Terpenoids from Laurencia luzonensis

Abstract

Luzodiol (4), a diterpene possessing a new carbon skeleton, and five new sesquiterpenes (5-9) of the snyderane class have been isolated from the red alga Laurencia luzonensis and their structures determined by spectroscopic analysis. The relative stereochemistry of the known luzonensol (3) was assigned by its conversion to palisadin B (10).

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

“…67,149,221,225,228 Irieane diterpenes were solely isolated from L. irieii (276−284), 189,190 L. pinnata (285− 287), 191 L. decumbens (288), 192,193 and more recently, from an unrecorded Laurencia species (289), 194 192 and L. similis (576, 577, and 584−586, 588), 185,355,357 352,353,356,358,410 Bromophenols with a 3-bromo-4,5-dihydroxybenzyl unit (598, 360 Despite of some of the characteristic metabolites were found in certain species of the Rhodomelaceae family, it is interesting to note that recollection of the same algal species at the same site and the same season over the consecutive years does not guarantee that only the same metabolites will be obtained. 98 It thus should be noted that, although the presence of these halogenated molecules can be informative, it is not advisable to rely solely on them to make taxonomic assignments, but instead to combine consideration of chemical composition with examination of morphological and cytological features.…”

Terpenes and Polybromoindoles from the Marine Red Alga Laurencia decumbens (Rhodomelaceae)

“…Structurally, this compound was closely related to luzodiol, a diterpene with a rarely described C-skeleton that was recently identified from L. luzonensis [12]. The IR spectrum of 1 indicated the presence of OH groups (3394 cm (Table), HMBC (Fig.…”

“…However, the relative configuration at C(3) and C(15) of 1 remain unknown. (12) to HÀC(14)) 1 ). The HMBC cross-peaks Me(20)/C(2), C(3), and C(4), Me(19)/C(6), C(7), and C(8), Me(18)/C(6), C(10), C(11), and C(12), Me(17)/C(14), C(15), and C(16), and Me(16)/C(14), C(15), and C(17) established the connectivities of the above four structural units at quaternary C-atoms C(3), C(7), C(11), and C(15) (Fig.).…”

Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review

“…The ethanolic extract of the Chinese L. saitoi (Hainan coastline) yielded 2-hydroxyluzofuranone A (163) and 2-hydroxyluzofuranone B (164) [96]. Another collection of the Okinawan L. luzonensis, a rich source of snyderane sesquiterpenes, afforded 3R*, 4S*-luzonolone (165), 3S*, 4R*-luzonolone (166), luzondiol (167), luzonenone (158) and the two isomeric compounds 168 and 169, beside the known compound, aplysistatin (170).…”

“…On the other hand, L. luzonensis was the source of palisadin B (172), palisadin A (173) and its oxidized product aplysistatin (170) [94]. L. saitoi (Hainan coastline, China) was the source of 5-acetoxypalisadin B (174) [100] and 4-hydroxypalisadin C (175) [96] (Figure 9). …”