Convergence in the biosynthesis of acetogenic natural products from plants, fungi, and bacteria

Bringmann, Gerhard; Irmer, Andreas; Feineis, Doris; Gulder, Tobias A. M.; Fiedler, Hans‐Peter

doi:10.1016/j.phytochem.2009.08.019

Cited by 33 publications

(19 citation statements)

References 56 publications

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“…These natural products are among the best studied examples of atropisomers, and have been extensively investigated; 9 including their isolation, identification, stereoselective syntheses, biological activities 10 and biosynthetic origin. 11 Here we depict one of the most recent examples reported by the Bringmann group; Mbandakamines A ( Figure 2, Compound 3) and B (not shown), which are unsymmetrical dimeric alkaloids isolated from an Ancistrocladus species collected from the Congo. 12 In recent years, there has also been a creative appreciation of 'non-traditional' atropisomerism associated with diazepine moieties.…”

Section: Natural Atropisomerism In Medicinal Chemistrymentioning

confidence: 93%

“…Additionally, phenotypic analysis of cells treated with 12, 14, and 16 showed elongated rod-like cells; an indicator for the induction of the bacterial SOS pathway in response to DNA interference. However, due to the fact that all compounds (11)(12)(13)(14)(15)(16) showed a reduction in B. subtilis growth, it was assumed that this was just one pathway through which inhibition occurred, and was reliant on the absolute configuration of the atropdiastereomers. This is promising as it evidences variable activity of therapeutic compounds based on their atropisomeric configuration, however the group concluded it is likely the natural products may have an additional, potentially novel, mode of action though this requires further investigation.…”

Section: Flavomannins and Talaromannins: Potential Novel Route For Anmentioning

confidence: 99%

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A twist of nature – the significance of atropisomers in biological systems

2015

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. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583. A twist of nature-the significance of atropisomers in biological systems AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized. AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Section: Natural Atropisomerism In Medicinal Chemistrymentioning

confidence: 93%

Section: Flavomannins and Talaromannins: Potential Novel Route For Anmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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“…Another example involves some basic polyketides made in plants for defense that are also synthesized by some bacteria and fungi, possibly for defense as well but against different organisms. However, the plant enzymes and reactions involved are distinct from those in the other taxa (7,30). Last, moths in the Zygaena family have evolved the ability to make cyanogenic glycosides, used for defense against predators, that are identical to those found in the plants on which they feed.…”

Section: Figurementioning

confidence: 99%

Convergent Evolution in Plant Specialized Metabolism

Pichersky

Lewinsohn

2011

Annu. Rev. Plant Biol.

408

323

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Plants synthesize a multitude of compounds that contribute to adaptation to their ecological niches. Such compounds serve as attractants of other living organisms beneficial to the plants or as defense against other biotic as well as abiotic agents. Selection for increased fitness, a never-ending process, has resulted in each plant lineage synthesizing a distinct set of specialized metabolites appropriate for its environment. The total number of specialized metabolites found in the plant kingdom far exceeds the capacity of any one plant genome to encode the necessary enzymes, and just as a plant lineage acquires the ability to make new specialized compounds during evolution, it also loses the ability to make others. Although the ability of plants to make novel, specialized metabolites continues to evolve, there are also many examples in which different plants have independently evolved the ability to make compounds already present in other plant lineages or to make different compounds that fulfill the same role-both are examples of convergent evolution. Here, we discuss many examples of convergent evolution in specialized metabolism. There are many genetic and biochemical mechanisms that can give rise to convergent evolution, and we conclude that, overall, convergent evolution in plant specialized metabolism is surprisingly common.

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“…Griffin and Lin, 2000;Merfort, 2011). One should not forget that solid research in chemotaxonomy has long shown the patterns of potentially interesting molecular scaffolds (Bringmann et al, 2009;Newman and Cragg, 2009;Wallwey and Li, 2011) and they do not necessarily correlate with plant families.…”

Section: Saslismentioning

confidence: 99%

“…The application of cheminformatics (chemotaxonomy; structural pharmacophores, etc.) (Zhu et al, 2011;Rollinger et al, 2009;Bringmann et al, 2009;Newman and Cragg, 2009;Wallwey and Li, 2011) or the emerging mechanistic ecological insights (Ramesha et al, 2011) seem to be more promising for bioprospecting and closer to pharmacological mechanisms than the obscure anecdotal evidence commonly found in ethnomedical systems. Anyone doing ethnobotanical field work will sooner or later realize that ethnomedical knowledge systems are belief systems.…”

Section: Saslismentioning

confidence: 99%

Cross-cultural comparisons of medicinal floras—What are the implications for bioprospecting?

Gertsch

2012

Journal of Ethnopharmacology

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Convergence in the biosynthesis of acetogenic natural products from plants, fungi, and bacteria

Cited by 33 publications

References 56 publications

A twist of nature – the significance of atropisomers in biological systems

A twist of nature – the significance of atropisomers in biological systems

Convergent Evolution in Plant Specialized Metabolism

Cross-cultural comparisons of medicinal floras—What are the implications for bioprospecting?

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