Sarcaglarols A—D, Lindenane−Monoterpene Heterodimers from Sarcandra glabra Based on Molecular Networks

Abstract

Sarcandra glabra | Molecular networks | Natural products | Structural elucidation | Peroxides Sarcaglarols AD (1-4), two pairs of lindenane−monoterpene heterodimers fused by a 1,2-dioxane moiety, were discovered and isolated from the leaves of Sarcandra glabra guided by MS/MS molecular networking-based strategy. Their planar structures, absolute configurations of basic skeleton and flexible polyhydric side chain were established by analysis of HRESIMS, NMR spectroscopic data, ECD spectrum, and the X-ray diffraction study of isopropylidene derivatives. An intermolecular [2+2+2] cycloaddition may play a key role in the biosynthesis pathway of the 1,2-dioxane moiety fused lindenane−monoterpene heterodimer skeleton, which can be recognized as the biogenetic precursors of our previous reported lindenane−normonoterpene conjugates. In addition, compounds 1, 3 and 4 exhibited moderate inhibitory effects of lipid accumulation in free fatty acid-exposed L02 cells.

Sarglaromatics A–E: A Class of Naphthalene-Like Architecture Fused Norlindenane Sesquiterpene Dimers from Sarcandra glabra

“…All dimers were tested for their inhibitory activity on fat deposition in free fatty acid (FFA)-exposed L02 cells based on the hepatoprotective and hypolipidemic effects of the S. glabra . ,, Compounds 1 and 2 could significantly attenuate lipid deposition in L02 cells at a concentration of 10 μM, as visualized by Bodipy staining (Figure ). The free hydroxyl groups seem to enhance the inhibitory activity of the compounds against lipid accumulation.…”

“…Nakai, which is widely distributed in southern Asia, is one of the renowned traditional Chinese medicines and is used as an anti-inflammatory and an adjuvant treatment for cancer . Modern pharmacological studies have shown that some of the components in S. glabra exhibit positive hepatoprotective and hypolipidemic effects. , Based on our previous research on sesquiterpenes from the Chloranthaceae plants, ,− a chemical investigation of the roots of S. glabra was carried out. As a result, five unprecedented norlindenane sesquiterpene dimers, sarglaromatics A–E ( 1 – 5 , respectively), were isolated (Figure ).…”

Spirolindemers A and B, Lindenane Sesquiterpenoid Oligomers Equipped with Oxaspiro[4.5]decane from Chloranthus henryi

“…In our previous phytochemical researches on the LDS oligomers from Chloranthaceae plants, several kinds of novel dimeric and trimeric oligomers have been discovered. [ 3,7,10‐13 ] According to their interesting biogenetic pathway, it is worthwhile and expectable to explore naturally‐occurring unique polymeric skeletons based on LDS units. Thus, Chloranthus henryi , a famous medicinal plant for the treatment of traumatic injuries, rheumatic arthralgia, fractures, pulmonary tuberculosis, and neurasthenia in southwestern China, [ 14 ] was selected as our research objective to discover novel LDS oligomers.…”

Natural and Pseudonatural Lindenane Heterodimers from Sarcandra glabra by Molecular Networking

“…7,11 carbon signals indicated that a new ring was formed in 2. The obvious downfield shift of C-6 (Δδ C + 10.9), C-8 (Δδ C + 5.8), and C-6′ (Δδ C + 12.1) along with oxygenated C-7 (δ C 87.2) suggested that the C-6′−O−C-7 linkage in 2 was formed…”