     

A new caffeoylgluconic acid derivative from the nearly ripe fruits of Evodia rutaecarpa

A new caffeoylgluconic acid derivative, trans-caffeoyl-6-O-d-gluconic acid methyl ester (1), together with two known compounds named trans-caffeoyl-6-O-d-glucono-γ-lactone (2) and trans-caffeoyl-6-O-d-gluconic acid (3), was isolated from the nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth.. These compounds were isolated by various separation methods associated with the UPLC-Q-TOF-MS technique. Their structures were elucidated on the basis of extensive spectroscopic methods.     

Evollionines A–C,Three New Alkaloids Isolated from the Fruits of Evodia rutaecarpa

A phytochemical study of the CHCl₃ extract of the dried unripe fruits of Evodia rutaecarpa (Juss. ) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A–C ( 1 – 3 , resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single‐crystal X‐ray analysis.     

Study on the source and characteristics of Evodia rutaecarpa based on chemical pattern recognition

In this study, the appearance and texture of E. rutaecarpa were linked with the chemical constituents to explore methods of classification of E. rutaecarpa. The Chemometrics such as Hierarchical cluster analysis (HCA), principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA) models were used for analysis. According to the models, samples of E. rutaecarpa were divided into three categories based on their source: Evodia, Stone Tiger and Sparse Evodia. The Evodia category could be subdivided into two categories, one representing large fruits with a greater degree of cracking and the other representing large fruits with little or no cracking. The method provided by this study combines chemometrics with HPLC fingerprints, which can provide a basis and reference for the identification of E. rutaecarpa and enables establishment of a grade standard.     

反相高效液相色谱法测定吴茱萸及制剂中吴茱萸碱和吴茱萸次碱

用反相高效液相色谱法测定了吴茱萸及制剂中吴茱萸碱和吴茱萸次碱，建立了中药及制剂中吴茱萸碱、吴茱萸次碱分离、测定的色谱方法。色谱条件：ＯＤＳ柱，乙腈＋水＋四氢呋喃＋乙酸（５２＋４８＋１＋０．１）为流动相，紫外检测波长２８０ｎｍ。方法简便、灵敏、准确、快速。     

New pyridocarbazole alkaloids from Strychnos nitida

Phytochemical investigation of Strychnos nitida has led to the isolation of three new racemic pyridocarbazole alkaloids, (±)-stritidas A-C (1–3) and three known monoterpenoid indole alkaloids (4–6). Compounds 2 and 3 represent the first examples of pyridocarbazole alkaloids featuring an N-2-hydroxyethyl moiety. Their structures were determined by combined spectroscopic data (MS, UV, IR and NMR) and chemical methods.     

蔬毛吴茱萸果实中新化合物吴茱萸塔宁的分离及结构表征

从传统中药蔬毛吴茱萸的干燥未成熟果实中分离得到一个稀有高氧化状态、新的柠檬苦素类化合物吴茱萸塔宁(evolimorutanin),同时还分离得到了已知结构的化合物柠檬苦素(limonin)。根据IR、MS、1DNMR(1HNMR,13C NMR,DEPT)和2D NMR(1H-1HCOSY,HSQC,HMBC)谱学数据确定了它们的结构,两者均归属为降三萜类化合物,A,A′,B,C,D五个环的取代和立体构型完全相同,只有E环氧化状态不同。此外,还分析了从柠檬苦素转化为吴茱萸塔宁的可能过程。     

Chromatographic fingerprint study on Evodia rutaecarpa (Juss.) Benth by HPLC/DAD/ESI‐MSn technique

The LC–ESI‐MSⁿ method was developed for the analysis and characterization of alkaloids in the extract of E. rutaecarpa (called Wuzhuyu in Chinese). Thirty‐six batches of Wuzhuyu from different locations of China were investigated and the common fingerprinting profile was established with a professional analytical software recommended by the State Food and Drug Administration. Fifteen chemical components of the common peaks were identified by multi‐stage MS. The effects on the chromatographic profile resulting from different collecting locations, harvesting times or storage times were studied. Hierarchical clustering analysis and principal components analysis were also performed to classify and differentiate the 36 batches of the samples. As a result, those which had same chemical properties were sorted into one cluster, which was very useful in evaluating and controlling the quality of Wuzhuyu.     

Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of Clausena excavata

A carbazole-pyranocoumarin conjugate, carbazomarin B (1), and two carbazole alkaloids, 6-methoxymukonidine (2) and 2-hydroxy-3-methoxycarbazole (3), together with 27 known compounds (4–30), were isolated from the stems of Clausena excavata. Their structures have been elucidated by spectroscopic analyses. Compound 2 showed moderate cytotoxicity to HuCCA-1, MOLT-3 and HepG2 cancer cell lines with IC₅₀ values of 15.09–28.50 μg/mL, but none to A549 cell line. Heptaphylline (6) and nordentatin (23) were found to show moderate cytotoxic activity against HepG2 cell line with IC₅₀ values of 12.33 and 11.33, respectively, while clausine K (27) exhibited strong cytotoxicity with IC₅₀ value of 1.05 μg/mL, better than a standard drug (etoposide, IC₅₀ 13.40 μg/mL).     

