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Herein, six previously undescribed steroids (1-6), were isolated from leaves and twigs of Aphanamixis polystachya (Wall.) R. N. Parker (Meliaceae). Their structures were elucidated by comprehensive spectroscopic analysis, including HRESIMS, 1D and 2D NMR, UV, and IR. Antiviral activity of these compounds were evaluated. Compounds 1-6 showed varying degrees of inhibitory activity against the severe acute respiratory syndrome coronavirus 2 main protease (SARS-CoV-2 M pro ) at 200 μM., Competing Interests: Declaration of competing interest All authors disclosed no relevant relationships., (Copyright © 2024. Published by Elsevier B.V.)

One new highly degraded steroid, namely 21-nor-4-ene-chaxine A (1) furnishing a 5/6/5-tricyclic, along with one known related analogue (2), were isolated from the South China Sea sponge Spongia officinalis. Their structures including absolute configurations were established by extensive spectroscopic data analysis, TDDFT-ECD calculation, and comparison with the spectral data previously reported in the literature. Compound 1 represent the new member of incisterols family with a highly degradation in ring B. In vitro bioassays revealed compound 2 exhibited significant anti-microglial inflammatory effect on lipopolysaccharide (LPS)-induced inflammation in BV-2 microglial cells., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

The genus Polygonatum Mill. belongs to the Liliaceae family, which is widely distributed all over the world. Modern studies have found that Polygonatum plants are very rich in chemical compounds such as saponins, polysaccharides and flavonoids. Steroidal saponins are the most commonly studied saponins in the genus Polygonatum and a total of 156 compounds have been isolated from 10 species of the genus. These molecules possess antitumor, immunoregulatory, anti-inflammatory, antibacterial, antiviral, hypoglycemic, lipid-lowering and anti-osteoporotic activities. In this review, we summarize recent advances in studies of the chemical constituents of steroidal saponins from Polygonatum, including their structural characteristics, possible biosynthetic pathways and pharmacological effects. Then, the relationship between the structure and some physiological activities is considered. This review aims to provide reference for further exploitation and utilization of the genus Polygonatum., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

New steroidal 3β,21-disulfates ( 2 - 4 ), steroidal 3β,22-disulfate ( 5 ), and the previously known related steroidal 3β,21-disulfate ( 1 ) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus , collected off Urup Island in the Sea of Okhotsk. The structures of these compounds were determined by intensive NMR and HRESIMS techniques as well as by chemical transformations. Steroids 2 and 3 have an oxo-group in the tetracyclic nucleus at position C-7 and differ from each other by the presence of the 5(6)-double bond. The Δ 24 -22-sulfoxycholestane side chain of the steroid 5 has not been found previously in the starfish or ophiuroid steroids. The cytotoxic activities of 1 , 4 , 5 , and the mixture of 2 and 3 were determined on the models of 2D and 3D cultures of human epithelial kidney cells (HEK293), melanoma cells (SK-MEL-28), small intestine carcinoma cells (HuTu80), and breast carcinoma cells (ZR-75-1). The mixture of 2 and 3 revealed a significant inhibitory effect on the cell viability of human breast carcinoma ZR-75-1 cells, but other tested compounds were less effective.

Gorgostane steroids are isolated from marine organisms and consist of 30 carbon atoms with a characteristic cyclopropane moiety. From the pioneering results to the end of 2021, isolation, biosynthesis, and structural elucidation using 13 C-NMR will be used. Overall, 75 compounds are categorized into five major groups: gorgost-5-ene, 5,6-epoxygorgostane, 5,6-dihydroxygorgostane, 9,11-secogorgostane, and 23-demethylgorgostane, in addition to miscellaneous gorgostane. The structural diversity, selectivity for marine organisms, and biological effects of gorgostane steroids have generated considerable interest in the field of drug discovery research.

Trillium govanianum , commonly known as Nag Chhatri and Teen Patra, is a popular herbal supplement traditionally used for curing different inflammatory and sexual disorders, infection and wound healing. Steroidal saponins are considered as active components of this species. The present study demonstrated the isolation of nine steroidal saponins, including one new compound named as govanoside B ( 9 ) and eight known, pregna-chacotrioside ( 1 ), pennogenin-triglycoside ( 2 ), borassoside E ( 3 ), pennogenin-tetraglycoside ( 4 ), protodioscin ( 5 ), clintonioside B ( 6 ), pennogenin-diglycoside ( 7 ) and borassoside D ( 8 ). This is the first report on the isolation of 1 , 2 , 4 , 5 , 6 , 7 and 8 from rhizomes of T. govanianum . The extract, fractions and isolated compounds were further evaluated for their DPPH and ABTS radical scavenging activity.

