Goniothalamin-Related Styryl Lactones: Isolation, Synthesis, Biological Activity and Mode of Action

: This review covers the chemistry and biological aspects of goniothalamin-related styryl lactones isolated from natural sources. This family of secondary metabolites has been reported to display diverse uses in folk medicine, but only a limited number of these compounds have been throughly investigated regarding their biological profile. Herein, we cover the goniothalamin-related styryl lactones having a C6-C3-C4 framework which appeared in the literature for the first time in the period 2000-2017, and the reports on the synthesis, biological activity and mechanism of action which were published from 2007-2017.

Styryl Lactones from Roots and Barks Goniothalamus lanceolatus

A new styryl lactone, 5 R,6 R-5-hydroxy-6-styryltetrahydropyrane-2-one 2 was isolated from the roots of an endemic Goniothalamus lanceolatus Miq. of Sarawak, Malaysia. Furthermore, seven previously undescribed diastereomers, 5 R,6 R-5-hydroxygoniothalamin 3, 5 R,6 R-5-acetylgoniothalamin 4, 6 S,7 S,8 S-goniodiol-7-monoacetate 5, 6 S,7 S,8 S-goniodiol-8-monoacetate 6, goniofupyrone B 7, deoxygoniopypyrone B 8 and 1 S,5 S,7 R,8 S,3- endo,7- endo-(+)-8- epi-9-deoxygoniopypyrone acetate 9, along with six known styryl lactones (1, 10–15) were also isolated and characterized. 6 S-goniothalamin 1 is reported for the first time from a Goniothalamus species. 1, 11 and 12 showed cytotoxic activity against human colon and lung cancer cell lines with IC50 values ranging from 2.38–7.59 μM.

Goniothalamus: Phytochemical and Ethnobotanical Review

Goniothalamusspecies are used in widespread medicines for abortion, anti-aging, body pains, rheumatism, skin complaints, typhoid fever, tympanites, stomach ache and fever. The present study reviews the distribution of species along with their synonyms, their traditional usage, and correlated chemical compounds ofGoniothalamusspecies with stress on the authentication of their ethnobotanical uses. The findings in someGoniothalamusspecies suggest that the chemical nature of their derivatives, such as acetogenins and styryl-lactones, may justify the use of these species against cancer in Asian traditional medicines due to their cytotoxic potential.

Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(−)-goniodiol

An unusual diastereoselective Grignard reaction has been explored, where the Grignard reagents are derived from 1,n-dihaloalkanes.