C15 acetogenins from the Laurencia complex: 50 years of research – an overview

Wanke, Tauana; Philippus, Ana Cláudia; Zatelli, Gabriele Andressa; Vieira, Lucas Felipe Oliveira; Lhullier, Cíntia; Falkenberg, Miriam

doi:10.1016/j.bjp.2015.07.027

Cited by 44 publications

(39 citation statements)

References 152 publications

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“…204 Eight-membered cyclic ethers are the most abundant C 15 acetogenins, and Laurencia spp. are common producers of these halogenated metabolites.…”

Section: Vanadium-dependent Haloperoxidasesmentioning

confidence: 99%

“…The eight-membered cyclic ethers can be divided into two subclasses: the lauthisan-type, which contains the metabolite laurencin ( 58 , Figure 18), and the laurenan-type, which contains the metabolites laureatin ( 59 ) and laurallene ( 60 ). 204 It was proposed that linear laurediols were a precursor to both subtypes, and that the assembly of the cyclic ether metabolites could proceed through a bromoetherification of the linear precursor. Incubation of ( 3E , 6R , 7R )-laurediol ( 61 ) with a crude preparation of a V-BPO from the red alga Laurencia nipponica produced the cyclic bromoether deacetyllaurencin ( 62 , Figure 18A).…”

Section: Vanadium-dependent Haloperoxidasesmentioning

confidence: 99%

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Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

et al. 2017

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Naturally produced halogenated compounds are ubiquitous across all domains of life where they perform a multitude of biological functions and adopt a diversity of chemical structures. Accordingly, a diverse collection of enzyme catalysts to install and remove halogens from organic scaffolds has evolved in nature. Accounting for the different chemical properties of the four halogen atoms (fluorine, chlorine, bromine, and iodine) and the diversity and chemical reactivity of their organic substrates, enzymes performing biosynthetic and degradative halogenation chemistry utilize numerous mechanistic strategies involving oxidation, reduction, and substitution. Biosynthetic halogenation reactions range from simple aromatic substitutions to stereoselective C-H functionalizations on remote carbon centers and can initiate the formation of simple to complex ring structures. Dehalogenating enzymes, on the other hand, are best known for removing halogen atoms from man-made organohalogens, yet also function naturally, albeit rarely, in metabolic pathways. This review details the scope and mechanism of nature’s halogenation and dehalogenation enzymatic strategies, highlights gaps in our understanding, and posits where new advances in the field might arise in the near future.

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“…204 Eight-membered cyclic ethers are the most abundant C 15 acetogenins, and Laurencia spp. are common producers of these halogenated metabolites.…”

Section: Vanadium-dependent Haloperoxidasesmentioning

confidence: 99%

Section: Vanadium-dependent Haloperoxidasesmentioning

confidence: 99%

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

et al. 2017

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“…The relative configuration at C-6 was assigned S * , identical to that of ( + )-7, based on a chemical shift (δ C 46. 4) Table 1) were almost identical to those of 8 except for the replacement of an olefinic methyl at C-14 in 8 by a vinyl carbinol unit in 2 [13]. Detailed assignment of 1 H-1 H COSY and HMBC correlations (▶Fig.…”

Section: Resultsmentioning

confidence: 77%

“…Red algae of the genus Laurencia are known to produce an array of diverse halogenated secondary metabolites represented as terpenoid, alkaloid and C 15 -acetogenin chemical skeletons [1][2][3][4]. Presence and quantity of the major halogenated metabolites within Laurencia populations often vary with their species and geographical distribution [5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity and Antibacterial Potential of Halogenated Chamigrenes from Malaysian Red Alga, Laurencia majuscula

Kamada

Phan

Okino

et al. 2019

PMIO

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Red algae of the genus Laurencia have been known to produce a wide array of bioactive secondary metabolites. Here, we report the isolation of two new halogenated chamigrenes, lauremantanones A (1) and B (2), along with seven known compounds, dendroidiol (3), (+)-elatol (4), cartilagineol (5), obtusol (6), (+)-laurencenone B (7), 2-chloro-3-hydroxy-α-chamigren-9-one (8), and puertitol A (9), from a population of Laurencia majuscula (Harvey) Lucas from Mantanani Island (North Borneo). The structures of the two new metabolites were determined based on spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds isolated from this alga exhibited potent cytotoxic (HeLa, MCF-7, P-388) and antibacterial (against antibiotic-resistant clinical bacteria) activities. The major metabolite of this population has significant importance in the geographical distribution of this species globally.

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“…Matsuura et al (2017) also reported the metabolites 10-bromo-β-chamigren-2-ol (64) and 10-bromo-β-chamigren-2,3-ol (65). The stereochemistries of aplydactone (60) and 8-epi-isoaplydactone (62) are reported according to revisions by Kutateladze and Reddy (2017). One sea hare population from Canary Island yielded the compound dactylomelatriol (66), a naturally occurring omphalene-derived sesquiterpene.…”

Section: Charmigrane Type Skeletonmentioning

confidence: 99%

Halogenated Metabolites from the Diet of Aplysia dactylomela Rang

et al. 2020

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Invertebrates are an important source of structurally-diverse and biologically-active halogenated metabolites. The sea hare Aplysia dactylomela Rang has long been known to possess halogenated metabolites of dietary origin that are used as a self-defense mechanism. The compounds from Aplysia dactylomela Rang are comprised mainly of terpenoids and small percentages of C-15 acetogenins, indoles, macrolides, sterols and alkaloids with potent cytotoxic, anti-microbial and anti-inflammatory properties. For decades the metabolites discovered have been investigated for their medical and pharmaceutical applications, so much so that the ecological role of the metabolites has been overlooked. The interaction between Aplysia dactylomela Rang and its diet that is comprised of seaweed can provide information into the distribution and diversity of the seaweed, the application of bioaccumulated secondary metabolites as part of its defense mechanism and the potential roles of these metabolites for adaptation in the marine environment. This paper compiles the diversity of halogenated secondary metabolites documented from Aplysia dactylomela Rang.

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C15 acetogenins from the Laurencia complex: 50 years of research – an overview

Cited by 44 publications

References 152 publications

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

Cytotoxicity and Antibacterial Potential of Halogenated Chamigrenes from Malaysian Red Alga, Laurencia majuscula

Halogenated Metabolites from the Diet of Aplysia dactylomela Rang

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