Diterpenes content of the brown alga Dictyota ciliolata (Dictyotales, Phaeophyceae) and recognition of a Brazilian haplotype based on psbA sequences

Figures & data

Figure 1. Hypothetical biosynthetic pathway for the production of Group I, II, and III diterpenes by Dictyota and Canistrocarpus (Teixeira and Kelecom 1988, 1989; Teixeira 2010).

Table 1. Chemotaxonomic groups of diterpenes produced by Canistrocarpus and Dictyota species from Brazil^a.

Group I and III	Group IIa	Group IIb
Dictyota jamaicensis W. R. Taylor	Dictyota pfaffii Schnetter	Canistrocarpus cervicornis (Kützing) De Paula & De Clerck
Dictyota guineensis (Kützing) P. Crouan & H. Crouan	Dictyota dolabellana De-Paula, Yoneshigue-Valentin and Teixeira	Canistrocarpus crispatus (J.V. Lamouroux) De Paula & De Clerck
Dictyota menstrualis (Hoyt) Schnetter, Hörning & Weber-Peukert
Dictyota mertensii (C. Martius) Kützing

^aKelecom and Teixeira 1988; Kelecom et al. 1991; Teixeira et al. 2001; Barbosa et al. 2003, 2004; De Clerck et al. 2006; Cavalcanti et al. 2006, 2011; Freitas et al. 2007; De-Paula et al. 2001, 2007a, 2008, 2012; De Paula et al. 2007b; Oliveira et al. 2008; Ortiz-Ramirez et al. 2008.

Figure 2. Dictyota ciliolata. A, Voucher specimen from Rocas Atoll (HRJ 5516) (scale bar = 10 cm). B, Detailed view of the same specimen showing margins with conspicuous teeth (scale bar = 1 cm). C, Voucher specimen from Preta beach (HUNI 5776) (scale bar = 5 cm). Insert: detailed view of the discoid holdfast (scale bar = 5 mm). D, Detailed view of the same specimen showing margins with very small teeth (black arrows) (scale bar = 1 cm). E, Voucher specimen from Prainha (HUNI 5010) (scale bar = 2 cm). F, Detailed view of the same specimen showing smoothed margins (scale bar = 5 mm). G, Voucher specimen from Prainha (HUNI 5011) (scale bar = 5 cm). H, Detailed view of the same specimen showing sparsely cilio-dentate margins (black arrows) (scale bar = 2 cm).

Figure 3. Diterpenes produced by the three populations of D. ciliolata.

Figure 4. Haplotype diversity of psbA sequences taken from D. ciliolata populations. A, Haplotype network of psbA showing the three geographically segregated groups; the haplotype shown in the intersection is the only haplotype found in all three regions. B, Distribution of the 10 haplotypes in the Atlantic and the Indo-West Pacific populations. Squares indicate locations where D. ciliolata had previously been studied. Red squares: DNA sequences available for a given population; blue squares: known diterpenes from a given population; green squares: DNA sequences and known diterpenes available for a given population. Map based on data from Cronin et al. (1995); Cronin and Hay (1996); De Clerck et al. (2006); Tronholm et al. (2010, 2012, 2013); Caamal-Fuentes et al. (2014b); Cheng et al. (2014); and the present study.

Table 2. Diterpenes produced by Brazilian populations of D. ciliolata.

Identified compounds	Preta Beach, Grande Island, Angra dos Reis, RJ (Brazil)^a	Itapuã beach, Salvador, BA (Brazil)^a	Rocas Atoll, RN (Brazil)^a	Skeletons
Dictyol B acetate	XX	XX	XX	Figure 3A
Dictyol B	tr		X	Figure 3B
Dictyol C	X		X	Figure 3C
Dictyoxide			X	Figure 3D
Isopachydictyol A		X	X	Figure 3E
Pachydictyol A	X	X	X	Figure 3F
4β-Acetoxydictyodial	X		X	Figure 3G
Crenulidanes	tr	X	X	Figure 3H–K

^aDiterpenes identified by HRGC/MS and 1H-NMR techniques combined spectra. Diterpenes Dictyol B acetate, Isopachydictyol A, and Pachydictyol A were isolated and identified via 1H-NMR spectra.

XX implies an abundance of more than 10% of total diterpenes; X corresponds to an abundance of more than 1% of the total diterpenes; tr = trace amounts.

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