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A focus on evaluating anticancer potency of various extracts of the heartwood of Calocedrus decurrens against human lung adenocarcinoma (A549) cell line was performed using in vitro MTT assay. The hexane extract displayed excellent cytotoxic effect, and the phytochemical investigation of the hexane and acetone extracts resulted in the isolation of five major compounds. The structure of the compounds was established as libocedrol (1), thymoquinone (2), libocedroquinone (3), diethylphthalate (4), and (1 R, 2 R, 4 R)-p-menthane-1,2,4-triol (5). Compounds 4 and 5 are reported for the first time from the Calocedrus genus. Compounds 1–3 were evaluated for their cytotoxicity against the lung cancer cell line along with a healthy control. Compound 3 was more potent than other compounds against the A549 cell line with an IC50 of 4.8 µM at 24 h. Moreover, compound 3 exhibited less toxicity with the normal lung fibroblast cell line WI-38. This is the first anticancer study of the species Calocedrus decurrens.

Chemoprofiling of the aerial parts of the unexplored wild nutmeg species M. beddomei subsp. Spherocarpa W.J. de Wilde led to the isolation of two new flavonoids, including an isoflavone 5,7-dihydroxy-3-(5'-hydroxybenzo[d](7',9')-dioxol-1'-yl)-4H-chromen-4-one (1) and a β-hydroxydihydrochalcone; (3(S)-hydroxy-3-phenyl-1-(2',4',6'-trihydroxyphenyl)propan-1-one (2) along with eleven known compounds (3-13) for the first time. The chemical structures of the isolates were elucidated by various spectroscopic analyses (1D and 2D NMR, HR-ESI-MS and IR). Chemotaxonomic significance of the isolates was discussed in detail. In addition the selected compounds were assessed for their in vitro cytotoxicity against human adenocarcinoma cell lines (MCF-7 and MDA-MB-231). Amongst malabaricones (3, 5-7) showed promising activity against both the cell lines whereas trimyristin (10) efficiently inhibited MCF-7 also partensein (8) and promalabaricone B (9) were found to be moderately toxic to MDA-MB-231 and MCF-7.

Artocarpus hirsutus Lam., or wild jack, a perennial tree of the Western Ghats of peninsular India, serves as a rich source of flavonoids. The indigenous knowledge of this multipurpose flora chronicles the efficient property of its bark as a natural treatment for various skin infections. Herein, we describe a rational explanation of this traditional knowledge via a broader evaluation of inhibitory activity of one of its phytoconstituents, cudraflavone C (Cud C), a prenyl flavone isolated from stem bark against diverse multidrug-resistant Staphylococcus aureus along with decidedly potent synergy combinations with a standard drug, gentamycin, especially against gentamycin-resistant S. aureus NRS 10119. Cud C exhibited equipotent MIC (4 μg/mL) against a varied array of MDR strains comprising MRSA, VRSA, and VRE and was nontoxic toward eukaryotic cells with a sizable selectivity index (SI 25-50). Cud C displayed concentration-dependent bactericidal activity against planktonic cells, an excellent biofilm disruption property exceeding that of levofloxacin and vancomycin against preformed S. aureus biofilm, and an enhanced capability to kill intracellular S. aureus more potently than vancomycin, thus exemplifying its position as an antibacterial lead candidate. In addition, S. aureus was unable to generate resistance to Cud C even after exposure for more than 40 days, whereas it generated resistance to levofloxacin within ∼20 days of exposure. Therefore, the naturally occurring prenylflavone Cud C can be accounted for as one of the reasons for the reported antibacterial properties of the bark of A. hirsutus. Taken together, detailed biological studies propose that Cud C can be considered as an effective antibacterial drug candidate against MDR S. aureus, which is fast becoming a significant threat to public health worldwide.

The genus

Five undescribed (2-6) rotenoid derivatives along with three known rotenoids (1, 7 and 8) were isolated from the rhizomes of white colored variety of Mirabilis jalapa Linn. The structures of these undescribed compounds were elucidated based on UV, IR, HR-MS (ESI), 1D and 2D NMR spectroscopic techniques. Selected compounds were evaluated for their cell viability and proliferation in two cancer cell lines namely, cervical (HeLa), breast (SKBR-3) and normal lung fibroblast (WI-38). Among them, the compounds Boeravinone C (1), Mirabijalone S (2), Mirabijalone T (3) and 4, 6, 11-trihydroxy-9-methoxy-10-methylchromeno [3, 4-b] chromen-12(6H)-one (8) showed moderate cytotoxicity against HeLa cells with IC50 values in the 8.40 − 12.9 μM range, and compound 8 exhibited cytotoxicity against SKBR-3 cells with IC50 value of 17.6 μM. Molecular docking studies of isolated compounds were performed with three apoptosis proteins, 3H11, 2AR9 and 1X0X. These results revealed that the isolated compounds were found to interact with Caspase 8 and 9 along with the anti-apoptotic protein Survivin. Since these compounds exhibit cytotoxic effects against SKBR3 and HeLa cells, they are expected to show apoptosis and may be further utilized for wet lab apoptotic studies.

Photoirradiation of (6E,9E)-zerumbone-2,3-epoxide afforded a diverse range of transannular cyclized products in the presence of a catalytic amount of Sc(OTf)3. At the behest of the geometrical isomers produced by photoirradiation, the diversity encompasses an unprecedented eudesmane core and oxo-bridged hydroxy-olefin skeletons. Structure elucidation and the stereochemical outcome of the products are described via extensive NMR analysis. The present study serves as a model for tandem photoisomerization and transannular cyclization of natural products with enone/dienone functionality.

Copper-mediated carbon–heteroatom bond-forming reactions involving a wide range of substrates have been in the spotlight for many organic chemists. This review highlights developments between 2010 and 2019 in both stoichiometric and catalytic copper-mediated reactions, and also examples of nickel-mediated reactions, under modified Chan–Lam cross-coupling conditions using various nucleophiles; examples include chemo- and regioselective N-arylations or O-arylations. The utilization of various nucleophiles as coupling partners together with reaction optimization (including the choice of copper source, ligands, base, and other additives), limitations, scope, and mechanisms are examined; these have benefitted the development of efficient and milder methods. The synthesis of medicinally valuable or pharmaceutically important nitrogen heterocycles, including isotope-labeled compounds, is also included. Chan–Lam coupling reaction can now form twelve different C–element bonds, making it one of the most diverse and mild reactions known in organic chemistry.1 Introduction2 Construction of C–N and C–O Bonds2.1 C–N Bond Formation2.1.1 Original Discovery via Stoichiometric Copper-Mediated C–N Bond Formation2.1.2 Copper-Catalyzed C–N Bond Formation2.1.3 Coupling with Azides, Sulfoximines, and Sulfonediimines as Nitrogen­ Nucleophiles2.1.4 Coupling with N,N-Dialkylhydroxylamines2.1.5 Enolate Coupling with sp3-Carbon Nucleophiles2.1.6 Nickel-Catalyzed Chan–Lam Coupling2.1.7 Coupling with Amino Acids2.1.8 Coupling with Alkylboron Reagents2.1.9 Coupling with Electron-Deficient Heteroarylamines2.1.10 Selective C–N Bond Formation for the Synthesis of Heterocycle-Containing Compounds2.1.11 Using Sulfonato-imino Copper(II) Complexes2.2 C–O Bond Formation2.2.1 Coupling with (Hetero)arylboron Reagents2.2.2 Coupling with Alkyl- and Alkenylboron Reagents3 C–Element (Element = S, P, C, F, Cl, Br, I, Se, Te, At) Bond Forma tion under Modified Chan–Lam Conditions4 Conclusions

We herein disclose an effective strategy for the synthesis of [5.3.0] and [6.3.0] fused polycyclic terpenoids, which are important structural elements of natural products and biologically active compounds. The method comprises of Lewis acid catalyzed interrupted Nazarov cyclization of zerumbone derivatives such as zerumbone epoxide, triazole-appended zerumbone, zerumbal, and zerumbenone with a wide substrate scope with different indoles. Zerumbone epoxide furnished [5.3.0] and [6.3.0] fused structurally diverse sesquiterpenoids and all other zerumbone derivatives furnished the [6.3.0] fused motifs.

Background: Self-renewal and proliferation of neural progenitor cells occur throughout humans' lives. However, aging, stress, and degenerative diseases can hinder or stop the process. If you can accelerate neurogenesis in adults, this is a promising way to recover from neurodegeneration and cognitive impairments. As the demand for a safer and natural therapeutic product has increased over the past decade, medicinal plants seem to be a viable alternative to synthetic medicines. Since early human civilization, various herbs have been used as medicines and are still a basis for different modern medications. With the advancements in science, researchers can isolate the active compounds in an herb and predict these herbs' line of action when used as a drug. Our current knowledge of medicinal plants with neurological functions is many, but only a few are scientifically validated. Method: A review of the scientific literature explaining plants' bioactive compounds that show neurogenesis was executed. All published data till the year 2021 have been taken to consideration. PubMed, Scopus, ScienceDirect, and Google Scholar directories were used to explore literature published using relevant keywords. Results: Plants like Panax ginseng, Lycium barbarum, Acorus tatarinowii, Curcuma longa, Salvia miltiorrhiza, Centella asiatica, Bacopa monnieri, Ginkgo biloba, Cuscuta japonica, Radix Astragali, Hericium erinaceus and Banisteriopsis caapi have shown to induce neurogenesis. Conclusions: The information on plants compiled in this review pertains to those with a therapeutic value that can be used for drug development to cope with neurodegenerative diseases and memory impairment.

Zerumbone is a naturally occurring humulene type sesquiterpene, isolated from the rhizomes of Zingiber zerumbet (L.) Smith with excellent therapeutic potential and is recognized as a valuable synthon for the construction of diverse array of natural product motifs. In this review, we intended to highlight our achievements in utilizing abundant natural product zerumbone and its derivatives for the development of pharmacologically relevant molecular scaffolds. We provided an account of the transition-metal catalyzed 1,4-conjugate addition reactions of zerumbone and its derivatives along with palladium-catalyzed cross-couplings, transition metal-based Lewis acid promoted interrupted Nazarov cyclisation reaction with substituted indoles and transannular cyclizations, photo-induced transformations of zerumbone and its epoxide.

Phytochemical investigation of the stem bark of Hopea parviflora resulted in the isolation of 9 compounds; which includes friedelin (1), friedelin-3β-ol (2), (-)-ampelopsin A (3), (-)-ɛ-viniferin (4), (-)-hopeaphenol (5), vaticaphenol A (6), 2,4,8-trihydroxyphenanthrene-2-O-glucoside (7), ellagic acid-3,3',4-trimethoxy-4'-O-α-L-rhamnopyranoside (8) and β-sitosterol-β-D-glucoside (9). Among them, compounds 1, 2, 6, 7, 8 and 9 are isolated for the first time from this species. Further, we evaluated the anti-inflammatory activity of compounds 4, 5, 6, 7 and 8. In this study, compound 8 inhibited the activity of proinflammatory mediators like NO, TNF-α, IL-6, 5-LOX and COX-2, also promoted the action of anti-inflammatory mediator like IL-10 via inhibition of the NF-κB pathway in LPS-stimulated RAW 264.7 macrophages.

Ethnopharmacological relevance Hopea ponga (Dennst.) Mabb. Is used in traditional herbal formulations for diabetes complications. The aim of this study is to evaluate the antidiabetic effect of extracts and compounds from H. ponga. Materials and methods Silica gel column chromatography was performed to identify various chemical components of the plant extract. Different extracts of H. ponga and isolated compounds were screened for their antidiabetic effect by modulation of digestive enzymes and protein glycation. The effect of glucose uptake by the compounds and the pathways through which the compounds mediate the glucose uptake potential were confirmed by fluorescent microscopy, flow cytometry and western blot analysis. Results Acetone and ethanol extracts of the stem bark of Hopea ponga (Dennst.) Mabb. Afforded six resveratrol oligomers namely, E-resveratrol (1), (−)-e-viniferin (2), (−)-α-viniferin (3), trihydroxyphenanthrene glucoside (THPG) (4), vaticaphenol A (5), (−)-hopeaphenol (6), along with four phytosterols. The structures were determined on the basis of spectroscopic analyses including nuclear magnetic resonance (NMR) spectroscopy and high resolution mass spectrometry (HRMS) data. Compounds 1–5 and 7–10 were tested for their α-glucosidase, α-amylase and glycation inhibitiory activities. All the resveratrol oligomers (1–5) showed prominent α-glucosidase inhibition with IC50 values, 12.56 ± 1.00, 23.98 ± 1.11, 7.17 ± 1.10, 31.74 ± 0.42 and 16.95 ± 0.39 μM, respectively. Molecular docking studies also supported the observed α-glucosidase inhibition. Compound 3 displayed IC50 values of 4.85 ± 0.06 and 27.10 ± 0.04 μM in α-amylase and glycation inhibitory assays activity. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay revealed that the compounds 3 and 4 were found to be less toxic at a concentration of 100 μM ( Conclusion This is the first report on the isolation of compounds from H. ponga. Altogether, the results of this study reveal the antidiabetic effects of H. ponga extracts and isolated compounds promoting traditional use of this plant in the treatment of diabetes.