The species of Paris genus is a prolific source of structurally diverse steroidal saponins responsible for multivarious biological properties. The first phytochemical investigation on the steroidal saponin constituents from the rhizomes of Paris vaniotii Lévl. led to the discovery and structural characterization of four new spirostanol saponins, named parisvaniosides A-D (1-4), and one new furostanol glycoside, named parisvanioside E (5), along with eleven known analogues (6-16). Their structures were unambiguously established on the basis of extensive spectroscopic analysis and comparison with the reported spectroscopic data. Compound 1 is a rare spirostanol saponin sharing with a C-9/C-11 double bond and a peroxy group located between C-5 and C-8 of the aglycone, whereas 3 and 4 are unusual C-27 steroidal sapoins with hydroxyl/methoxyl at both C-5 and C-6. Furthermore, 5 is the first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B. All isolated saponins were evaluated for their anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW 264.7 macrophages., (Copyright © 2021 Elsevier Inc. All rights reserved.)

Fourteen polyhydroxylated steroids including six new compounds, ehrensteroids A - F (1-6), were isolated from the Vietnamese soft coral Sarcophyton ehrenbergi after applying various chromatographic separations. The structure elucidation was done by detailed analysis of 1D, 2D NMR and HR QTOF mass spectra. In addition, significant cytotoxicity (IC 50 values ranging from 8.45 ± 0.56 to 38.27 ± 2.39 μM) against all five tested cancer cell lines as LU-1 (lung cancer), HepG2 (hepatoma cancer), MCF-7 (breast cancer), HL-60 (acute leukemia), and SW480 (colon adenocarcinoma) was observed for compounds 1, 2, 6-10, and 12-14, whereas this activity on LU-1 (IC 50  = 21.91 ± 2.72 μM) and HepG2 (IC 50  = 20.32 ± 0.03 μM) cell lines was also observed for 4., (Copyright © 2021 Elsevier Inc. All rights reserved.)

Context: Ircinia mutans Wilson (Irciniidae) is a sponge with antimicrobial and cytotoxic constituents., Objective: Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans ., Materials and Methods: The sponges were extracted in methanol-dichloromethane and their constituents were purified and characterised using column chromatography, GC-MS, 1 D and 2 D NMR. Anti-proliferative activities of the compounds, were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay (0.25-100 μg/mL, 72 h) against leukaemia (MOLT-4), breast (MCF-7) and colon cancer (HT-29) human cells., Results: Three furanosesquiterpoids; furodysin ( 1 ), ent -furodysinin ( 2 ) and furoircin ( 3 ) and ten sterols were characterised in I. mutans , for the first time. Cholesterol ( 4 ), cholesta-5, 7-dien-3β-ol ( 5 ) and ergosterol ( 6 ) were determined in the sponge from the winter collections, while cholesta-5, 22-dien-3β-ol ( 7 ), 24-methyldesmosterol ( 8 ), campesterol ( 9 ), stigmasterol ( 10 ), γ-ergostenol ( 11 ), chondrillasterol ( 12 ) and γ-sitosterol ( 13 ) were detected in the summer samples. The steroids from the winter collection exhibited cytotoxic activity with IC 50 values of 13.0 ± 0.9, 11.1 ± 1.7 and 1.1 ± 0.4 µg/mL, against the mentioned cancer cell lines, respectively, while those from the summer sample, showed greater activity, IC 50 = 1.1 ± 0.2 μg/mL against MOLT-4. The purified steroids showed potent MOLT-4 cytotoxic activity, IC 50 values = 2.3-7.8 µg/mL., Discussion and Conclusion: The present study suggests that I. mutans is a rich source of cytotoxic steroids, and introduces 3 as new natural product. Considering the high cytotoxic activity of the steroids, these structures could be candidates for anticancer drug development in future research.

A unique C30 steroid, solitumergosterol A (1), was isolated from the deep-sea-derived fungus Penicillium solitum MCCC 3A00215. The planar structure and relative configuration of 1 were established mainly on the basis of extensive analysis of its 1D and 2D NMR as well as HRESIMS data, while its absolute configuration was clarified by comparison of the experimental and theoretical ECD spectra. Noteworthily, 1 is a Diels-Alder adduct of a heterogeneous steroid bearing a 6/6/6/6/5 pentacyclic carbon skeleton. Solitumergosterol A (1) exhibited weak in vitro anti-tumor activity against MB231 cells by a RXRα-dependent mechanism.

