Furanoditerpenoids of the Labdane Series: Occurrence in Plants, Total Synthesis, Several Transformations, and Biological Activity

Шульц, Э. Э.; Mironov, M. E.; Kharitonov, Yu. V.

doi:10.1007/s10600-014-0861-8

Cited by 30 publications

(24 citation statements)

References 89 publications

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“…(-)-Ambrox (82) a constituent of ambergris and very important product in perfumery is produced on large scale by partial synthesis from (-)-sclareol [77]. Furthermore, (-)-15oxopuupehenoic acid (83) [78], (+)-coronarin E (84) [79], (+)subersic acid (85) [80] as well as the complex sesterterpenoids (-)sesterstatin 4 and (+)-scalarolide [56d] can be prepared from (-)sclareol (48), emphasizing its importance as starting material to produce a variety of natural products and analogues thereof.…”

Section: (-)-Sclareolmentioning

confidence: 99%

Terpenoids with Special Pharmacological Significance: A Review

Jaeger

Cuny

2016

Natural Product Communications

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Terpenoids are a very prominent class of natural compounds produced in diverse genera of plants, fungi, algae and sponges. They gained significant pharmaceutical value since prehistoric times, due to their broad spectrum of medical applications. The fragrant leaves of Eucalyptus trees are a rich source of terpenoids. Therefore this review starts by summarizing the main terpenoid compounds present in Eucalyptus globulus, E. citriodora, E. radiata and E. resinifera and describing their biosynthetic pathways. Of the enormous number of pharmaceutically important terpenoids, this paper also reviews some well established and recently discovered examples and discusses their medical applications. In this context, the synthetic processes for (-)-menthol, (-)-cis-carveol, (+)-artemisinine, (+)-merrilactone A and (-)-sclareol are presented. The tricyclic sesquiterpene (-)-englerin A isolated from the stem bark of the Phyllanthus engleri plant (Euphorbiaceae) is highly active against certain renal cancer cell lines. In addition, recent studies showed that englerin A is also a potent and selective activator of TRPC4 and TRPC5 calcium channels. These important findings were the motivation for several renowned research labs to achieve a total synthesis of (-)-englerin A. Two prominent examples-Christmann and Metz-are compared and discussed in detail.

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Section: (-)-Sclareolmentioning

confidence: 99%

Terpenoids with Special Pharmacological Significance: A Review

Jaeger

Cuny

2016

Natural Product Communications

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“…Common structural features of V. agnus‐castus bioactive diterpenoids are the presence of furan, lactone or 3‐hydroxy‐3‐methyl‐pent‐4‐enyl groups (König, ). Furan or lactone groups, in particular, are frequent features of bioactive diterpenoids and appear, in some cases, to be important for their activity (Lim et al ., ; Shul′ts et al ., ). For example, work on elucidating the pharmacophore of salvinorin A, indicates that the furan ring influences its kappa opioid receptor agonist activity (Munro et al ., ; Riley et al ., ).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

et al. 2018

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Summary Vitex agnus‐castus L. (Lamiaceae) is a medicinal plant historically used throughout the Mediterranean region to treat menstrual cycle disorders, and is still used today as a clinically effective treatment for premenstrual syndrome. The pharmaceutical activity of the plant extract is linked to its ability to lower prolactin levels. This feature has been attributed to the presence of dopaminergic diterpenoids that can bind to dopamine receptors in the pituitary gland. Phytochemical analyses of V. agnus‐castus show that it contains an enormous array of structurally related diterpenoids and, as such, holds potential as a rich source of new dopaminergic drugs. The present work investigated the localisation and biosynthesis of diterpenoids in V. agnus‐castus. With the assistance of matrix‐assisted laser desorption ionisation‐mass spectrometry imaging (MALDI‐MSI), diterpenoids were localised to trichomes on the surface of fruit and leaves. Analysis of a trichome‐specific transcriptome database, coupled with expression studies, identified seven candidate genes involved in diterpenoid biosynthesis: three class II diterpene synthases (diTPSs); three class I diTPSs; and a cytochrome P450 (CYP). Combinatorial assays of the diTPSs resulted in the formation of a range of different diterpenes that can account for several of the backbones of bioactive diterpenoids observed in V. agnus‐castus. The identified CYP, VacCYP76BK1, was found to catalyse 16‐hydroxylation of the diol‐diterpene, peregrinol, to labd‐13Z‐ene‐9,15,16‐triol when expressed in Saccharomyces cerevisiae. Notably, this product is a potential intermediate in the biosynthetic pathway towards bioactive furan‐ and lactone‐containing diterpenoids that are present in this species.

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“…The present protocol offered the opportunity to explore structural diversity by variation of the diazide structures and leaves room for further exploration of (10,12), tetra(triazole) macrocycles (11,13).…”

Section: Discussionmentioning

confidence: 99%

“…[11] As a member of the diterpenoids family, furanolabdanoid lambertianic acid 1 could be considered an ideal scaffold for receptors, due to its low toxicity and biocompatibility. [12,13] In recent years the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), the most frequently used "click" reaction, have emerged as efficient methodologies for the construction of a range of different macrocyclic structures for different purposes. [14][15][16] CuAAC has been utilized as an efficient protocol to close macrocycles of different sizes by the formation of 1,4-triazoles.…”

Section: Synthesis Of Novel Labdanoid-based Macroheterocyclesmentioning

confidence: 99%