Arteannoides U-Z: Six undescribed sesquiterpenoids with anti-inflammatory activities from the aerial parts of Artemisia annua (Qinghao).

Four previously unreported sesquiterpenoid diasteromers, arteannoides U-X (1-4), together with one new norsesquiterpenoid 5 (arteannoide Y) and one undescribed rearranged cadinene sesquiterpenoid 6 (arteannoide Z) were obtained from the dried aerial parts of Artemisia annua (Qinghao). Notably, arteannoides U-X (1-4) are four stereoisomers that possess the same molecules and the same planar connectivity, but differ from each other in configuration at a certain stereocenter. Their accurate structures were unambiguously identified and distinguished by extensive spectroscopic analyses, NMR calculations with DP4+ analysis, electronic circular dichroism (ECD) calculations and X-ray diffraction analyses. Compounds 1, 3, and 4 showed inhibitory activities against the production of inflammatory cytokines (PGE2, NO, IL-6 and TNF-α) in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages.

[Research on chemical constituents from Artemisia annua â ].

Chemical constituents were isolated and purified from the water extract of Artemisia annua by column chromatography of HP-20 macroporous resin, silica gel, ODS, Sephadex LH-20, HW-40, and semi-preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. As a result, Fifteen compounds were isolated and identified as vitexnegheteroin M(1), sibricose A5(2), securoside A(3), citrusin D(4), annphenone(5), E-melilotoside(6), esculetin(7), scopoletin-7-O-ß-D-glucoside(8), eleutheroside B_1(9), chrysosplenol D(10), patuletin-3-O-ß-D-glucopyranoside(11), quercetin-7-O-ß-D-glucoside(12), rutin(13), apigenin 6,8-di-C-ß-D-glucopyranoside(14), isoschaftoside(15), among them, compounds 1-4 were identified from Artemisia for the first time. Additionally, the isolates were evaluated for their inhibitory effects on the production of PGE_2 in LPS-simulated RAW264.7 macrophages. The results showed that compounds 1, 2, 8, and 10-15 could reduce PGE_2 levels, to a certain extent.

Structurally diverse sesquiterpenoids from the aerial parts of Artemisia annua (Qinghao) and their striking systemically anti-inflammatory activities.

Thirteen new sesquiterpenoids, arteannoides F-R (1-13), along with 13 known analogues (14-26), were isolated from the dried aerial parts of Artemisia annua L. Their structures, including absolute configurations, were unambiguously determined by a combination of physical data analyses (HRESIMS, 1D and 2D NMR, and ECD) as well as the crystal structures of 1, 5, 6, 15, 19, and 23. Among the isolated compounds, 1 features an unusual 11-oxatricyclo[6.2.1.04,9]undecan-2-ene ring system, 5 possesses an uncommon 4,11-ether bridged tricyclic framework, whereas 6 is a new eudesmane-type sesquiterpenoid formed via rearrangement of its carbon backbone. The systemically anti-inflammatory activities of all isolates were evaluated by measuring their inhibitory effects on PGE2, NO, TNF-α, and IL-6 production in LPS-stimulated RAW 264.7 macrophages. Moreover, the structure activity relationships of some compounds are summarized, this study will provide new structural templates for discovering potential anti-inflammatory agents.

Populeuphrines A and B, two new cembrane diterpenoids from the resins of Populus euphratica.

Two new cembrane diterpenoids, named populeuphrines A and B (1 and 2), together with three known analogues (3-5) were isolated from the resins of Populus euphratica. The planar structures and relative configurations of 1 and 2 were elucidated by detailed 1 D and 2 D NMR spectroscopic analyses. The absolute configurations of 1 and 2 were determined by X-ray diffraction analysis and quantum chemical computation. Biological activities of all the isolates against proliferation of human cancer cells and umbilical cord mesenchymal stem cells were evaluated.

Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins.

