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Sea cucumbers are benthic marine invertebrate members of the phylum Echinodermata. Due to the absence of a rigid skeleton, these species have developed chemical defenses based on the production of saponins (triterpene glycosides). These secondary metabolites are bioactive molecules with a broad biological, ecological, and pharmaceutical spectrum. However, the saponin profiles of several species of sea cucumbers are not known yet. The present study aims to highlight the mixture of saponins in two sea cucumber species from the Algerian coast, namely Holothuria (Holothuria) algeriensis, which has been recently described in central and western Algerian waters, and Holothuria (Roweothuria) arguinensis, originating from the Atlantic Ocean and reported in Algeria for the first time in 2014. Saponin extracts from three individuals of H. (H.) algeriensis and two individuals of H. (R.) arguinensis were analyzed using mass spectrometry, i.e., Matrix-assisted Laser Desorption/Ionization mass spectrometry (MALDI-MS), MALDI-High Resolution MS (MALDI-HRMS), Liquid Chromatography MS (LC-MS) and tandem MS (LC-MS/MS). These analyses allow us to detect 11 and 18 elemental compositions for H. (H.) algeriensis and H. (R.) arguinensis, respectively, each presenting several isomers. In total, 13 new saponin structures are proposed, of which four are common between the two species, six are specific to H. (H.) algeriensis and three to H. (R.) arguinensis. The saponin profiles of the two species were compared to those of other species of the same genus existing on the Algerian coast and the results showed that they share non-sulfated saponins with Holothuria (Panningothuria) forskali and Holothuria (Platyperona) sanctori and sulfated saponins with Holothuria (Holothuria) tubulosa and Holothuria (Roweothuria) poli. [ABSTRACT FROM AUTHOR]

A new oleanane-type triterpene glycoside, 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl ester, was isolated from the aqueous-ethanolic extract of the seeds of Nephelium lappaceum L. The structure elucidation of this compound was based on analyses of spectroscopic data, including 1D and 2D NMR and HR-ESI-MS techniques, and by comparing their NMR data with those reported in the literature. [ABSTRACT FROM AUTHOR]

In this study, nine triterpene glycosides including seven previously undescribed compounds (1–7), were isolated from leaves of Cryptolepis buchananii R.Br. ex Roem. and Schult. using various chromatographic methods. The chemical structures of the compounds were elucidated to be 3-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyluncargenin C 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (1), 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyluncargenin C 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (2), 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyluncargenin C 28-O-β-d-glucopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (3), 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosylhederagenin 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (4), 3-O-β-d-glucopyranosylarjunolic acid 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (5), 3-O-β-d-glucopyranosyl-(1 → 2)-β- d-glucopyranosyl-6β,23-dihydroxyursolic acid 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (6), 3-O-β-d-glucopyranosyl-6β,23-dihydroxyursolic acid 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (7), asiatic acid 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (8), and 3-O-β-d-glucopyranosylasiatic acid 28-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (9), through infrared, high-resolution electrospray ionization mass spectrometry, one- and two-dimensional nuclear magnetic resonance spectral analyses. The isolates inhibited nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells, with half-maximal inhibitory concentration (IC50) values of 18.8–58.5 µM, compared to the positive control compound, dexamethasone, which exhibited an IC50 of 14.1 µM. [ABSTRACT FROM AUTHOR]

ABSTRACT A new triterpene 3-O-[α-L-Rhamnopyranosyl (1 ->2)-(β-D-xy-lopyranosyl 16β,23 (R): 16α,30α-diepoxy-20(S)-hydraxydammar-24-ene (1) was isolated from roots of Centrosema bracteosum. The structure of this triterpenoid glycoside was elucidated by spectroscopic analysis of the natural product (1) and its peracetyl derivative (1a), including 2D NMR experiments.