New pyrazinoquinazoline alkaloids Isolated from a culture of Stenotrophomonas maltophilia QB-77

Two new pyrazinoquinazoline alkaloids, epi-fiscalin D (1) and epi-fiscalin E (2), as well as three known analogues, norquinadoline A (3), quinadoline A (4), and fiscalin C (5), were isolated from ethyl acetate extract of the fermentation broth of Stentrophomonas maltophilia QB-77. The structures of new compounds were elucidated on the basis of extensive spectroscopic data analysis including UV, HRESIMS, and 1D and 2D NMR experiments. All the isolated compounds were tested for their in vitro cytotoxicity against five human cancer cell lines (SMMC-7721, MCF-7, HL-60, SW480, and A-549) and antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus.     

A New Indole Alkaloid from Limonia Crenulata

Limonia crenulata Roxb. (Rutaceae), a small tree widely distributed in dry warm regions of southeastern Asia, has been reported to have antiepileptic, purgative and sudorific effects and is used for colic trouble and cardialgia1. Various parts of this plant have been employed in indigenous medicine. Our investigation on its stems led to the isolation of one new alkaloid, crenulatine 1, together with three known ones, 4-methoxy-6- hydroxy-1-methyl-2-quinolone2, N-benzoyltyramine methyl ether2,…     

在线SFE—GC技术在中药吴茱萸化学成分研究中的应用

建立了分析型超临界流体萃取(SFE)技术通过界面与气相色谱直接偶合分析中药吴茱萸化学成分的方法,样品不经预处理。讨论了界面设计及其应用中的一些问题。列出了吴茱萸某些化学成分的GC-MS鉴定结果。     

Cytotoxic monoterpenoid indole alkaloids isolated from the barks of Voacanga africana Staph.

A new monoterpenoid indole alkaloid compound (1) and six known monoterpenoid indole alkaloids compounds (2–7) were isolated from the barks of Voacanga africana Staph. The structures were established by spectral analysis as ibogamine-16-carboxylic acid,17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester (1), voacamine (2), vobasine (3), voacangine (4), voacristine (5), 19-epi-voacristine (6) and 19-epi-heyneanine (7). Compound 1 was confirmed by X-ray crystallographic analysis. All of the isolated compounds were evaluated for cytotoxicity against five cell lines (HEPG-2, A375, MDA-MB-231, SH-SY5Y, CT26). Among them, compounds 2 and 6 displayed significant inhibitory activities, compounds 3, 4 and 5 showed moderate inhibitory activities, while compounds 1 and 7 showed no inhibitory activities against the five cell lines.     

Soyauxinine,a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2–10. In addition, six semi-synthetic derivatives 3a–c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2–4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1–7 and 9, and semi-synthetic derivatives 3a–c, 4b, 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.     

Two new alkaloids from the leaves of Uncaria hirsuta Haviland

Two new alkaloids, uncaric acid A and hirsutaside A, were isolated from Uncaria hirsuta. Their structures were determined by spectroscopic evidences and chemical means.     

New prenylated indole alkaloids from fungus Penicillium sp. derived of mangrove soil sample

Three diprenylated indole alkaloids, mangrovamides A–C (1–3), featured a bicyclo [2.2.2] diazaoctane core and possessed a novel γ-methyl proline and isoprene derived dimethyl γ-pyrone functionalities hitherto unknown among the family of paraherquamides, were isolated from the fungus Penicillium sp., which was separated from a mangrove soil sample. The structures were elucidated based on NMR, X-ray, and CD methods. The possible biosynthetic pathway of these compounds is proposed.     

Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata

Two new monoterpenoid indole alkaloids, tabervarines A (1) and B (2), along with seven known monoterpenoid indole alkaloids, were isolated from the methanol extract of the twigs and leaves of Tabernaemontana divaricata. The structures including the absolute configurations of the new alkaloids were elucidated based on MS, NMR, and ECD calculation. The in vitro cytotoxic activities of the isolated alkaloids against several human cancer cell lines were also evaluated.     

Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2)

Evodiamine and rutaecarpine have been intensively studied due to their pharmacological actions and clinical applications. In this report, supercritical fluid was used to extract evodiamine and rutaecarpine from the unripe fruit of Evodia rutaecarpa. Response surface methodology using Box-Behnken experimental design was utilized to optimize parameters for supercritical carbon dioxide extraction with methanol as co-solvent. The effect of various values of dynamic extraction time (30-90min), temperature (50-70°C) and pressure (200-400bar) on extraction yields of the two compounds was evaluated. Determinations of the extracts were performed by high-performance liquid chromatography. The experimental data obtained were fitted to second-order polynomial equations and analyzed by analysis of variance. The highest yields predicted were 1.217mg/g for evodiamine and 0.969mg/g for rutaecarpine at the optimal values (time 78min, temperature 62°C, pressure 280bar and co-solvent flow rate 0.4mL/min), based on the selected range of experimental conditions.     

New alkylamide from the stems of Zanthoxylum nitidum

A new alkylamide, named (2E,6E,8E)-N-(2-methylpropyl)-10-oxo-2,6,8-decatrienamide (1), together with 22 known compounds (2–23), were isolated from the stems of Zanthoxylum nitidum. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR spectroscopy. The isolated compounds exhibited slightly antioxidant activities through DPPH and ABTS radical scavenging assays but showed no antibacterial activity against Streptococcus mutans ATCC2517, a dental caries causing bacteria.