Antiproliferative activity was confirmed in the various extracts of rhizomes of Hedychium flavescens (Zingiberaceae). The phytochemical investigation of the rhizomes of Hedychium flavescens led to the isolation of four labdane diterpenes. Their structures were established as coronarin E (1), C-14 epimers of isocoronarin D (2), C-15 epimers of coronarin D methyl ether (3) and isocoronarin D (4). The structure of the compounds was identified based on spectroscopic analysis and on comparison with literature reports. All these compounds were assessed for their in vitro cytotoxicity against human lung adenocarcinoma (A549) cell line and showed significant cytotoxicity as reflected in IC50 value, that is, 0.52, 0.59, 0.68 and 1.22 μM compared with the control doxorubicin (IC50 0.92 μM). Moreover, all the compounds were nontoxic towards the normal lung fibroblast (WI-38) cells. The chemo-profiling and cytotoxicity study of Hedychium flavescens is reported for the first time.

An approach to expand the diversity of terpenes to novel polycyclic skeletons with contiguous stereogenic centers is described. An unprecedented 8-oxabicyclo[3.2.1]octane motif was obtained in quantitative yield by photoirradiation of zerumbone in the presence of a catalytic amount of Lewis acid. The vital role of light in the isomerization of double bonds in zerumbone, which ensued cyclization via tertiary carbocation intermediate, emulates a biosynthetic route. Synthetic diversification of the phototransformed product afforded epoxy derivatives with up to seven contiguous stereogenic centers and eight-member ring fused tricyclic motifs. The present work sheds light on the possible role of UV irradiation in the biosynthesis of oxo-bridged tricyclic structures from polyene terpenes.

A facile synthesis of biologically important trans-functionalized cyclopentenes by a mild Rh(III)-catalyzed alkylation of strained ­diazabicyclic olefins with aryl ketones in the presence of ammonium ­acetate has been developed. The reaction proceeds through C–H bond activation of the aryl ketone groups by transforming them in to an ­autocleavable directing group, such as in situ-formed imine.

Three previously undescribed dihydro-β-agarofuran sesquiterpenoids (1–3) along with eight known sesquiterpenoids (4–11) were isolated from the seeds of C. paniculatus. The structures of these compounds were determined on the basis of UV, IR, HR-MS (ESI), 1D and 2D NMR data obtained, and their absolute configurations were further confirmed by single-crystal X-ray diffraction. All these compounds were evaluated for their α-glucosidase and α-amylase inhibition, and antiglycation properties. Compounds 1, 3, 4, 5, 7 and 11 showed good α-glucosidase inhibition with IC50 values, 39.56 ± 0.761, 35.60 ± 0.843, 36.54 ± 0.173, 44.83 ± 0.453, 42.58 ± 0.209 and 45.84 ± 0.356 μM respectively. Molecular docking studies revealed that these compounds bind effectively to the active sites of the protein 3A4A, which supports the observed α-glucosidase inhibitory activity.

