Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons

1989 ◽  
Vol 67 (2) ◽  
pp. 213-219 ◽  
Author(s):  
Daniel Gardette ◽  
Jean-Claude Gramain ◽  
Marie-Eve Lepage ◽  
Yves Troin
Keyword(s):  
Steric Hindrance ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Aromatic Substituent ◽  
Aromatic Moiety ◽  
Efficient Route

The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety. This reaction was studied in order to achieve the synthesis of indole alkaloid synthons. Trials of regioselectivity control were made by using groups with enhanced steric hindrance. The reactivity of secondary enaminones was tested, and the ratio of C-alkylation to N-alkylation was shown to be dependent on the nature of the aromatic substituent. During this work, new hexahydrocarbazolones were synthesized, with substituents on the A ring or the modified C ring. Keywords: photocyclization, aryl enaminones, indole alkaloids, hexahydrocarbazolones-4, cyclopenta[b]indoles.

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

5-Methyltryptophan Resistant Cells of Catharanthus roseus

1979 ◽  
Vol 34 (7-8) ◽  
pp. 541-545 ◽  
Author(s):  
Jürgen Schallenberg ◽  
Jochen Berlin
Keyword(s):  
Catharanthus Roseus ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Synthetase Activity ◽  
Wild Type ◽  
Free Tryptophan ◽  
Alkaloid Synthesis ◽  
Resistant Cells

Several cell lines resistant to 5-methyltryptophan were selected from wild type cells of different Catharanthus roseus suspension cultures. The resistant cells had up to 30 times tne normal levels of free tryptophan. Despite the increased pool size of tryptophan anthranilate synthetase activity of resistant cells was as sensitive to inhibition by ʟ-tryptophan as wild type cells. The overproduction of tryptophan did not lead to intensified accumulation of tryptamine nor of indole alkaloids. This was supported by a low conversion of tryptophan to tryptamine in vivo and in vitro. The overpro­duction of one of the primary precursors was evidently not sufficient to stimulate the rate of indole alkaloid synthesis in Catharanthus cells.

scholarly journals MATARANINE A AND B: A NEW DIASTOMERIC INDOLE ALKALOID FROM Alstonia scholaris R.Br. OF LOMBOK ISLAND

2010 ◽  
Vol 9 (3) ◽  
pp. 466-469 ◽  
Author(s):  
Surya Hadi
Keyword(s):  
Spectral Data ◽  
Bioactive Compounds ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Mass Spectral Data ◽  
Acid Base ◽  
Mass Spectral ◽  
Alstonia Scholaris ◽  
Lombok Island

Alstonia scholaris R. Br., (Apocynaceae) is widely distributed in Indonesia and in Lombok Island, the plant locally known as ";lolon nita"; has been used to treat malaria. To locate potential bioactive compounds, acid-base extraction was carried out. From the base fraction, two new indole alkaloids with diastomeric structure, named Mataranine A and B, were isolated. The structures of the two alkaloids were elucidated on the basis of UV, NMR and mass spectral data.   Keywords: alkaloids, Alstonia scholaris, Lombok, mataranine

scholarly journals Terpenoid indole alkaloid biosynthesis in Catharanthus roseus: effects and prospects of environmental factors in metabolic engineering

2021 ◽  
Vol 43 (11) ◽  
pp. 2085-2103
Author(s):  
Yongliang Liu ◽  
Barunava Patra ◽  
Sanjay Kumar Singh ◽  
Priyanka Paul ◽  
Yan Zhou ◽  
...  
Keyword(s):  
Gene Expression ◽  
Metabolic Engineering ◽  
Environmental Factors ◽  
Catharanthus Roseus ◽  
Abiotic Factors ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Terpenoid Indole Alkaloids ◽  
Madagascar Periwinkle ◽  
Specialized Metabolites

Abstract Plants synthesize a vast array of specialized metabolites that primarily contribute to their defense and survival under adverse conditions. Many of the specialized metabolites have therapeutic values as drugs. Biosynthesis of specialized metabolites is affected by environmental factors including light, temperature, drought, salinity, and nutrients, as well as pathogens and insects. These environmental factors trigger a myriad of changes in gene expression at the transcriptional and posttranscriptional levels. The dynamic changes in gene expression are mediated by several regulatory proteins that perceive and transduce the signals, leading to up- or down-regulation of the metabolic pathways. Exploring the environmental effects and related signal cascades is a strategy in metabolic engineering to produce valuable specialized metabolites. However, mechanistic studies on environmental factors affecting specialized metabolism are limited. The medicinal plant Catharanthus roseus (Madagascar periwinkle) is an important source of bioactive terpenoid indole alkaloids (TIAs), including the anticancer therapeutics vinblastine and vincristine. The emerging picture shows that various environmental factors significantly alter TIA accumulation by affecting the expression of regulatory and enzyme-encoding genes in the pathway. Compared to our understanding of the TIA pathway in response to the phytohormone jasmonate, the impacts of environmental factors on TIA biosynthesis are insufficiently studied and discussed. This review thus focuses on these aspects and discusses possible strategies for metabolic engineering of TIA biosynthesis. Purpose of work Catharanthus roseus is a rich source of bioactive terpenoid indole alkaloids (TIAs). The objective of this work is to present a comprehensive account of the influence of various biotic and abiotic factors on TIA biosynthesis and to discuss possible strategies to enhance TIA production through metabolic engineering.

