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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.

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.

Three pregnene steroids, two of them new, were isolated from ethyl-acetate partition of liquid-cultivation of the extremophyle fungus Exophiala oligosperma , found in a pH 1.5 hydrochloric acid aqueous solution. Spectroscopic studies using NMR and HRMS, allowed the identification of the molecular structures of both Δ 8,9 -pregnenes, still not described in the literature.

As our ongoing chemical investigation, two new pregnane steroidal glycosides, cynataihosides G ( 1 ), with a new aglycone, and H ( 2 ) were isolated from the 95% ethanol extract of Cynanchum taihangense . Their structures were elucidated on the basis of 1 D and 2 D NMR spectral data, HR-ESI-MS analysis and qualitative chemical methods. The compounds were subjected to detect the cytotoxicity against three human tumor cell lines (HL-60, THP-1 and PC-3). The compounds displayed no significant cytotoxicity.Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2019.1672682.

A new withanolide glycoside ( 1 ), two new ergostanol glycosides ( 2 and 3 ), and a new furostanol glycoside ( 4 ), along with nine known steroidal derivatives ( 5 - 12 ) were isolated from the seeds of Withania somnifera . The structures of the new compounds were determined using spectroscopic analysis and hydrolysis. The cytotoxic activities of the isolated compounds were evaluated against Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, and HL-60 human promyelocytic leukemia cells. Only 12 exhibited cytotoxic activity against these cell lines with IC 50 values of 0.38, 0.54, and 1.5 μM, respectively.

Chemical investigation on the ethyl acetate extract of the aerial parts of Begonia sp. afforded a new steroid glycoside, 9(11)α,16(17)α-dioxirane-20,25-dihydroxy-β-sitosterol-3- O -β-glucopyranoside ( 1 ) along with a known steroidal glycoside, β-sitosterol-3- O -β-D-glucopyranoside ( 2 ). The Chemical structures were elucidated by 1D and 2D NMR and mass spectroscopic analysis. Cytotoxicity against four different cancer cell lines (HeLa, T47D, WiDr and Vero) was assessed. Compound 1 was more potent and selective against breast cancer cell line (T47D) than other cell lines with an IC 50 value of 0.16 µg/mL. Further docking study of 1 exhibited the preference of molecule to bind in the epidermal growth factor receptor tyrosine kinase (EGFR-TK) binding pockets with docking scores of -97.8800 (PLANTS) and -3.56 kcal/mol (AutoDock 4.2.6).

Henryiosides F and G ( 1 and 2 ), two new steroidal saponins along with two known analogues ( 3 and 4 ) were obtained from the roots and rhizomes of Maianthemum henryi . Their structures were determined by physicochemical properties and spectroscopic methods including 1D, 2D-NMR, IR and HR-ESI-MS data analysis. Cytotoxic activity in human HepG2 and SW620 tumour cells were evaluated by the MTT method and all of the saponins exhibited cytotoxicity with IC 50 values ranging from 15.33 μ M to 57.85 μ M.

A new coprostanol glycoside, 26-trihydroxy-16, 22-dioxo-3 β -[( α -L-rhamnopyranosyl)oxy]-5 β -cholestan-1 β -yl O - α -L-rhamnopyranosyl-(1→2)- β -D-fucopyranoside ( 1 ) (25 S )-5 β -spirostan-1 β ,2 β ,3 β , 4 β ,5 β , 6 β -hexol ( 2 ), a new C-22 steroidal lactone saponin, (20  R )-16 β -trihydroxy-3 β -[( α -L-rhamnopyranosyl)oxy]-1 β -[( O - α -L-rhamnopyranosyl-(1→2)- β -D-xylopyranosyl)oxy]-5 β -pregnane-20-oic acid γ-lactone ( 3 ) along with two known pregnane glycosides ( 4 and 5 ) were obtained from the roots of Reineckia carnea . Their structures were determined by 1 D, 2 D NMR, IR and MS data analysis. In addition, the cytotoxic activities in HT-29, HCT116, H1299 and A549 tumor cells of the isolated compounds ( 1  -  5 ) were determined by the MTT method. The results showed that only compound 1 exhibited weak effect against these cells with IC 50 values ranging from 63.36  μ M to 105.01  μ M.

