New Polyhydroxylated Steroidal Saponins from Solanum paniculatum L. Leaf Alcohol Tincture with Antibacterial Activity against Oral Pathogens

Author(s)

Valerino-Diaz, Alexander B. ^[1] ; Gamiotea-Turro, Daylin ^[1] ; Zanatta, Ana C. ^[1] ; Vilegas, Wagner ^[2] ; Gomes Martins, Carlos Henrique ^[3] ; Silva, Thayna de Souza ^[3] ; Rastrelli, Luca ^[4] ; dos Santos, Lourdes Campaner ^[1]

Affiliation

^[1] Sao Paulo State Univ, UNESP, Inst Chem, Rua Prof Francisco Degni 55, BR-14800060 Araraquara, SP - Brazil

^[2] Sao Paulo State Univ, UNESP, Inst Biosci, Praca Infante Dom Henrique S-N, BR-11330900 Sao Vicente, SP - Brazil

^[3] UNIFRAN Univ Franca, Lab Res Appl Microbiol, Av Dr Armando Salles Oliveira 201, BR-14404600 Franca, SP - Brazil

^[4] Univ Salerno, Dipartimento Farm, Via Giovanni Paolo 2, I-84084 Salerno - Italy

• Document type: Journal article
• Source: Journal of Agricultural and Food Chemistry; v. 66, n. 33, p. 8703-8713, AUG 22 2018.
• Web of Science Citations: 2

Abstract

Solanum paniculatum L. is widely used in Brazilian folk medicine for the treatment of liver and gastrointestinal disorders as well as for culinary purposes and beverage production. Fractionation of hydroalcoholic {[}ethanol (EtOH) 70%] tincture from S. paniculatum leaves led to the isolation of six new spirostanic saponins which included 6-O-alpha-L-rhamnopyranosyl-(1{''}-> 3')-beta-D-quinovopyranosyl-(22S,23R,25S)-3 beta,6 alpha,23-trihydroxy-5 alpha-spirostane (1), 6-O-beta-D-xylopyranosyl-(1{''}-> 3')-beta-D-quinovopyranosyl-(22S,23R,25R)-3 beta,6 alpha,23-trihydroxy-5 alpha-spirostane (4), 3-O-alpha-L-rhamnopyranosyl-(1{''}-> 3')-beta-D-quinovopyranosyl-(22S,23S,25R)-3 beta,6 alpha,23-trihydroxy-5 alpha-spirostane (5), 3-O-beta-D-xylopyranosyl-(1{''}-> 3')-beta-D-quinovopyranosyl-(22S,23S,25R)-3 beta,6 alpha,23-trihydroxy-5 alpha-spirostane (6), 6-O-alpha-L-rhamnopyranosyl-(1{''}-> 3')-beta-D-quinovopyranosyl(22S,25S)-1 beta,3 beta,6 alpha-trihydroxy-5 alpha-spirostane (7), and 6-O-beta-D-xylopyranosyl-(1{''}-> 3')-beta-D-quinovopyranosyl-(22S,25S)-3 beta,4 beta,6 alpha-trihydroxy-5 alpha-spirostane (8) together with two known spirostanic saponins (2, 3). The structures of these compounds were determined by one-dimensional (1D) and two-dimensional (2D) NMR experiments in addition to high resolution electrospray ionization mass spectrometry (HRESIMS) analyses. The 70% alcohol tincture, used as phytomedicine, exhibited promising activities against oral pathogens, including, Steptococcus sanguinis, St. oralis, St. mutans, St. mitis, and Lactobacillus casei with minimal inhibitory concentration (MIC) values ranging from 6.25 to 50 mu g/mL. The saponin fraction, nonetheless, showed lower activity against all the strains tested (from 100 to >400 mu g/mL). (AU)

• FAPESP's process: 15/04899-3 - Chemical study of the extracts produced by endophytic fungi associated with the aerial parts of Eriocaulaceae species and its antimicrobial activity
• Grantee: Lourdes Campaner dos Santos
• Support Opportunities: Regular Research Grants
• FAPESP's process: 09/52237-9 - Standardized herbal medicines for the treatment of chronic diseases
• Grantee: Wagner Vilegas
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants