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Phyllaciduloids E (1) and F (2), two new cleistanthane diterpenoids, were isolated from the leaves of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Their planar structures were established by spectroscopic analysis and comparison with literature values. The relative configurations of phyllaciduloids E and F were confirmed by DFT-NMR chemical shift calculations and subsequent CP3 probability methods. Phyllaciduloids E and F were evaluated for their cytotoxicity. However, no significant activities were detected at concentrations up to 40 μM. [ABSTRACT FROM AUTHOR]

Four new protopanaxatriol-type triterpenes (1–2) and glucosides (3–4), were isolated from the rot roots of Panax notoginseng (Burk.) Chen, along with four known ones (5–8). Their structures were elucidated on the basis of extensive spectroscopic analysis (HRESIMS, NMR, UV, IR, and OR) and acidic hydrolysis. The possible transformation pathway of these compounds were also speculated from ginsenoside Rg1. Compound 1, with a unique α,β-unsaturated ketene in its side chain, showed significant inhibitory effects against NO production on Murine macrophage cells (IC50 = 4.12 ± 0.20 μM) and comparable cytotoxicities against five human cancer cell lines (myeloid leukemia HL-60, lung cancer A-549 cells, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480) to positive control, cisplatin (DDP). [ABSTRACT FROM AUTHOR]

Two new sphingofungins G (1) and H (2) with a five-membered lactone ring were identified from the solid-state fermentation of Aspergillus penicilliodes Speg., a dominant microorganism isolated previously from the post-fermentation of ripe Pu-er tea, together with six known metabolites. Their structures were elucidated by extensive spectroscopic methods. All of them were isolated from the mycelia culture of A. penicilliodes for the first time. The known compound, trypacidin, exhibited potent cytotoxities against five human cancer cell lines, e.g. myeloid leukemia HL-60, lung cancer A-549, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480, with IC50 values of 0.55, 11.45, 10.95, 3.58, and 3.49 μM, resp., while cisplatin as the positive control, with IC50 values of 8.63, 24.15, 21.99, 27.29, and 23.61 μM, resp. [ABSTRACT FROM AUTHOR]

Two new compounds, (Z,R)-1-phenylethylcinnamate (1) and (1R,2R,3R,6S)-pipoxide (2) were isolated from the aerial part ofPiper hainanense, along with 12 known compounds, including nine benzene derivatives (4–11), one isobutylamide (12), and two polyoxygenated cyclohexene derivatives (13–14). Their structures were elucidated on the basis of the HRESIMS, 1D and 2D NMR spectroscopic analyses, and ECD in cases of2and3. The absolute configuration of ellipeiopsol B (3) was determined for the first time. All these compounds1–14were reported from the titled plant for the first time. Most of the isolates were tested for their cytotoxicities against five human cancer cell lines. Four of which,2,3,9,14showed moderate bioactivities. Among them, the new compound2showed potential cytotoxicity against SMMC-7721, MCF-7, and SW-480 with IC50values of 9.7, 15.0, and 13.2 μM, respectively. [ABSTRACT FROM PUBLISHER]

[Display omitted] • Four new rare dichapetalins (1–4) were isolated from Phyllanthus acidus. • Their structures were elucidated by extensive spectroscopic data and X-ray diffraction analysis. • The isolated dichapetalins showed cytotoxicity against seven human cancer or normal cell lines. The young leaves of Phyllanthus acidus (Euphorbiaceae) are commonly used as edible vegetables in Indonesia, Thailand, and India, and their water infusions as dieting aids for people trying to remain slim. However, it is regarded as a poisonous plant in Malaya, and current researches are insufficient to provide a conclusion on its toxicity and safety under large doses. In this study, we firstly found that the refined nonpolar extracts of P. acidus leaves showed significant cytotoxic effect against BEAS-2B and L02 normal cell lines with IC 50 values of 2.15 and 1.64 mg/mL, respectively. Further bioactivity-guided isolation produced four new rare dichapetalins (pacidusins A – D) from the most active fraction. Their structures including absolute configurations were elucidated by extensive spectroscopic data and X-ray diffraction analysis. All the isolated dichapetalins exhibited moderate cytotoxicity against, BEAS-2B and L02 normal cell lines with IC 50 values ranging from 12.44 to 22.55 μM, as well as five human cancer cell lines with IC 50 values ranging from 3.38 to 22.38 μM. Furthermore, the content of the main dichapetalins in the leaves were determined by analytical HPLC, which showed that the leaves contained a very high amount of the four isolated dichapetalins with a total yield of 0.488 mg/g of dry plant material. These toxic dichapetalins may lead to adverse health effects in higher doses. Our findings indicate that the dichapetalin containing leaves may not be suitable for consumption in large quantities as food, but demonstrate their potency as anti-cancer agents for new drug discovery. [ABSTRACT FROM AUTHOR]

