JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH

Special issue commemorating the 40th anniversary of the College of Traditional Chinese Medicine, Shenyang Pharmaceutical University
Song SJ
A new verrucosane diterpenoid from the Vietnamese liverwort
Thi-Kim-Dung L, Thi-Nhu-Quynh N, Thanh-Nguyen L, Nguyen-Khanh-Trinh T, Thi-Phuong N, Nguyen TH, Nguyen NH, Sichaem J and Duong TH
A new verrucosane-type diterpenoid, bantamenside (), along with six known compounds (), was isolated from the Vietnamese liverwort . The structure of the new compound was determined using comprehensive spectroscopic methods, including 1D and 2D NMR techniques as well as high-resolution mass spectrometry. Furthermore, all isolated compounds were evaluated for their ability to inhibit nitric oxide (NO) production. Compounds and demonstrated notable NO inhibitory activity, with IC values ranging from 12.85 to 51.37 µM, outperforming or comparable to that of the positive control L-NMMA (IC 41.30 ± 6.60 µM).
Two new polyacetylenes from
Li CH, Jiang GH, Yao JC, Zhou HL, Jiang HQ, Liu XJ, Ma XQ, Li YN, Huo LG, Zhang LX and Shen T
Two novel polyacetylenic compounds were successfully separated from the dichloromethane extract of the aerial parts of Willd., known for its ethnomedicinal use in traditional Dai medicine. These compounds were structurally elucidated and identified as (2)-trideca-3,5,11-triene-7,9-diyne-1,2,13-triol (), and (2)-trideca-11-ene-5,7,9-triyne-1,2,13-triol (). Their chemical structures were confirmed through a comprehensive analysis involving ultraviolet (UV) spectroscopy, infrared (IR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), as well as detailed one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopic data, and measurements of specific optical rotation.
Dihydroagarofuran sesquiterpene derivatives from the roots of
Hu YL, Hong PT, Lei YT, Chen WJ, Wang C, Huang JL, Li Z, Li ZJ and Li W
Two new () and five known () dihydro--agarofuran derivatives were isolated from the roots of . The structures of new compounds were elucidated by spectroscopic techniques, such as UV, IR, HRESIMS and NMR. And the structure of compound was confirmed by X-ray crystallographic. Cytotoxic activity assays against four human tumor cell lines (SK-MEL-2, HCC1806, HUH-7, PANC-1) were assessed for compounds . Compound exhibited pronounced cytotoxicity against SK-MEL-2 cells with an IC value of 9.18 μM. Additionally, compound showed significant cytotoxic effects on SK-MEL-2 and HCC1806 cells with IC values of 4.59 μM and 8.14 μM, respectively.
Secondary metabolites with anti-inflammatory activity isolated from a marine-derived fungus sp. 8703
Zheng L, He QM, He D, Chen SH, Wu QL, Luo GY, Chen J, Guo H, Hu ZB, Chen LT, Liu L and Li J
Four new compounds (-), along with 22 known metabolites (-), were isolated from the fungus sp. 8703. The structures of the new compounds were elucidated based on NMR, MS, and ECD analysis. Compounds and were identified as heliannuol D analogs, which exhibited anti-inflammatory activity by inhibiting NO production in LPS-induced RAW 264.7 cell, with IC values of 7.14 and 25.25 M, respectively.
Targeting GPX4-dependent ferroptosis by natural compounds in multiple sclerosis
Zhou N, Dong YR, Wang JR, Zang CX, Ma JW, Yang Y, Chen QZ, Jiang YQ, Yang X, Cao SP, Zhou MC, Zeng SX, Li FF, Bao XQ and Zhang D
Multiple sclerosis (MS) is an autoimmune-mediated, heterogeneous, multifactorial central nervous system degenerative disease influenced by genetics and environment. Ferroptosis, an iron-dependent lipid peroxidation/reactive oxygen species-induced programmed cell death, exacerbates MS pathology. Glutathione peroxidase 4 (GPX4) regulates ferroptosis by clearing peroxides to sustain cells. Targeting GPX4-mediated ferroptosis, especially via safe, potent natural compounds, is a promising MS treatment. This review explores GPX4-dependent ferroptosis's role in MS progression and summarizes natural compounds for MS therapy.