scholarly journals Indole Alkaloids from Vinca major and V. minor Growing in Turkey

2012 ◽  
Vol 7 (6) ◽  
pp. 1934578X1200700
Author(s):  
Fatemeh Bahadori ◽  
Gülaçtι Topçu ◽  
Mehmet Boǧa ◽  
Ayla Türkekul ◽  
Ufuk Kolak ◽  
...  
Keyword(s):  
Indole Alkaloids ◽  
Radical Scavenging ◽  
Indole Alkaloid ◽  
Aerial Parts ◽  
High Lipid ◽  
Vinca Major ◽  
Alkaloid Extracts ◽  
First Time ◽  
Dpph Radical Scavenging ◽  
High Lipid Peroxidation

A new indole alkaloid, 11-hydroxypolyneuridine, was isolated from Vinca major subsp. major L. and the known indole alkaloids vallesiachotamine and isovallesiachotamine from Vinca minor L. This is the first report on the alkaloids of both Vinca species growing in Turkey; vallesiachotamine and isovallesiachotamine were isolated from a Vinca species for the first time. V. minor may be considered as a new source for these two alkaloids due to their occurrence in high amount in the aerial parts of the plant. The alkaloid extracts of the two Vinca species were found to have high lipid peroxidation inhibitory and DPPH radical scavenging activities. Anticholinesterase activity of the extracts was also very strong.

scholarly journals Monoterpenoid Indole Alkaloids from Catharanthus roseus Cultivated in Yunnan

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001
Author(s):  
Bei Wang ◽  
Lu Liu ◽  
Ying-Ying Chen ◽  
Qiong Li ◽  
Dan Li ◽  
...  
Keyword(s):  
Catharanthus Roseus ◽  
Spectroscopic Data ◽  
Spectroscopic Analysis ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Monoterpenoid Indole Alkaloids ◽  
Monoterpenoid Indole Alkaloid ◽  
First Time

A new monoterpenoid indole alkaloid, 15,20-dehydro-3α-(2-oxopropyl) coronaridine (1), along with sixteen analogues (2–17) were isolated from the leaves of Catharanthus roseus cultivated in Yunnan. The new alkaloid was elucidated on the basis of extensive spectroscopic analysis, and the known alkaloids were identified by comparison with the reported spectroscopic data. Among them, alkaloid 16 was isolated from Catharanthus for the first time.

scholarly journals Studies on plants containing indole alkaloids. VIII. Indole alkaloid glycosides and other constituents of the leaves of Uncaria rhynchophylla Miq.

1982 ◽  
Vol 30 (11) ◽  
pp. 4046-4051 ◽  
Author(s):  
NORIO AIMI ◽  
TOSHIAKI SHITO ◽  
KAYOKO FUKUSHIMA ◽  
YUMIKO ITAI ◽  
CHIFUMI AOYAMA ◽  
...  
Keyword(s):  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Uncaria Rhynchophylla

ChemInform Abstract: Photocyclization of Aryl Enaminones. An Efficient Route to Indole Alkaloid Synthons.

ChemInform ◽  
1989 ◽  
Vol 20 (32) ◽  
Author(s):  
D. GARDETTE ◽  
J.-C. GRAMAIN ◽  
M.-E. LEPAGE ◽  
Y. TROIN
Keyword(s):  
Indole Alkaloid ◽  
Efficient Route

scholarly journals Development of a Cell Suspension Culture System for Promoting Alkaloid and Vinca Alkaloid Biosynthesis Using Endophytic Fungi Isolated from Local Catharanthus roseus

Plants ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 672
Author(s):  
Tran My Linh ◽  
Nguyen Chi Mai ◽  
Pham Thi Hoe ◽  
Ninh Thi Ngoc ◽  
Phan Thi Hong Thao ◽  
...  
Keyword(s):  
Suspension Culture ◽  
Cell Suspension ◽  
Endophytic Fungi ◽  
Catharanthus Roseus ◽  
Cell Suspension Culture ◽  
Indole Alkaloids ◽  
Vinca Alkaloid ◽  
Indole Alkaloid ◽  
Cell Suspension Cultures ◽  
Cell Extracts

Cell and tissue cultures of Catharanthus roseus have been studied extensively as an alternative strategy to improve the production of valuable secondary metabolites. The purpose of this study was to produce C. roseus callus and suspension cell biomass of good quality and quantity to improve the total alkaloids and bis-indole alkaloids. The young stem derived-callus of C. roseus variety Quang Ninh (QN) was grown on MS medium supplemented with 1.5 mg/L 2,4-dichlorophenoxyacetic acid (2,4-D) plus 1.5 mg/L kinetin, and the growth rate increased by 67-fold after 20 days. The optimal conditions for maintaining the cell suspension culture were 150 mg/50 mL cell inoculum, a medium pH of 5.5 and a culture temperature of 25 °C. The low alkaloid content in the culture was compensated for by using endophytic fungi isolated from local C. roseus. Cell extracts of endophytic fungi—identified as Fusarium solani RN1 and Chaetomium funicola RN3—were found to significantly promote alkaloid accumulation. This elicitation also stimulated the accumulation of a tested bis-indole alkaloid, vinblastine. The findings are important for investigating the effects of fungal elicitors on the biosynthesis of vinblastine and vincristine, as well as other terpenoid indole alkaloids (TIAs), in C. roseus QN cell suspension cultures.

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