Isolation of Guaianoid Pigments from the Gorgonian Calicogorgia granulosa

Abstract

Three pigments of the guaiazulene class have been isolated from the gorgonian Calicogorgia granulosa. Structures of these compounds have been determined as guaiazulene, 2,2'- diguaiazulenylmethane, and a new compound, 2,2'-biguaiazulenyl, by combined chemical and spectroscopic methods. 2,2'-Biguaiazulenyl exhibited moderate antimicrobial activity.

Study on the photostability of guaiazulene by high‐performance liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry

“…Similarly, the parabolas (2), (3) and (4) could be ascribed to the [M+H] + ions of guaiazulene dimer, trimer and tetramer with addition of oxygen atoms, respectively. In fact, [M+H] + at 443 m/z (parabola (2)) is derived from the addition of three oxygen atoms to the GA dimer (MW 394, 2,2′‐biguaiazulenyl structure proposed by Seo et al 2…”

“…Moreover, GA has been isolated from marine red algae and is widely distributed among marine octocorals of the order of gorgonacea . In octocorals, guaiazulene‐related sesquiterpenoids, as 2,2′‐biguaiazulenyl and 2,2′‐diguaiazulenylmethane, were also present 2. Reports from various sources show that azulene and GA are widely used as ingredients in cosmetic, beauty, skin and body‐care products 3.…”

Chemical and biological aspects of octocorals from the Brazilian coast

“…For other species of the family Acanthogorgiidae, 9,10-secosterols isolated from methanolic extract of a gorgonian octocoral collected in Japan was lethal to Artemia salina, (LD 50 values ranging from 1.0 to 10 ppm) and inhibited insect growth in the silkworm, Bombyx mori (Ochi et al, 1990). From species of the family Acanthogorgiidae, steroids as Acanthovagasteroid A (47) (Zhang et al, 2004) and a diversity of terpenes such as eunicellin diterpenes from Muricella subogae (48) (Li et al, 2013b), xenicane norditerpenes and diterpenes from Acalycigorgia inermis, such as 9-deoxy-xeniolide-A (49) (Rho et al, 2001), and guaiazulene-based terpenoids (50, 51) (Seo et al, 1996;Chen et al, 2012a,b) were isolated.…”

2,12′-bis-hamazulenyl from Ajania fruticulosa essential oil

“…Dimeric guaianolids are encountered in plants and are possible precursors of dimeric hamazulene 1 and its analogs that have not yet been prepared [12].…”