Sea cucumbers are benthic marine invertebrate members of the phylum Echinodermata. Due to the absence of a rigid skeleton, these species have developed chemical defenses based on the production of saponins (triterpene glycosides). These secondary metabolites are bioactive molecules with a broad biological, ecological, and pharmaceutical spectrum. However, the saponin profiles of several species of sea cucumbers are not known yet. The present study aims to highlight the mixture of saponins in two sea cucumber species from the Algerian coast, namely Holothuria (Holothuria) algeriensis, which has been recently described in central and western Algerian waters, and Holothuria (Roweothuria) arguinensis, originating from the Atlantic Ocean and reported in Algeria for the first time in 2014. Saponin extracts from three individuals of H. (H.) algeriensis and two individuals of H. (R.) arguinensis were analyzed using mass spectrometry, i.e., Matrix-assisted Laser Desorption/Ionization mass spectrometry (MALDI-MS), MALDI-High Resolution MS (MALDI-HRMS), Liquid Chromatography MS (LC-MS) and tandem MS (LC-MS/MS). These analyses allow us to detect 11 and 18 elemental compositions for H. (H.) algeriensis and H. (R.) arguinensis, respectively, each presenting several isomers. In total, 13 new saponin structures are proposed, of which four are common between the two species, six are specific to H. (H.) algeriensis and three to H. (R.) arguinensis. The saponin profiles of the two species were compared to those of other species of the same genus existing on the Algerian coast and the results showed that they share non-sulfated saponins with Holothuria (Panningothuria) forskali and Holothuria (Platyperona) sanctori and sulfated saponins with Holothuria (Holothuria) tubulosa and Holothuria (Roweothuria) poli.

Three undescribed triterpene glycosides syzybullosides A-C (1–3) along with fourteen known compounds were isolated from the leaves of Syzygium bullockii (Hance) Merr.& L.M. Perry, including six triterpene glycosides (1–6), four phenolics (7–9, 17), four megastigmanes (10–13), and three flavonoids (14–16). The structures of 1–17 were elucidated by extensive spectroscopic analysis, including IR, HR-ESI–MS, 1D and 2D NMR spectra. Compounds 1–10 and 12–17 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW264.7 cells with IC50 values ranging from 1.30 to 13.70 µM, lower than that of the positive control compound, L-NMMA (IC50 = 33.8 µM). [ABSTRACT FROM AUTHOR]

Two undescribed triterpene glycosides, 3-[(O -α- L -rhamnopyranosyl-(1→2)-α- L -arabinopyranosyl)oxy]olean-12-en-28-oic acid O -β- D -xylopyranosyl-(1→2)- O -[β- D -xylopyranosyl-(1→6)]-β- D -glucopyranoside (1) and 3-[(O -β- D -xylopyranosyl-(1→3)- O -α- L -rhamnopyranosyl-(1→2)-α- L -arabinopyranosyl)oxy]olean-12-en-28-oic acid O -α- L -rhamnopyranosyl-(1→2)]- O -[β- D -xylopyranosyl-(1→6)]-β- D -glucopyranoside (2), named longanosides A and B, respectively, were isolated from the seeds of Dimocarpus longan Lour. by various chromatography methods. The structures of the isolated compounds were established by interpretation of spectroscopic data (1D and 2D NMR) and mass spectrometry (HR-ESI-MS). [Display omitted] • A phytochemical study was achieved on the seeds of Dimocarpus longan. • Two new triterpene glycosides were isolated for the first time. • Their structures were fully determined by spectroscopic data. [ABSTRACT FROM AUTHOR]