A phytochemical investigation of the leaf extract of Costus lucanusianus J. Braun & K. Schum (Family Costaceae) a tropical African medicinal plant known for curing several infectious diseases such as venereal disease, cough and urinary tract infection led to the isolation of two new steroids. The identification of these isolates was achieved by modern spectroscopic methods, including 2D NMR. The in vitro antimicrobial activity and Minimum Inhibition Concentration (MIC) values of the isolated compounds against six bacterial and four fungi strains were evaluated. Compound Xp named 3,27-dihydroxy-1-methoxy-22-cholest-5-enone and compound 1 named β-sitosterol-3-O-β-D-3-deoxyxylo-4-hydroxy4,5-dimethyl-pent-2-one displayed broad antimicrobial activity at concentration 12.5 µg/mL-100 µg/mL. Compound Xp displayed MIC value 25.0 µg/mL against tested micro-organisms except for P. notatum and R. stolonifer which showed no prominent growth. Compound 1 was insufficient to determine the MIC value. This present study may be helpful in discovering new chemical groups of antimicrobial compounds that could be useful as an agent against infectious diseases., (Copyright © 2021 Elsevier Inc. All rights reserved.)

Gymnema sylvestre (Retz.) Schult is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of G. sylvestre , a chemical investigation was thus performed. In this research, four new C 21 steroidal glycosides sylvepregosides A-D ( 1 - 4 ) were isolated along with four known compounds, gymnepregoside H ( 5 ), deacetylkidjoladinin ( 6 ), gymnepregoside G ( 7 ) and gymnepregoside I ( 8 ), from the ethyl acetate fraction of G. sylvestre . The structures of the new compounds were established by extensive 1D and 2D nuclear magnetic resonance (NMR) spectra with mass spectroscopy data. Compounds 1 - 6 promoted glucose uptake by the range of 1.10- to 2.37-fold, respectively. Compound 1 showed the most potent glucose uptake, with 1.37-fold enhancement. Further study showed that compounds 1 and 5 could promote GLUT-4 fusion with the plasma membrane in L6 cells. The result attained in this study indicated that the separation and characterization of these compounds play an important role in the research and development of new anti-diabetic drugs and pharmaceutical industry.

In the ongoing research on potent antitumor agents from the rhizomes of Asparagus cochinchinensis, seven undescribed steroidal saponins asparagusoside A-G (1-7), along with twenty known ones (8-27), were isolated and elucidated via analyzing their 1D, 2D NMR, mass spectroscopic data and chemical methods. All isolated compounds were evaluated for their cytotoxic effects against human large cell lung carcinoma cells (NCI-H460) in vitro. Among them, compounds 7, 9 and 27 showed more significant antitumor activities than the positive control cisplatin (11.56 μM) with IC 50 values of 1.39, 3.04, and 2.25 μM, respectively. Further research about asparagusoside G (7) showed G0/G1 arrest in NCI-H460 cell line cycle and induced cell death by apoptosis in a dose‑dependent way., (Copyright © 2021 Elsevier Inc. All rights reserved.)

Chemical investigation of the marine sponge Dysidea avara, collected from the South China Sea, yielded 13 steroids, including nine new (1-9) and four known (10-13) ones. The new structures were elucidated as (3S,14R)-3,14-dihydroxycholesta-5,8-dien-7-one (1), (22E,24R)-7α-ethoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol (2), 3β-hydroxy-7α-ethoxy-5α,6α-epoxy-8(14)-cholestene (3), 3β,5α-dihydroxy-6α-ethoxychofesta-7,9(11)-diene (4), 3β,5α-dihydroxy-6β-ethoxycholest-7-ene (5), (22E,24R)-24-ethoxy-3β,5α-dihydroxy-6β-ethoxyergosta-7,22-diene (6), (22E)-3β,5α-dihydroxy-6β-ethoxycholesta-7,22-diene (7), 24-ethoxy-3β,5α-dihydroxy-6β-ethoxycholest-7-ene (8 and 9), by extensive spectroscopic analyses, such as HR-ESI-MS, 1D and 2D NMR data. The absolute configuration of 1 was assigned by comparison the experimental ECD spectra with the calculated ones. Among the 13 metabolites, compounds 1, 4, 11, 12, and 13 showed NF-κB inhibitory activities in human HER-293 cells with IC 50 values of 6.4, 18.7, 8.1, 9.6, and 7.5 μM, respectively. Preliminary structure-activity relationship analysis unveiled that the conjugated ketones or unsaturated double bonds might be the functional groups for the five active steroids., (© 2021 Wiley-VHCA AG, Zurich, Switzerland.)

A phytochemical study on the fruits of Artocarpus heterophyllus caused the isolation of a previously undescribed steroid, artoheterophoid ( 1 ), together with seven known analogues ( 2 - 8 ). The chemical structure of 1 was elucidated on the basis of comprehensive spectroscopic methods and the known compounds ( 2 - 8 ) were identified by comparing their spectroscopic data with those reported in the literatures. All known compounds ( 2 - 8 ) were separated from A. heterophyllus for the first time. All isolated compounds ( 1 - 8 ) were assessed for their anti-inflammatory activities in vitro by measuring the inhibitory effect against nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells. Compounds 1 - 8 displayed remarkable inhibitory effects against NO production with the IC 50 values in the range of 0.72 ± 0.07 to 5.93 ± 0.12 μM.