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Two new compounds, adinandrolide (1) and adipoiloside (2), together with twelve known compounds 3–14, were isolated and identified from Adinandra poilanei leaves. In the α-glucosidase activity evaluation, compounds 5–7 and 10 strongly inhibited enzyme activity with IC50 values ranging from 1.29 ± 0.03 μg/mL to 3.13 ± 0.07 μg/mL. Compounds 9, 11, and 13–14 showed significant inhibition with IC50 values of 13.01 ± 0.32 μg/mL to 16.00 ± 0.35 μg/mL, while adipoiloside (2) displayed moderate inhibitory activity. In addition, pomolic acid (10) showed strong cytotoxicity against four tested cancer cell lines.

Two previously undescribed 3(4), 8(9), 9(10)-trisecocycloartane triterpene dilactones with a featured eleven-membered ring, pseudoladilactones A and B (1-2), together with three known ones (4-5), were isolated from the 80 % ethanol extract of the cones of Pseudolarix amabilis. The structures of compounds 1 and 2 were determined on the basis of analysis of 1D- and 2D-NMR spectroscopic data. The absolute configuration of pseudoladilactones A (1) was elucidated by single crystal X-ray diffraction (CuKα). All isolates were tested for cytototoxicity against four human tumor cell lines A549, HCT116, SK-BR-3, and HepG2.

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 IC50 values over 50 μM.

Two undescribed ursane-type triterpene saponins, named asiaticoside H (1) and I (2), were isolated from the whole plants of Centella asiatica. The chemical structures of 1 and 2 were mainly characterized by extensive analysis of their 1D and 2D NMR and HRESIMS spectroscopic data and chemical derivation.

The investigation of the methanolic extracts of the roots, stem bark and leaves of Manilkara obovata (Sabine & G. Don) J. H. Hemsl. (Sapotaceae), synonym Manilkara argentea Pierre ex Dubard, has led to the isolation and characterization of a new 4-phenylcoumarin derivative, in form of a racemic mixture of obovacoumaric acid (1a) and the previously reported callophyllic acid (1b) as well as a new taraxerane type triterpene named obovatol (2), alongside twenty-five known compounds. In addition, ethylcanophyllate (3a), obtained by esterification of canophyllic acid (3) is reported here for the first time. The structures of compounds were determined by comprehensive spectroscopic analyses of their 1D and 2D NMR, EI/ESI-MS and single crystal X-ray diffraction (SC-XRD) analysis for 1a and 1b, accompanied by comparison with reported records. In addition, the antibacterial activity of crude extracts, fractions and some of the isolated compounds including the hemi-synthesized ethylcanophyllate (3a) was determined against Salmonella typhi, Staphylococcus aureus ATCC4330, Enterobacter cloacae, Pseudomonas aeruginosa HM801, Streptococcus pneumoniae ATCC491619 and Escherichia coli ATCC25322 applying the broth microdilution method. While the methanolic stem bark extract showed good to significant activity against all bacterial test strains with MICs between 7.8 and 62.5 μg/mL, its fractions A and B were less active, indicating synergistic effects. This effect was also observed for the methanolic root extract, which gave a significant MIC against Staphylococcus aureus ATCC4330 with MIC < 3.9 μg/mL, but only MICs of 31.2 and 7.8 μg/mL for its fractions D and E. Likewise, though fractions F3 and F4 of the methanolic leaf extract displayed good MICs of 31.2 and 15.6 μg/mL, respectively, against Staphylococcus aureus ATCC4330, tested compounds were not stronger active. Interestingly, the hemi-synthesized ethylcanophyllate (3a) based on the completely antibacterial inactive canophyllic acid (3) displayed a good MIC of 15.6 μg/mL against Staphylococcus aureus ATCC4330, pointing here to a dominant role of the ester function in compound 3a in the structure-activity relationship.

Two new oleanane-type triterpene saponins, named polythosides A and B (1 and 2), together with a known compound, silphioside E (3), were isolated from the roots of Acacia polyacantha. Their structures were elucidated by analysis of 1D and 2D-NMR experiments, and mass spectrometry (HR-ESITOF-MS) as oleanolic acid 3-O-β- d -galactopyranosyl-(1→2)-β- d -xylopyranosyl-(1→6)-[β- d -xylopyranosyl-(1→4)]-[β- d -xylopyranosyl-(1→2)]-β- d -galactopyranoside (1), 3-O-[β- d -galactopyranosyl-(1→2)-β- d -xylopyranosyl-(1→6)-[β- d -xylopyranosyl-(1→4)]-[β- d -xylopyranosyl-(1→2)]-β- d -galactopyranosyl] oleanolic acid-28-O-β- d -glucopyranosyl ester (2) and 3-O-β- d -glucopyranosyl-(1→2)-β- d -glucopyranosyl] oleanolic acid 28-O-β- d -glucopyranosyl ester (3). The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. The results show that none of the compounds (assayed at 100 μM) showed cytotoxicity against H4IIE cells.

