The Chemistry of the Sesquiterpene Alkaloids

Brocksom, Timothy J.; Oliveira, Kléber T. de; Desiderá, André L.

doi:10.21577/0103-5053.20170049

Cited by 6 publications

(9 citation statements)

References 14 publications

(17 reference statements)

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“…Guaipyridine sesquiterpenoids obtained from Artemisia are pseudo alkaloids that exist as bicyclic molecular architectures, consist of a seven‐membered carbocyclic ring fused to the pyridine ring with two stereogenic centers. Rupestine A‐M ( 1 – 13 ) belongs to a very rare class of guaipyridine sesquiterpene alkaloid with one carboxyl group and two chiral centers that have never been reported before (for biosynthesis see scheme 1, Supporting Information; Brocksom, Oliveira, & Desiderá, ). These alkaloids are biosynthetically derived from guaiane‐type sesquiterpenes that are the characteristic compounds widely distributed within Artemisia species, and chemotaxonomically, guaiane‐derived compounds are considered as the biomarker of Artemisia ‐derived natural products (Liu et al, ; Phan et al, ).…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

The chemistry and pharmacology of alkaloids and allied nitrogen compounds from Artemisia species: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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Several reviews have been published on Artemisia's derived natural products, but it is the first attempt to review the chemistry and pharmacology of more than 80 alkaloids and allied nitrogen compounds obtained from various Artemisia species (covering the literature up to June 2018). The pharmacological potential and unique skeleton types of certain Artemisia's alkaloids provoke the importance of analyzing Artemisia species for bioactive alkaloids and allied nitrogen compounds. Among the various types of bioactive Artemisia's alkaloids, the main classes were the derivatives of rupestine (pyridine–sesquiterpene), lycoctonine (diterpene), pyrrolizidine, purines, polyamine, peptides, indole, piperidine, pyrrolidine, alkamides, and flavoalkaloids. The rupestine derivatives are Artemisia's characteristic alkaloids, whereas the rest are common alkaloids found in the family Asteraceae and chemotaxonomically links the genus Artemisia with the tribes Anthemideae. The most important biological activities of Artemisia's alkaloids are including hepatoprotective, local anesthetic, β‐galactosidase, and antiparasitic activities; treatment of angina pectoris, opening blocked arteries, as a sleep‐inducing agents and inhibition of HIV viral protease, CYP450, melanin biosynthesis, human carbonic anhydrase, [3H]‐AEA metabolism, kinases, and DNA polymerase β1. Some of the important nitrogen metabolites of Artemisia include pellitorine, zeatin, tryptophan, rupestine, and aconitine analogs, which need to be optimized and commercialized further.

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Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

The chemistry and pharmacology of alkaloids and allied nitrogen compounds from Artemisia species: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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“…With increasing age, the increase of Dendrobium ‐specific glycosides and the decrease of dendrobine‐type alkaloids in D. nobile may be related. Dendrobine is one of the typical structures of sesquiterpene alkaloids 28 . Dendrobine has only been isolated from D. nobile , while dendrobine‐type alkaloids have been detected in various Dendrobium species.…”

Section: Resultsmentioning

confidence: 99%

“…Dendrobine is one of the typical structures of sesquiterpene alkaloids. 28 Dendrobine has only been isolated from D. nobile, while dendrobine-type alkaloids have been detected in various Dendrobium species. The structures of dendrobine-type alkaloids are complex; thus, multiple biosynthesis pathways may exist.…”

Section: Statistics Of the Structure-confirmed Constituents With Age-...mentioning

confidence: 99%

Opposite trends of glycosides and alkaloids in Dendrobium nobile of different age based on UPLC‐Q/TOF‐MS combined with multivariate statistical analyses

Jiang

Wu³

et al. 2022

Phytochemical Analysis

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Introduction Alkaloids and glycosides are the active ingredients of the herb Dendrobium nobile, which is used in traditional Chinese medicine. The pharmacological effects of alkaloids include neuroprotective effects and regulatory effects on glucose and lipid metabolism, while glycosides improve the immune system. The pharmacological activities of the above chemical components are significantly different. In practice, the stems of 3‐year‐old D. nobile are usually used as the main source of Dendrobii Caulis. However, it has not been reported whether this harvesting time is appropriate. Objective The aim of this study was to compare the chemical characteristics of D. nobile in different growth years (1–3 years). Methods In this study, ultra‐high‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry (UPLC‐Q/TOF‐MS) was employed to analyze the constituents of D. nobile. The relative abundance of each constituent was analyzed with multivariate statistical analyses to screen the characteristic constituents that contributed to the characterization and classification of D. nobile. Dendrobine, a component of D. nobile that is used for quality control according to the Chinese Pharmacopoeia, was assayed by gas chromatography. Results As a result, 34 characteristic constituents (VIP > 2) were identified or tentatively identified as alkaloids and glycosides based on MS/MS data. Moreover, the content of alkaloids decreased over time, whereas the content of glycosides showed the opposite trend. The absolute quantification of dendrobine was consistent with the metabolomics results. Conclusion Our findings provide valuable information to optimize the harvest period and a reference for the clinical application of D. nobile.

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“…Guaipyridine sesquiterpene alkaloids are a family of natural compounds that share a unique structure consisting of a fused pyridine ring and seven-membered carbocycle [1]. For example, patchoulipyridine (1, figure 1) and epiguaipyridine (2, figure 1) were first isolated from the essential oil of Pogostemon patchouli Pellet by Büchi et al in 1966 [2].…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of rupestine G and its epimers

et al. 2018

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Rupestine G is a guaipyridine sesquiterpene alkaloid isolated from Artemisia rupestris L. The total synthesis of rupestine G and its epimers was accomplished employing a Suzuki reaction to build a terminal diene moiety. The diene was further elaborated into the desired guaipyridine structure by a ring-closing metathesis reaction. Over all, rupestine G and its three epimers were obtained as a mixture in a sequence of nine linear steps with 18.9% yield. Rupestine G and its optically pure isomers were isolated by chiral preparative HPLC and fully characterized by 1H ,13C NMR, HRMS, optical rotation value, and experimental and calculated electronic circular dichroism spectroscopy.

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The Chemistry of the Sesquiterpene Alkaloids

Abstract: We present the occurrence, structures, biological activities, biosynthesis, and syntheses of the sesquiterpene alkaloids.

Cited by 6 publications

References 14 publications

The chemistry and pharmacology of alkaloids and allied nitrogen compounds from Artemisia species: A review

The chemistry and pharmacology of alkaloids and allied nitrogen compounds from Artemisia species: A review

Opposite trends of glycosides and alkaloids in Dendrobium nobile of different age based on UPLC‐Q/TOF‐MS combined with multivariate statistical analyses

Total synthesis of rupestine G and its epimers

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