Two new macrocyclic cembrane diterpenoids from gum resin
Metta D, Kothapalli RB, Paidi R and Singuru R
Two previously undescribed macrocyclic diterpenoids, cycloserratol () and isopapyrifuranol A () were isolated from the gum resin of Compound was confirmed as trihydroxy substituted 12-membered macrocyclic cembrane-type diterpenoid skeleton and was a new 1,12-oxygen fused trihydroxy cembrane skeleton. The structures of these new metabolites were characterized by HRESIMS, 1D NMR and 2D NMR analysis.
Synthesis and biological activity of the marine-derived leonurine analogue N-(4-guanidinobutyl)-2-(4-hydroxyphenyl)-2-oxoacetamide
Li N, Dai XL, Xiong GX, Meng WL, Hao J and Hao JJ
N-(4-Guanidinobutyl)-2-(4-hydroxyphenyl)-2-oxoacetamide (), a marine-derived leonurine analogue, was synthesized via a six-step route with 38% total yield. Biological evaluation demonstrated potent anticoagulant activity through significant prolongation of APTT (20 mM) and PT (5 mM). dose-dependently (100-200 μM) suppressed LPS-induced NO production in RAW 264.7 macrophages without cytotoxicity and modulated phagocytosis. In LPS-induced acute lung injury rats, reduced proinflammatory cytokines in BALF. These findings highlight 's dual anticoagulant and anti-inflammatory properties as a promising lead compound.
Glutinol, main component of , inhibits TGF-β-induced epithelial mesenchymal transition of human cancer cells
Bang C, Jang EH, Lee DE, Kim GL, Jung Y, Shin H, Na JH, Lee S and Kim JH
Glutinol (GT), a major triterpenoid component of , suppresses TGF-β-induced epithelial-mesenchymal transition (EMT) in human cancer cells. GT treatment restored epithelial characteristics by upregulating E-cadherin and downregulating Snail, thereby reducing cancer cell migration and invasion in A549 and MCF-7 cells. , GT significantly inhibited lung metastasis of TGF-β-treated A549-luc cells in mice. These findings demonstrate that GT exerts potent anti-metastatic effects through modulation of the TGF-β/Snail/E-cadherin signaling axis, highlighting its potential as a natural therapeutic agent against cancer metastasis.
Rutin inhibits hepatic gluconeogenesis and increases glycogen synthesis through the IRS/PI3K/akt signaling pathway in insulin resistant hepatocytes
Li QH, Lu MX, Feng YH, Zhao M, Mo TD, Jiang WW, Zhang X and Wang L
Rutin, a dietary flavonoid, can relieve insulin resistance to improve hyperglycemia, while the precise mechanism remains unclear. In this study, we found that rutin bound well to the insulin receptor, alleviated glucosamine-induced insulin resistance in HepG2 cells and observably increased glucose consumption and glucose uptake . Furthermore, rutin increased the levels of IRS-1, IRS-2, PI3K, p-AKT, p-GSK3β and p-FOXO1 and decreased the expression of p-IRS-1, p-GS, PEPCK and G6Pase, indicating that rutin could promote glycogen synthesis and inhibit gluconeogenesis via the IRS/PI3K/Akt signaling pathway. Overall, the findings confirmed that rutin potentially mitigates glucosamine-induced insulin resistance in hepatocytes via activation of IRS/PI3K/Akt pathways.
First total synthesis and antimicrobial evaluation of xanthone V1
Tan F, Wang MQ, Shi HF, Zhang CR, Cui DX and Dong HB
Antibiotic resistance demands new agents. We disclosed the first total synthesis of the natural xanthone V1 (), which featured a regioselective Claisen cyclization and a Claisen/Cope rearrangement that installed the pyran ring and isopentenyl unit. The synthetic compound showed moderate antibacterial potency (MICs 16-64 μg/ml) across multiple strains and synergized with ciprofloxacin against MRSA. It exhibited low cytotoxicity toward mammalian cells and minimal hemolysis, thereby supporting xanthone V1 as a promising lead for anti-MRSA therapy.