Eugenia lisboae M.A.D. Souza (Myrtaceae) is a species found in the Amazon biome, recently described and has not yet been studied regarding its chemical properties. This study aims to identify the main chemical constituents of crude ethyl acetate and ethanolic extracts from E. lisboae leaves. These crude extracts were fractionated using chromatographic methods (LC and HPLC). The identified compounds are a triterpene (1), three organic acids (2 - 4), and two flavonoids (5 and 6). These structures were determined by analyzing the spectroscopic (NMR and MS) data. Compound 6 was named lisboaeflavanonol A {(−)-2R,3R-dihydrokampferol 3-O-β- d -xylopyranosyl-(1”'→2”)-α- l -rhamnopyranoside}, undescribed in the literature. These were the first compounds described in this matrix, and the chemical composition is in line with chemistry of the Eugenia genus. In addition, preliminary molecular docking analysis indicated lisboaeflavanonol A as a potential inhibitor of 3-chymotrypsin-like cysteine protease (3CLpro) and RNA-dependent RNA polymerase (RdRp), which are important SARS-CoV-2 non-structural proteins (NSPs).

Two new oleanane-type triterpene glycosides, 3-O-β- d -glucuronopyranosyl -echinocystic acid-28-O-β- d -apiofuranosyl-(1→3)[O-β- d -xylopyranosyl)(1→4)]-O- α- l -rhamnopyranosyl-(1→2)-β- l -arabinopranoside (1) and 3-O-β- d -glucurono pyranosyl-echinocystic acid-28-O-β- d -apiofuranosyl-(1→3)[O-β- d -xylopyranosyl -(1→4)]-O-α- l -rhamnopyranosyl-(1→2)-β- d -xylopyranoside (2) along with two known compounds impatienoside G (3) and scaberoside A2 (4), were isolated from an n-butanol fraction of the 50 % aqueous ethanol extract of the rhizome of Impatiens pritzellii var. hupehensis. The compounds were separated by silica gel column chromatography and RP-HPLC. Their structures were elucidated through the analysis of 1D and 2D NMR spectra and HRESIMS data. The T-lymphocyte proliferation activity of the isolated terpenoid saponins was evaluated by using the CCK-8 colorimetric method.

A new pentacyclic triterpene 3-O-β-(E)-(4-O-acetylferuloyl)-lupeol (1) possessing an unusual (E)-acetylferuloyl moiety at C-3 and a new bicoumarin 7,7′-dimethoxy-6,6′-dicoumarinyl ether (2) were isolated from the liana Landolphia lucida K. Schum, along with fourteen previously known compounds 3-16, where methandriol dipropionate (3) and 2,3-bis-(4-hydroxy-3-methoxy-benzyl)-dimethyl- succinate (5) were obtained for the first time from natural sources. The structures of the new compounds were established on the basis of extensive 1D and 2D NMR spectroscopy, and HRMS data analyses. The absolute configuration of 1 was determined by circular dichroism (CD) spectroscopy. Furthermore, compounds 1 and 2 had exhibited a significant antibacterial activity against Escherichia coli (ATCC 25922) with MIC values of 2.3 μM and 4.6 μM, respectively; while compounds 4 and 5 showed antiglycation and α-glucosidase inhibitory activities.

Three new triterpene glycosides, mussapilosides A–C (1-3) together with six known triterpene glycosides, cincholic acid-28-O-β- d -glucopyranosyl ester (4), mussaendoside S (5), quinovic acid 28-O-β- d -glucopyranosyl ester (6), glycoside A (7), glycoside B (8), and quinovic acid 3-O-β- d -glucopyranosyl(1→2)-β- d -glucopyranoside (9) were isolated from the leaves of Mussaenda pilosissima. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR, and HR ESI MS spectra. All these compounds were examined for their inhibitory activity against PTP1B. The results indicated that compounds 2, 6, and 8 exhibited potent inhibitory effects with IC50 values of 3.4 ± 0.2, 4.2 ± 0.2, and 6.4 ± 0.2 μM, respectively. Compound 5 showed the moderate inhibitory effect with IC50 value of 63.0 ± 3.2 μM.