A new triterpene glycoside, silviridoside, was isolated from the aerial parts of Silene viridiflora (Caryophyllaceae) using different chromatographic techniques. The structure of silviridoside was comprehensively elucidated as 3-O-β-D-galacturonopyranosyl-quillaic acid 28-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-fucopyranosyl ester by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). Silviridoside showed promising antioxidant activity in different antioxidant assays such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) (2.32 mg TE/g), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (1.24 mg TE/g), cupric-reducing antioxidant capacity (CUPRAC) (9.59 mg TE/g), ferric-reducing antioxidant power (FRAP) (5.13 mg TE/g), phosphomolybdenum (PHD) (0.28 mmol TE/g), and metal-chelating (MCA) (6.62 mg EDTA/g) assays. It exhibited a good inhibitory potential on acetylcholinesterase (AChE) (2.52 mg GALAE/g), butyrylcholinesterase (BChE) (7.16 mg GALAE/g), α-amylase (0.19 mmol ACAE/g), α-glucosidase (1.21 mmol ACAE/g), and tyrosinase (38.83 mg KAE/g). An in silico evaluation of the pharmacodynamic, pharmacokinetic, and toxicity properties of silviridoside showed that the new compound exhibited reasonable pharmacodynamic and pharmacokinetic properties without any mutagenic effect, but slight toxicity. Thus, it could be concluded that silviridoside could act as a promising lead drug for pharmaceutical and nutraceutical developments to combat oxidative stress and various disorders, but a future optimization is necessary. [ABSTRACT FROM AUTHOR]

This study aimed to determine the optimal light conditions for the protected cultivation of Centella asiatica—a herbaceous medicinal plant with high bioactive content and antioxidant potential. The growth, triterpene glycoside content, total phenol content (TPC), total flavonoid content (TFC), and antioxidant activities of seedlings grown for five weeks under different light intensities (150 and 200 μmol m−2 s−1) and qualities (red and blue light ratios: 10:0, 8:2, and 6:4) were evaluated. Light intensity and quality significantly affected the studied parameters. At 150 μmol m−2 s−1 photosynthetic photon flux density (PPFD), most growth parameters decreased as the blue light ratio increased; however, the plants showed extreme epinasty under the sole red light treatment. Growth performance was highest under 20% blue light and 200 μmol m−2 s−1 PPFD. At both light intensities, the total triterpene glycoside content was higher for the sole red light and 20% blue light treatments than the 40% blue light treatment. Moreover, the TPC, TFC, and antioxidant activity increased as the blue light ratio increased. In conclusion, artificial light conditions affect the growth and secondary metabolite production of C. asiatica differentially, and 20% blue light at a higher light intensity (200 μmol m−2 s−1) is optimum for growing C. asiatica. [ABSTRACT FROM AUTHOR]

Four new sesquiterpene glycosides and one triterpene glycoside were isolated from flowers of Yucca gloriosa L. introduced into Georgia. [ABSTRACT FROM AUTHOR]

The broth of sea cucumber was decolorized with mineral sorbents, as perlite and bentonite, and with chitosans of crab carapace and shrimp shell. The chitosans were the most effective in sorption and subsequent removal of the protein-pigment complex, providing the decolorization degree of 35–55 %. Besides, the content of glycosides in the broth was twice decreased. The amino sugars content changed in dependence on the chitosan origin: the chitosan of crab carapace did not influence on this parameter, but the chitosan of shrimp shell caused its halving. For the optimal combination of chemical compounds in the broth, the chitosan with high molecular weight (1300 kDa) extracted from crab carapace should be used for decolorizing. Preliminary fermentation of the broth with Protamex increased concentration of biologically active peptides with low molecular weight in the solution. The fermented and decolorized broth of sea cucumber has good organoleptic properties and high content of biologically active components, as glycosides, amino sugars and low molecular weight peptides, so could be used as the basis for nonalcoholic tonic drinks.

One previously undescribed triterpene glycoside ( 1 ) and two known compounds were isolated from the leaves of Cyclocarya paliurus ( 2-3 ). Their structures were elucidated based on methods of spectroscopic analysis and NMR data comparison with those in the literature. Compound 1 showed a moderate inhibitory effect on melanogenesis with an IC 50 value of 282.3 μM, with the positive drug arbutin showing an IC 50 value of 168.5 μM.

