A syn-ent-labdadiene derivative with a rare spiro-β-lactone function from the male cones of Wollemia nobilis

Phytochemistry, Chemotaxonomy, and Biological Activities of the Araucariaceae Family—A Review

“…Yet, biflavonoids and, in particular, agathisflavone and its derivatives represent the most common compounds in this context. By the way, these compounds have actually been used as chemotaxonomic markers at the genus level [ 22 , 28 , 29 , 30 , 31 , 32 , 33 ], even if their occurrence seems, now, to be extended at the whole family level. Some diterpenes have also been reported for this genus from A. lanceolata [ 14 , 15 ], A. macrophylla from China [ 16 ] and from Fiji [ 18 , 19 ] and the resin of A. microstachya [ 20 ].…”

“…Yet, diterpenes and biflavonoids represent the most common compounds in this context. By the way, these compounds have actually been used as chemotaxonomic markers at the genus level even if their occurrence seems, now, to be extended at the whole family level [ 22 , 28 , 29 , 30 , 31 , 32 , 33 ]. Several other sub-classes of natural compounds, including triterpenes, lignans, simple flavonoids, and organic acids, have been recorded for this genus [ 44 , 45 , 46 , 47 , 50 , 51 , 54 , 55 , 57 , 58 , 62 , 68 , 69 , 71 , 73 , 75 , 77 , 80 , 82 , 84 , 88 ].…”

“…As Table 3 clearly shows, most of the phytochemical works reported in the literature about this species regard exemplars collected in Italy [ 28 , 29 , 30 , 31 , 32 , 33 ]. Yet, this fact is not so unusual since, as already mentioned, Italy is one of the main places where this species has been introduced in order to favor its survival.…”

“…In addition, there are two works regarding the essential oil content of a sample collected in Belgium [ 106 ] and one regarding the polar fraction metabolites of an exemplar purchased from a company in Poland [ 107 ]. The studied organs were mainly the leaves [ 8 , 32 , 106 ] but also other organs were taken into considerations i.e., twigs [ 106 , 107 ], half-matured female cones [ 33 ], male reproduction organs [ 29 ], unripe female cones [ 31 ], and male cones for two different studies in the time distance of one year [ 28 , 30 ]. For what concerns the identified compounds, also W. nobilis is known to biosynthesize both components of the essential oil and polar fraction metabolites.…”

“…For none of the studied samples, both essential oil and polar fraction composition were studied. In particular, only the essential oil composition was analyzed for the exemplar from Australia [ 8 ] and for the leaves and twigs of the exemplar coming from Belgium [ 106 ], whereas only the polar fraction composition was analyzed in all the other cases [ 28 , 29 , 30 , 31 , 32 , 33 , 107 ]. Among the essential oil metabolites, only β-pinene and germacrene D are present in all the studied samples [ 8 , 106 ].…”