Phytochemical investigation of the stem bark of Myristica fatua Houtt. led to the isolation of a new compound 1 (3-tridecanoylbenzoic acid), along with six known acylphenols (2–7). All the compounds displayed moderate inhibitory activity on α-amylase and significant activity on α-glucosidase; however malabaricone B (6) and C (7) were identified as potent α-glucosidase inhibitors with IC50 values of 63.70 ± 0.546, and 43.61 ± 0.620 µM respectively. Acylphenols (compounds 3–7) also showed significant antiglycation property. The molecular docking and dynamics simulation studies confirmed the efficient binding of malabaricone C with C-terminus of human maltase-glucoamylase (2QMJ). Malabaricone B also enhanced the 2-NBDG [2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxy glucose] uptake in L6 myotubes. These findings demonstrate that acylphenols isolated from Myristica fatua Houtt. can be considered as a lead scaffold for the treatment of type II diabetes mellitus.

A facile Lewis-acid-catalyzed method for the synthesis of structurally diverse sesquiterpenoid derivatives from readily available and abundant 11-membered natural product zerumbone has been developed. Starting from zerumbone, we have developed an efficient cyclization process for the creation of [5.7], [5.8], and [5.8.3] fused-ring systems. This process was exemplified by the selective functionalization of zerumbone; by controlling the conformation of the 11-membered ring, the ring-closing process could be tuned to afford the fused-ring system of choice.

A palladium-catalyzed aminocarbonylation strategy exploiting chloroform as a CO source has been developed for the synthesis of biologically potent 2-amidoimidazopyridine scaffolds. The aminocarbonylation reaction was found to be general with a range of amines and substituted imidazopyridines. Preliminary biological evaluation of cytotoxicity on selected examples provides scope for future investigations.

A newly synthesised zerumbone pendant derivative (ZPD) was studied in human cervical cancer cells (HeLa) for its anticancer properties. ZPD significantly inhibited the growth of human cervical cancer cells with a GI50 value of 6.35 ± 1.30 μM, which also induced morphological changes and apoptosis in a dose-dependent manner. Our data indicated that ZPD actively encouraged programmed cell death in HeLa cells which were confirmed by DNA fragmentation, phosphatidylserine translocation, increased activity of caspase 3, upregulation of the expression of the pro-apoptotic protein Bax, cleaved PARP, cleaved caspase 3 and downregulation of anti-apoptotic protein Bcl-2. ZPD also inhibited cell migration of HeLa cells, decreasing the production of MMP-2,-9 and downregulation of expression of MMPs and pro-angiogenic factor VEGF. Also it is nontoxic to normal rat cardiac myoblasts. Overall, ZPD is a promising candidate for inducing cytotoxicity, apoptosis and anti-migratory effects in cervical cancer cells.

Herein we report a ratiometric naturally occurring fluorescent pH probe, berberrubine (BBn) for the direct detection of diabetic ketoacidosis (DKA) conditions of patients having type I diabetes mellitus. The photophysical properties of the probe during pH titrations showed remarkable changes in absorption spectra where two absorption bands at 377 and 326 nm have disappeared followed by the emergence of an absorption maxima at 346 nm in highly acidic conditions. In addition, a fluorescence enhancement effect was observed in the alkaline pH, with a bathochromic shift of 33 nm. Moreover, the solution switches the color from light yellow to light pink with the change of pH from acidic to basic. A pKa value of 7.57 and a good linearity between pH 5.0–9.0 indicate that the probe can be used efficiently for the DKA condition, where pH variations are in the range of 6–7. The excellent water solubility, photostability, reversibility, and selectivity of BBn make it a potential pH sensing agent for acidic microenvironments. The reversible sensing of pH variations during DKA could be effective in primary detection and diagnosis which can assist in avoiding further complications of acidosis.

The conventional methods for carrying out fluorination of organic compounds are typically conducted using a pre-modified starting material, usually expensive and toxic reagents. In this regard, electrochemical fluorination has been recognized as a sustainable and scalable strategy. Electrofluorination has proven to be an environmentally benign, highly effective, and versatile platform for the synthesis of selective organofluorine compounds under mild conditions. This review provides an overview on the use of anodic electrochemical methods for vicinal difluorination, iodofluorination, fluoroalkynylation, fluorodecarboxylation, fluoro desulfurization, radiofluorination, and synthesis of fluorinated heterocycles. Modern advances in the field of electrochemical fluorination, such as ionic liquids mediated electrochemical fluorination, triethylammonium halides, mixed non-aqueous solvents, alkali–metal fluoride, and split-bipolar electrodes in the field of electrochemical fluorination are also discussed.

trans-3-Styryl-4-hydrazinocyclopentenes have been synthesized via palladium-catalyzed desymmetrization of diazanorbornenes with (Z)-β-bromostyrenes. The reaction also works well with (Z)-β-bromostyrenes generated in situ from 2,3-dibromohydrocinnamic acids. The synthesized hydrazinocyclopentenes provide an easy route towards synthetic intermediates of many scaffolds of biological potential.

