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

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.

Dereplication-guided isolation of a new indole alkaloid triglycoside from the hooks of Uncaria rhynchophylla by LC with ion trap time-of-flight MS

2018 ◽  
Vol 41 (7) ◽  
pp. 1532-1538 ◽  
Author(s):  
Jian-Gang Zhang ◽  
Xiao-Yan Huang ◽  
Yun-Bao Ma ◽  
Xue-Mei Zhang ◽  
Ji-Jun Chen ◽  
...  
Keyword(s):  
Ion Trap ◽  
Time Of Flight ◽  
Indole Alkaloid ◽  
Uncaria Rhynchophylla

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.

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.

Chemical and biological comparison of different sections of Uncaria rhynchophylla (Gou-Teng)

2017 ◽  
Vol 23 (1) ◽  
pp. 11-21 ◽  
Author(s):  
Jian-Gang Zhang ◽  
Chang-An Geng ◽  
Xiao-Yan Huang ◽  
Xing-Long Chen ◽  
Yun-Bao Ma ◽  
...  
Keyword(s):  
Hek293 Cell ◽  
Indole Alkaloids ◽  
Hypotensive Effect ◽  
Uncaria Rhynchophylla ◽  
Traditional Chinese Medicine Theory ◽  
Chemical Profiles ◽  
Well Differentiated ◽  
Chinese Medicine Theory ◽  
Different Parts

Uncaria rhynchophylla (Gou-Teng in Chinese) is officially documented in Chinese pharmacopoeia as one of the authentic sources for the crude drug of Gou-Teng which has long been used for mental and cardiovascular diseases. Indole alkaloids are the characteristic constituents responsible for the desired hypotensive effect; however, the psychiatric active constituents of Gou-Teng are still unclear. According to traditional Chinese medicine theory, only the hook-bearing stems of U. rhynchophylla are used as the crude materials for Gou-Teng, while its leaves and fruits are scarcely used. The present study aimed to compare the metabolic fingerprints of different parts (hooks, stems, leaves and fruits) of U. rhynchophylla by LC-DAD-MS/MS analysis and further evaluate their psychiatric activities on HEK293 cell line in vitro. A total of 38 constituents including 26 alkaloids, six flavonoids, two triterpenoids, two chlorogenic acid analogs and two other compounds were characterized. The different parts of U. rhynchophylla can be well differentiated from their chemical profiles. Leaves displayed the most potent activity on both MT1 and MT2 receptors, with agonistic rates of 39.7% and 97.6%. For 5-HT1A and 5-HT2C receptors, hooks showed the strongest activity with agonistic rates of 92.6% and 83.1%, respectively. This investigation provided valuable information for understanding the chemical divergence between different parts of U. rhynchophylla, and their substantial bases for psychiatric purposes.

Glucoconjugated Monoterpene Indole Alkaloids from Uncaria rhynchophylla

2019 ◽  
Vol 82 (12) ◽  
pp. 3288-3301 ◽  
Author(s):  
Qiang Guo ◽  
Xiali Si ◽  
Yuntao Shi ◽  
Hongshuai Yang ◽  
Xinyu Liu ◽  
...  
Keyword(s):  
Indole Alkaloids ◽  
Uncaria Rhynchophylla ◽  
Monoterpene Indole Alkaloids

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.

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