Marine natural products. I. Pacifenol, a rare sesquiterpene containing bromine and chlorine from the red alga, Laurencia pacifica

Sims, James J.; Fenical, William; Wing, Richard M.; Radlick, Phillip

doi:10.1021/ja00744a041

Cited by 89 publications

(28 citation statements)

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“…Among these, pacifenol (29) was the first natural product reported to contain both Br and Cl in the structure. 41 As can be seen from Figure 3, the bromine atom is usually located on the secondary carbon (C 2 ) whereas the chlorine is often attached to the tertiary center (C 3 ) on the opposite face of Br-atom, representing a characteristic 2,3-trans-halide arrangement observed for 5,10-epoxychamigrane sesquiterpenes (29−31 and 37−40). This halogenation pattern is also commonly observed in other chamigrane sesquiterpenes, as shown in Figures 4−6, which indicates that C 2 and C 10 are the most favored positions for Br-substitution, whereas C 3 appears to be favored for Cl-substitution.…”

Section: Halogenated Sesquiterpenesmentioning

confidence: 96%

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

et al. 2013

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Section: Halogenated Sesquiterpenesmentioning

confidence: 96%

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

et al. 2013

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“…We have been examining the secondary metabolites from a number of such algae and have found compounds with potent antimicrobial activity. Described here are the results of preliminary tests of chondriol (4) and cycloeudesmol (3) from Chondria oppositiclada, pre-pacifenol (9) from Laurencia filiformis, and laurinterol and debromolaurinterol from Laurencia pacifica (5,8).…”

mentioning

confidence: 99%

Antimicrobial Agents from Marine Algae

Sims

Donnell

Leary

et al. 1975

Antimicrob Agents Chemother

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The antimicrobial activity of five compounds extracted from marine algae was tested against Staphylococcus aureus, Salmonella choleraesuis, Mycobacterium smegmatis, Candida albicans , and Escherichia coli . Three of the compounds, cycloeudesmol, laurinterol, and debromolaurinterol, exhibited activity at concentrations approaching that of streptomycin. None of the compounds inhibited all of the organisms tested. There appeared to be selectivity for gram-positive microbes.

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“…Interestingly, the major component of the crude extract of Laurencia caduciramulosa from Brazil was pacifenol, a compound that has been reported for Laurencia species from the Pacific Ocean and Mediterrenean Sea (Sims et al, 1971;Caccamese et al, 1986;Argandoña et al, 1993) and that was isolated for the first time from Laurencia species introduced into Brazilian waters by transoceanic shipping.…”

Section: Specimens Examinedmentioning

confidence: 97%

Comparative analysis of the corps en cerise in several species of Laurencia (Ceramiales, Rhodophyta) from the Atlantic Ocean

Fujii¹,

Cassano

Sentíes³

et al. 2012

Rev. bras. farmacogn.

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Different species of Laurencia have proven to be a rich source of natural products yielding interesting bioactive halogenated secondary metabolites, such as terpenoids and acetogenins. It is shown that such compounds are accumulated in the spherical, reniform to claviform refractive inclusions called corps en cerise (CC), which are intensively osmiophilic and located mainly in the cortical cells of the thalli and also in trichoblast cells. Up to now, it was believed that CC were present only in these two kinds of cells. Recently, however, a species of Laurencia, L. marilzae, with CC in all cells of the thallus, i.e., cortical, medullary, including the pericentral and axial cells, as well as in the trichoblasts, was described from the Canary Islands, and subsequently also reported to Brazil and Mexico. Within the Laurencia complex, only Laurencia species produce CC. Since the species of Laurencia are targets of interest for the prospection of bioactive substances due to their potential antibacterial, antifungal, anticholinesterasic, antileishmanial, cytotoxic, and antioxidant activities, the present paper carries out a comparative analysis of the corps en cerise in several species of Laurencia from the Atlantic Ocean to obtain basic information that can support natural product bioprospection projects. Our results show that the number and size of the CC are constant within a species, independent of the geographical distribution, corroborating their use for taxonomical purposes to differentiate groups of species that present a lower number from those that have a higher number. In this regard, there was a tendency for the number of CC to be higher in some species of Laurencia from the Canary Islands. The presence of CC can also be used to distinguish species in which these organelles are present in all cells of the thallus from those in which CC are restricted to the cortical cells. Among the species analyzed, L. viridis displayed the most varied secondary metabolites composition, such as sesquiterpenes, diterpenes, triterpenes, all of which showed potent antiviral, cytotoxic, and antitumoral activities, including protein phosphatase type 2A (PP2A) inhibitory effects.

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Marine natural products. I. Pacifenol, a rare sesquiterpene containing bromine and chlorine from the red alga, Laurencia pacifica

Cited by 89 publications

References 1 publication

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

Antimicrobial Agents from Marine Algae

Comparative analysis of the corps en cerise in several species of Laurencia (Ceramiales, Rhodophyta) from the Atlantic Ocean

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