Cadinanes are a class of bicyclic sesquiterpenes with complex stereochemistry and broad pharmacological activities, such as antibacterial, anti-inflammatory, and hypoglycemic activities. To date, structurally diverse and bioactive cadinane sesquiterpenes have been isolated and identified from a variety of plants and microorganisms. Moreover, deeper understandings on cadinane sesquiterpene synthases have been made. This article categorized the 124 new cadinanes which were published in the literatures in the past four years (2017-2020) into five structural types, and presented their pharmacological activities. We also illustrated the elucidation of the biosynthetic pathways for typical cadinanes, summarized the research progress on cadinane sesquiterpene synthases. Finally, current challenges and future prospects were proposed and discussed.
Anti-Inflammatory Agents ; Polycyclic Sesquiterpenes ; Sesquiterpenes

Sarglanoids A-F, six new sesquiterpenoids belonging to eudesmane (1-5) and eremophilane (6) types, were isolated from the leaves of Sarcandra glabra, a famous traditional Chinese medicine (TCM). Their structures including absolute configurations were elucidated through extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. Compounds 1-2 were rare N-containing eudesmane-type sesquiterpenoids. Compound 3 exhibited inhibitory activity against nitric oxide (NO) production in lipopolysaccharides (LPS)-induced RAW 264.7 cells with IC₅₀ values at 20.00 ± 1.30 μmol·L^-1. These findings provide scientific evidence for sesquiterpenoids as the material foundation of S. glabra.
Molecular Structure ; Plant Leaves ; Polycyclic Sesquiterpenes ; Seeds ; Sesquiterpenes/pharmacology*

Sesquiterpenoids are comprised of three C₅ units and derived from farnesyl diphosphate. In these C₁₅ family of terpenoids, drimane-type sesquiterpenoids are unique as their chemical structure of decahydronaphthalene along with the methyl group decorations resemble the A/B rings of labdane derived diterpenoids and the eastern part of many meroterpenoids. In the past decades, based on their chemical structural features and diverse bioactivities, great efforts have been made to perform chemical and biological research on this family of natural products, leading to the characterization of a large of new compounds and a few biosynthetic pathways. In this review, we collected 164 new drimane-type sesquiterpenoids from fungi between January 2004 and October 2021 and classified them into three major subfamilies, so as to highlight their diverse chemical structures, biological activities, and biosynthetic pathways,.
Polycyclic Sesquiterpenes ; Sesquiterpenes/chemistry* ; Fungi ; Terpenes/chemistry* ; Diterpenes

Drimane-type sesquiterpenoids are widely distributed in fungi. From the ethyl acetate extract of the earwig-derived Aspergillus sp. NF2396, seven new drimane-type sesquiterpenoids, named drimanenoids A-G (1-7), were isolated. Their structures were elucidated by diverse spectroscopic analysis including high-resolution ESI-MS, one- and two-dimensional NMR spectroscopy. Drimanenoids A-F (1-6) are new members of drimane-type sesquiterpenoid esterified with unsaturated fatty acid side chain at C-6. Drimanenoids C (3), D (4) and F (6) showed antibacterial activity against five types of bacteria with different inhibition diameters. Drimanenoid D (4) exhibited moderate cytotoxicity against human myelogenous leukemia cell line K562 with an IC₅₀ value of 12.88 ± 0.11 μmol·L^-1.
Humans ; Polycyclic Sesquiterpenes ; Sesquiterpenes/chemistry* ; Aspergillus/chemistry* ; Magnetic Resonance Spectroscopy ; Molecular Structure

Cerebral ischemia-reperfusion(I/R) injury is an important cause of acute ischemic stroke. Timely elimination of damaged proteins and organelles by regulating autophagy during cerebral ischemia-reperfusion plays an important role in relieving brain damage. In order to investigate whether β-caryophyllene(BCP) could protect neurons from cerebral I/R injury by regulating auto-phagy, C57 BL/6 J male mice were randomly divided into sham operation group, model group, and drug-administered group. After intra-gastric administration was given for 5 days, the middle cerebral artery occlusion(MCAO) model was established by suture method. Twenty four hours after surgery, the infarct volume and neurological function were assessed; the pathological changes of cortical tissue were observed by HE staining; Western blot was used to detect the expression of autophagy-related proteins beclin1, p62, LC3 B and apoptosis-related protein Bcl-2; immunofluorescence was used to observe the expression of LC3 B in the ischemic cortex. The autophagy of cortical tissue in the ischemic area was observed by transmission electron microscopy. The experimental results showed that as compared with the model group, the BCP pretreatment significantly reduced the neurological deficit, decreased the percentage of cerebral infarction volume, reduced the death of brain tissue cells in the ischemic area, up-regulated the expression of beclin1, LC3 B and Bcl-2 protein, down-regulated p62 protein expression, and significantly increased the number of autophagosomes in the cortical tissue of the ischemic area. It was finally determined that BCP could protect neurons from cerebral ischemia-reperfusion injury by activating autophagy.
Animals ; Autophagy ; Brain Ischemia/drug therapy* ; Infarction, Middle Cerebral Artery ; Male ; Mice ; Mice, Inbred C57BL ; Polycyclic Sesquiterpenes/therapeutic use* ; Random Allocation ; Reperfusion Injury/drug therapy*

Essential oils of the resins of Pinus brutia and Pinus pinea were evaluated for their biological potential. Essential oils were characterized using GC-MS and GC/FID. in vitro antimicrobial, phytotoxic, antioxidant, and insecticidal activities were carried out using the direct contact and the fumigant assays, respectively. The chemical profile of the essential oils of the resins of P. pinea and P. brutia included mainly α-pinene (21.39% and 25.40%), β-pinene (9.68% and 9.69%), and caryophyllene (9.12% and 4.81%). The essential oils of P. pinea and P. brutia exerted notable antimicrobial activities on Micrococcus luteus and Bacillus subtilis, insecticidal activities on Ephestia kuehniella eggs, phytotoxic activities on Lactuca sativa, Lepidium sativum, and Portulaca oleracea, as well as antioxidant potential. Indications of the biological activities of the essential oils suggest their use in the formulation of ecofriendly and biocompatible pharmaceuticals.
Animals ; Anti-Infective Agents ; analysis ; pharmacology ; Antioxidants ; analysis ; pharmacology ; Bacillus subtilis ; drug effects ; Bicyclic Monoterpenes ; Bridged Bicyclo Compounds ; analysis ; pharmacology ; Gas Chromatography-Mass Spectrometry ; Insecta ; drug effects ; Insecticides ; analysis ; pharmacology ; Lepidium ; drug effects ; Lettuce ; drug effects ; Mediterranean Region ; Micrococcus luteus ; drug effects ; Monoterpenes ; analysis ; pharmacology ; Oils, Volatile ; chemistry ; pharmacology ; Pinus ; chemistry ; Plant Extracts ; chemistry ; pharmacology ; Plant Oils ; chemistry ; pharmacology ; Polycyclic Sesquiterpenes ; Portulaca ; drug effects ; Resins, Plant ; chemistry ; Sesquiterpenes ; analysis ; pharmacology ; Terpenes ; analysis ; pharmacology