Two new cyclic diarylheptanoids, casuaritriol A (1) and casuaritriol B (2), were isolated from the EtOAc extract of litters (including branches and leaves) of Casuarina equisetifolia, along with a new triterpene casuariene (3), and two known compounds diarylheptanoids adanin (4) and ostryopsitriol (5). Their structures were elucidated by spectroscopic analysis (including HRESIMS, 1D NMR and 2D NMR data), and the absolute configuration of 3 was determined by analysis of the ECD data according to the octant rule. Compound 1 exhibited inhibitory activity against α-glycosidase with inhibition rate of 45.1 ± 1.4 % at a concentration of 500 μg/mL. In addition, compound 4 showed weak inhibitory activity against acetyl cholinesterase (AChE) with inhibition rate of 14.9 ± 1.1 % at a concentration of 50 μg/mL.

Five new cycloartane saponins, mussaglaosides A–E (1–5) together with five known saponins, mussaendoside O, mussaendoside, G mussaendoside U, mussaendoside P, and mussaendoside Q (6–10) were isolated from the leaves of Mussaenda glabra. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR, and MS data. All compounds were evaluated for ANO1 inhibitory activity using calcium-activated chloride channel and YFP expressing HT29 cells. Among the tested compounds, compound 6 strongly inhibited chloride channel activity with IC50 value of 22.0 ± 1.7 μM without any cytotoxicity.

Anchietea pyrifolia, commonly known as woody liana, belongs to the Violaceae family and is being used in Brazil as a herbal medicine with anti-inflammatory, anti-allergic, and depurative properties. However, our knowledge on the phytochemicals that confer pharmacological properties to the plant extract remains limited. We report the identification of three new friedelane-type triterpenes (1, 2a, 2b) and a new 30-norfriedelane triterpene (3) together with nine known compounds (4-12) that were isolated from the liana stems of A. pyrifolia. The structures of these compounds were elucidated by spectroscopic methods, including HRMS, and 1D/2D-NMR. In vitro cytotoxicity was assessed against two human cancer cell lines, HeLa and HL-60. The new triterpenes 1-3 and known compounds 9, 11, and 12 exhibited moderate activity with IC50 values ranging from 5.7 to 45.0 μM.

Polemonium caeruleum L. is a Chinese medicinal plant used in the treatment of tuberculosis, whooping cough, fever, infertility, epilepsy, endometritis and insomnia. It was also used as sedative and anaesthetic agent. In this work the phytochemical investigation using LC-ESI-QTOF-MS and GC–MS techniques was done for chemical characterization of methanol extracts of underground and aerial plant parts. In the course of our studies on medicinal plants, we evaluated the extracts of P. caeruleum for their biological activities as antimicrobial, antimalarial, anti-leishmanial and antitrypanosomal agents and we investigated their cytotoxicity towards mammalian cells – HEK293 and Vero cell lines, both originating from kidney and also against pharyngeal squamous cell carcinoma, FaDu cell line. LC-ESI-QTOF-MS analysis confirmed the presence of triterpene saponins – oleanane derivatives (polemoniumsaponins, glycosides of theasapogenol derivatives and β-amyrin among others), as well as flavonoid glycosides with most predominant acacetin derivatives. Saponins were more abundant and varied in the extract from underground parts of the plant, while flavonoids dominated in the extract from aerial parts. GC–MS performed after silanization enabled the identification of carbohydrates, fatty acid esters, amino acids and carboxylic acids. In the present study, the antibacterial activity of crude extract of the aerial parts of P. caeruleum against Escherichia coli with an IC50 of 137.0 μg/mL and antitrypanosomal activity of crude extract of the underground parts of P. caeruleum with an IC50 of 16.03 μg/mL were reported. The cytotoxicity of the extract from underground parts of P. caeruleum was in a range 44.5–63.5 μg/ml, while cytotoxicity of the extract from aerial parts ranged from 93.8 to 178.0 μg/ml.

The phytochemical investigation of Echinops spinosissimus aerial parts led to the isolation of nine triterpenoids, one oleanane-type (1), four taraxastane-type (2, 3, 5, 6), three lupane-type (4, 7, 9) and one phytosterol (8). Their structures were elucidated through extensive analysis of NMR and HRMS spectra data. Compound 6, 20-oxo-30-nortaraxast-21-en-3β-ol, represent a previously undescribed taraxastane-type triterpene while compound 2, 21-hydroxytaraxasterol-3β-acetate, is described herein for the first time as a natural product. Furthermore, this is the first report of isolation of compound 3-5, 8, 9 from Echinops species. Isolated compounds were tested for their inhibitory activity on acetyl cholinesterase. Only compound 4 showed a moderate activity at 25 μM (35.61 ± 1.42%).

