Records of Natural Products

Antileishmanial activity guided studies on the methanolic extract of the tubers of Cyclamen rohlfsianum Asch. resulted in the isolation and characterization of six saponins. All saponins were established as tri-, tetra-, and pentaglycosidic derivatives of 13β-28- epoxy-oleanane-type triterpenic sapogenols. Two of them were found to be newly described saponins, rohlfsianosides A and B. Their structures were identified as 3-O-β-{[β-Dxylopyranosyl-( 1→2)-β-D-lucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}- 13β,28-epoxy-16α-hydroxy-30-acetoxy-oleanane (rohlfsianoside A), and 3-O- β-{{[β-D-xylopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→4) ]}-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-protoprimulagenin A (rohlfsianoside B), respectively. Additionally, three known compounds, cyclamiretin A (3β,16α- dihydroxy-13β-28-epoxy-oleanan-30-al) glycosides; cyclaminorin, deglucocyclamin and cyclamen, and protoprimulagenin A (13β-28-epoxy-3β,16α-dihydroxy-oleanane) derivative, lysikoianoside I, were identified. The structure elucidation of the saponins was established by means of spectroscopic methods (1D and 2D NMR, HR-MS). All the saponins showed notable growth inhibitory activity against Leishmania  ropica, with IC50 values ranging from 17.5 to 21.9/mL.

A new isoflavone apiosisoflavone A (1) and five known isoflavones (2–6) were isolated fromthe ethanol extracts of Apios fortuneiMaxim. The structures were elucidated by spectroscopic data analysis of NMR, HR-ESI-MS, and experimental and calculated ECD. All compounds were evaluated on the anti-inflammatory activity against RAW264.7 cell lines. The levels of NO and TNF-α released by RAW264.7 cells were detected by the kit. All the compounds displayed moderate anti-inflammatory activity.

Kaempferol, a naturally occurring flavonoid found in hair growth-promoting plants, was investigated for its direct effects on hair loss prevention. This study assessed its impact on human dermal papilla (HDP) cells, essential regulators of hair follicle activity. Kaempferol significantly enhanced HDP cell proliferation in a dose-dependent manner, exceeding the effect of minoxidil. It markedly inhibited TGF-β1-induced Smad-binding activity (65.8%) and IL-4-induced STAT6 activity (72.5%), compared to finasteride (35%) and tofacitinib (96%), respectively. Western blot analysis showed suppression of phosphorylated Smad2/3 and STAT6, along with upregulation of CDK2, CDK4, cyclin D3, ERK1/2, IGF-1R, and VEGFR-2. In vivo, topical application of Kaempferol in C57BL/6 mice significantly promoted hair growth, increased follicle numbers, and improved hair thickness. These findings suggest that Kaempferol enhances hair growth through modulation of TGF-β/Smad and JAK3/STAT6 pathways and may serve as a promising natural therapeutic agent for hair loss treatment.

In our study, chemical exploration of the Nicotiana tabacum L. symbiotic fungus Aspergillus sp. TE-65L led to the discovery of a new himeic acid derivative, japonimeic acid J (1), along with two previously reported compounds 2 and 3. The structure of the new compound was unequivocally elucidated using nuclear magnetic resonance spectroscopy and high-resolution electrospray ionization mass spectrometry. Furthermore, compounds 1 and 2 displayed strong anti-phytopathogenic potency against Alternaria alternata and Botrytis cinerea, with a minimum inhibitory concentration of 4 μg/mL. This result suggests that they have considerable potential as new, naturally sourced agro-antibiotics for controlling fungal plant diseases.