Two new octanorlanostane-type triterpenes, euphraticanoids A and B (1 and 2), two new trinorsesquiterpenoids, euphraticanoids C and D (3 and 4), and eight known triterpenoids (5, 6, 8-13) along with one steroid (7) were isolated from Populus euphratica resins. The structures of these new compounds, including their absolute configurations, were characterized by spectrocsopic, chemical, and computational methods. Biological evaluation revealed that compounds 4, 7-9, 12, and 13 display neuroprotective activities in H2O2-induced HT-22 cells with 4, 8, and 9 occurring in a concentration-dependent manner and 7, 12, and 13 reaching the maximum effects at 20 µM. Meanwhile, the neuroprotective properties of all isolates were accessed using glutamate-induced SH-SY5Y cells and disclosed that compounds 3, 4, 8, and 9 could dose-dependently protect neural cell injury in a concentration range of 10-40 µM. Finally, a brief structure-activity relationship was briefly discussed.

Anti-Mycobacterium tuberculosis Terpenoids from Resina Commiphora.

Four new compounds including two new sesquiterpenoid dimers, commiphoroids E (1) and F (2), a new triterpenoid (3), and a new sesquiterpenoid (4), along with three known terpenoids (5-7) were isolated from Resina Commiphora, whose structures were identified by NMR spectra, HRESIMS, and X-ray diffraction analysis. Compounds 1 and 2 both bear an O-bridge ring and feature a plausible [4 + 2] Diels-Alder cycloaddition reaction. Antimycobacterial activities show that all the tested compounds (200 µM) could inhibit the growth of both sensitive and clinically multi-drug resistant (MDR) isolated strains. In addition, cellular toxicity of the isolates against human cancer cells and THP-1 monocyte cells was examined.

Commipholactam A, a cytotoxic sesquiterpenoidal lactam from Resina Commiphora.

Diverse terpenoids including a novel sesquiterpenoidal lactam, commipholactam A (1), and a structurally related new cadinane sesquiterpenoid, commiphorane H (2), a new eudesmane sesquiterpenoid, commiphorane I (4), a new guaiane sesquiterpenoid, commiphorane J (5), and two new nor-abietane diterpenoids, commiphoranes K1 and K2 (6 and 7) along with two known terpenoids (3 and 8), were isolated from Resina Commiphora. Their structures with absolute configurations were characterized by spectroscopic methods and calculated electronic circular dichroism (ECD). Notably, commipholactam A represents the first example of cadinane sesquiterpene alkaloids isolated from Resina Commiphora. Biological assessment toward human cancer cells showed that the IC50 values of 1 against HepG2 and A549 cells were 21.73 µM and 128.50 µM, respectively.

Lonimacranaldes A-C, three iridoids with novel skeletons from Lonicera macranthoides.

Lonimacranaldes A and B (1 and 2), along with one biogenetically related intermediate, lonimacranalde C (3), were isolated from the flower buds of Lonicera macranthoides. Characterized by an iridoid structure and an additional C-6 unit with an aldehyde group, compounds 1 and 2 are the first examples of hybrid iridoids possessing an unexpected 6/5/6 fused tricyclic ring system, while compound 3 serves as an important precursor for their generation. The structures of lonimacranaldes A-C (1-3) were revealed by extensive spectroscopic and X-ray diffraction analyses. A plausible biogenetic pathway for them was proposed. Compound 3 showed anti-inflammatory activities by inhibiting the production of IL-6 on LPS-induced RAW 264.7 cells with an IC50 value of 6.33 µM.

Meroterpenoids from the Fungus Ganoderma sinensis and First Absolute Configuration Clarification of Zizhine H.

Five new meroterpenoids, zizhines P-S and U (1-4,7), together with two known meroterpenoids (5 and 6) were isolated from Ganoderma sinensis. Their structures including absolute configurations were assigned by using spectroscopic, computational, and chemical methods. Racemics zizhines P and Q were purified by HPLC on chiral phase. Biological evaluation found that 4, 5 and 6 are cytotoxic toward human cancer cells (A549, BGC-823, Kyse30) with IC50 values in the range of 63.43-80.83 µM towards A549, 59.2 ± 2.73 µM and 64.25 ± 0.37 µM towards BGC-823, 76.28 ± 1.93 µM and 85.42 ± 2.82 µM towards Kyse30.

