An overview of odoriferous marine seaweeds of the <i>Dictyopteris</i> genus: insights into their chemical diversity, biological potential and ecological roles

Zatelli, Gabriele Andressa; Philippus, Ana Cláudia; Falkenberg, Miriam

doi:10.1016/j.bjp.2018.01.005

Brasil

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Review • Rev. bras. farmacogn. 28 (2) • Mar-Apr 2018 • https://doi.org/10.1016/j.bjp.2018.01.005 linkcopy

An overview of odoriferous marine seaweeds of the Dictyopteris genus: insights into their chemical diversity, biological potential and ecological roles

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

Since the middle of the twentieth century the marine algae have attracted attention as a source of new drugs. Dictyopteris is an important group of marine seaweeds and is widely distributed in tropical, subtropical and temperate regions. This genus is known by its characteristic “ocean smell”. Some species show a distinct phytochemistry, with specific secondary metabolites, including C₁₁-hydrocarbons, sulfur compounds and quinone derivatives, not usually found in marine seaweeds and described for the first time in the literature. Furthermore, several terpenes, steroids and halogenated compounds have been described. This chemical diversity gives it interesting biological properties, including cytotoxic, antimicrobial, antioxidant, anti-inflammatory and anti-herbivory activities. These findings highlight the importance to continue investigations on this genus and the need to compile the data available so far, since the species are quite heterogeneous, notably in relation to the chemical constitution. This paper reviews the literature on the Dictyopteris genus, focusing on its secondary metabolites and biological activities, in order to build the base for further studies.

Keywords: Dictyopteris; Beach odor; C11-hydrocarbons; Sesquiterpene quinones; Sulfur compounds

Species	Compounds	Activity	Reference
D. divaricata	66, 73, 76-79, 81, 83, 84, 108-117, 135, 138, 143, 154	Cytotoxicity against several human cancer cell lines (KB, PC-3M, Ketr 3, A549, Bel7402, BGC-823, HCT-8, and MCF-7): inactive	Song et al., 2004; Song et al., 2005a; Song et al., 2006
D. polypodioides	44, 45, 47-50, 53	Antibacterial against resistant strains of S. aureus and E. coli (inactive)	Dimou et al., 2016
D. polypodioides		Anti-inflammatory (LPS stimulation assay): 45 and 53 were active (IC₅₀ = 3.8 and 14.2 µM, respectively) and showed growth inhibition above 45 and 85 µM, respectively	Dimou et al., 2016
D. sp	53	Phospholipase A2 inhibition (inactive)	Mayer et al., 1993
D. undulata	125, 126	Antifungal (Phytophthora cinnamomi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Sclerotium rolfsii): moderate	Fenical et al., 1973
	125	Anti-angiogenic properties	Castro et al., 2004
	126	Phospholipase A2 inhibition: 52%	Mayer et al., 1993
	126	Inhibition of inflammatory bowel disease in a mouse model of ulcerative colitis	Yamada et al., 2014
	126	Neuroprotection by activating the Nrf2/ARE pathway	Shimizu et al., 2015
	130	Phospholipase A2 inhibition: 76%	Mayer et al., 1993
	137	Antifungal (12.5-25 µg/ml) against Saccharomyces cerevisiae, Sclerotinia libertiana, Aspergillus niger, and A. oryzae	Ochi et al., 1979a,b
	Mixture of 163 and 164, and 168	Inhibition of PTP1B (IC₅₀ = 1.88 and 3.47 mM)	Feng et al. (2018)
	Mixture of 163 and 164, and 165, 166, 167, 168, 169	Cytotoxicity against human cancer cell lines HL-60 (IC₅₀ from 1.02 to 2.70 mM) and A-549 (IC₅₀ from 1.35 to 2.85 mM)	Feng et al. (2018)

