Natural and Pseudonatural Lindenane Heterodimers from Sarcandra glabra by Molecular Networking

Abstract

Sarglaoxolane A (1), the first lindenane−normonoterpene heterodimer fused by tetrahydrofuran, was discovered in Sarcandra glabra guided by the first proposed single-node-based molecular networking approach. Moreover, two pseudonatural derivatives (2 and 3) with an oxa-difuranofurone moiety were transformed from 1 and confirmed by X-ray diffraction, and also proven to exist in the plant extract. A combination of molecular networking and biomimetic transformation can significantly promote the discovery and structural elucidation of novel natural products.

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

“…Although LSs have been discovered for 100 years and 354 natural LSs with 50 diverse carbon skeletons have been reported; [5][6][7][8][9][10][31][32][33][34][35][36][37] however, a clear and rational structural clas-sication for LSs and their oligomers is lacking. Thus, a classi-cation based on the basic framework and plausible biogenetical pathways of LSs will be proposed in this review.…”

“…30 It is worth noting that LS and non-LS units (e.g., monoterpene and geranylbenzofuranone) can form heterooligomers with unprecedented structural diversity, which have remarkable differences compared with that of other sesquiterpenoids. [31][32][33][34][35][36][37] Plants containing LSs have been used as famous natural medicines to treat blood stasis, inammation, drainage, and detoxication. 38,39 Thus, the diverse LSs also show various and signicant biological activities, such as anti-inammation, [40][41][42][43] antitumor, [44][45][46] and anti-infection.…”

Machine learning-assisted structure annotation of natural products based on MS and NMR data

“…Cosine-based scoring is the most commonly used spectral similarity measurement, which serves as the core algorithm in the extensively employed molecular networking Natural Product Reports Review approach. [36][37][38][39] Cosine similarity evaluation is highly sensitive to molecular structural changes, which means that even slight structural differences between two molecules may result in a low cosine similarity score. However, in many NPs structure elucidation cases based on MS/MS matching, the primary focus is oen not on the overall similarity between two MS/MS spectra, but rather on the structural similarity between fragmented compounds.…”

Dipeniroqueforins A–B and Peniroqueforin D: Eremophilane-Type Sesquiterpenoid Derivatives with Cytotoxic Activity from Penicillium roqueforti

“…Natural products have fascinating chemical skeletons and potential bioactivities, which makes them play an indispensable role in many aspects of humanity. − Over the past few decades, traditional cultivation methods have become challenging to avoid repeated isolation of known compounds and discover structurally unique molecules with attractive bioactivities. − Recently, a Global Natural Products Social (GNPS) molecular networking strategy has been widely applied to solve the aforementioned problems. Molecular networking on the GNPS platform can help us to analyze the MS/MS fragment data and assess the structural similarities from the predicted metabolites, in which structurally similar compounds are clustered together in a visual network. − Consequently, the new structures of secondary metabolites can be precisely predicted from a crude extract before intensive chromatographic isolation, thereby speeding up their rapid discovery.…”