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

Abstract

Sarglaromatics A−E (1−5, respectively), five unprecedented naphthalene-like architecture-fused norlindenane sesquiterpene dimers, were discovered from the roots of Sarcandra glabra. The unique naphthalene core skeleton was obtained from classical lindenane [4 + 2] dimers via a free-radical-mediated C11− C11′ bond formation reaction and 12'-decarboxylation. The highly fused octonary ring skeleton was elucidated by HRMS, NMR, ECD, quantum chemical calculations, and biogenetic inspiration. Compounds 1 and 2 showed significant anti-nonalcoholic steatohepatitis (NASH) activity by inhibiting lipid deposition in L02 cells.

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

“…and carbonyl (1755 and 1701 cm −1 ) groups. The 1 H NMR spectrum (Table 1) showed a pair of high-field methylene signals of the 1,2-substituted cyclopropane ring, indicating the presence of a lindenane-type sesquiterpenoid in 1, [9][10][11] which was further identified by the cross peaks of H-1 (δ H 1.94, m)/H-2 (δ H 0.79, m, 0.65, m)/H-3 (δ H 2.01, m) in the 1 H-1 H COSY spectrum. In the 13 C NMR spectrum, only 10 carbons remained to be Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.…”

Coumarins from Sarcandra glabra (Thunb.) Nakai and Acetylcholinesterase Inhibiting Activity

“…As a traditional Chinese medicinal material, the xylem of S. glabra can clear away heat and detoxification, dispel wind and activate blood circulation, reduce swelling and pain, and resist bacteria and inflammation. In recent years, many studies had shown that S. glabra has acetylcholinesterase (AchE) inhibitory activity, [4] anti-inflammatory, [5] anti-tumor, anti-bacterial, [6] antifungal activities, [7,8] and inhibitory activity of lipid accumulation. Previous phytochemistry researches of this plant revealed the presence of coumarins, sesquiterpenes, and neolignans.…”

Natural and Pseudonatural Lindenane Heterodimers from Sarcandra glabra by Molecular Networking

“…The unchanged degree of unsaturation and disappearance of Δ Subsequently, the X-ray diffraction (XRD) experiment on the crystal of 2 under Cu Kα radiation was successful, and the XRD data (CCDC 2158552, MeOH/H 2 O) confirmed its planar structure and absolute configuration as 1R,3S,5S,7S,8R,9S,10S,11R,4′S,5′R [Figure 4; Flack parameter = 0.04 (10)]. To validate the structural relationship of 1/3 and 2, the electronic circular dichroism (ECD) calculations of 1−3 at the B3LYP/6-311+G(2d,p) level with the PCM in methanol were conducted.…”