Triterpene saponins from the leaves of red beet (Beta vulgaris L.) were qualitatively profiled using electrospray ionization tandem mass spectrometry (ESI-MS/MS). Results indicated that red beet leaves contain 11 saponins, including oleanolic acid aglycone and a varying number of sugars plus acetyl or methyl groups. We identified and studied two additional saponins other than the nine reported previously from red beets. Relative quantification was undertaken of saponins in leaves, compared to those in the roots of four cultivars (Egyptian, Forono, Red Sphere, and Round Dark Red). Saponins were quantitated using ultra-performance reverse-phase liquid chromatography (UPLC) coupled with ESI-MS/MS. Leaves of Egyptian and Round Dark Red contained higher total amount of saponins than the roots, whereas relatively higher levels of saponins were observed in roots in cultivars Red Sphere and Forono. The differential accumulation of specific triterpene saponins is indicative of spatially differentiated biosynthesis and/or biological function.

As a part of our ongoing search for bioactive compounds from the dried latex of Euphorbia resinifera (Euphorbium), a new rearranged tirucallane triterpene with a spiro [5,6] ring system, euphorol K (1), and a novel euphane triterpene hydroperoxide, euphorol J (2), together with a known compound, kansuinone (3) have been isolated. Their structures were established on the basis of extensive analyses of their spectroscopic, circular dichroism (CD) measurement and theoretical calculation (ECD) methods. The cytotoxicity of all compounds against MCF-7, U937 and C6 cancer cell lines was evaluated. Compounds 1−3 exhibited various degrees of cytotoxic effect against MCF-7.

Four undescribed triterpenoid saponins together with five known and oleanolic acid were isolated from root bark of Olax obtusifolia De Wild. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, in combination with mass spectrometry as 3-O-α- l -rhamnopyranosyl-(1→4)-α- l -rhamnopyranosyl-(1→3)-β- d -glucuronopyranosyloleanolic acid, 3-O-α- l -rhamnopyranosyl-(1→4)-α- l -rhamnopyranosyl-(1→3)-β- d -glucuronopyranosyloleanolic acid 28-O-β- d -glucopyranosyl ester, 3-O-α- l -rhamnopyranosyl-(1→3)-β- d -glucopyranosyl-(1→2)-[β- d -glucopyranosyl-(1→3)]-β- d -glucuronopyranosyloleanolic acid and 3-O-α- l -rhamnopyranosyl-(1→3)-β- d -glucopyranosyl-(1→2)-[β- d -glucopyranosyl-(1→3)]-β- d -glucuronopyranosyloleanolic acid 28-O-β- d -glucopyranosyl ester.

Three new terpenes, classified as one cembrane-type diterpenoid (rel)-(1S,5R,7E,11E)-1-isopropyl-8,12-dimethyl-4-methylenecyclotetradeca-7,11-diene-1,5-diol (1), one dinortirucallane-type triterpene 20,21-dinortirucalla-8,24-diene-3β-ol-7-one (2) and one ursane-type triterpene 21β-hydroxy-3-O-acetyl-11-keto-boswellic acid (3), respectively, along with four known triterpenes, were isolated from the gum resin of Boswellia carterii. Their structure elucidations were achieved by in-depth spectroscopic examination, mainly including experiments and analyses of multiple 1D- and 2D-NMR and HR-ESI-MS. The effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 cells of all the isolated compounds were evaluated in vitro. Compound 1, 4, 5 and 7 exhibited potent inhibitory effects on NO production with IC50 values of 1.32, 3.04, 1.42, and 3.25 μM.

Four previously undescribed triterpene saponins (1-4) were isolated from the EtOH/H2O extract of the aerial parts of Bupleurum rigidum, together with a known structural analogue. Their structures were elucidated by analysis of 1D-(1H, 13C) and 2D-NMR (1H-1H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data and mass spectrometry (ESI- and HR-ESI-MS) and by comparison with those of related metabolites. An unusual structure was characterized as 3-O-β-D-glucopyranosyl-(1 → 2)-[ β-D-glucopyranosyl-(1 → 3)]- β-D-fucopyranosyl-21-O-β-D-glucoyranosyl-3β,16β,21β,23-tetrahydroxy-13,28-epoxyolean-11-ene (1). The three other compounds shared the same sugar sequence as 1 and differed by the structure of the aglycons, 3β,16α,23,28,29-pentahydroxyoleana-11,13(28)-diene for 2, and 3β,16α,23-trihydroxy-13,28-epoxyolean-11-ene for 3, and 4.

