Sesterterpenoids: chemistry, biology, and biosynthesis

Abstract

Over the last seven years, expanding research efforts focused on sesterterpenoids has led to the isolation, identification, and characterization of numerous structurally novel and biologically active sesterterpenoids.

A Cryptic Plant Terpene Cyclase Producing Unconventional 18‐ and 14‐Membered Macrocyclic C25 and C20 Terpenoids with Immunosuppressive Activity

“…and considered to function as kairomones (Figure 1). [4a–c] Sesterterpenoids with 5/15, 5/12, 6/12 or 5/12/5 ring systems have been mainly obtained from fungi (Figure 1), and reported to show cytotoxic, antiangiogenic and phytotoxic activities or serve as inhibitors of syncytium formation in HIV infection [4d] . So far, no macrocyclic sesterterpenoid has been directly isolated from plants [4e]…”

Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae

“…Sesterterpenes are a small class of terpene natural products that are not commonly isolated from bacteria . As a result, only a few bacterial geranylfarnesyl polyprenyl synthases have been biochemically characterized, such as those involved in the biosynthesis of somaliensenes A and B, atolypenes, and the sestermobaraenes .…”

An extremely promiscuous terpenoid synthase from the Lamiaceae plant Colquhounia coccinea var. mollis catalyzes the formation of sester-/di-/sesqui-/mono-terpenoids

“…Naturally occurring alotane sesterterpenoids have been reported from only a handful of marine sponges and also as the enzymatic products of a bacterial sesterterpenoid cyclase from the UbiA superfamily. Some serve as potent activators of cAMP cell signaling or exhibit cytotoxic activity ( Yang et al., 2018 ; Li and Gustafson, 2021 ). In addition, compound 3 is a new member of the prenylbisabolane-type diterpenoids, a relatively rare subclass of diterpenoids previously discovered in a few plants of the Asteraceae, Lamiaceae, and Euphorbiaceae families and in marine organisms.…”