Unusual derivatives from Hypericum scabrum

Abstract

Three new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

Valorization of bio-colorants extracted from Hypercium scabrum L. plant for sustainable and ecological coloration of wool yarns

“…The random use of antibiotics and subsequent antibiotic resistance have compelled scientists to search for alternative drugs which will act quickly and effectively. H. Scabrum aerial plant parts possess many aromatic compounds of which three compounds with unusual skeletons were extracted and exhibited moderate level of effectivenes against T. brucei and P. falciparum [ 27 ]. The isolated chemical components of H. scabrum have antioxidant and antibacterial properties that are attributed to the presence of phenolic groups or oxygen-bound derivatives [ 28 ].…”

Anatomical and Phytochemical Characteristics of Different Parts of Hypericum scabrum L. Extracts, Essential Oils, and Their Antimicrobial Potential

“…Just in 2020, the scientists found three new compounds with untypical skeletons that were segregated from the air-dried aerial parts of H. scabrum plant. The compounds revealed a moderate activity against T. brucei and P. falciparum [23]. These structures mostly consist of phenolic structure or oxygen-bound derivatives of these structures.…”

Prenylated acylphloroglucinols from aerial parts of Hypericum scabrum

“…Hypericum is one of the biggest genus of family Hypericasease, with multifarious applications in traditional medicine around the world. H. scabrum , one of the species of Hypericum , growing in Iran, has been used in Iranian folk medicine as an antiseptic, a sedative, an analgesic, and for the treatment of headaches 1 . Several classes of compounds were reported from Hypericum genus, and polyprenylated acylphloroglucinols (PPAPs) are among those well-known secondary metabolites isolated from this genus to date.…”