Phytochemical investigation of the roots, stems and leaves of Mostuea thomsonii (Loganiaceae) resulted in the isolation of two new alkaloids of indolic and quinolinic types, named Thomsonines A (1) and B (2) respectively. Eleven additional known compounds, including one alkaloid namely camptothecine 3 and ten triterpene derivatives: 2α,3α,19α-trihydroxy-24-norurs-4(23),12-dien-28-oic acid 4, 3β-acetoxy-2α,19α-dihydroxy-24-norurs-4(23),12-dien-28-oic acid 5, oleanol 6, 3-O-s- d -glucopyranosideolean-28-oic acid 7, 3-β-acetoxyoleanol 8, 2α, 3α, 19α-trihydroxy-24-nurs-4(23), 12-dien 9, 3-O-s- d -glucopyranoside oleanane 10, friedelan-3-ol 11, 3-O-s- d -glucopyranosylfriedelane 12 and decanol 13, have been isolated from the same sources. The structures of the new compounds were determined by detailed analyses of 1D and 2D NMR spectra, in combination with high-resolution mass spectrometry data and by direct comparison with related data from literature. Compounds 1–4 were evaluated in vitro for their antimicrobial activities against a wide range of micro-organisms using the broth micro-dilution technique, but none of them exhibited noticeable activity.

Two new triterpene saponins named congmuyenoside V (1) and congmuyenoside VI (2), together with eleven known ones (3-13) were isolated from the leaves of Aralia elata. Structures of compounds 1-13 were determined by comprehensive spectroscopic analyses, principally including 1D, 2D NMR and HRESIMS techniques. In addition, all compounds were evaluated for their inhibitory effects on α-glucosidase and protein tyrosine phosphatase 1B (PTP1B). Compounds 1, 7 and 9-13 exhibited stronger α-glucosidase inhibitory activities than acarbose (the positive control). Simultaneously compounds 1 and 13 also demonstrated significant inhibitory effects on PTP1B.

Three previously undescribed oleanane-type saponins acylated with monoterpenic acid, kamerunosides A, B, and C were isolated from the stem liana of Acacia kamerunensis . Their structures were elucidated on the basis of extensive 1D and 2D NMR data and HRESIMS analyses. Their cytotoxicities were evaluated against HL60 cells. Kamerunoside B was the most cytotoxic.

A new 3,4- seco -27-norlanostane triterpene, ganoboninketal D ( 1 ), a new lanostane, (24 S )-3-oxo-7α,24,25-trihydroxylanosta-8-ene ( 2 ), together with six known lanostanes ( 3 – 8 ), were isolated from cultivated fruiting bodies of the basidiomycete Ganoderma orbiforme . The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data, and the structures 1 and 2 were further confirmed by chemical correlations to ganoboninketal C and ganodermanondiol, respectively. All isolated compounds were inactive in the antitubercular and antimalarial activity assays against Mycobacterium tuberculosis H37Ra and Plasmodium falciparum K1, respectively, except that compound 8 exhibited weak antitubercular activity (MIC 50 μg/ml).

Four new oleanane-type triterpene glycosides namely 3-O-[β- d -glucopyranosyl-(1 → 2)-β- d -glucopyranosyl-(1 → 2)-α- l -arabinopyranosyl] oleanolic acid, 3-O-[β- d -glucopyranosyl-(1 → 2)-β- d -glucopyranosyl-(1 → 2)-α- l -arabinopyranosyl]-28-O-[α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl] oleanolic acid, 3-O-[β- d -quinovopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranosyl]-28-O-[β- d -glucopyranosyl] oleanolic acid, 3-O-[β- d -quinovopyranosyl-(1 → 3)-α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranosyl]-28-O-[α- l -rhamnopyranosyl(1 → 4)-β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl] oleanolic acid, were isolated from methanol extract of the roots of Nigella arvensis var. involucrata along with five known oleanane-type triterpene glycosides and a steroid glucoside. Structures of the new compounds were established as by using 1D and 2D NMR techniques and mass spectrometry.