Species	Algal material	Active compounds	Activity	Reference
D. acrostichoides	CH₂Cl₂ surface extract and whole-cell extracts	-	Antifouling test: whole-cell extract inhibits settlement and germling development of Ulva australis gametes, while the CH₂Cl₂ extract had no significant effect. Both whole-cell and CH₂Cl₂ extracts had no effects in inhibition of settlement of Polysiphonia spores	Nylund et al., 2007
D. delicatula	Whole alga	16, 19	Herbivory test: D. delicatula was intermediate in the preference of the fishes, while amphipods preferentially consumed D. delicatula. Compounds 16 and 19 significantly deterred fish grazing but had no effect on grazing by amphipods	Hay et al., 1988
	CH₂Cl₂ extract	-	Antifouling test: no fouling inhibition using the common fouling organism mussel Perna perna	Medeiros et al., 2007
	Aqueous extract	-	Antiparasitic activity: Weak effect on the life cycle of the monogenean ectoparasite, Neobenedenia sp., infecting farmed barramundi (Lates calcarifes)	Hutson et al., 2012
D. divaricata	MeOH extract	-	Herbivory test: deterred feeding by the sea urchin Strongylocentrotus nudus and the abalone Haliotis discus hannai	Shiraishi et al., 1991
D. hoytii	Whole alga	-	Herbivory test: no activation of chemical defenses following damage by herbivores	Cetrulo and Hay, 2000
D. hoytii	Whole alga	-	Herbivory test: feeding preference of amphipod A. longimana in comparison of D. polypodioides (which contains C₁₁-sulfur compounds)	Schnitzler et al., 2001
D. jamaicensis	Whole alga	-	Herbivory test: no feeding preference by fishes	Marques et al., 2006
D. jolyana	Whole alga		Herbivory test: the alga was less consumed by fishes in comparison to other alga species	Longo et al., 2015
D. justii	CHCl₂/MeOH and MeOH extract	156	Herbivory test: The crude extracts were inactive, but the mixture of epimers 156 has inhibitory effect against the crab Pachygrapsus transversus	Teixeira et al., 2006
D. plagiogramma	Whole alga	-	Herbivory test: least susceptibility to consumption by herbivorous fishes	Mendes et al., 2015
D. plagiogramma	Whole alga	-	Herbivory test: the alga was less consumed by fishes in comparison to other alga species	Longo et al., 2015
D. polypodioides	Whole alga	53	Herbivory test: deterring feeding by the amphipod A. longimana, without effect on feeding by the sea urchin Arbacia punctulata	Schnitzler et al., 1998
	Whole alga	-	Herbivory test: not preferred by the amphipod A. longimana in the herbivory test when compared to D. hoytii and D. polypodioides that had lost the ability to produce C₁₁ sulfur compounds	Schnitzler et al., 2001
	Whole alga	-	Herbivory test: reducing feeding but not palatability in response to direct amphipod-attacks	Yun et al., 2007
	Whole alga	-	Herbivory test: predominated in the diet of Lessepsian migrant Siganus luridus	Stergiou, 1988
	Diethyl ether extract	-	Antifouling activity and variable antimicrobial activity against some representative species of the major groups. of fouling organisms	Hellio et al., 2001
D. undulata	Methanol extract	125-127, 129, 130, 135, 142	Piscicidal activity: the extract and isolated compounds were toxic to fish	Dave et al., 1984
	Neutral and acidic fractions methanol extract	125, 126, 129-131, 135	Herbivory test: potent inhibitory activity against young abaone Haliotis discus hanai	Kurata et al., 1996
	Methanol extract	125, 126, 132, 134-137	Algicidal activity: moderate to high cell lysis activity against the red tide microalgal species	Ishibashi et al., 2013
	Ethanol extract	-	Antifouling test: no activity against Ciona intestinalis, Bugula neritina, Spirorbis sp., but enhanced the settling of Ciona intestinalis	Bakus and Kawaguchi, 1984
	Methanol extract	125, 126	Antifungal activity: moderate activity against Phytophthora cinnamomi, Rhizoctonia solani, Sclerotinia sclerotiorum and Sclerotium rolfsii	Fenical et al., 1973

	Dac	Dau	Dde	Ddi	Dju	Dla	Dpl	Dpo	Dpr	Dun
C₁₁	15	12	2	2	0	14	12	16	16	8
Suphur	0	5	0	0	0	0	9	10	1	0
Terpenes	0	0	5	53	0	2	2	21	1	4
Meroditerpenes	0	0	1	4	0	0	0	2	0	13
Halogenated	0	0	0	2	0	0	0	2	0	0
Steroids	0	0	8	2	1	0	8	3	0	12
Other volatile	0	0	0	1	2	15	4	29	1	1
Total	15	17	16	64	3	31	35	83	19	38

Species	Activity	Algal material	Reference
D. dichotoma	Tyrosine inhibition	EtOH extract	Kwak et al., 2016
D. jamaicensis	Antibacterial, antifungal	CHCl₃/MeOH extract (2:1)	Ballantine et al., 1987
D. jolyana	Antibacterial, antifungal, antiprotozoal (all inactive)	CH₂Cl₂/MeOH extract (2:1)	Bianco et al., 2013b
D. longifolia	Antibacterial	EtOH extract	Vlachos et al., 1997, 1999
	Antioxidant	EtOH, MeOH, Aqueous extracts	Matsukawa et al., 1997; Lee et al., 2011; Lee and Kim, 2015
	Cytotoxic, anti-inflammatory	EtOH extract	Lee et al., 2008

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Sociedade Brasileira de Farmacognosia Universidade Federal do Paraná, Laboratório de Farmacognosia, Rua Pref. Lothario Meissner, 632 - Jd. Botânico, 80210-170, Curitiba, PR, Brasil, Tel/FAX (41) 3360-4062 - Curitiba - PR - Brazil
E-mail: revista@sbfgnosia.org.br

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[TFN1] Dac, D. acuostichoides; Das, D. australis; Dde, D. delicatula; Ddi, D. divaricata; Dju, D. justii; Dla, D. latiuscula; Dpl, D. plagiogramma; Dpo, D. polypolioides; Dpr, D. prolifera; Dun, D. undulata.