Chlospicenes A and B, cyclopropane cracked lindenane sesquiterpenoid dimers with anti-nonalcoholic steatohepatitis activity from Chloranthus henryi

Visible-light enabled synthesis of cyclopropane-fused indolines via dearomatization of indoles

“…1 Due to its inherent ring strain, cyclopropane-containing compounds can undergo a ring-opening process and serve as versatile intermediates and building blocks for the synthesis of complex molecules. 2 In this regard, cyclopropane-fused indolines exist as the key units in many biologically active alkaloids, such as lundurines A–D (Scheme 1a). 3 Typically, strategies for the construction of cyclopropane-fused indolines rely on cyclopropanation of indoles with diazo compounds, 4 cyclopropenes, 5 ene–yne ketones 6 or tosylhydrazones 7 catalyzed by transition-metal complexes or enabled by visible light (Scheme 1b).…”

Sarcaglarone A, a lindenane–monoterpene heterodimer from the seeds of Sarcandra glabra

“…2 Due to their highly reactive conjugated groups, LSs are prone to intermolecular polymerization reactions, such as [2 + 2] cycloaddition, Michael addition, Diels–Alder addition, and acetal formation, to form LS oligomers with various skeleton types. 2–4 This polymerization usually occurs between LSs, and a few occur with other types of sesquiterpenoids, such as eudesmane- and aromodendrane-types, 5,6 or monoterpenes. 7–10 The lindenane–monoterpene heterodimers formed by the Diels–Alder reaction were first isolated from Hedyosmum angustifolium in 2007, 7 and a similar polymer was later discovered from Sarcandra glabra by Kashiwada et al 8 Another type of lindenane–monoterpene heterodimer, formed by [2 + 2 + 2] cycloaddition, was isolated by our group from the seeds and leaves of S. glabra .…”

Natural and Pseudonatural Lindenane Heterodimers from Sarcandra glabra by Molecular Networking

“…Recently, our group has focused on the lindenane sesquiterpenoid dimers possessing diverse architectures and bioactivities from Chloranthaceae plants. − The classic MN method was also established in our group, resulting in the efficient discovery of sarcaglarols A–D and chlospicenes A . Lindenane heterodimers, composed of lindenane and another terpenoid moiety, showing great potential in possessing fascinating skeletons and bioactivities, − also captured our interest.…”

“…7−12 The classic MN method was also established in our group, resulting in the efficient discovery of sarcaglarols A−D 11 and chlospicenes A. 12 Lindenane heterodimers, composed of lindenane and another terpenoid moiety, showing great potential in possessing fascinating skeletons and bioactivities, 11−13 also captured our interest. However, lindenane heterodimers were difficult to identify by the classical MN because of the noncluster features with other lindenane sesquiterpenoid dimers and their trace amounts in plants.…”