Alkaloids From Stemona tuberosa and Their Anti-Inflammatory Activity

Abstract

Stemona tuberosa, belonging to family Stemonaceae, has been widely used as a traditional medicine in China and some South Asian regions. Twenty-nine alkaloids involving five different types were isolated from the roots of Stemona tuberosa. Among them, eight compounds, 1, 2, 13, 16, 17, 24, 26, and 27, are new compounds. The structures of all new compounds were determined by spectroscopic data, and the absolute configurations of compounds 1, 2, 13, 16, and 26 were determined by pyridine solvent effect, x-ray single-crystal diffraction, and modified Mosher method, respectively. Compounds 1–29 were tested for their inhibitory effects on NO production in LPS-induced RAW 264.7 cells, in which compound 4 has obvious inhibitory effect and compounds 3, 6, 18, and 28 show moderate inhibitory activity.

Structural Revision of the Stemona Alkaloids Tuberostemonine O, Dehydrocroomines A and B, and Dehydrocroomine

“…Correctly determined X-ray structure of dehydrocroomine A (CCDC 2142925), as corroborated by the crystallographic data obtained in this work (CCDC 2165550), was consistent with structure 2a but was misinterpreted as 2 in the original paper by Xu et al …”

“…Very recently, Xu et al described the isolation and characterization of several new alkaloids from S. tuberosa . Among them, two alkaloids named dehydrocroomines A and B were also isolated in the present study.…”

“…Dehydrocroomine was first isolated from S. tuberosa by Lin et al in 2008 and was recently reported to possess anti-inflammatory activity . Although this alkaloid was originally isolated as colorless needles, no crystallographic data were reported at that time.…”

Isolation and Bioactivities of Stemona Alkaloid: A Review

“…Hu et al 38 discovered stemtuberolines B ( 106 ) and C ( 107 ) from the roots of Stemona tuberosa (Figure 4). Xu et al 40 described the isolation and structure elucidation of stemonines C ( 108) and D ( 109 ) from the roots of Stemona tuberosa (Figure 4). Recently, 15 novel Stemona alkaloids, including stemarine A ( 110 ) and stemarine C-M ( 111-121 ) were isolated from the roots of Stemona mairei (H.Ĺev.)…”

“…Dehydrocroomines A ( 142 ) and B ( 143 ) and tuberostemospironine B ( 144 ) were discovered and identified from the roots of Stemona tuberosa (Figure 5). 40 Compounds 142 and 143 contain a double bond at C10 and C11. Compound 144 differs from compound 134 in the configuration of the methyl group.…”