Halogenated monoterpenes of the red alga Microcladia

Crews, Phillip; Ng, Patricia; Kho-Wiseman, Ernest; Pace, C. S.

doi:10.1016/s0031-9422(00)97461-2

Cited by 16 publications

(6 citation statements)

References 20 publications

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“…Inquisitively, bromine is the most occurring halogen in marine natural products, despite that its concentration in seawater is lower than that of chlorine. To the best of our knowledge, the isolation of halogenated monoterpenes is limited to three families of marine red algae, the Plocamiaceae and Rhizophyllidaceae [112,113], and Ceramiaceae [114]. The chemical structure of Rhodophyta monoterpenes is characterized by multiple halogen substitutions (chlorine and bromine) and by uncommon carbon cycle structures in the case of cyclic compounds.…”

Section: Halogenated Terpenes From Red Algae (Rhodophyta)mentioning

confidence: 99%

“…The chemical structure of Rhodophyta monoterpenes is characterized by multiple halogen substitutions (chlorine and bromine) and by uncommon carbon cycle structures in the case of cyclic compounds. All halogenated acyclic seaweed monoterpenes appear to be derived from the halogenation of myrcene or ocimene [114]. As indicated in the rich bibliography dedicated to this purpose [45,113,[115][116][117], the almost majority of halogenated terpenoids (monoterpenes, sesquiterpenes, and diterpenes) described in red algae are isolated from crude solvent extracts.…”

Section: Halogenated Terpenes From Red Algae (Rhodophyta)mentioning

confidence: 99%

“…The same species collected along the central coast of Chile [119] conduct to the isolation of eight monoterpenes (88)(89)(90)(91)(92)(93)(94)(95), four of which are based on the 1-(2-chlororovinyl)-2,4,5-trichloro-1,5-dimethylcyclohexane skeleton (Figure 7). As in the genus Plocamium, the chemical study of the genera Portieria [120], Ochtodes [121], and Microcladia [114,122] has led to the isolation of over 100 of acyclic, cyclic, and tetrahydrofuran halogenated monoterpenes. A large number of halogenated sesquiterpenes, more than monoterpenes, were described in red algae especially in the genus Laurencia (Ceramiales).…”

Section: Halogenated Terpenes From Red Algae (Rhodophyta)mentioning

confidence: 99%

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Algae Essential Oils: Chemistry, Ecology, and Biological Activities

Hattab¹

2020

Essential Oils - Bioactive Compounds, New Perspectives and Applications

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This chapter focuses on the essential oils and volatile fractions of seaweed. It includes an introduction to the essentials and volatile fractions and the main chemical classes found. This part is completed by a presentation of the fundamental aspects of biodiversity and the chemodiversity of the marine environment followed by the taxonomy and systematics of marine macroalgae. The heart of this chapter concerns the chemistry of volatile products extracted from marine algae. It reports the specificities of the marine natural products chemistry in comparison to that of terrestrial organisms. The description of volatile compounds in seaweed is divided into two parts, the first reports the common compounds identified in main volatile fractions and the second cover the specific volatile components. These include C11 hydrocarbons, sulfur compounds, and halogenated hydrocarbons. These latter are playing a very important role in communication and chemical defense. The last part includes aspects of chemical ecology and biological activities of volatile products.

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Section: Halogenated Terpenes From Red Algae (Rhodophyta)mentioning

confidence: 99%

Section: Halogenated Terpenes From Red Algae (Rhodophyta)mentioning

confidence: 99%

Section: Halogenated Terpenes From Red Algae (Rhodophyta)mentioning

confidence: 99%

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Algae Essential Oils: Chemistry, Ecology, and Biological Activities

Hattab¹

2020

Essential Oils - Bioactive Compounds, New Perspectives and Applications

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“…Gardner from the Galapagos Islands. In 1976, Crews et al [72] observed that halogenated monoterpenes found in Microcladia differ in the composition between different collection locations. They compared Microcladia with Plocamium species [73] with respect to the similarity of monoterpenes profile.…”

Section: Isolation and Biodiversity Of Monoterpenes From Macroalgaementioning

confidence: 99%

Update on Monoterpenes from Red Macroalgae: Isolation, Analysis, and Bioactivity

et al. 2019

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Macroalgae produce a wide range of monoterpenes as secondary metabolites of mevalonate (MVA) and/or methylerythritol phosphate (MEP) pathway (often including haloperoxidase action). Great biodiversity of macroalgal monoterpenes was reported including acyclic, monocyclic, and bicyclic structures. Halogenated monoterpenes exhibited significant biological activity (e.g., anticancer, antiplasmodial, and insecticidal) that is influenced by the number of present halogens (higher halogen content is preferable, especially bromine) and their position within the monoterpene skeleton. In distinction from the existing reviews, the present review provides novelty with respect to: (a) exclusively monoterpenes from red macroalgae are targeted; (b) biosynthesis, isolation, and analysis, as well as bioactivity of monoterpenes are represented; (c) the methods of their isolation, analysis, and structure elucidation are summarized; (d) the bioactivity of macroalgal monoterpenes is systematically presented with emphasis on anticancer activity; (e) the literature references were updated.

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“…This activity was assumed to be due to the presence of polyhalogenated indoles 265-270 (Brennan and Erickson, 1978). (Crews et al, 1976).…”

Section: Rhodophyllis Membranaceamentioning

confidence: 99%

Volatile halogenated metabolites from marine red algae

2004

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A significant number of halogenated low molecular weight metabolites have exhibited an impressive array of biological properties ranging from antimicrobial to insecticidal activities. Studies on the natural products chemistry of the red seaweeds were recently stimulated by the discovery of the acyclic monoterpene halomon, which exhibits selective antitumor activity in the National Cancer Institute's human tumor and disease oriented in vitro screen.The present review is a taxonomy based compilation of the available literature on the halogenated volatile metabolites (C 1 -C 10 ) produced by red seaweeds, with a short description of the reported ecological and pharmaceutical activities. The review begins with a presentation of simple halogenated hydrocarbons and phenols, showing their wide occurrence in rhodophyta, along with a description of simple halogenated lipids in some of the most frequently investigated red algae species and finally focuses on the chemical composition of individual red algae species.

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Halogenated monoterpenes of the red alga Microcladia

Cited by 16 publications

References 20 publications

Algae Essential Oils: Chemistry, Ecology, and Biological Activities

Algae Essential Oils: Chemistry, Ecology, and Biological Activities

Update on Monoterpenes from Red Macroalgae: Isolation, Analysis, and Bioactivity

Volatile halogenated metabolites from marine red algae

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