Two new polyketides, xerucitrinin A ( 1 ) and coniochaetone M ( 8 ), and one new steroid, 16 α -methylpregna-17 α ,19-dihydroxy-(9,11)-epoxy-4-ene-3,18-dione-20-acetoxy ( 13 ), together with eleven known analogues were isolated from fungus Penicillium citrinum SCSIO 41017 associated with the sponge Callyspongia sp. Their structures and absolute configurations were elucidated by NMR spectra, MS, CD, optical rotation, X-ray crystallography, and compared with literature data. Biological evaluation results revealed that 5 exhibited significant cytotoxic activity against MCF-7 cell line with IC 50 values of 1.3  μ M. Compound 13 showed moderate activity against all cell lines with IC 50 values of 13.5-18.0  μ M, and compounds 9 and 14 showed weak activity with MIC values of ranging from 125  μ g/mL to 250  μ g/mL respectively.[Formula: see text].

Two new steroidal saponins ( 1 and 2 ), along with four known ones ( 3  ∼  6 ) were obtained from the roots and rhizomes of Maianthemum henryi , their structures were determined to be spirost-5, 25(27)-diene-l β , 3 β -diol 1- O - α -L-rhamnopyranosyl-(1 → 2)-4- O -acetyl- β -D-fucopyranoside ( 1 ), (23 S , 24 S )-spirost-5, 25(27)-diene-l β , 3 β , 23, 24-tetrol 1- O - α -L-rhamnopyranosyl-(1 → 2)-4- O -acetyl- β -D-fucopyranoside ( 2 ), spirost-5, 25(27)-diene-l β , 3 β -diol 1- O - α -L-rhamnopyranosyl-(1 → 2)- β -D-fucopyranoside ( 3 ), spirost-5, 25(27)-diene-l β , 3 β -diol 1- O - α -L-rhamnopyranosyl-(1 → 2)- β -D-xylopyranoside ( 4 ), Henryioside A ( 5 )、Henryioside B ( 6 ), by physicochemical properties and spectroscopic methods. In addition, their cytotoxic activity against human HepG2 tumor cells was evaluated by MTT method and all of the compounds exhibited cytotoxicity with the cells.

A new pregnane steroid, named aspergillon A ( 1 ), together with two known compounds, (22 E ,24 R )-ergosta-5,7,22-trien-3 β -ol ( 2 ) and (22 E , 24 R )-ergosta-4,6,8(14),22-tetraen-3-one ( 3 ) were isolated from cultures of the tin mine tailings-associated fungus Aspergillus versicolor . The new structure and absolute configuration were determined with the help of extensive spectroscopic analyses and quantum chemical calculations of the electronic circular dichroism (ECD) spectra.

A new steroid, (3S,5R,9R,10S,13R,17R,20R,24S,22E)-ergosta-6,8,22-triene-3,25-diol (1), and its sulfonated analogue (2) together with a known one, 5α,8α-epidioxy-cholest-6-en-3β-ol (3) were isolated from the marine sponge Dactylospongia elegans collected from the South China Sea. The new structures including absolute configurations were established by the HRESIMS and 1D and 2D NMR analysis coupled with the X-ray crystal analysis. Both of 1 and 2 exhibited cytotoxicity against cancer cell line MCF-7 with IC 50 values of 9.7 and 8.5 μM, respectively.

The phytochemical investigation of an alkaloidal extract of Holarrhena pubescens roots led to the isolation and identification of a new pregnene-type alkaloid, mokluangin D (1), together with nine known steroidal alkaloids (2-10). The structure of the new metabolite was determined on the basis of spectroscopic analyses including 1D- and 2D-NMR spectroscopy and mass spectrometry. Compounds 3 and 4 showed potent antimalarial activity against Plasmodium falciparum K1 stain with IC 50 values of 1.2 and 2.0 μM, respectively, and showed weak cytotoxic activity against the NCI-H187 cell line with IC 50 values of 27.7 and 30.6 μM, respectively. The substituent groups at C-3 and the carbonyl group at C-18 are important for the activity against the P. falciparum K1 stain.

Two new seco-lanostane-type triterpenes, named mayomlactones A (1) and B (2) were isolated from the fruits of Leplaea mayombensis together with 10 known compounds (3-12). Structures of the new compounds were elucidated by extensive spectroscopic studies. Except compounds 11 and 12, all the other chemical compounds are newly reported from Leplaea genus. From the results of this investigation, compounds 1-10 were examined for antiproliferative activity against HeLa cells as well as cytotoxicity against 3T3 cell line. Compounds 3 and 4 showed moderate antiproliferative activity with IC 50 values of 10.4 ± 0.1 and 18.6 ± 0.2 μM, respectively. On the other hand, compounds 1, 4 and 9 showed weak cytotoxicity with IC 50 values 44.1 ± 0.5, 55.8 ± 0.7 and 55.1 ± 0.5 μM. Overall, none of the tested compounds showed good selectivity (SI ranging from 0.51 to 3.06) but high toxicity against the 3T3 cell line.

