Peduncin, A New Indole Alkaloid from Pueraria peduncualris

Pueraria peduncularis (Grah. ex Benth.) Benth. is a plant of Leguminosae which grows in the southwest of China. Different from other plants of Pueraria, it could not be used as a medicine due to its toxicity1. In order to use the Pueraria plants safer, we studied the constituents of P. peduncularis. Previous phytochemical studies of an n-BuOH extract afforded three triterpenoid saponins2-3. The continuing investigation on CHCl3 extract led to the isolation of a new indole alkaloid. …     

A New Indole Alkaloid from Cleome droserifolia

The phytochemical investigations on Cleome droserifolia resulted in the isolation and characterization of a new indole alkaloid, 5‐hydroxy‐2‐methoxy‐1‐methyl‐1H‐indole‐3‐carbaldehyde ( 1 ). The structure elucidation was carried out on the basis of 1D‐ and 2D‐NMR techniques. In addition to 1 , two known aromatic derivatives, veratrol ( 2 ) and 2‐methoxy‐4‐methylacetophenone ( 3 ), were also obtained. All these compounds were purified by repeated column chromatography of the CH₂Cl₂ fraction obtained from MeOH extract of Cleome droserifolia. The structure of the new compound 1 was finally confirmed by the combined 1D (¹H‐ and ¹³C‐) and 2D (H? C correlations; HMBC and HSQC) NMR and IR spectroscopy, mass spectrometry (MS), and UV absorption spectroscopy techniques. The comparison of the physical and spectroscopic data with those in the literature provided evidence for the structure confirmation of known compounds. All the purified compounds were subjected to urease and α‐glucosidase enzymes inhibition. The results showed that compound 1 was more potent with an IC₅₀ value 11.97±2.067 μg/ml towards urease inhibition, while the activity of α‐glucosidase enzyme was marginal.     

Dasycarine, a New Quinoline Alkaloid from Dictamnus dasycarpus

Dasycarine, a new quinoline alkaloid along with five known compounds, dictamine, dihydroobacunone, obacunone, fraxinellone and b -sitosterol, were isolated from Dictamnus dasycarpus. The structure of dasycarine was identified as 4, 5, 8- trimethoxyl –3- (3- methyl –2- butenyl)- 2- quinone by 1D and 2D NMR techniques.     

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…     

Matrix-Assisted DOSY for Analysis of Indole Alkaloid Mixtures

Diffusion-ordered spectroscopy (DOSY) is a powerful tool for investigating mixtures and identifying peaks of chemical components. However, similar diffusion coefficients of the components, particularly for complex mixtures that contain crowded resonances, limit resolution and restrict application of the DOSY technique. In this paper, matrix-assisted DOSY were used to explore whether the diffusion resolution of a complex model involving indole alkaloid mixtures can be realized. Furthermore, we investigated the influence of different factors on the separation effect. The results showed that the changes in diffusion coefficient differences were achieved more obviously when using sodium dodecyl sulfate (SDS) micelles as the matrix. In addition, we also found that increasing the concentration of SDS can improve the resolution of the DOSY spectrum. Finally, after investigating the influence factors and NMR conditions, we demonstrated the applications of the SDS-assisted DOSY on analyzing the total alkaloid extract of Alstonia Mairei, and the virtual separation of mixtures was achieved.     

New alkaloids from the leaves of Evodia rutaecarpa

One new indole alkaloid (1) and one new indole alkaloidal glycoside (2), together with nine known alkaloids (3–11), were isolated from the leaves of Evodia rutaecarpa. Their structures were determined on the basis of spectroscopic and chemical methods. Compound 4 exhibited potent activity against Pseudomonas aeruginosa with an MIC value of 7.13 μg/ml.     

Two New Indole Alkaloids from Tabernaemontana hystrix Steud. (Apocynaceae)

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).     

A New Nitro Alkaloid from Corydalis saxicola Bunting

A new nitro tetrahydronprotoberberins alkaloid, 1-nitro-apocavidine was isolated from Corydalis saxicola Bunting. The structure was established by spectroscopic methods.     

A new Dendrobine-Type Alkaloid from Dendrobium nobile

A new dendrobine-type alkaloid has been isolated from stems of Dendrobium nobile lindl.Its structure has been identified on the basis of spectroscopic method.     

Total Synthesis of the Monoterpenoid Indole Alkaloid (±)‐Aspidophylline A

Aspidophylline A belongs to the akuammiline alkaloid family, the members of which possess intriguing cagelike structures and diverse biological activities. Herein we report a 15‐step synthesis of this alkaloid from conveniently available starting materials. The key elements of the synthesis include an intramolecular oxidative coupling to create the tetracyclic furoindoline motif of the natural product and a [Ni(cod)₂]‐mediated cyclization to install its piperidine ring.     

