A 7,8-secolabdanoid from the liverwort Pallavicinia subciliata

Novel Diterpenoids Incorporating Rearranged Labdanes from the Chinese Liverwort Anastrophyllum joergensenii and Their Anti-inflammatory Activity

“…Anajoerin J (10) possessed a molecular formula of C 16 H 24 O 3 and was arranged on a norditerpenoid, as confirmed based on its 13 C NMR and HRESIMS (m/z 265.1798 [M + H] + , calcd 265.1798) data. The NMR spectroscopic data of 10 closely resembled that of scapairrin Q, 37 excluding that the position of the hydroxyl was shifted from C-5 to C-6 in 10, which was determined derived from the HMBC interrelations from H 3 -14 to C-3, C-4, C-5, and C-15 and from H 3 -15 to C-3, C-4, C-5, and C-14, further supported by the 1 H− 1 H COSY interrelations of H-5/H-6, H-6/H 2 -7, and H-6/OH-6.…”

“…Bryophytes were reported as an emergency food source, which are known to have been utilized as human food by the Laplanders, who historically incorporated it into their bread . Notably, Bryophytes are also used as medicine, which is closely related to the function of their metabolites. , Liverworts are taxonomically classified as members of the bryophytes, which are an abundant source of structurally complex aromatic compounds and terpenoids, − several of which show various biological activities, such as anti-inflammatory, antifungal, antibacterial, antiviral, cytotoxic, insect antifeedant, antiobesity, and plant growth regulatory activities …”

“…1 and 3. (3.67) nm; IR ν max : 3536, 2926, 1723, 1577, 1461, 1302, and 975 cm −1 ; 1 H and 13 C NMR data are shown in Tables 2 and 3. 13 C NMR data are shown in Tables 1 and 3.…”

Diels–Alder adducts of a labdane diterpenoid from the Chinese liverwort Pallavicinia subciliata

“…Previous chemical investigations on the Pallaviciniaceae family have led to the treatment of labdane-type diterpe-noids, 11 which form various intriguing carbon skeletons [12][13][14][15][16][17] through enzymatic or nonenzymatic pathways. 18 Our ongoing phytochemical studies on the genus Pallavicinia have led to the discovery of one novel labdane monomeric diterpenoid (1) and its dimeric derivatives (2-4) (Fig.…”

Remote B-Ring Oxidation of Sclareol with an Engineered P450 Facilitates Divergent Access to Complex Terpenoids

“…In the same vein, we designed a model study toward the pallavicinin 23 skeleton via a biomimetic Grob fragmentation− aldol cyclization sequence (Scheme 1C). Toward this goal, the C3-OH of 23 was protected as the TBS ether and the resulting product was subjected to reduction with LiAlH 4 , followed by protection of the resulting primary alcohol to afford intermediate 24.…”