Synthesis of Sulfur-Containing Analogues of Hedychenone, a Labdane Diterpenoid from Hedychium spicatum

Abstract

The labdane diterpene hedychenone, isolated from Hedychium spicatum, is an example of a furan-containing natural product. Herein, a new and efficient method for the synthesis of 19 new thio analogues of hedychenone is reported. The present methodology exhibits a broad substrate scope with good to excellent yields without metal or base under mild reaction conditions. The natural compound 1 and four semisynthetic derivatives (3a, 3b, 3i, and 3j) exhibited strong α-glucosidase inhibition activity with IC 50 values of 15.93 ± 0.29, 9.70 ± 0.33, 11.82 ± 0.06, 12.23 ± 0.33, and 12.15 ± 0.14 μg/mL, respectively. In addition, compound 3e (6.0 ± 0.04 mm; zone of inhibition) displayed antibacterial activity against Staphylococcus aureus. This study increases the chemical diversity of bioactive hedychenone derivatives and provides a direction for the development of antidiabetic agents.

Extending the Structural Diversity of Labdane Diterpenoids from Marine-Derived Fungus Talaromyces sp. HDN151403 Using Heterologous Expression

“…The transformants of A. nidulans were grown on solid CD-ST medium for 5 days and extracted with ethyl acetate (EtOAc). Two compounds (1 and 2) were obtained from the core genes transformant AN-labdAB, and eleven compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), including five undescribed ones, talarobicins A-E (3-7), were obtained from the whole genes transformant AN-labdABCDEFG (Figures 2 and 3, Figure S10). [23].…”

“…Labdane-related diterpenes are widely distributed secondary metabolites discovered from fungi, insects, higher plants, and marine organisms [1], possessing high structural diversity and a broad spectrum of biological activities [2][3][4][5][6][7][8][9][10]. The basic core structure of labdane diterpenes is composed of a fused decalin system (C1-10) and a branched six-carbon side chain (C11-16, with C16 attached to C13) at C9, generally with additional four carbons (C17-20) on C8, C4 (with C18 and C19 being attached), and C10 of the decalin system, respectively [6,11].…”

Chemical Diversity and α‐Glucosidase Inhibitory Activity in Needles Essential Oils of Four Pinus Species from Northwestern Himalaya, India

“…The EOs were evaluated for inhibitory activity against α-glycosidase according to previously described protocol with minor modification. [46][47][48] Each sample in DMSO (1 mg/ml) (from 2, 2.5, 5, 10 and 20 μg/ml) was added to 10 μl α-glycosidase solution (0.4 U/ml). Reaction mixtures were kept at room temperature for 5 min.…”

Chemodiversity and α‐Glucosidase Activity of Eucalyptus Species from Northwestern Himalaya, India

“…[23,25,26] Furthermore, EO and its metabolites have been used as flavoring agents in the preparation of several food, pharmaceutical and cosmetic products. [23,27] In continuing study from Himalayan bioresources, [28][29][30][31][32] the objective of current work was to reveal variation in the EOs content, composition, and αglucosidase inhibitory activity of E. citriodora, E. globulus and E. camaldulensis. These results enriched us the awareness on chemodiversity of targeted samples and provide the direction to utilize its function.…”