An efficient rhodium (III) catalyzed C-H activation approach for the construction of fused heterocyclic motifs with urea derived bicyclic olefins has been demonstrated. Rhodium catalyzed reaction of O-acetyl ketoximes with these bicyclic motifs furnished isoquinoline derivatives whereas isoquinolone fused bicyclic olefins were obtained with the reaction of N-methoxy benzamides.

Herein, we describe a metal-free, iodosobenzenediacetate mediated trans-aziridination of zerumbone by the direct use of sulphonamides. The preliminary in vitro-screening showed better anti-proliferative and anti-diabetic activity compared to parent compound zerumbone.

A facile route toward the synthesis of pentaleno(1,2- b )indoles via multicomponent reaction of indole, aldehyde, and pentafulvene is realized. The reaction proceeds through Lewis acid catalyzed [3+2] cycloaddition of in situ generated indolylmethanol and pentafulvene. This methodology provides an easy access to biologically relevant indole derivatives.

A series of zerumbone pendant derivatives were synthesized and evaluated for their α-glucosidase, α-amylase and glycation inhibition activities. In our study, some of the derivatives showed potent inhibitory activity in micromolar concentration. In addition, investigations were carried out to screen the cytotoxic effects of some selected derivatives against various cancer cell lines viz., A549, HCT116, HeLa, HT1080 and MDAMB231. Two of the derivatives showed potent activity towards HCT116 and HeLa cell lines.

The design, synthesis, and comprehensive utilization of diazanorbornene systems incorporating a flexible hydroxy group are described. The Lewis acid catalyzed intramolecular rearrangement of these strained alkenes gave cyclopentannulated dihydro-2H-pyrans, whereas the intermolecular sequential Lewis acid/palladium-mediated reaction with o-iodoanilines gave pentacyclic frameworks through multiple bond formation (C–C, C–N, C–O).

Selective C-2 functionalization of N-protected and free indoles is reported. The ruthenium-catalyzed C-2 activation of indoles provided an easy access to cyclopentenylated indoles. Hydroheteroarylated bicyclic motifs were synthesized via iridium-catalyzed C-2 activation of NH indoles. The methodology was extended to different bicyclic adducts such as diaza- or urea-derived bicyclic olefins.

The carbonyl moiety is one of the indispensable sub-units in organic synthesis with significant applications in medicinal as well as materials chemistry. Hence the insertion of a carbonyl group via simple and highly efficient routes has been one of the most challenging tasks for organic chemists. Though the direct utilisation of CO gas in carbonylation is the fundamental procedure for the construction of carbonyl compounds, it has certain drawbacks due to its toxic and explosive nature. As a result, the need for cheap and efficient CO surrogates has gained much attention nowadays by which CO gas can be easily generated in situ or ex situ. In this review we discuss the advantages of chloroform as CO surrogate and have surveyed recent carbonylation reactions where chloroform has been used as CO source.

Promalabaricone B (PMB), an acylphenol was isolated from dichloromethane-soluble extract of the seeds of Myrisitica fatua Houtt. PMB exhibited significant inhibitory activity on α-glucosidase enzyme. The molecular docking and dynamics studies of PMB with human maltase-glucoamylase were performed. PMB exhibited an enhanced glucose uptake in L6 myotubes with 46.3% in 2.5 µM. Encouraged with these results; we investigated the molecular mechanism of PMB through the upregulation of AMPK. The results revealed that PMB promoted the glucose uptake in myocytes by stimulating the translocation and expression of GLUT4. From this, it is clear that PMB can acts as a potential therapeutic option for diabetes treatment, and its hypoglycaemic effect may be mediated by AMPK upregulation and induction of GLUT4 translocation.