Two new acylated triterpenoid saponins named pendulaosides A and B as well as the known phenolic compounds methyl gallate, gallic acid, 1,2,3,6-tera- O -galloyl-β- d -glucose and 1,2,3,4,6-penta- O -galloyl-β- d -glucose, were isolated from the seeds of Harpullia pendula . The structures of pendulaosides A and B were determined using extensive 1D and 2D NMR analysis and mass spectrometry as well as acid hydrolysis, as 3- O -β- d -glucopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→3)]-β- d -glucuronopyranosyl-22- O -angeloyl-3β,16α,22α,24β,28-pentahydroxylolean-12-ene and 3- O -β- d -glucopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→3)]-β- d -glucuronopyranosyl-16- O -(2-methylbutyroyl)-3β,16α,22α,24β,28-pentahydroxylolean-12-ene, respectively. To the best of our knowledge the two triterpene parts 22- O -angeloyl-3β,16α,22α,24β,28-pentahydroxylolean-12-ene and16- O -(2-methylbutyroyl)-3β,16α,22α,24β,28-pentahydroxylolean-12-ene have never been characterized before. The two isolated saponins were assayed for their in-vitro cytotoxic activity against the three human tumor cell lines HepG2, MCF7 and PC3. The results showed that pendulaoside A exhibited moderate activity on PC3 cell line with IC50value equal to 13.0 μM and weak activity on HepG2 cell line with IC50 value equal to 41.0 μM. Pendulaoside B proved to be inactive against the three used cell lines.

Two new hopane-type triterpenes, 1-oxo-3α-hydroxy-22(30)-hopen-29-oic acid (1) and 3α-hydroxy-22(30)-hopen-29-oic acid (2), and the known compounds dihydrosanguinarine (3), dl-stylopine (4), dihydrochelirubine (5), dihydromacarpine (6), dihydrochelerythrine (7), dihydrochelilutine (8), and norsanguinarine (9) were isolated from the aerial part of Chelidonium majus. The structures of the new compounds were elucidated based on extensive spectroscopic evidence, especially from 1D and 2D NMR and HRESIMS experiments. The shared structure features of the hopane-type triterpenes are the presence of a mono-hydroxyl substitution at the 3-position and an acrylic acid-2-yl moiety, as a manifestation of the isopropyl group connected to C-21 of the hopane skeleton. Phytotaxonomically, the hopane-type triterpenes might be another important chemical marker in addition to the benzophenanthridine alkaloids of C. majus.

Further chemical investigation of the metabolites in the fruiting bodies of Ganoderma lingzhi resulted in isolation of eight triterpenes; two of them are new triterpene acid ethyl esters. Their structures were established based on spectroscopic studies and comparison with the known related compounds. The anticancer potential of the isolates were tested with an in vitro cytotoxic assay against five human cancer cell lines (MCF-7, HeLa, HCT-116, Caco-2 and HepG2) and two normal human cell lines (TIG-1 and HF19). Results showed that the new compounds have a strong to moderate selective cytotoxic activity against MCF-7 while they showed moderate to weak activity against HeLa cell line. Potent cytotoxic activities of some of the known isolated compounds are reported for the first time.

Investigation of the n-BuOH extract of the whole plant of Beesia calthaefolia led to the isolation of three new cycloartane triterpenoids (1–3) and two known compounds (4, 5). Their structures were elucidated by 1D and 2D NMR, HRESIMS and optical rotation spectral data. All of the isolates were investigated for their inhibitory effects on the classical pathway of the complement system. Among them, compound 3 showed stronger inhibitory activity (IC50 148.0 μM) than the positive control (rosmarinic acid, IC50 181.8 μM), while other compounds (1, 2, 4 and 5) showed moderate activity. The chemical compound studied in this article was rosmarinic acid (PubChem CID: 5281792).

The CH 2 Cl 2 -MeOH (1:1) extract of the whole plant of Rhynchospora corymbosa (L.) Britton, led to the isolation of two new secondary metabolites 1 , 2 ( 1 and 2a ) together with nine known compounds 3–11. The flavone named tricin (11) was partially modified by esterification reaction to three semi-synthetic derivatives 11a–11c ). Their structures were elucidated on the basis of spectroscopic analysis. The antimicrobial, tyrosinase and butyrylcholinesterase inhibitory activities revealed that, extract and compounds 1 , 2a , 6 , 11, 11a - c exhibited variable MICs (1–512 μg/mL) and significant antimicrobial activity, depending on the microbial species; Antifungal activity of 11 and 11c was more important than that of nystatine used as reference antifungal drugs. The inhibitory activity of 4 (IC 50 = 43.28 μg/mL) was higher than that of the kojic acid (IC 50 = 49.62 μg/mL) which is known tyrosinase inhibitor. The extract, compounds 1 , 7–10 , and 11a-c exhibited significant ( p 50 ). These results suggest that the, R. corymbosa could be exploited as a potential source of natural antimicrobial, and antibutyrylcholinesterase agents as well as tyrosinase inhibitors.