A new triterpene glycoside, silviridoside, was isolated from the aerial parts of Silene viridiflora (Caryophyllaceae) using different chromatographic techniques. The structure of silviridoside was comprehensively elucidated as 3-O-β-D-galacturonopyranosyl-quillaic acid 28-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-fucopyranosyl ester by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). Silviridoside showed promising antioxidant activity in different antioxidant assays such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) (2.32 mg TE/g), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (1.24 mg TE/g), cupric-reducing antioxidant capacity (CUPRAC) (9.59 mg TE/g), ferric-reducing antioxidant power (FRAP) (5.13 mg TE/g), phosphomolybdenum (PHD) (0.28 mmol TE/g), and metal-chelating (MCA) (6.62 mg EDTA/g) assays. It exhibited a good inhibitory potential on acetylcholinesterase (AChE) (2.52 mg GALAE/g), butyrylcholinesterase (BChE) (7.16 mg GALAE/g), α-amylase (0.19 mmol ACAE/g), α-glucosidase (1.21 mmol ACAE/g), and tyrosinase (38.83 mg KAE/g). An in silico evaluation of the pharmacodynamic, pharmacokinetic, and toxicity properties of silviridoside showed that the new compound exhibited reasonable pharmacodynamic and pharmacokinetic properties without any mutagenic effect, but slight toxicity. Thus, it could be concluded that silviridoside could act as a promising lead drug for pharmaceutical and nutraceutical developments to combat oxidative stress and various disorders, but a future optimization is necessary.

[Display omitted] • Chenoalbumosides A–D, four new triterpene glycosides isolated from the aerial parts of Chenopodium album. • Chemical structures were successfully determined by HR ESI MS and NMR spectroscopic methods. • Chenoalbumosides A–D exhibited weak cytotoxic effects on HT-29, SW480, AGS, and MKN7 cancer cells. Six triterpene glycosides including four new ones, chenoalbumosides A–D (1 - 4), and two known triterpene glycosides, chikusetsusaponin IVa (5) and ginsennoside Ro (6), were isolated from the aerial parts of Chenopodium album Linn (Chenopodiaceae). Their structures were determined by extensive analyses of HR-ESI-MS and NMR spectral data. The cytotoxic activity of compounds 1 - 6 were evaluated against HT-29, SW480, AGS, and MKN7 cell lines. Unfortunately, our results indicated that none of these compounds were potential cytotoxic agents, showing IC 50 values over 50 μM. [ABSTRACT FROM AUTHOR]

The 2 new oleanane-type triterpene glycosides, 23-hydroxyoleanolic acid-[28-O-ß-D-glucopyranosyl]-3-O-{ß-D-glucopyranosyl-(1-2)- [ß-D-glucopyranosyl-(1-3)]-ß-D-galactopyranoside}, (1) and oleanolic acid-[28-O-ß-D-glucopyranosyl]-3-O-{ß-D-glucopyranosyl- (1-2)-[ß-D-glucopyranosyl-(1-3)]-ß-D-galactopyranoside} (2) were isolated from the roots of Aralia armata. Their chemical structures were elucidated by using a combination of high resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1 dimensional (1D), and 2 dimensional (2D) nuclear magnetic resonance spectral data, as well as by comparison with the previous literature. Compounds 1 and 2 displayed weak cytotoxic activity toward KB and HepG2 cell lines with IC50 values of 25.1±1.2 and 23.7± 0.9 µM (for 1) and 29.5±1.3 and 23.9±0.7 µM (for 2), respectively, compared to that of the positive control compound, ellipticine (IC50: 1.3±0.1 and 1.6±0.1 µM, respectively) in in vitro assay. [ABSTRACT FROM AUTHOR]

