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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]

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.

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.

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.)

Sea cucumber Apostichopus japonicus Selenka, as a traditional tonic, has great edible value and a large-scale aquaculture variety in China. As its spawn has similar nutrients as body wall, residents in many countries often use spawn to make various delicious food, especially Japanese ferment it to make sauce. In this study, four new triterpene glycosides (1 - 4) together with a known holotoxin B (5) were obtained from it. New compounds were holotoxin S 1 -S 3 (1 - 3) with rare 18(16)-lactone ring as well as holotoxin S 4 (4) with an 18(20)-lactone group belonging to holostane type. Holotoxin B was firstly isolated from spawn of A. japonicus. The structures of four new molecules were elucidated based on extensive spectroscopic analysis and chemical tools. • Four new compounds were obtained in this paper. • Rare lactone ring produced by sea cucumber spawn. • Saponins differ in body wall and spawn. • First report on chemical constituents in sea cucumber spawn. [ABSTRACT FROM AUTHOR]

[Display omitted] • Six triterpene and nine steroidal glycosides were isolated from Digitalis purpurea seeds. • The structures of seven novel compounds were determined by spectroscopic analyses. • Gitonin (7) synergistically enhanced the cytotoxicity of etoposide against SBC-3 cells. • Gitonin (7) induced the HMGB1 release, ATP secretion, and CALR exposure in SBC-3 cells. The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of six triterpene glycosides (1 – 6), six spirostanol glycosides (7 – 12), and three furostanol glycosides (13 – 15), including seven previously unidentified compounds (1 – 3 , 10 – 12 , and 14). Here, the structures of 1 – 3 , 10 – 12 , and 14 were determined via extensive spectroscopic analyses, including two-dimensional (2D) NMR; hydrolysis, followed by chromatographic and spectroscopic analyses; and X-ray crystallographic analysis. The cytotoxic activities of the isolated compounds (1 – 15) against SBC-3 small cell lung carcinoma and TIG-3 normal human diploid fibroblast cells were evaluated. Triterpene glycoside 3 and spirostanol glycoside 9 exhibited considerable cytotoxicity with IC 50 values of 1.0 and 1.7 µM, respectively; they induced apoptotic cell death, which was accompanied by the activation of caspase-3 in SBC-3 cells. Spirostanol glycoside 7 exhibited cytotoxicity toward the SBC-3 cells (IC 50 1.3 μM). Additionally, 7 at 0.1 and 1.0 µM synergistically enhanced the cytotoxicity of etoposide against SBC-3 cells; compound 7 induced the release of DAMPs; the release of HMGB1, the secretion of ATP, and the exposure of CALR in the SBC-3 cells. Furthermore, the combination of 7 and etoposide resulted in increasing the extracellular release of DAMPs. These data indicated that 7 , as well as its combination with etoposide, might potentially cause immunogenic cell death. [ABSTRACT FROM AUTHOR]

Saponaria officinalis L., commonly known as "Soapwort", is a rich source of triterpene glycosides; however, the chemical constituents of S. officinalis seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of the seeds of S. officinalis and obtained 17 oleanane-type triterpene glycosides (1–17), including seven new glycosides (1–7). The structures of 1–7 were determined based on a detailed analysis of NMR spectroscopic data and chromatographic and spectroscopic analyses following specific chemical transformation. The cytotoxicities of the isolated compounds were evaluated against HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells. The cytotoxicities of 1, 4, and 10 toward HL-60 cells and SBC-3 cells were nearly as potent as that of cisplatin. Compound 1, a bisdesmosidic triterpene glycoside obtained in good yield, arrested the cell cycle of SBC-3 cells at the G2/M phase, and induced apoptosis through an intrinsic pathway, accompanied by ROS generation. As a result of the mitochondrial dysfunction induced by 1, mitochondria selective autophagy, termed mitophagy, occurred in SBC-3 cells. [ABSTRACT FROM AUTHOR]

Two novel triterpene glycosides (1 and 2), 17 known triterpene glycosides (3-19), two known flavonoid glycosides (20 and 21), and two known norsesquiterpene glucosides (22 and 23) were isolated from Hedera rhombea (Araliaceae) leaves. The structures of 1 and 2 were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The cytotoxicity of the isolated triterpene glycosides (1-19) against HL-60 human promyelocytic leukemia cells was evaluated. Compounds 9, 10, and 11 were cytotoxic to HL-60 cells with IC 50 values of 7.2, 21.9, and 32.8 µM, respectively. Other compounds isolated from the leaves were not cytotoxic at sample concentrations of 50 μM.