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.

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.

Diterpenoids from Euphorbia peplus possessing cytotoxic and anti-inflammatory activities.

Phytochemical investigation into the medium polar fraction of the ethanol extract of Euphorbia peplus led to the identification of 32 diterpenoids with five structural types. Compounds 1-5 and 7-11 are reported for the first time, while the configuration of 6,7-epoxy group of 6 was revised to be β-oriented. Compounds 1-5 feature a rare structural variation of the double bond at Δ migrating to Δ in the tigliane-type diterpenoid family.

Sesquiterpenoids and Cytochalasins with Immunosuppressive Activity from Sonchus wightianus.

The plant species, Sonchus wightianus DC., was historically used in China for both medicinal and dietary uses. In present study, seven new guaiane sesquiterpenoids (1-7) and one cytochalasin (8), along with five known guaianes (9-13) and two known cytochalasins (14 and 15), were isolated from the whole plants of S.

Monoterpenoid indole alkaloids from Alstonia scholaris and their Toxoplasma gondii inhibitory activity.

Nine previously unreported various types of monoterpenoid indole alkaloids, together with seven known analogues were isolated from the stem barks of Alstonia scholaris through a silica gel free methodology. The structures of 1-9 were elucidated by spectroscopic data analysis, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Compound 1 is a modified echitamine-type alkaloid with a novel 6/5/5/7/6/6 hetero hexacyclic bridged ring system, and 8 and 9 exist as a zwitterion and trifluoroacetate salt, respectively.

Unprecedented sesterterpenoids, orientanoids A-C: discovery, bioinspired total synthesis and antitumor immunity.

Sesterterpenoids are a very rare class of important natural products. Three new skeletal spiro sesterterpenoids, named orientanoids A-C (1-3), were isolated from . Their structures were determined by a combination of spectroscopic data, X-ray crystallography, and total synthesis.

Densely Functionalized Macrocyclic Sesquiterpene Pyridine Alkaloids from .

Eleven densely functionalized new dihydro-β-agarofuran sesquiterpenoid derivatives, named maytenoids A-K (-), as well as one known analog, were isolated and characterized from . Their structures were assigned based on analysis of spectroscopic data and X-ray crystallography. Compounds - are macrocyclic sesquiterpene pyridine alkaloids generated by the respective acylation of the hydroxy groups at C-3 and C-13 of dihydro-β-agarofuran sesquiterpenoids via diverse pyridine dicarboxylic acids.

A new class of potent liver injury protective compounds: Structural elucidation, total synthesis and bioactivity study.

A new class of potent liver injury protective compounds, phychetins A-D (-) featuring an unique 6/6/5/6/5 pentacyclic framework, were isolated and structurally characterized from a Chinese medicinal plant . Compounds - are three pairs of enantiomers that were initially obtained in a racemic manner, and were further separated by chiral HPLC preparation. Compounds - were proposed to be originated biosynthetically from a coexisting lignan an intramolecular Friedel-Crafts reaction as the key step.

Highly Modified Sesquiterpene Lactones with Cytotoxic Activities from .

Three new germacranolide sesquiterpene lactones (SLs), strochunolides A-C (-, respectively), and a new guaianolide SL, strochunolide D (), were isolated from and structurally characterized. Compound is the first example of a dihomo-germacranolide SL, characterized by an unprecedented 6/10/5 tricyclic scaffold incorporating an additional fused δ-lactone C-ring. The structure of a known germacranolide SL, spicatolide C (), was revised as its 8-epimer.

Sumatranins A-J: Lignans with Immunosuppressive Activity from .

Chemical investigation of the twigs of (Phyllanthaceae) led to the isolation of 10 undescribed lignans, sumatranins A-J (-). Compounds - are unprecedented furopyran lignans characterized by a unique 2,3,3a,9a-tetrahydro-4-furo[2,3-]chromene heterotricyclic framework. Compounds and are rare 9'--dibenzylbutane lignans.

Diterpenoids from Euphorbia lactea and their anti-HIV-1 activity.

Nine undescribed diterpenoids, euphlactenoids A-I (1-9), including four ingol-type diterpenoids (1-4) with a 5/3/11/3-tetracyclic framework and five ent-pimarane-type diterpenoids (5-9), together with thirteen known diterpenoids (10-22), were identified from the leaves and stems of Euphorbia lactea Haw. The structures and absolute configurations of compounds 1-9 were unequivocally elucidated on the basis of spectroscopic analysis, ECD calculations and single crystal X-ray diffraction. Compounds 3 and 16 showed anti-HIV-1 effects with IC values of 1.

Laeviganoids A-T, -Clerodane-Type Diterpenoids from .

Laeviganoids A-T (-), 20 new -clerodane-type diterpenoids featuring a 2-furanone (-) or a furan (-) ring, as well as six analogues (-), were isolated from the roots of . Their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallographic studies. Compounds -, , -, and could influence the anti-inflammatory protumoral phenotype of macrophages.