Pacifenol from the Mediterranean Red Alga Laurencia majuscula

Caccamese, Salvatore; Compagnini, Anna; Toscano, Rosa Maria

doi:10.1021/np50043a033

Cited by 24 publications

(18 citation statements)

References 5 publications

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“…Based on the finding from this investigation, it is clear that there are two chemical types of L. majuscula in North Borneo waters. To date, L. majuscula populations are known to exist as four distinct chemical types and the other remaining types are the pacifenol producing population in Eastern Sicily, Italy (Caccamese et al 1986) and a (2R,3R,5S)-5-acetoxy-2-bromo-3-chloro-chamigra-7(14),9-dien-8-one producing population found in Ryukyu Islands, Japan (Masuda et al 1997b). All four halogenated metabolites showed potent antibacterial activities against the seaweed pathogens as compared to the human pathogenic bacteria.…”

Section: Discussionmentioning

confidence: 99%

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

et al. 2009

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Carrageenophyte farming is an expanding economical activity in North Borneo Island, Malaysia. During routine monitoring of "ice-ice" disease and epiphyte outbreak at commercial farms, it was apparent that culture lines were heavily (60-80%) infested with biofoulers, particularly Acanthophora spp. and Laurencia majuscula. However, only L. majuscula showed dominance and flourished even during "ice-ice" disease outbreak. Presence of chemical defense against seaweed pathogens was investigated in two populations of L. majuscula collected from three major carrageenophyte farms in two districts; (A) Lohok Butun, Selakan Island, and Bum-Bum Island, in Semporna district, and (B) Telutuh, Carrington Reef, and Balambangan Island, in Kudat district. The first population contained elatol (1), and iso-obtusol (2), and, second population contained (Z)-10,15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene (3) and (E)-10-15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene (4), as their antibacterial metabolites. All four metabolites showed highly selective inhibition against "ice-ice" disease bacteria compared to human pathogens at 30µg disk −1 . In addition, seasonal variation of these compounds at two representative farms (Selakan Island [P-1] and Balambangan Island [P-2]) revealed a 120-170% increase in concentration during "ice-ice" disease outbreak. Microscopy of fresh specimens showed the presence of corps en cerise, which is the synthesis and storage site of halogenated metabolites at superficial cortical cells, branch tips, and trichoblasts. This suggests the importance of these metabolites as defense chemicals against "ice-ice" disease bacteria in L. majuscula that grows on seaweed culture lines.

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Section: Discussionmentioning

confidence: 99%

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

et al. 2009

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“…In contrast, four sesquiterpenes were previously reported for L. majuscula from different localities. The sesquiterpenes pacifenol and dehydrochloroprepacifenol were isolated from L. majuscula from the Mediterranean Sea (Caccamese et al. 1986, 1987), whereas isoobtusol and elatol were reported for L. majuscula from the Gran Canaria (Masuda et al.…”

Section: Discussionmentioning

confidence: 99%

LAURENCIA MARILZAE SP. NOV. (CERAMIALES, RHODOPHYTA) FROM THE CANARY ISLANDS, SPAIN, BASED ON MORPHOLOGICAL AND MOLECULAR EVIDENCE¹

Gil-Rodríguez

Sentíes

Díaz‐Larrea

et al. 2009

Journal of Phycology

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Laurencia marilzae Gil-Rodríguez, Sentíes et M.T. Fujii sp. nov. is described based on specimens that have been collected from the Canary Islands. This new species is characterized by distinctive yelloworange as its natural habitat color, a terete thallus, four pericentral cells per vegetative axial segment, presence of secondary pit-connections between adjacent cortical cells, markedly projecting cortical cells, and also by the presence of corps en cerise (one per cell) present in all cells of the thallus (cortical, medullary, including pericentral and axial cells, and trichoblasts). It also has a procarp-bearing segment with five pericentral cells and tetrasporangia that are produced from the third and fourth pericentral cells, which are arranged in a parallel manner in relation to fertile branchlets. The phylogenetic position of this taxon was inferred based on chloroplast-encoded rbcL gene sequence analyses. Within the Laurencia assemblage, L. marilzae formed a distinctive lineage sister to all other Laurencia species analyzed. Previously, a large number of unique diterpenes dactylomelane derivatives were isolated and identified from this taxon. L. marilzae is morphologically, genetically, and chemically distinct from all other related species of the Laurencia complex described.