Chemical investigation of the resinous exudates of Commiphora myrrha has led to the isolation of four sesquiterpenes (1a/1b, 2, and 3), including one pair of new sesquiterpene enantiomers (1a/1b), one new racemic mixture 2, and two steroids (4 and 5). Their structures were elucidated by spectroscopic analysis, and the absolute configurations of 1a/1b were determined by CD analysis. The antimigratory potential of compounds 1-5 were evaluated and compound 3 was found to inhibit human hepatocellular liver carcinoma HepG2 cell migration in dose-dependent manner.

A new steroidal alkaloid, 4-dehydroxyepisarcovagine A (1), along with seven known alkaloids, sarcovagine D (2), sarcovagenine C (3), epoxysarcovagenine D (4), Pachysamine L (5), Pachysamine E (6), sarcovagine A (7) and sarcovagine B (8), was isolated from the roots and stems of Sarcococca pruniformis Lindl. The structure of compound 1 was elucidated by means of spectroscopic analysis.

Six pregnane steroids including one new compound namely 15β-hydroxypregna-4,20-dien-3-one (1), were isolated and structurally elucidated from the octocoral Carijoa riisei. The cytotoxic activity against a panel of eight human cancer cell lines of isolated compounds was also evaluated by SRB method. As the results, 18-acetoxypregna-1,4,20-trien-3-one (5) showed significant cytotoxicity against all the tested cell lines with the IC 50 values from 22.29 ± 1.47 to 48.73 ± 3.93 μM, whereas 15β-acetoxypregna-1,4,20-trien-3-one (3) and 20R-acetoxypregna-1,4-dien-3-one (6) only exhibited weak effect on KB cell line with IC 50 values of 93.62 ± 7.32 and 71.38 ± 5.45 μM, respectively.

Timosaponin AIII (TAIII) exhibits extensive pharmacological activities and has been reported as a potent antitumour agent for various human cancers. In the present study, a potential industrial process for producing TAIII that involves biotransformation directly in the crude extract liquid of rhizoma anemarrhenae (RA) was developed. β-D-glycosidase was used to transform timosaponin BII (TBII) into TAIII, and monofactor experiments were conducted to optimise the enzymolysis conditions. In addition, AB-8 macroporous resin column chromatography, preparative liquid chromatography, and crystallisation technique were applied for yielding TAIII crystals with a purity > 97%. Approximately, 7 g of TAIII with a high purity of > 97% was obtained from 1 kg of RA through this five-step preparation method, which can be used to produce TAIII on a large scale.

Nephthea are soft coral species rich in sesquiterpenoids and steroids. An organic extract of Nephthea sp. resulted in the isolation of a new steroid (1), as well as several previously reported metabolites (2-9). Structures were elucidated by employing NMR and HR-EI-MS analyses. The total extract, fractions and purified compounds exhibited differential cytotoxicity against the breast cancer MCF-7 cell line.

Chemical investigation of the soft coral Lobophytum lobophytum collected from the Red Sea led to the isolation of a new compound gorgostan-5,25-dien-3β-ol (1), and two known compounds gorgosterol (2), and alismol (3). Structures were elucidated by employing extensive NMR and HR-ESI-MS experiments.

The structures of two novel steroidal derivatives (1 and 4) were elucidated. Steroidal derivatives namely fologenin (1) and hoyagenin (4) have been isolated from chloroform-soluble extract of the whole plant of Hoya longifolia (family: Asclepiadaceae), and their structures were determined by using (1)H NMR, (13)C NMR, (1)H-(1)H COSY and FAB-MS techniques as well as chemical degradation and derivatisation.

A new 19-oxygenated steroid, 25-acetate-nebrosteroid K (1), and five known steroids (2-6), along with one known 19-hydroxy steroidal glycoside (7) were obtained from the gorgonian Dichotella gemmacea collected from the South China Sea. The structure and relative configuration of 1 were elucidated by using comprehensive spectroscopic data including NOESY spectra. Compound 1 represents the first example of 19-oxygenated steroid with a 19-oic acid methyl ester group isolated from gorgonians. All of the isolated compounds were evaluated for lethal activity to brine shrimp Artemia salina and cytotoxicity against A549 and HL-60 cell lines. Among them, 1 showed strong lethality towards A. salina.

