A new steroidal glycoside from the fruits of Solanum myriacanthum

Abstract

A new cholestane-type steroidal glycoside, solamyriaside A (1), was isolated from the fruits of Solanum myriacanthum Dunal (Solanaceae), along with two known steroidal glycosides, namely, solaviaside A (2) and aculeatiside A (3), and three known steroidal alkaloid glycosides, namely, solamargine (4), khasianine (5) and solasonine (6), which were isolated for the first time from this plant. Based on spectroscopic data as well as chemical evidence, 1 was determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-22R,25R-cholest-5-ene-3β,16α,22,26-tetraol 26-O-β-D-glucopyranoside. The cytotoxic activity of 1–6 against HL-60 human promyelocytic leukaemia cells was examined. Compounds 4–6 showed cytotoxic activity. Among them, 4 exhibited the strongest activity with an IC₅₀ value of 4.64 ± 0.17 μM, similar to the activity of cisplatin, a positive control.

Graphical Abstract

Keywords:

• Solanum myriacanthum
• Solanaceae
• cholestane-type steroidal glycoside
• cytotoxic activity

Acknowledgements

We express our appreciation to Mr. H. Harazono of Fukuoka University for the measurement of the FAB-MS. We also sincerely thank to Ms. Nami Tanaka, Mr. Shuhei Hashimoto and Mr. Yuji Hashihara of Kyushyu Tokai University for the collaboration of extraction and isolation of compounds.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

A part of this work was supported by Research and Study Project of Tokai University General Research Organisation (Kanagawa, Japan).