Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Ishikura, Minoru; Abe, Takumi; Choshi, Tominari; Hibino, Satoshi

doi:10.1039/c5np00032g

Cited by 219 publications

(61 citation statements)

References 337 publications

(384 reference statements)

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“…products. [1] These compounds have attracted tremendous interest from the synthetic community as ar esult of their diverse biological activities as well as their challenging molecular architectures. [2] In particular spiroindoline alkaloids ( Figure 1) have garnered much attention, as demonstrated by the high number of approaches to construct the spirocyclic unit.…”

Section: Indolealkaloidsconstitutealargeanddiverseclassofnaturalmentioning

confidence: 99%

Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

et al. 2018

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The N-iodosuccinimide-mediated spirocyclization of tryptamine-derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow-up chemistry.N ucleophilic addition typically occurs chemoselectively on the imine moiety with complete diastereoselectivity,p roviding opportunities for the construction of complex molecular frameworks. The synthetic potential of the method was showcased in the formal total synthesis of (AE)-aspidofractinine.

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Section: Indolealkaloidsconstitutealargeanddiverseclassofnaturalmentioning

confidence: 99%

Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

et al. 2018

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“…the Fischer, Bischler, Reissert, and Madelung indole syntheses), were developed, several of which are still widely used today . The interest in this “privileged scaffold” originates in part from the numerous naturally occurring bioactive indole alkaloids (Figure ) …”

Section: Introductionmentioning

confidence: 99%

Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3‐Chloroindolenines

et al. 2019

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C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ‐generated 3‐chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3‐substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.

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“…It has been further demonstrated that alkaloids are the main bioactive components responsible for therapeutic efficacy of Kumu and its preparations for their potent activities against infection and abscesses of the respiratory, digestive, and urinary systems [13,14,15,16,17,18]. Up to now, more than sixty β -carboline and canthinone alkaloids have been isolated from P. quassioides , including nigakinone (5-hydroxy-4-methoxycanthin-6-one), 4,5-dimethoxycanthin-6-one, 3-methylcanthin-5,6-dione, β -carboline-1-carboxylic acid, β -carboline-1-propanoic acid, and so on.…”

Section: Introductionmentioning

confidence: 99%

Quality Assessment of Kumu Injection, a Traditional Chinese Medicine Preparation, Using HPLC Combined with Chemometric Methods and Qualitative and Quantitative Analysis of Multiple Alkaloids by Single Marker

Wang

Zheng

et al. 2018

Molecules

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Kumu injection (KMI) is a common-used traditional Chinese medicine (TCM) preparation made from Picrasma quassioides (D. Don) Benn. rich in alkaloids. An innovative technique for quality assessment of KMI was developed using high performance liquid chromatography (HPLC) combined with chemometric methods and qualitative and quantitative analysis of multi-components by single marker (QAMS). Nigakinone (PQ-6, 5-hydroxy-4-methoxycanthin-6-one), one of the most abundant alkaloids responsible for the major pharmacological activities of Kumu, was used as a reference substance. Six alkaloids in KMI were quantified, including 6-hydroxy-β-carboline-1-carboxylic acid (PQ-1), 4,5-dimethoxycanthin-6-one (PQ-2), β-carboline-1-carboxylic acid (PQ-3), β-carboline-1-propanoic acid (PQ-4), 3-methylcanthin-5,6-dione (PQ-5), and PQ-6. Based on the outcomes of twenty batches of KMI samples, the contents of six alkaloids were used for further chemometric analysis. By hierarchical cluster analysis (HCA), radar plots, and principal component analysis (PCA), all the KMI samples could be categorized into three groups, which were closely related to production date and indicated the crucial influence of herbal raw material on end products of KMI. QAMS combined with chemometric analysis could accurately measure and clearly distinguish the different quality samples of KMI. Hence, QAMS is a feasible and promising method for the quality control of KMI.

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Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Abstract: This review covers the literature on simple indole alkaloids and those with a nonrearranged monoterpenoid unit from the beginning of 2012 up to the end of 2013, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.

Cited by 219 publications

References 337 publications

Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3‐Chloroindolenines

Quality Assessment of Kumu Injection, a Traditional Chinese Medicine Preparation, Using HPLC Combined with Chemometric Methods and Qualitative and Quantitative Analysis of Multiple Alkaloids by Single Marker

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