A new nor-oleanane triterpene 24-nor-4(23)-12-oleanadien-2α,3α,28-triol (1) and two new sesterterpenes salvidominicolide A (2), salvidominicolide B (3) together with fifteen known compounds were isolated from Salvia dominica L. growing wild in Jordan. The known compounds comprised six flavones, three triterpenes, one diterpene, one sesterterpene, two oxygenated monoterpenes, one sterol glucoside and one flavone glucoside. The isolated compounds were elucidated by extensive spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRMS).

Three new cycloartane triterpene glycosides, cycloramosides A–C (1–3), were isolated from Thalictrum ramosum B. Boivin. Those compounds were determined as 3-O-α-l-arabinopyranosyl-3β,16β,24S,25,30-pentaolcycloartane-16-O-β-d-glucopyranoside (1), 3-O-α-l-arabinopyranosyl-3β,16β,24S,25,30-pentaolcycloartane-24-O-β-d-glucopyranoside (2) and 3-O-α-l-arabinopyranosyl-3β,16β,24S,25-tetrahydoxylcycloartane-16-O-β-d-glucopyranoside (3), respectively. Their structures were elucidated by hydrolysis and extensive spectroscopic methods including 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, ROESY, HSQC, HMBC) along with HR-ESI–MS analyses.

Two new 29-nor-cycloartane triterpenes, amooratsanols A and B (1, 2) along with nine known compounds including two 29-nor-cycloartane triterpenes (3, 9), two lupane triterpenes (4, 5), two cycloartane triterpenes (6, 10), two dammarane triterpenes (7, 8), as well as one dinorcycloartane triterpene (11) were isolated from the leaves and twigs of Amoora tsangii (Merr.) X. M. Their structures were established by spectroscopic methods (IR, HRESIMS, and NMR). The cytotoxicity of 1-11 was evaluated against the human fibro sarcoma HT1080, esophageal cancer TE, and non-small cell lung cancer A549 cell lines by the CCK8 assay. Cycloartanes (1-3, 6, and 9-11) displayed significant cytotoxic activity with IC50 values ranging from 2.56 to 19.05 mu M. Among these triterpenes, mooratsanol A (1) showed the most potent cytotoxic activity, with IC50 values ranging from 2.56 to 5.10 mu M. (C) 2016 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

A phytochemical study of the MeOH-soluble portion from the CH2Cl2/MeOH extract of the fruits of Paullinia pinnata resulted in the isolation of a new triterpenoid, cyclopinnatol (1), and a new eicosanoic acid ester, paulliniester (2), together with five known compounds including cycloart-22(E)-ene-3β,25-diol (3), cycloartenol (4), β-sitosterol (5), betulonic acid (6) and oleanonic acid (7). The structures of the new compounds were elucidated by spectroscopic analyses (NMR and MS) and comparisons with published data. Cyclopinnatol (1) and the MeOH-soluble portion exhibited significant and weak antibacterial activities against Staphylococcus aureus, with MICs of 32 and 50 μg/mL, respectively.

Alisol G, also named 25-anhydroalisol A, is a major triterpene obtained from dried rhizomes of Alisma orientalis. This paper investigated the transformation of alisol G by fungi and evaluated the hCE2 inhibitory effects of the transformed products. By screening whole cells of 10 strains of filamentous fungi, Penicillium janthinellum AS 3.510 exhibited a special capability to transform alisol G. Four metabolites were obtained, which were determined to be new compounds on the basis of spectroscopic data, including UV, 1D- and 2D-NMR, and HRESIMS. In addition, in an in vitro bioassay, metabolites 1–4 showed significant hCE2 inhibitory activities with IC50 values of 6.81, 16.66, 3.38, and 6.33 μM, respectively.