This study aimed to determine the optimal light conditions for the protected cultivation of Centella asiatica—a herbaceous medicinal plant with high bioactive content and antioxidant potential. The growth, triterpene glycoside content, total phenol content (TPC), total flavonoid content (TFC), and antioxidant activities of seedlings grown for five weeks under different light intensities (150 and 200 μmol m−2 s−1) and qualities (red and blue light ratios: 10:0, 8:2, and 6:4) were evaluated. Light intensity and quality significantly affected the studied parameters. At 150 μmol m−2 s−1 photosynthetic photon flux density (PPFD), most growth parameters decreased as the blue light ratio increased; however, the plants showed extreme epinasty under the sole red light treatment. Growth performance was highest under 20% blue light and 200 μmol m−2 s−1 PPFD. At both light intensities, the total triterpene glycoside content was higher for the sole red light and 20% blue light treatments than the 40% blue light treatment. Moreover, the TPC, TFC, and antioxidant activity increased as the blue light ratio increased. In conclusion, artificial light conditions affect the growth and secondary metabolite production of C. asiatica differentially, and 20% blue light at a higher light intensity (200 μmol m−2 s−1) is optimum for growing C. asiatica.

One new triterpene glycoside, asiaticoside I (1), along with seven known ones (2–8), were isolated from the aerial parts of Cimicifuga dahurica (Turcz.) Maxim. The structure of 1 was elucidated on the basis of extensive spectroscopic methods including 1D-NMR, 2D-NMR and MS data. The structures of known compounds were determined by comparison with the literature data. Compound 1 exhibited moderate cell growth inhibitory activities in vitro against HELF, non-small cell lung cancer A549, and pancreatic cancer PANC-1 cell lines, with IC50 values of 62.97, 43.19, and 60.40 μM, respectively. [ABSTRACT FROM AUTHOR]

From the MeOH extract of the Vietnamese sea cucumber Holothuria edulis, eight triterpene glycosides (1–8), including one new compound namely holothurin A5 (1), were isolated by using various chromatographic separations. Their structures were established by spectroscopic experiments including 1D, 2D NMR and HR-ESI-MS. Holothurin A5 (1) has a hydroperoxy group at C-25. To the best of our knowledge, this is the first report of this group in triterpene saponins obtained from sea cucumbers to date. In addition, the in vitro cytotoxicity against five human cancer cell lines (HepG2, KB, LNCaP, MCF7 and SK-Mel2) of all isolated compounds was also evaluated using SRB assays. [ABSTRACT FROM AUTHOR]

From the methanol extract of the Cryptolepis buchananii fruits, four undescribed pentacyclic triterpenene glycosides (1-4) and five known pentacyclic triterpenenes (5-9) were isolated. Their structures were determined to be uncargenin C 28-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester (1), 3-O-β-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester (2), 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-6β,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester (3), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester (4), asiatic acid (5), 2α,3β,23-trihydroxyoleana-11,13(18)-dien-28-oic acid (6), arjunolic acid (7), 6β-hydroxyarjunolic acid (8), and actinidic acid (9) based on analyses of their HR-ESI-MS, 1D and 2D NMR spectra. All the isolates showed significantly NO production inhibition in LPS-activated RAW264.7 cells with the IC 50 values ranging from 18.79 to 37.57 μM, compared to that of the positive control compound, dexamethasone, which showed IC 50 value of 14.05 μM., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Abstract Previous studies indicate that the herb black cohosh (Actaea racemosa L.) and the triterpene glycoside actein inhibit the growth of human breast cancer cells and activate stress-associated responses. This study assessed the transcriptomic effects of black cohosh and actein on rat liver tissue, using Ingenuity and ToxFX analyses. Sprague-Dawley rats were treated with an extract of black cohosh enriched in triterpene glycosides (27%) for 24 h or actein for 6 and 24 h, at 35.7 mg/kg, and liver tissue collected for gene expression analysis. Ingenuity analysis indicates the top canonical pathways are, for black cohosh, RAR Activation, and, for actein, Superpathway of Cholesterol Biosynthesis, at 24 h. Actein alters the expression of cholesterol biosynthetic genes, but does not inhibit HMG-CoA reductase activity. Black cohosh and actein inhibited the growth of human breast and colon cancer cells and synergized with the statin simvastatin. Combinations of black cohosh with certain classes of statins could enhance their activity, as well as toxic, such as inflammatory liver, side effects. Transcriptomic analysis indicates black cohosh and actein warrant further study to prevent and treat cancer and lipid disorders. This study lays the basis for an approach to characterize the mode of action and toxicity of herbal medicines. Graphical abstract Image 1 Highlights • Transcriptomic analysis of effects of black cohosh and actein on rat liver tissue: Ingenuity Pathway and ToxFX analysis. • Black cohosh alters Acute Phase Response Signaling at 24 h. • Actein alters the Superpathway of Cholesterol Biosynthesis at 6 and 24 h. • Actein does not inhibit HMG-CoA reductase activity. • Black cohosh and actein inhibited the growth of colon cancer cells and synergized with the statin simvastatin. [ABSTRACT FROM AUTHOR]

