A chemotaxonomic study of diterpenes from marine brown algae of the genus Dictyota

Algal terpenes constitute a wide and well-documented group of marine natural products with structures differing from their terrestrial plant biosynthetic analogues. Amongst macroalgae, brown seaweeds are considered as one of the richest source of biologically and ecologically relevant terpenoids. These metabolites, mostly encountered in algae of the class Phaeophyceae, are mainly diterpenes and meroditerpenes (metabolites of mixed biogenesis characterized by a toluquinol or a toluquinone nucleus linked to a diterpene moiety).In this chapter, we describe analytical processes commonly employed for the isolation and structural characterization of the main terpenoid constituents obtained from organic extracts of brown algae. The successive steps include (1) extraction of lipidic content from algal samples; (2) purification of terpenes by column chromatography and semi-preparative high-performance liquid chromatography; and (3) structure elucidation of the isolated terpenes by means of 1D and 2D nuclear magnetic resonance (NMR). More precisely, we propose a representative methodology which allows the isolation and structural determination of the monocyclic meroditerpene methoxybifurcarenone (MBFC) from the Mediterranean brown alga Cystoseira amentacea var. stricta. This methodology has a large field of applications and can then be extended to terpenes isolated from other species of the family Sargassaceae.

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“…Fig. 5 Chemical structure of methoxybifurcarenone (MBFC) isolated from the brown alga Cystoseira amentacea var. stricta 4.…”

Section: Methodsmentioning

confidence: 99%

“…In Dictyotaceae, a majority of the terpenes are described from species of the genus Dictyota (Fig. 2a), these compounds being exclusively cyclic diterpenes which could be classified into three main chemical groups: dolabellanes, prenylated guaianes, and xenicanes [4,5] (Fig. 3).…”

Section: Introductionmentioning

confidence: 99%

Extraction, Purification, and NMR Analysis of Terpenes from Brown Algae

Gaysinski

Ortalo-Magné

Thomas

et al. 2015

Methods in Molecular Biology

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“…Its fragmentation spectrum revealed ions at m/z 333.0627/335.0609/ 337.0566 (4 : 5 : 1), m/z 253.1281/255.0815 (3 : 1), m/z 217.1458; the rst fragment was formed aer the loss of HBr (80 Da), while the second fragment resulted from the elimination of 2 HBr (160 Da); the last fragment was produced aer the elimination of 2 HBr and HCl (196 Da). The foregoing data in conjunction to the data reported in the literature led to the structure of some chamigrane-type sesquiterpenes, such as 9hydroxy-4,10-dibromo-3-chloro-a-chamigrene (10) 22-24 and 2,10dibromo-3-chloro-8-hydroxy-b-chamigrene (11), 25 along to the irregular rearranged bisabolane-related sesquiterpene laucapyranoid A (12). 26 The metabolite detected at 7.74 and 8.11 min might be related, due to similar fragmentation behavior.…”

Section: Resultsmentioning

confidence: 67%

“…10 In addition, Dictyota and Canistrocarpus are chemically composed of diterpenes. [11][12][13][14][15][16] The metabolites produced by algae mainly serve as chemical defenses against herbivorous or pathogenic micro-organisms. 16 Many of these metabolites have been conrmed as presenting anticoagulant, antifouling, antimicrobial, antioxidant, herbivore-deterrent and cytotoxic activities.…”

Section: Introductionmentioning

confidence: 99%

Molecular networking prospection and characterization of terpenoids and C₁₅-acetogenins in Brazilian seaweed extracts

et al. 2018

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“…In the present study we isolated fucoxanthin (7), which is a dominant pigment in most of the phaeophyceae species, and five C-29 steroids (2-6), including two new ones (2, 5) from the brown alga Cystoseira trinodis (order Fucales, family Fucaceae), which are found to be adequate chemotaxonomic markers of such type of macro-algae [18,19]. However, one more metabolite was isolated from this organism, identified as (12E)-cis-maneonene-E (1), a halogenated cyclic ene-yne ether isolate belonging to the class of natural occurring compounds acetogenins (nonterpenoid C15 compounds).…”

