A tocotrienol series with an oxidative terminal prenyl unit from Garcinia amplexicaulis

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

“…Besides g-(Z)and g-(E)deoxy-amplexichromanol (38) as well as d-(Z)and d-(E)-deoxyamplexichromanol, two aldehydes, namely g-(E)-deoxyamplexichromanal (39) (which is identical to g-(E)-garcinal) and d-(E)-amplexichromanal (40) were isolated from Garcinia amplexicaulis. 43,48 d-(E)-Deoxy-amplexichromanol (32) has also been described in Cedrus atlantica. 45 d-(Z)-Deoxy- amplexichromanol was earlier described by Teixeira et al in Clusia obdeltifolia.…”

“…An additional methoxy-group is introduced at position C-5 of the chromane ring for litchocotrienols B, D, F and G, respectively. Position C-12 0 is hydroxylated for A, B, G or methoxylated for C and D. Macrolitchtocotrienol A (48) derives from an intramolecular condensation between C-12 0 and C-6 to form an ansa-chromane. The structural motive is similar to the smenochromene sesquiterpenes.…”

“…24). 48 5.2 Marine organisms 5.2.1 Brown algae. Next to the large number of di-and sesqui-terpenes, only a few monoterpenes have been described in the literature.…”

Synthesis and Liver Microsomal Metabolic Stability Studies of a Fluorine‐Substituted δ‐Tocotrienol Derivative

“…To address these questions, the proposed C−F bond hydrolysis products, M1 and M2 , of DT3‐F2 ( 1 ) in mouse liver microsomes were synthesized (See supporting information for the synthesis). Interestingly, M2 , also known as δ‐amplexichromanol, is a natural product present in the stem bark of Garcinia amplexicaulis , a shrug found in New Caledonia . To the best of our knowledge, the synthesis of this natural product has never been reported.…”

“…Interestingly, M2, also known as δ-amplexichromanol, is a natural product present in the stem bark of Garcinia amplexicaulis, a shrug found in New Caledonia. [19,20] To the best of our knowledge, the synthesis of this natural product has never been reported. Normal phase chromatography and fluorescence detection (λ excitation = 292 nm, λ emission = 330 nm) was used for better separation of Z/E isomers and improved detection limits.…”