Manauealides, Some of the Causative Agents of a Red Alga <i>Gracilaria coronopifolia</i> Poisoning in Hawaii

Nagai, Hiroshi; Yasumoto, Takeshi; Hokama, Y.

doi:10.1021/np970193c

Cited by 43 publications

(20 citation statements)

References 19 publications

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“…G. coronopifolia and G. edulis were also toxic to humans [65,49] (See Table 1). Carbohydrate, heparin [97], agar [101], manauealide A, manauealide B [64], manauealide C [102], palmitic, palmitoleic, oleic, lauric and myristic acids [103], steroids and alkaloids malyngamide [104] were found in these species (Figure 1). …”

Section: Resultsmentioning

confidence: 99%

“…A variety of lactones are present in Gracilaria from the Pacific Ocean, such as aplysiatoxin isolated from G. confervoides [64,65], polycavernoside B, polycavernoside B 2 , and polycavernoside A 2 and A 3 isolated from G. crassa [49,66]. Other constituents are also containedin this genus such as proteins r-phycoerythrin from G. salicornia [67] and G. longa [68], gigartinine from G. chilensis [69] and proteoglycan from G. longa [70].…”

Section: Introductionmentioning

confidence: 99%

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Bioactivities from Marine Algae of the Genus Gracilaria

Almeida

Falcão

Lima

et al. 2011

IJMS

200

102

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Seaweeds are an important source of bioactive metabolites for the pharmaceutical industry in drug development. Many of these compounds are used to treat diseases like cancer, acquired immune-deficiency syndrome (AIDS), inflammation, pain, arthritis, as well as viral, bacterial, and fungal infections. This paper offers a survey of the literature for Gracilaria algae extracts with biological activity, and identifies avenues for future research. Nineteen species of this genus that were tested for antibacterial, antiviral, antifungal, antihypertensive, cytotoxic, spermicidal, embriotoxic, and anti-inflammatory activities are cited from the 121 references consulted.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bioactivities from Marine Algae of the Genus Gracilaria

Almeida

Falcão

Lima

et al. 2011

IJMS

200

102

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“…Their biological activities have prompted numerous synthetic studies [71,72]. It is interesting to note at this point that aplysiatoxin (43) is the para-isomer of manauealide B (46) reported from a red alga [73] (Fig. (9)).…”

Section: Other Sea Hare Isolates Of Postulated Cyanobacterial Originmentioning

confidence: 99%

“…The analogy between the aurisides (55, 56) and the lyngbyalosides (57, 59) includes the brominated conjugated diene functionality. Related glycoside macrolides, polycavernosides, have been isolated from a red alga [87,88], and, as for the manauealides [73], might actually be derived from a cyanobacterium. Finally, the doliculols (60, 61) [89] do not structurally resemble a cyanobacterial metabolite, but show stunning similarities to laurencin (62) [90,91] and other closely related analogues from the red alga Laurencia (Fig.…”

Section: Other Sea Hare Isolates Of Postulated Cyanobacterial Originmentioning

confidence: 99%

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Luesch¹,

Harrigan²,

Goetz³

et al. 2002

CMC

133

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It is increasingly evident that the true biological origin of many metabolites originally isolated from certain marine macroorganisms is cyanobacterial. For example, several dolastatins, potent cytotoxic compounds originally derived from the sea hare Dolabella auricularia, have now been isolated from marine cyanobacteria of the genera Lyngbya and Symploca. This review discusses the isolation of dolastatins and close structural analogues from cyanobacteria. Biosynthetic signatures of metabolites isolated from sea hares, but which are most probably cyanobacterial in origin, are also presented. Finally, some more complex ecology involving movement of cyanobacterial metabolites through the marine food web is presented.

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“…Fatal intoxication due to ingestion of lyngbyatoxin A contaminated flesh of the turtle Chelonia mydas has been reported [8,9]. In addition, aplysiatoxin and related toxins were revealed to be the causative agents of food poisoning by the red alga Gracilaria coronopifolia [10,11,12]. The true producer of these toxins involved in these poisoning cases was deduced to be M. producens [8,10].…”

Section: Introductionmentioning

confidence: 99%

A New Lyngbyatoxin from the Hawaiian Cyanobacterium Moorea producens

et al. 2014

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Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of “swimmer’s itch” with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicated that the compound was a new lyngbyatoxin A derivative, 12-epi-lyngbyatoxin A (1). While 12-epi-lyngbyatoxin A showed comparable toxicities with lyngbyatoxin A in cytotoxicity and crustacean lethality tests, it showed more than 100 times lower affinity for protein kinase Cδ (PKCδ) using the PKCδ-C1B peptide when compared to lyngbyatoxin A.

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Manauealides, Some of the Causative Agents of a Red Alga Gracilaria coronopifolia Poisoning in Hawaii

Cited by 43 publications

References 19 publications

Bioactivities from Marine Algae of the Genus Gracilaria

Bioactivities from Marine Algae of the Genus Gracilaria

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

A New Lyngbyatoxin from the Hawaiian Cyanobacterium Moorea producens

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