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confidence: 99%

Two New Cytotoxic C-29 Steroids from the Red Sea Brown Alga Cystoseira trinodis

et al. 2015

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Chromatographic fractionation of the organic extract obtained from the brown alga Cystoseira trinodis led to the isolation of a known carotene pigment (7), five C-29 steroids (2-6), including two new ones (2 and 5), and an unexpected metabolite, halogenated cyclic ene-yne ether (1). Compound 1 was isolated from the genus Cystoseira for the first time. This finding plays an important role in the chemo-taxonomical differentiation of C. trinodis from other Cystoseira species. All compounds (1-7) were evaluated for their in vitro cytotoxic activities against four human tumor cell lines HepG2, WI 38, and Vero. They showed moderate cytotoxicity with IC 50 in the range 7-33 PM, where 7 exhibited the highest antioxidant activity with 72.1% inhibition.Marine macro-organisms, particularly algae, are considered as a platform of metabolites that possess a diversity of chemical structures as well as potent pharmacological activities [1]. Recently, the literature showed a wide range of biological activities of secondary metabolites isolated from algae, including anti-HIV, anticoagulant, anticonvulsant, anti-inflammatory, antineoplastic, and cytotoxic activities [2-4]. Generally, but not exclusively, diterpenes and sterols are isolated from brown algae [5] belonging to the genus Cystoseira [6][7][8]. For instances, four acetate cytotoxic hydroazulene diterpenes, dictyone acetate, dictyol F monoacetate, isodictytriol monoacetate, and cystoseirol monoacetate, were isolated from Cystoseira myrica [9]. A meroditerpenoid metabolite was isolated from the brown alga Cystoseira tamariscifolia [10].As a part of our systematic endeavors to isolate bioactive metabolites from Saudi Red Sea organisms, we investigated the constituents of C. trinodis (order: Fucales; family: Fucaceae) collected off the coast of Jeddah, KSA. We report here the isolation and characterization of two new metabolites, (24E)-stigmasta-5,24(28)-dien-3D-ol (2) and stigmasta-5,24(28)-dien-3E,29-diol (5), along with five known compounds: a halogenated cyclic ene-yne ether, (12E)-cis-maneonene-E (1) [11]; three steroids, stigmast-5-en-3E-ol (3) [12], 24-vinylcholesterol (4) [13], and fucosterol (6) [12]; and the allenic carotenoid fucoxanthin (7) [14].Compound 1 was identified as (12E)-cis-maneonene-E [11] and reported herein for the first time from C. trinodis (kingdom: Chromalveolata; phylum: Heterokontophyta; class: Phaeophyceae; order: Fucales; family: Fucaceae; genus: Cystoseira L). It represents a new trend in the isolation of unique natural compounds from marine brown algae of the order Fucales. Compound 1 was isolated from the red algae Laurencia papillosa and L. obtuse [15] which were collected from the same location as C. trinodis.Compound 2 was isolated as an amorphous solid material; it gave a molecular ion peak in the HR-EI-MS at 412.3693 corresponding to a molecular formula of C 29 H 48 O requiring six unsaturation sites. Its ESI-MS showed a molecular ion at m/z 412.

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A chemotaxonomic study of diterpenes from marine brown algae of the genus Dictyota

Cited by 35 publications

References 50 publications

Extraction, Purification, and NMR Analysis of Terpenes from Brown Algae

Extraction, Purification, and NMR Analysis of Terpenes from Brown Algae

Molecular networking prospection and characterization of terpenoids and C₁₅-acetogenins in Brazilian seaweed extracts

Two New Cytotoxic C-29 Steroids from the Red Sea Brown Alga Cystoseira trinodis

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A chemotaxonomic study of diterpenes from marine brown algae of the genus Dictyota

Cited by 35 publications

References 50 publications

Extraction, Purification, and NMR Analysis of Terpenes from Brown Algae

Extraction, Purification, and NMR Analysis of Terpenes from Brown Algae

Molecular networking prospection and characterization of terpenoids and C15-acetogenins in Brazilian seaweed extracts

Two New Cytotoxic C-29 Steroids from the Red Sea Brown Alga Cystoseira trinodis

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Molecular networking prospection and characterization of terpenoids and C₁₅-acetogenins in Brazilian seaweed extracts