A demethylation chloroisosulochrin and a chromone metabolite from the endophytic fungus sp
Chen KL, Wang X, Liu Y and Liu YB
A newly discovered chloroisosulochrin derivative, involving demethychloroisosul (), and a novel chromone metabolite, reduchromone (), were extracted from sp., an endophytic fungus residing in . The structures of these compounds were elucidated through a comprehensive analysis of their 1D and 2D NMR and HRESIMS data. In addition, the X-ray diffraction analysis of demethychloroisosul () is the first example to confirm the structure of chloroisosulochrin by single-crystal data. Notably, demethychloroisosul () exhibited moderate cytotoxic efficacy against HepG2 liver cancer cells, with a half-maximal inhibitory concentration value of 30.18 μM.
Scuregeliolides a-C: new -clerodane diterpenoids from and their anti-inflammatory activities
Zhang DW, Yue XD, Wang Y, Liu JH and Dai SJ
Three new -clerodane diterpenoids, named scuregeliolides AC (-), were isolated from the whole plant of . Their chemical structures, including absolute stereochemical configurations, were fully elucidated by means of integrated spectroscopic techniques and Electronic Circular Dichroism (ECD) calculations. , three undescribed -clerodane diterpenoids showed significant anti-inflammatory activities due to inhibiting the release of TNF-, IL-6 and IL-1 in the LPS-induced RAW264.7 cells, as well as preventing the release of -glucuronidase from the PAF-stimulated PMNs.
Hyperwightianols I-N, six new meroterpenoids from
Fu CL, Ying P, Huang WM, Liu Z, Jia ZW, Zheng Q, Wu YJ, Kong LY and Xu WJ
Six undescribed meroterpenoids, designated as hyperwightianols I-N (), were isolated from the dried whole herb of . The structures of these compounds were elucidated through comprehensive spectroscopic analyses, including high-resolution mass spectrometry (HRMS), 1D & 2D nuclear magnetic resonance spectroscopy (NMR), as well as electronic circular dichroism (ECD). Compounds featured a chromone core hybridized with a monoterpene unit (geranyl or geranyl-derived groups), while were characterized by benzoic acid or cinnamic acid cores hybridized with a lavandulyl unit. In all cases, the monoterpene fragments were linked to the core structures via C-4 ether bond.
A comprehensive review on phytosomes as an emerging technology for delivering herbal medicines
Aneja P, Guleria R, Aneja S, Dahiya DP, Goyal A, Roy D, Singh J and Rangra NK
A "novel drug delivery system" is a new and effective alternative pathway to administer drugs that evade the limitations of traditional methods. The natural medications can be a good approach for delivering the active ingredients to the target-specific area. However, many plant extracts and compounds face challenges like poor solubility and poor absorption. To overcome these issues, the emergence of "phytosomes" has been developed. Phytosomes are advanced herbal delivery systems that improve the absorption and effectiveness of plant extracts. This review highlights the key advancements in phytosomal technology, their practical benefits, and cost-effectiveness.
Two new polymethoxyflavones with fully substituted A-ring from the peels of "dahongpao"
Li J, Liu YH, Zheng HY, Zhan Q, Xiao B, Liu D and Zhang CL
Phytochemical investigation of the peels of "Dahongpao" resulted in the isolation and characterization of six polymethoxyflavones. Their structures were elucidated as 5,6,7,3'-tetrahydroxy-8,4'-dimethoxyflavone (), 5,6,7-trihydroxy-8,3',4'-trimethoxyflavone (), 5,7,8-trihydroxy-6,3',4'-trimethoxyflavone (), 5,8-dihydroxy -6,7,3',4'-tetramethoxyflavone (), 5,6,7,8-tetrahydroxy-3',4'-dimethoxyflavone (), and nobiletin () by analysis of their spectroscopic data. They feature a characteristic fully substituted A-ring and a 3',4'-disubstituted B-ring, analogous to nobiletin. Among them, compounds and are new compounds. Full assignment of NMR data for compounds and is presented here for the first time. Furthermore, the discrepancies in the previously reported NMR spectroscopic data of compound are discussed.