Timosaponin B-III (TB-III) is a steroidal saponin isolated from the rhizome of Anemarrhenae asphodeloides (Liliaceae). The biotransformation of TB-III by β-glucosidase was investigated. Three biotransformation products were isolated and their structures were identified as timosaponin B-III-a (M1), (20R,25S)-5β-spirostane-3β-ol-3-O-β-D-glucopyranosyl-(1 → 2)-β-D-galacopyanoside (M2) and timosaponin AIII (M3). Then the four compounds were evaluated for their anti-depressive activity in mice by the open field test, tail suspension test and forced swimming test. As a result, TB-III, M1 and M3 exhibited modest anti-depressive activity. Structure-activity relationships were investigated and the preliminary conclusions are summarised as follows: the glycosyl at C-3 and C-26 can increase the activity, the double bond between C-20 and C-22 might be important for the anti-depressive activity, the R-configuration at C-22 and S-configuration at C-20 are necessary for its anti-depressive activity.

Three new steroid glycosides, pectiniosides H-J (1-3), were isolated along with three known compounds (4-6) including a steroid glycoside and two polyhydroxysteroids, from the alcoholic extract of the starfish Asterina pectinifera. The structures of 1-3 were determined by extensive NMR and HR-ESI-MS experiments. Compounds 1-4 did not show cytostatic activity on HL-60 cells below 100 μM, while compounds 5-6 showed moderate cytostatic activity, with IG50 values of 80.3 and 40.5 μM, respectively.

Quantitative analysis of miroestrol (1) and kwakhurin (3) by HPLC, leading to standardisation of commercially available Thai miracle herb 'Kwao Keur' which has been identified with Pueraria mirifica, was established using independent solvent systems. The simple isolation procedure of highly estrogenic miroestrol (1) and deoxymiroestrol (2) from P. mirifica was also proposed.

A phytochemical investigation of the EtOH extract from the rhizomes and roots of Smilax scobinicaulis resulted in the isolation of a new isospirostanol-type steroidal saponin, namely (25 R)-5α-spirostan-3β,6β-diol 3-O-β-D-glucopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside (1), along with four known steroidal saponins (2-5). The structures of these compounds were determined by 1D- and 2D-NMR spectroscopic analysis, FABMS and HR-ESI-MS as well as chemical degradation. The isolated saponins were evaluated for their in vitro cytotoxicity against A549, LAC and Hela human cancer cell lines, which demonstrated that only compound 1 possessed significant cytotoxic activity with IC₅₀ values of 3.70, 5.70 and 3.64 µM, respectively.

A new polyoxygenated ergostane-type sterol, 3β,5α,6β,8β,14α-pentahydroxy-(22E,24R)-ergost-22-en-7-one (1), has been isolated from the liquid culture of the basidiomycete Ganoderma applanatum together with four known sterols, 3β,5α,9α-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (2), ergosterol peroxide (3), 6-dehydrocerevisterol (4) and cerevisterol (5). Two of these sterols (2, 4) are reported to have been isolated from this species for the first time. The structures of these compounds were determined by chemical and spectroscopic analyses, including 1D- and 2D-NMR, as well as by comparison of their spectroscopic data with those reported in the literature.

The steroids 3,6,17-trihydroxy-stigmasta-4,7,24(28)-triene (A) and 14,15,18,20-diepoxyturbinarin (B) were isolated from the cyclohexane extract of brown alga, Turbinaria conoides (J. Agardh) Kutzing, and have been reported for their antimicrobial activity by us. In this study, the isolated compounds were evaluated for comprehensive antihistaminic, antiviral and cytotoxicity screening. The antihistaminic study was performed using in vitro standard animal models. Evaluation of the potency (EC(50)), affinity (pA(2)) and the maximal response (E(max)) of the histamine alone and in the presence of the compounds were determined. Antiviral activity and cytotoxicity were performed in Crandell-Rees feline kidney (CRFK) cells by a colorimetric formazan-based MTS assay. No significant antiviral activity or cytotoxicity were observed for the compounds in the CRFK cells. Compound A inhibited the histamine-induced concentration at 20 µg mL(-1)(p < 0.05). The most significant inhibition (97%) was observed for compound B (p < 0.01) at the same concentration, which was comparable to that of the positive control chlorpheniramine maleate (10 µg mL(-1)). This potentiality suggests that 14,15,18,20-diepoxyturbinarin (B) can be developed as a new lead antihistaminic agent.