Four new triterpene glycosides, variegatusides C–F (1–4), together with three structurally known triterpene glycosides, variegatusides A and B (5, 6), and holothurin B (7), were isolated from the sea cucumber Stichopus variegates Semper (Holothuriidae), collected from the South China Sea. Their structures were elucidated on the basis of extensive spectral analysis (nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS)) and chemical evidence. Variegatusides C–F exhibit the same structural feature consisting of the presence of a 23-hydroxyl group at the holostane-type triterpene aglycone side chain. Variegatuside C (1) has a double bond (24, 25) in this same chain, while variegatuside D (2) exhibits a 8(9)-ene bond in the holostane-type triterpene aglycone, which has not been extracted from other sea cucumber species. Compound 4 is a native compound from the sea cucumber S. variegates Semper, which has been reported to be desacetylstichloroside B1. Except for holothurin B, these glycosides have no sulfate group in their sugar chain and show potent antifungal activities in vitro biotests.

The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of triterpene glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of triterpene glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography-electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of triterpene glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated glycosides were detected and described. Triterpene glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the triterpene glycosides contents from the five different body components revealed that the profiles of triterpene glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed. [ABSTRACT FROM AUTHOR]

Using various chromatographic separation techniques, eight triterpene diglycosides ( 1 – 8 ), including four new compounds namely stichorrenosides A–D ( 1 – 4 ), were isolated from a methanol extract of the Vietnamese sea cucumber S. horrens . Their structures were elucidated based on spectroscopic analyses, including HR ESI MS, 1D and 2D NMR. Their in vitro cytotoxic activity against five human cancer cell lines, Hep-G2 (hepatoma cancer), KB (epidermoid carcinoma), LNCaP (prostate cancer), MCF7 (breast cancer), and SK-Mel2 (melanoma), was evaluated using SRB methods. Stichorrenoside D ( 4 ), stichoposide A ( 5 ), and 3 β - O -[ β - d -xylopyranosyl-(1→2)- β - d -xylopyranosyl]-23 S -acetoxyholost-7-ene ( 7 ) showed strong cytotoxicity on all five tested cancer cell lines, whereas significant effect was observed for stichorrenoside C ( 3 ) and stichoposide B ( 6 ). [ABSTRACT FROM AUTHOR]

