Alstolarsines A-E, Indoline Alkaloids with Two Different Carbon Skeletons from .

Five complex indoline alkaloids, alstolarsines A-E (-) possessing two unprecedented carbon skeletons of 6/5/5/7/6/6(5) fused polycyclic systems, were isolated from . Their structures were characterized using various methods including spectroscopic data, ECD spectra, and single-crystal X-ray diffraction. The inhibitory activities of alstolarsines A-D (-) on DRAK2 phosphorylation and ATP-citrate lyase were evaluated, but all of them were inactive.

Asptertides A-H, C-Polyketides From a Marine-Derived Aspergillus terreus.

In the present study, 11 C-polyketides comprising a monocyclic skeleton of an aromatic (1-6 and 11) or a cyclohexanone moiety (7) and an oxygenated bicyclic nucleus (8-10) were isolated from a mutated strain of endophytic fungus Aspergillus terreus RA2905. Five pairs of enantiomers (2a/b-5a/b and 7a/b) were achieved by chiral-phase HPLC separation. The structures of previously unreported asptertides A-H (1-8) were determined by analysis of the spectroscopic data and electronic circular dichroism (ECD) calculations.

Isolation and Bioinspired Synthesis of Lauenones A and B, Skeleton-Rearranged Diterpenoids with Antiadipogenic Activity from .

Two skeleton-rearranged labdane diterpenoids, lauenones A () and B () were isolated from . Their bioinspired synthesis was accomplished in 9 and 10 steps, respectively, without using any protecting groups. Key steps include a semipinacol rearrangement and a substrate-controlled one-pot reaction cascade involving photooxidation and aldol condensation.

Talaromyketides A-I: Nine polyketides with anti-inflammatory activity from a soil fungus Talaromyces sp. KYS-41.

A chemical investigation into fermentation product of Talaromyces sp. KYS-41, a fungus isolated from Kunyu Mountain soil, resulted in the discovery and identification of 27 polyketides. Notably, talaromyketides A-I (1-9) are reported for the first time, with talaromyketides A-C (1-3) being three pair of enantiomers.

Macoligophones A-I, prenylated acetophenone dimers and monomers from Maclurodendron oligophlebium.

Chemical investigation of the bark of Maclurodendron oligophlebium resulted in the isolation of three prenylated acetophenone (PAP) dimers (1-3) and seventeen monomers (4-20). Among them, macoligophones A-I (1, 2, and 4-10) are previously undescribed. Utilizing chiral column, compounds 1-7 were separated into their individual enantiomers.

Harnessing Functional Food Sources: Deriving Anti-Inflammatory and Antibacterial Naphthalene Derivatives from the Edible Bulbs of .

The red bulbs of , commonly used as a daily dietary ingredient in cooking, are well-known for their rich nutritional profile and potential medicinal properties. This study focused on identifying bioactive components from by a bioactivity-guided approach combined with global natural products' social molecular networking, which led to the characterization of 12 new naphthalene derivatives, eleuthalenes A-L (-), and 22 known analogues. The structures of these compounds were determined through spectroscopic data, X-ray crystallography, and quantum chemical calculations.

Effect of soil conditioner on alleviating saline-alkali stress damage of maize.

Soil conditioners are efficacy in ameliorating saline-alkali soils and fostering crop growth. To explore the effect and physiological mechanism of soil conditioner on improving the adaptability of maize to saline-alkali stress, we conducted a field randomized block experiment in Liuzhong Village, Pingluo County, Ningxia Province in 2022. We investigated the variations of antioxidant capacity, key enzyme activities and photosynthetic fluorescence properties of maize induced by soil conditioners under saline-alkali stress, with "Xianyu 1255" maize as the experimental material under four treatments: T(no conditioner, control), T(humic acid), T(microsilica fume + wood vine-gar solution), T(humic acid + wood vinegar solution + microsilica fume).

Triterpenoids with bioactivities from Oenothera biennis.

Phytochemical investigation into the whole plants of Oenothera biennis led to the isolation and identification of 28 triterpenoids, of which oenothebienoids A-G (1-7) are reported for the first time. Oenothebienoids A-D (1-4) have an unnormal 20-epi-ursane type triterpenoid framework, which is rarely documented. To swiftly and precisely differentiate the C-20 configurations, a rule was summarized by analysis of the NMR data from the two pairs of simultaneously obtained C-20 epimers, namely 1/8 and 3/9.