In this study, cholest-5-en-3β,7β-diol and 3β-hydroxy-cholest-5-en-7-one were isolated from Oviductus Ranae by column chromatographies on Sephadex LH-20, octadecylsilyl (ODS) and pre high-performance liquid chromatography (HPLC). Their structures were elucidated on the basis of chemical and spectral analyses, including electrospray ionisation-mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR). The above two compounds were obtained from Oviductus Ranae for the first time.

Three steroidal saponins were isolated and characterised from the rhizomes of Polygonatum odoratum. The structure of the compounds were determined as 3-O-beta-D-glucopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranosyl-(1 --> 4)-galactopyranosyl-25(S)-spirost-5(6)-en-3beta-ol (1), 3-O-beta-D-glucopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranosyl-(1 --> 4)-galactopyranosyl-25(S)-spirost-5(6),14(15)-dien-3beta-ol (2) and 3-O-beta-D-glucopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranosyl-(1 --> 4)-galactopyranosyl-25(S)-spirost-5 (6)-en-3beta, 14alpha-diol (3). Compound 2 was identified as a new compound. Compounds 1-3 were found to be strong against the growth of bacteria and plant pathogenic fungi.

From the n-butanol soluble fraction of the methanol extract of the rhizomes of Smilax excelsa, three new furostanol saponins 3-O-[4-O-acetyl-alpha-L-rhamnopyranosyl-(1 --> 2)-{alpha-L-rhamnopyranosyl-(1 --> 4)}-beta-D-glucopyranosyl]-26-O-[beta-D-glucopyranosyl]-22alpha-hydroxy-(25R)-furost-5-ene-3beta,26-diol (1), 3-O-[2-O-acetyl-alpha-L-rhamnopyranosyl-(1 --> 2)-{alpha-L-rhamnopyranosyl-(1 --> 4)}-beta-D-glucopyranosyl]-26-O-[beta-D-glucopyranosyl]-22alpha-hydroxy-(25R)-furost-5-ene-3beta,26-diol (2), 3-O-[3-O-acetyl-alpha-L-rhamnopyranosyl-(1 --> 2)-{alpha-L-rhamnopyranosyl-(1 --> 4)}-beta-D-glucopyranosyl]-26-O-[beta-D-glucopyranosyl]-22alpha-hydroxy-(25R)-furost-5-ene-3beta,26-diol (3), and three known saponins: protodioscin (4), pseudoprotodioscin (5) and dioscin (6) were isolated.

The search for antileishmanial constituents from the medicinal plant Sarcococca hookeriana (Buxaceae) of Nepalese origin has resulted in the isolation of 17 (1-17) active steroidal alkaloids. Compounds 1, 2, and 10 were subjected to derivatization and five chemically derived derivatives (1a, 2a, 10a, 10b, 10c) were also obtained. All these natural compounds and derivatives were found to have potent to mild antileishmanial properties. The IC(50) values were found to be in the range of 0.20-61.44 microg mL(-1) (IC(50) value of standard drug amphotericin B = 0.12 microg mL(-1)). The structure activity relationship indicated that the varieties of functionalities present in ring A of the steroidal alkaloids were found to play a characteristic role to increase the antileishmanial activity.

Chemical investigation of the organic extract of a soft coral belonging to the genus Alcyonium furnished a steroid, 3alpha,7alpha,12alpha-triacetoxy-5beta-cholanic acid (1). The structure of steroid 1 was assigned on the basis of spectroscopic evidence, particularly in 1D and 2D NMR experiments. The configuration of steroid 1 was further supported by molecular mechanics calculations.

Two new 19-oxygenated polyhydroxy steroids, 24-methylcholesta-5, 24(28)-diene-3 beta, 7 beta, 19-triol-19-monoacetate (1), 24-methylcholesta-5, 24(28)-diene-3 beta, 7 beta, 19-triol-7 beta, 19-diacetate (3), together with a known steroid, 24-methylcholesta-5, 24(28)-diene-3 beta, 7 beta, 19-triol-7 beta-monoacetate (4), have been isolated from the soft coral Sinularia sp. collected from the South China Sea and characterized through interpretation of spectral data.