Synthesis and anti- activity of oleanolic acid derivatives
Zou F, Jiang LY, Chen F, Fan ZF, Zhang TY, Yang TY, Wang RR and Ni GH
With the increase incidence of infections and the widespread use of azole drugs, particularly fluconazole, the emergence of drug-resistant strains has become a significant concern. In this study, the derivatives were prepared by nucleophilic substitution at the 3-OH position of oleanolic acid, utilizing the reactivity of triphosgene, and by electrophilic coupling at the 28-COOH position through photoredox reactions. The antifungal activity of all compounds was evaluated, revealing that most derivatives exhibited good synergistic antifungal activity with fluconazole against the drug-resistant strain ATCC14053, with FICI values ranging from 0.45 to 0.14.
A new cyclohexenone and two new phenanthrones from
Thien DD, Sa NH, Thang LQ and Tam NT
A new cyclohexenone, 5-(3,4-dihydroxyphenethyl)cyclohex-2-en-1-one (), along with two new phenanthrones, (4a,10a)- 1,9,10,10a -tetrahydro-4a,6,7-trihydroxy-4(4a)-phenanthrone () and (4a,10a)-4a-hydroxy-7-methoxy-1,9,10,10a-tetrahydro-4(4a)-phenanthrone 6-O--D-glucopyranoside () were isolated from the whole plant of The structures were determined by spectroscopic methods including 1D, 2D NMR and HR-ESI-MS. The absolute configurations of compounds were determined by their experimental and calculated ECD spectral data. The isolates were evaluated for inhibitory activity on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophage cells, and compound showed the strongest activity with an IC value of 9.5 ± 1.2 μM.
Isolation and structural characterization of an iridoid glycoside and a pyridine derivative, both previously undescribed, from the flowers of
Hou-Run Z, Qi C, Hu DB, Wang JA, Chen X, Xiao-Xu B, He JB and Wang Y
An iridoid glycoside, rhododeoside C (), and a pyridine derivative, rhododeodine A (), both previously undescribed, were isolated from the flowers of . The structures were elucidated using 1D and 2D NMR spectroscopy, along with high-resolution electrospray ionization mass spectrometry (HRESIMS). The absolute configurations of both compounds were unambiguously assigned using electronic circular dichroism (ECD) computational methods. Furthermore, all isolated compounds were assessed for their cytotoxic activities against HepG2 and HeLa cell lines.
Effects of bergapten-loaded long-circulating liposomes on osteogenic differentiation of human dental pulp stem cells
Ding HN, Wang XW, Qian YX, Liu K and Jin L
Bergapten is a natural compound with the potential to regenerate bone. However, its poor solubility and instability hinder its clinical use. We developed bergapten-loaded long-circulating liposomes (BP-LCL) to overcome these challenges. The liposomes were spherical, stable, and highly effective at delivering bergapten. We found that BP-LCL were biocompatible and enhanced the osteogenic differentiation of human dental pulp stem cells. It did this by increasing key markers like RUNX2, COL1, and OCN, and by activating the Wnt/β-catenin signaling pathway. This study suggested that BP-LCL could be a promising new approach for bone regeneration settings.
Unraveling the mechanisms of matrine in esophageal cancer treatment: insights from network pharmacology, bioinformatics, and molecular biology experiments
Wen SM, Lv T, Lei L and Shi LY
Matrine, a natural compound from traditional Chinese medicine, demonstrates anti-esophageal cancer (EC) efficacy via multi-target mechanisms. In this study, integrated network pharmacology and WGCNA identified MGLL, EPHX2, and CES2 as key targets for matrine. Clinical nomograms indicated their prognostic value, and bioinformatics analysis confirmed their downregulation in EC, correlating with tumor stage, survival, and immune infiltration. Molecular docking confirmed stable binding between matrine and these targets. In vitro experiments showed matrine upregulates their expressions, concurrently inhibiting EC cell proliferation and inducing apoptosis. In conclusion, matrine treats EC through dual actions-direct antitumor effects and immunomodulation-highlighting its therapeutic potential.