Easterfield and his colleague J.C McDowell proposed the name “totarol” in a follow-up paper in 1915,[5] as the crystalline substance was believed to possess a tertiary alcohol group.
[21] Totarol may also function by disrupting the structural integrity of the phospholipid bilayer of bacteria by weakening Van der Waals interactions with its phenolic group,[22][23][24] which also results in bacterial cells unable to synthesize ATP.
The use of Podocarpus totara extract in Māori medicines for treatment of fevers, asthma, coughs, cholera, distemper, chest complaints and venereal disease dates back to over 100 years.
The tōtara tree was accorded divine status by Māori based on its immense size and its use in making waka employed on long, dangerous voyages.
It has a strong link to Māori creation stories as it reaches down to Papatūānuku (Mother Earth) and up towards Ranginui (Sky Father).
The roots in the symbolism of the tōtara mark out a genealogical reference point which Māori believe ties them to the natural world, the whenua (land) and their ancestral rohe (territory).
[31] In Māori tradition tōtara is the first born child of Tāne-Mahuta and the forest goddess Mumuwhango and is considered a noble tree.
[33] European settlers of New Zealand used the wood for wharf piles, bridges, railway sleepers, telegraph poles, lighthouses, mining equipment, fence posts and foundation blocks.
Houses, churches, grave markers, and even cobbles and kerbs were made of tōtara; strips of the bark were used as a roofing material.
Scientists have suggested that totarol from Cupressaceae resin at the site was used for its antibacterial and antifungal properties to preserve meat, as well as for its ability to repel insects.
[36] Totarol has been observed in the endemic Mexican plant Buddleja perfoliata, used in traditional medicine as a topical antiseptic and diuretic against headaches, colds, tuberculosis, heart disease, dizziness and nervousness.
Additionally, it was used to treat oral wounds, disorders of the digestive and urinary systems, diarrhea, peptic ulcers, hemorrhoids and inflammations.
[41] Totarol's anti-cancer activity is hypothesized to be due to the natural product's ability to form an o-quinone methide in vivo.
The first total synthesis of totarol (Scheme 3)[46] utilized 6 and the alkyne 7 to yield 8 which was converted to the corresponding ketone 9 via hydrogenation followed by cyclization with polyphosphoric acid.
[48] Subsequent hydrogenation of 13 followed by intramolecular cyclization with aluminium chloride forms the B ring and totarylmethyl ether which is demethylated by boron tribromide to yield totarol.
A more recent organic synthesis of totarol was achieved by utilizing 14, a lamdane diterpene named zamoranic acid (Scheme 5).
The key step in the synthesis was the cyclization of ring C: 16 was treated with SmI2 to yield totarane diastereomers which were separated by column chromatography.
The synthesis was completed by a halogenation-dehydrogenation sequence and subsequent bromination to yield 18 and ring aromatization with elimination via a lithium complex.
Consequently, totarol can aid in the characterization of different types of gin or commercial brands, vouching for the authenticity and quality of the product.
[95] Totarol has been found on the posterior tibia of Frieseomelitta silvestrii languida, a species of stingless bees from Brazil.