Eleutherlenes A-D, Diverse Types of Naphthalene Derivatives with Anti-inflammatory Activity from .

Eleutherlene A (), an unprecedented carbon skeleton featuring an aryl-fused 6-methyl-2,7-dioxabicyclo[3.2.1]octane unit, and eleutherlene B (), a naphthoquinone derivative with interesting ring fusion of an α,β-unsaturated γ-lactam and a tetrahydropyran moiety, along with two novel naphthoquinone alkaloids, eleutherlenes C () and D (), were isolated from and identified.

Jatrophane and ingenane diterpenoids with anti-inflammatory activity from Euphorbia esula.

A phytochemical investigation into the plants of Euphorbia esula L. has yielded 19 diterpenoids, comprising 17 jatrophane-type (1-7 and 9-18) and two ingenane-type (8 and 19). The structures of these compounds were elucidated by a combination of spectrum elucidations, quantum chemical calculations, and X-ray single crystal diffraction.

Spirocyclic iridoid alkaloids from .

Plumerianoids A-D (1-4) with a new intact spirocyclic iridoid alkaloid skeleton, along with a new degraded alkaloid 8--plumerianine (5), and a known one (6), were isolated and characterized from . The structure of 6 was revised as (8,13)-plumerianine. These alkaloids consist of three epimeric pairs (1/2, 3/4, and 5/6), exhibiting virtually identical NMR spectra within each pair.

Design, Synthesis, and Biological Evaluation of HDAC Inhibitors Containing Natural Product-Inspired -Linked 2-Acetylpyrrole Cap.

Drawing inspiration from the structural resemblance between a natural product -(3-carboxypropyl)-2-acetylpyrrole and phenylbutyric acid, a pioneer HDAC inhibitor evaluated in clinical trials, we embarked on the design and synthesis of a novel array of HDAC inhibitors containing an -linked 2-acetylpyrrole cap by utilizing the pharmacophore fusion strategy. Among them, compound exhibited potential inhibitory activity on HDAC1, and demonstrated notable potency against RPMI-8226 cells with an IC value of 2.89 ± 0.

Immunosuppressive Breviane Spiroditerpenoids from Isolated from a Medicinal Plant.

Breviane spiroditerpenoids are a small group of structurally interesting and complex meroterpenoids. This work focused on an endophytic fungus ZBWPQ-27 that was isolated from a medicinal plant , leading to the isolation of 15 breviane spiroditerpenoids with four types of polycyclic systems (- and -), and two new carotane sesquiterpenoids ( and ). The structures including absolute configurations of the new compounds - were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations.

Cytotoxic diterpenoids from Croton kongensis inhibiting tumor proliferation and migration.

Thirty-two diterpenoids including 18 ent-kauranes (1-6, and 12-23), nine 8,9-seco-ent-kauranes (7-8, and 24-30), four ent-abietanes (9-10, and 31-32), and one crotofolane (11) were isolated from the twigs and leaves of Croton kongensis. The structures of previously unreported crokokaugenoids A-H (1-8), crokoabiegenoids A-B (9-10), and crokocrotogenoid A (11) were determined by spectroscopic data analyses, TDDFT-ECD and GIAO NMR calculations, and X-ray crystallographic studies. All compounds were evaluated for their cytotoxic activity against five human tumor cell lines, and the structure-activity relationships were discussed.

Intriguing steroid glycosides for cancer therapy by suppressing the DNA damage response and mTOR/S6K signaling pathways.

Two rare 8-hydroxysteroid glycosides (6-7), and their downstream metabolites (1-5) with an unprecedented 6/6/5/5/5-pentacyclic scaffold, together with seven known analogues (8-14) were isolated from the twigs and leaves of Strophanthus divaricatus. Their structures were fully assigned by analysis of the spectroscopic and ECD data, NMR calculations, X-ray crystallographic study, and chemical methods. In addition, the inhibitory effects of 1-14 on liver and lung cancer cell lines were evaluated, and preliminary structure-activity relationship was discussed.

Stereochemical insights into enantioselective antiplasmodial lignanamides from the twigs and leaves of Solanum erianthum.