Novel Terpenoids with Potent Cytotoxic Activities from Resina Commiphora.

A novel sesquiterpene dimer, spirocommiphorfuran A (1); two new cadinane sesquiterpenoids, commiphorenes A (2) and B (3); along with three known terpenoids (4⁻6), were isolated from Resina Commiphora. The structures of these new compounds were characterized by NMR, HRESIMS, quantum chemical computation, and X-ray diffraction analysis. Compound 1 features a 7-oxabicyclo[2.2.1]heptane-2-ene core, representing the first example of germacrane-type sesquiterpene dimer fused via a spiro ring system. Compound 2 is a novel sesquiterpene with a completely new carbon skeleton, which is characteristic of an additional carbon attaching to the cadinane backbone via a carbon⁻carbon bond. Additionally, compounds 2 and 4 exert acceptable cytotoxicity toward normal cells and high selectivity in cancer cells, especially in HepG2 cells.

Nardochinoids A-C, Three Dimeric Sesquiterpenoids with Specific Fused-Ring Skeletons from Nardostachys chinensis.

Three unusual sesquiterpenoid dimers, nardochinoids A-C (1-3), were isolated from Nardostachys chinensis Batal. Compound 1 features a rare fused 3,8-dioxatricyclo[7.2.1.01,6]dodecane-11-one ring system, compound 2 is the first nitrogen-containing nornardosinane-aristolane sesquiterpene conjugate, and compound 3 represents the first example of the dimer of a nornardosinane and a nardosinane sesquiterpene. Their structures were characterized by NMR spectroscopic methods and X-ray single-crystal diffraction analysis. Compound 3 showed significant anti-inflammatory activities.

Belamchinanes A-D from Belamcanda chinensis: Triterpenoids with an Unprecedented Carbon Skeleton and Their Activity against Age-Related Renal Fibrosis.

Belamchinanes A-D (1-4), four triterpenoids with an unprecedented skeleton, were isolated from the seeds of Belamcanda chinensis and fully characterized. The structures of belamchinanes feature a 4/6/6/6/5 polycyclic system in which a four-membered carbocyclic ring bridges the C-1 and C-11 positions of a classical triterpenoid framework. A plausible pathway for the biosynthesis of 1-4 is proposed. Biological studies reveal that 1-4 dose-dependently protect age-related renal fibrosis in vitro .

Dimeric Cadinane Sesquiterpenoid Derivatives from Artemisia annua.

Arteannoide A (1), an unusual cadinane dimer featuring a rare fused 6,8-dioxabicyclo[3.2.l]octan-7-one ring system, arteannoides B and C (2 and 3), two novel heterodimers incorporating a rearranged cadinene sesquiterpenoid and a phenylpropanoid, together with two new rearranged cadinene sesquiterpenoids 4 and 5, were isolated from Artemisia annua L. Their structures were determined by a combination of NMR spectroscopy, electronic circular dichroism calculations, and X-ray diffraction analyses. Compounds 2 and 3 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 mouse macrophage cell lines with IC50 values of 4.5 and 2.9 µM, respectively.

Two new coumarins from Talaromyces flavus.

Two new coumarins, talacoumarins A (1) and B (2), were isolated from the ethyl acetate extract of the wetland soil-derived fungus Talaromyces flavus BYD07-13. Their structures were elucidated by spectroscopic data (NMR, MS) analyses. The absolute configuration of C-12 in 1 was assigned using the modified Mosher's method, whereas that of C-12 in 2 was deduced via the circular dichroism data of its corresponding [Rh2(OCOCF3)4] complex. Compounds 1 and 2 were evaluated for their anti-Aß42 aggregation, cytotoxic, and antimicrobial activities. The results showed that the two compounds had moderate anti-Aß42 aggregation activity, and this is the first report on the Aß42 inhibitory aggregation activity of coumarins.