Two new ursane-type triterpene saponins, 3- O -β- d -glucopyranosyl(1 → 3)-[α- l -rhamnopyranosyl(1 → 2)]-α- l -arabinopyranosylurs-12,19(29)-dien-28-oic acid 28- O -α- l -rhamnopyranosyl(1 → 2)-β- d -glucopyranosyl ester ( 1 ) and 3- O -β- d -glucopyranosyl(1 → 3)-[α- l -rhamnopyranosyl(1 → 2)]-α- l -arabinopyranosyl-19α,20α-dihydroxyurs-12-en-28-oic acid 28- O -α- l -rhamnopyranosyl(1 → 2)-β- d -glucopyranosyl ester ( 2 ), along with thirteen known triterpene saponins were isolated from the n -BuOH part of the MeOH extraction of the leaves of Ilex kudingcha C.J. Tseng (also called “Ku-Ding-Cha”). The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis, including HR-ESI-TOF-MS, 1D and 2D-NMR experiments, and by acid hydrolysis. All the compounds were screened for antiplatelet aggregation activity in vitro , and compounds 1 , 2 , 3 , 7 , 12 and 15 showed significant inhibition of platelet aggregation induced by ADP (5 μM) with IC 50 values of 14.7 ± 3.7, 11.3 ± 2.5, 17.4 ± 4.6, 20.5 ± 3.1, 8.1 ± 1.5 and 18.9 ± 4.2 μM, respectively.

Two new acylated triterpene saponins, named as securioside C (1), securioside D (2), and one pair of isomers 3/4, the (Z)–isomer securioside E (3) being new, together with a known triterpene saponin polygalasaponin XLIV (4) were isolated from the roots of Securidaca inappendiculata Hassk. Their structures were established by HRESIMS, 1D and 2D NMR experiments and comparison of their NMR data with previous reported data. In addition, Compounds 1–2, 3/4, 4 were evaluated for cytotoxicities against LLC (Lewis lung carcinoma) and MCF-7 (human breast cancer) cell lines. Compounds 1 and 2 exhibited moderate cytotoxic activities against LLC cells with IC50 values of 45.56 μM and 85.98 μM.

Two new 18,19-secoursane triterpenes and three triterpene glucosides, together with twelve known compounds, were isolated from the aerial parts of Rubus lambertianus Ser. The structures of the new compounds were determined by spectroscopic analyses (HR-ESI-MS, 1D/2D NMR). The protective effects of compounds 1–17 on high glucose-induced oxidative stress injury in human umbilical vein endothelial cells (HUVECs) were evaluated using cell viability assay. Compounds 1, 2, 7, 10, 12, 15 and 17 significantly attenuated high glucose-induced oxidative damage on HUVECs at the concentration of 3.10 μM.

Two new triterpene saponins, namely, ilexpublesnin S (1) and T (2), and six known saponins were isolated from the roots of Ilex pubescens. The structures of the new compounds were elucidated through extensive spectroscopic methods (IR, HR-ESI-MS, 1D and 2D NMR). Sugar residues obtained after acid hydrolysis were identified through TLC and HPLC. Compound 1 contains a 24-aldehyde group, which is rare for triterpene saponins from Ilex.

Two new triterpene rhamnosides, 3 beta-O-[alpha-L-(2',3',4'-O-triacetyl)-rhamnopyranosyl]-aleuritolic acid (1), and 3 beta-O-[alpha-L-(2',3'-O-diacetyl)-rhamnopyranosyl]-aleuritolic acid (2), together with four known triterpenoids (3-6) were isolated from the petroleum ether fraction of the 70% aqueous acetone extract of the aerial parts of E. dracunculoides Lam. Their structures were elucidated by means of extensive spectroscopic analysis, acid hydrolysis, and comparison with data reported in the literatures. Among them, compounds 1 and 2 are the first examples of taraxerene-type triterpene rhamnosides, and compounds 3-6 were isolated from this plant for the first time. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

Fucosterol, a triterpene derivative encountered in several alga species, provides a wide range of biological activities, such as protection against metabolic syndrome, or against UV-induced skin damage. We describe here the comparison of extraction by supercritical fluid (SFE) and pressurized solvent (PSE) of the brown alga Lessonia vadosa mainly abundant in the coastal water of Patagonia, followed by the isolation of fucosterol, using centrifugal partition chromatography (CPC), in association with HPLC–UV quantification. After collection, the seaweed was dried, ground and extracted either by PSE or by SFE under various conditions. The yield and the content in fucosterol of each extract were determined by HPLC–UV. Optimization of a biphasic solvent system and K D calculation led to the isolation of pure fucosterol with high recovery rate. Extraction by SFE using CO 2 at 180 bar and 50 °C with 20 to 30 % of cellulose as modifier and CPC purification by cyclohexane/acetone/methanol/water 10/1/10/1 with lower layer as mobile phase led to the best results in terms of yield, purity, time and solvent consumption. Natural and semisynthetic steroid derivatives have been previously shown to be potential drug candidates against parasitic diseases including leishmaniasis. In this context fucosterol was evaluated and demonstrated noticeable antileishmanial activity (IC 50