吲哚类生物碱的合成研究进展

吲哚类生物碱是具有吲哚分子骨架的一类化合物,具有多种良好的生理活性。文章综述了近年来新发现吲哚类生物碱的合成研究进展,介绍了(-)-Arboricine,(±)-cis-Trikentrin A,(-)-Corynantheidol等化合物的合成方法。     

A New Binary Carbazole Alkaloid from Murraya koenigii

A new binary carbazole alkaloid,8,8″-biskoenigine (1), along with its monomer, koenigine,was isolated from the dried leaves of Murraya koenigii collected in Xishuangbanna, Yunnan province. The structure of 1 was established spectroscopic methods.     

藏药蓝翠雀花中的新二萜生物碱

蓝翠雀花(Delphinium caeruleum Jacq.ex Camb.)~[1]在甘肃西南部、西藏、青海等地分布较广,藏民常用其治疗牙痛、跌打损伤.其化学成分迄今未见报道.我们将其全草用乙醇浸泡,石油醚脱脂,乙醚除去色素,酸碱常法处理,氯仿萃取得总生物碱.用氧化铝、硅胶进行多次柱层析及硅胶薄层制备层析,分得碱(1)～(4).     

New Indole Alkaloids from Kopsia. Alkaloid Variation in Kopsia singapurensis

Five new indole alkaloids, viz., kopsiloscine G ( 2 ), kopsidarine ( 4 ), kopsimaline F ( 6 ), kopsidine C N‐oxide ( 7 ), and aspidophylline B ( 9 ), in addition to 17 other known alkaloids, were obtained from the leaf and stem‐bark extract of the Malaysian Kopsia singapurensis. The structures were determined by using NMR and MS analysis. The results are compared with the alkaloidal composition of another sample of K. singapurensis, collected from the same location but at a different time of the year, as well as with other samples of K. singapurensis collected from different locations.     

Huperzine V, A New Lycopodium Alkaloid from Huperzia serrata

Huperzine V, a new Lycopodium alkaloid, was isolated from the whole plant of Huperzia serrata, and the absolute stereochemistry was determined by X-ray crystallographic analysis.     

云南萝芙木花新吲哚生物碱

从云南萝芙木(Rauvolfia yunnanensis Tsiang)花乙酸乙酯提取物中分离得到9个化合物(其中4个为吲哚类生物碱), 即(18Z)-11-methoxypicrinine(1), caberoline(2), 11-methoxystrictamine(3)和strictamine(4), 以及russulamide(5), ursolic acid(6), urs-12(13)-en-3α-yl acetate(7), β-amyryl nonanoate(8)和β-sitosterol(9); 采用UV, IR, MS和1D, 2D NMR方法对化合物的结构进行了鉴定, 其中化合物1为新吲哚生物碱, 化合物5, 7和8系首次从该植物中分离得到, 但未得到利血平和育亨宾.     

Plant-Based Indole Alkaloids: A Comprehensive Overview from a Pharmacological Perspective

Plant-based indole alkaloids are very rich in pharmacological activities, and the indole nucleus is considered to contribute greatly to these activities. This review’s fundamental objective is to summarize the pharmacological potential of indole alkaloids that have been derived from plants and provide a detailed evaluation of their established pharmacological activities, which may contribute to identifying new lead compounds. The study was performed by searching various scientific databases, including Springer, Elsevier, ACS Publications, Taylor and Francis, Thieme, Wiley Online Library, ProQuest, MDPI, and online scientific books. A total of 100 indole compounds were identified and reviewed. The most active compounds possessed a variety of pharmacological activities, including anticancer, antibacterial, antiviral, antimalarial, antifungal, anti-inflammatory, antidepressant, analgesic, hypotensive, anticholinesterase, antiplatelet, antidiarrheal, spasmolytic, antileishmanial, lipid-lowering, antimycobacterial, and antidiabetic activities. Although some compounds have potent activity, some only have mild-to-moderate activity. The pharmacokinetic profiles of some of the identified compounds, such as brucine, mitragynine, 7-hydroxymitragynine, vindoline, and harmane, were also reviewed. Most of these compounds showed promising pharmacological activity. An in-depth pharmacological evaluation of these compounds should be performed to determine whether any of these indoles may serve as new leads.     

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.     

A New Lycopodine-type Alkaloid from Lycopodium japonicum

A new lycopodine-type alkaloid, 12β-hydroxy-acetylfawcettiine N-oxide (1), together with seven known analogues, acetyllycoposerramine M (2), lycopodine (3), lycoclavine (4), diphaladine A (5), lycoposerramine K (6), 11β-hydroxy-12-epilycodoline (7) and fawcettiine (8), were isolated from Lycopodium japonicum. Their structures were established by mass spectrometry and 1D and 2D NMR techniques. The isolated alkaloids were assayed for their inhibition activities against acetylcholinesterase, but no inhibitory activities for the compounds were detected.