Stereochemical investigations on the twigs and leaves of Solanum erianthum afforded five pairs of lignanamide enantiomers and a previously undescribed phenolic amide (3). Particularly, two pairs of previously undescribed lignanamide racemates (1a/1b-2a/2b) represent the first case of natural products that feature an unreported 5/5-fused N/O-biheterocyclic core. Their structures, including the absolute configurations, were determined unambiguously by using spectroscopic analyses and electronic circular dichroism calculations.

Terpenoids of plants from Chloranthaceae family: chemistry, bioactivity, and synthesis.

Covering: 1976 to December 2023Chloranthaceae is comprised of four extant genera (, , , and ), totaling about 80 species, many of which have been widely used as herbal medicines for diverse medical purposes. Chloranthaceae plants represent a rich source of structurally interesting and diverse secondary metabolites, with sesquiterpenoids and diterpenoids being the predominant structural types. Lindenane sesquiterpenoids and their oligomers, chemotaxonomical markers of the family Chloranthaceae, have shown a wide spectrum of bioactivities, attracting significant attention from organic chemists and pharmacologists.

Lauinoids A-X: Labdane-type diterpenoids with anti-inflammatory activity from Croton laui.

Croton laui (Euphorbiaceae) is a traditional medicinal plant used by the Li ethnic group in China to treat headaches, stomachaches, and diphtheria. To understand the pharmacological basis of its medicinal use, an extensive investigation of the ethanolic extract of the bark of C. laui was performed.

Crotonoids A-H, Labdane-Type Diterpenoids with Anti-Inflammatory Activity from Croton Sublyratus.

Croton sublyratus (Euphorbiaceae) is a traditional medicinal plant used by the Thai populace to treat helminthic infections and dermatologic conditions. In present study, eight new labdane-type diterpenoids, crotonoids A-H (1-8) and one known analogue (9) were isolated from the aerial parts of C. sublyratus.

Drymariamides A-J, Antiadipogenic Cyclopeptides Incorporating Noncanonical Amino Acids from .

Herein, we report an extensive phytochemical study on the whole plant of , which led to the isolation of ten new orbitides, named drymariamides A-J (-). Compounds , , and incorporate rare residues of noncanonical amino acids of kynurenine (Kyn) or 3a-hydroxypyrroloindoline (HPI). Their structures with absolute configurations were elucidated by a combination of spectroscopic analysis, advanced Marfey's method, X-ray diffraction, and electronic circular dichroism analysis.

Anti-Inflammatory Salicin Derivatives from the Barks of .

The genus L. is traditionally used in folk medicine to alleviate pain caused by various kinds of inflammation. In the present study, 10 undescribed salicin derivatives along with 5 known congeners were isolated from the barks of , and their structures were elucidated by spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and chemical conversions.

Design and Synthesis of Cyclolipopeptide Mimics of Dysoxylactam A and Evaluation of the Reversing Potencies against P-Glycoprotein-Mediated Multidrug Resistance.

Inspired by the structure of dysoxylactam A (DLA) that has been demonstrated to reverse P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) effectively, 61 structurally simplified cyclolipopeptides were thus designed and synthesized via an effective method, and their reversing P-gp-mediated MDR potentials were evaluated, which provided a series of more potent analogues and allowed us to explore their structure-activity relationship (SAR). Among them, a well-simplified compound, , with only two chiral centers that all derived from amino acids dramatically reversed drug resistance in KBV200 cells at 10 μM in combination with vinorelbine (VNR), paclitaxel (PTX), and adriamycin (ADR), respectively, which is more promising than DLA. The mechanism study showed that reversed the MDR of tumor cells by inhibiting the transport function of P-gp rather than reducing its expression.

Cephalotane diterpenoids: structural diversity, biological activity, biosynthetic proposal, and chemical synthesis.

Covering: up to the end of 2023Cephalotane diterpenoids are a unique class of natural products exclusive to the genus , featuring a rigid 7,6,5,6-fused tetracyclic architecture. The study of cephalotanes dates back to the 1970s, when harringtonolide (1), a troponoid with a peculiar norditerpenoid carbon skeleton, was first discovered. In recent years, prototype C diterpenoids proposed as cephalotane were disclosed, which triggered intense studies on this diterpenoid family.