Momilactones are allelochemicals in rice and moss defense. Momilactone-like compounds are therefore considered important secondary metabolites for plant defense. They may serve as promising lead compounds for crop-friendly herbicides as well as antifungal and antibacterial agents. Many of these substances possess potent cytotoxicity property against cancer cell lines as well. The present paper is the first review on these versatile molecules, focusing on the structure, biological activity, chemical synthesis, and biosynthesis of the naturally occurring momilactone-like molecules reported from 1973 to 2017.

Six new pimarane derivatives, including two dinor-pimaranes (1, 2), two 17-nor-pimaranes (3, 4), and two 17-nor-(9β-H)-pimaranes (5, 6) were isolated from the tuber of Icacina trichantha. Their structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 1 and 5 were determined by single-crystal X-ray diffraction, and that of 2 was established by electronic circular dichroism data analysis. Compound 3 possesses a unique C-20 acetal moiety. It is the first report of the isolation of dinor-(9β-H)-pimarane derivatives from Icacina plants. Compounds 5 and 6 showed moderate cytotoxicity against MDA-MB-435, MDA-MB-231, and OVCAR3 cell lines, with IC50 values of 2.91–7.60 µM and 1.48–3.23 µM, respectively.

Two modified diterpenoids featuring a novel 4,12-dioxatetracyclo[8.6.0.02,7.010,14]hexadecane core, together with a 3,4-seco-pimarane, a 3,4-seco-cleistanthane, and eight pimarane derivatives were isolated from the tuber of Icacina oliviformis.

Data measured in methanol-d 4 . b Data measured in DMSO-d 6 .