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“…Furthermore, our material is in agreement with an Australian specimen of L. majuscula that was collected from Kangaroo Island, southern Australia (SAP 039946), which is rather near the type locality of this species, Rottnest Island. Masuda et al (1997bMasuda et al ( , 1998 have pointed out the possibility that at least four chemical races are present among chamigrane-type sesquiterpenoid-producing populations of L. majuscula, although interfertility between these populations have not been tested: (i) populations from Okino-shima in Japan (Suzuki and Kurosawa 1978, Suzuki et al 1979a, Hinchinbrook Island and Magnetic Island in north Queensland, Australia (Coll and Wright 1989;Wright et al 1990), which produce (Z)-10,15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene as a major compound; (ii) a population of eastern Sicily, Italy (Caccamese et al 1986(Caccamese et al , 1987, which includes pacifenol as a major compound; (iii) populations from Woodmans Point 30 km south of Perth, Western Australia, which is the closest to the type locality of L. majuscula (Capon et al 1988), and Gran Canaria ), which produce elatol as a major compound; and (iv) populations from Taketomi Island and Hateruma Island, the Ryukyu Islands, Japan (Masuda et al 1997b), which produce (2R,3R,5S)-5-acetoxy-2-bromo-3-chlorochamigra-7(14),9-dien-8-one as a major compound. The Tanegashima population of L. majuscula sampled is assigned to the race that produces (Z)-10,15dibromo-9-hydroxy-chamigra-1,3(15), 7(14)-triene.…”

Section: Laurencia Majusculamentioning

confidence: 99%

Additional analysis of chemical diversity of the red algal genus Laurencia (Rhodomelaceae) from Japan

Masuda¹,

Kawaguchi²,

Abe³

et al. 2002

Phycological Res

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The halogenated secondary metabolite constitution of four species of the red algal genus Laurencia (Rhodomelaceae) from southern Japan is reported. Laurencia composita Yamada from Tanegashima Island (Kagoshima Prefecture) bears five sesquiterpenoids (2,10-dibromo-3-chloro-α-chamigrene and 2,10-dibromo-3-chloro-9-hydroxy-α-chamigrene, in addition to prepacifenol epoxide, johnstonol and pacifenol, which are known in other populations of this species). Laurencia intricata Lamouroux from Chinzei (Saga Prefecture) and Oomura Bay (Nagasaki Prefecture) bear a C 15 acetogenin, okamurallene. Laurencia majuscula (Harvey) Lucas from Tanegashima Island produces three sesquiterpenoids, (Z )-10,15-dibromo-9-hydroxy-chamigra-1, 3(15),7(14)-triene, 10-bromo-7-hydroxylaurene and 10,11-dibromo-7-hydroxylaurene, corresponding to those of one of its chemical races. Laurencia venusta Yamada from Tanegashima Island produces two sesquiterpenoids, cupalaurenol and cyclolaurenol, which were known only from a sea hare, Aplysia dactylomela Rang. This strongly suggests that Aplysia consumes L. venusta and concentrates these halogenated compounds.

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Pacifenol from the Mediterranean Red Alga Laurencia majuscula

Cited by 24 publications

References 5 publications

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

LAURENCIA MARILZAE SP. NOV. (CERAMIALES, RHODOPHYTA) FROM THE CANARY ISLANDS, SPAIN, BASED ON MORPHOLOGICAL AND MOLECULAR EVIDENCE¹

Additional analysis of chemical diversity of the red algal genus Laurencia (Rhodomelaceae) from Japan

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Pacifenol from the Mediterranean Red Alga Laurencia majuscula

Cited by 24 publications

References 5 publications

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

LAURENCIA MARILZAE SP. NOV. (CERAMIALES, RHODOPHYTA) FROM THE CANARY ISLANDS, SPAIN, BASED ON MORPHOLOGICAL AND MOLECULAR EVIDENCE1

Additional analysis of chemical diversity of the red algal genus Laurencia (Rhodomelaceae) from Japan

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LAURENCIA MARILZAE SP. NOV. (CERAMIALES, RHODOPHYTA) FROM THE CANARY ISLANDS, SPAIN, BASED ON MORPHOLOGICAL AND MOLECULAR EVIDENCE¹