Phytochemical investigations on n-butanol extract of Cephalaria balansae Raus. (Caprifoliaceae) led to the isolation of four previously undescribed triterpenoid saponins based on hederagenin type aglycone, namely, balansoides A-D, along with ten known compounds. Their structures were proposed based on 1D and 2D NMR spectroscopic data, HRESIMS analysis and chemical evidence as 3- O -α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin, 3- O -α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28- O -β-D-glucopyranosyl ester, 3- O -α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28- O -β-D-galactopyranosyl-(1 → 6)-β-D-glucopyranosyl ester and 3- O -α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28- O -β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester. The four saponins were evaluated for their potential cytotoxic activity against HEK-293, A-549, HeLa cells and for hemolytic properties on human blood cells. Balansoide A displayed significant inhibitory effects on cancerous A-549 and HeLa cells, and non-cancerous HEK-293 cells with IC 50 values of 12, 15 and 8 μM, respectively. Balansoides A-D together with n -butanol extract exhibited considerable hemolysis in human erythrocyte cells. Immunomodulatory properties of balansoides A-D were also evaluated in activated whole blood cells by PMA plus ionomycin. While balansoides A-C increased IL-1β concentration with values of 1004.47, 991.57 and 966.50 pg/ml, only balansoide B augmented a slight IFN-γ secretion with value of 5219.14 pg/ml. None of the compounds changed IL-2 levels significantly. [ABSTRACT FROM AUTHOR]

A new oleanolic-type triterpene glycoside, (3β,21β)-21-[(β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl)oxy]-3-hydroxyolean-12-en-28-oic acid (1), together with five analogues, oleanazuroside 1 (2), oleanazuroside 2 (3), 24-hydroxytormentic acid ester glucoside (4), 24-epi-pinfaensin (5), and oleanolic acid 3-O-α-l-arabinoside (6) were isolated from the n-butyl alcohol extract of Anchusa italica. Their structures were determined spectroscopically and compared with previously reported spectral data. Compounds 3–4 and 6 were evaluated for their cytotoxic activities against five human cancer cell lines, but only compound 6 showed moderate cytotoxicity. [ABSTRACT FROM AUTHOR]

From the bark of Ladenbergia hexandra Klotzsch, ten triterpenoid glycosides were isolated along with five known compounds, and their structures were determined based on extensive NMR and mass spectroscopic, GC and HPLC analyses. Some triterpenoid glycosides contained 6-deoxy-D-allose or D-allose as a sugar moiety. The absolute stereochemical assignment of the sugars was determined by comparison with synthetic samples, as well as by GC and HPLC analysis. [ABSTRACT FROM AUTHOR]

Background: Holothuria scabra is the potential source of terpene with high antioxidant capacity and one of the most valuable species in the trade. Results: The results indicated that antioxidant activity of crude methanol extracts and three pure compounds, Friedelin, 3-Hydroxybenzaldehyde and 4-Hydroxybenzaldehyde, from sea cucumber was determined using DPPH, Folin-Cioccalteau reagent. The results indicated the total phenolic contents at 30.52.28 ± 0.21 GAE/g dry weight equivalent and the effective concentration (EC) value were found to be 33.77 ± 0.24, 14.63 ± 0.01, 14.62 ± 0.01 and 14.78 ± 0.11 mg/ml whole body of Holothuria scabra, Friedelin, 3-Hydroxybenzaldehyde and 4-Hydroxybenzaldehyde, respectively. Conclusion: In conclusion, the methanol extract and pure compounds of whole body parts of sea cucumber showed the highest antioxidant activity with EC value of 33.77 ± 0.24, 14.63 ± 0.01, 14.62 ± 0.01 and 14.68 ± 0.11 mg/ml. It also showed the highest total phenolic content at 30.52 ± 0.21 GAE/g dry weight. [ABSTRACT FROM AUTHOR]

A new triterpene glycoside, 3-O-[(α-L-rhamnopyranosyl)(1→2)]-[β-D-glucuronopyranosyl-6-O-methyl ester]-olean-12-ene-28-olic acid (1) and a new indole alkaloid, 5-methoxy-2-oxoindolin-3-acetic acid methyl ester (5) were isolated from the leaves of Acanthopanax senticosus Harms along with six known compounds. The structures of the new compounds were determined by means of 2D-NMR experiments and chemical methods. All the isolated compounds were evaluated for their glycosidase inhibition activities and compound 6 showed significant α-glucosidase inhibition activity.