Phytochemical investigation on the nonpolar extracts of P. acidus leaves afforded three new cleistanthane diterpenoids, named phyllanacidins A–C (1 – 3), in addition to three known ones (4 – 6). Among them, compounds 2 and 3 represent the first examples of 17- nor cleistanthane diterpenoids. Their structures including absolute configurations were elucidated on the basis of extensive spectroscopic data and single crystal X-ray diffraction analysis. All the isolated cleistanthane diterpenoids were evaluated for their cytotoxic activities against five human cancer cell lines. Compounds 4 – 6 exhibited moderate cytotoxicity with IC 50 values ranging from 16.11 to 30.82 μM. Unlabelled Image • Three new cleistanthane diterpenoids (1 – 3) were isolated from Phyllanthus acidus. • Their structures were elucidated on the basis of spectroscopic analysis. • 2 and 3 represent the first examples of 17- nor cleistanthane diterpenoids. [ABSTRACT FROM AUTHOR]

Quantitative analysis of Rumex nepalensis var. remotiflorus revealed that its roots contain rich anthraquinones, which has emodin, chrysophanol, and physcion contents of up to 0.30, 0.67, and 0.98 mg/g, respectively. Further phytochemical study led to the isolation and purification of seven undescribed phenolic constituents, including one flavan derivative with a 13-membered ring, polygorumin A (1), two dianthrone glucosides, polygonumnolides F and G (2 , 3), two diphenylmethanones, rumepalens A and B (4 , 5), and a pair of epimeric oxanthrone C -glucosides, rumejaposides K and L (6a , 6b) from the roots of R. nepalensis var. remotiflorus. Furthermore, 1 undescribed natural product, 1- β -D-glucoside-6′-[(2 E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate]-3-hydroxy-5-methylphenyl (19), and 21 known phenolic compounds were obtained from the aforementioned plant for the first time. Their structures were elucidated through extensive spectroscopic data analysis. Notably, compounds 1 , 4 – 5 , and 7 – 9 exhibited inhibitory activity on α -glucosidase with IC 50 values ranging from 1.61 ± 0.17 to 32.41 ± 0.87 μM. In addition, the isolated dianthrone, chrysophanol bianthrone (14), showed obvious cytotoxicity against four human cancer cell lines (HL-60, SMMC-7721, A-549, and MDA-MB-231) with IC 50 values ranging from 3.81 ± 0.17 to 35.15 ± 2.24 μM. In silico target prediction and molecular docking studies demonstrated that the mechanism of the anticancer activity of 14 may be related to the interaction with protein kinase CK2. [Display omitted] • The chemical constituents of R. nepalensis var. remotiflorus were studied firstly. • Emodin, chrysophanol and physcion are major anthraquinones in the roots. • Seven undescribed phenols and one undescribed natural product were obtained. • Some isolates showed obvious inhibition on α -glucosidase and HL-60 cell lines. [ABSTRACT FROM AUTHOR]

Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23 S ,26 R -hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A‒C, were isolated from the fruits of Solanum violaceum , together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16 β -methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16 β -methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A‒C, (22 R ,23 S ,25 R ,26 R)-spirost-5-ene-3 β ,23,26-triol3- O - β - d -xylopyranosyl-(1→3)- β - d -glucopyranoside, solanindins A and B, and (1 S ,2 S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2 S ,3 R ,4 R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1 S ,2 S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2 S ,3 R ,4 R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC 50 = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC 50 value of 37.32 ± 0.793 μM. In addition, (1 S ,2 S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2 S ,3 R ,4 R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells. [Display omitted] • Three undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A-C were isolated. • One rare 23S,26R-hydroxylated spirostanoid saponin was obtained. • Acid hydrolysis gave two undescribed aglycones, solanindins A and B. • A known lignan showed cytotoxicity on MCF-7 cells (IC 50 = 4.39 ± 0.10 μM). • Solanindin B showed inhibitory effects on Staphylococcus aureus. [ABSTRACT FROM AUTHOR]

Six diterpenoids including three ent -kauranes (1 – 2 , 4) and three cleistanthanes (3 , 5 – 6) were isolated from the roots and stems of Phyllanthus acidus (L.) Skeels. Of them, (16 S)- ent -16,17,18-tri-hydroxy-19-nor-kaur-4-en-3-one (1), phyllanthone A (2), and 6-hydroxycleistanthol (3) are new compounds, while the ent -kaurane diterpenoids were reported from the titled plant for the first time. Their structures were elucidated on the basis of the extensive spectroscopic analyses. Compounds 2 and 4 – 6 displayed cytotoxic potential with IC 50 values ranging from 1.96 to 29.15 μM. They also showed moderate anti-inflammatory activities (IC 50 = 6.30–12.05 μM). Particularly, the new ent -kaurane 2 displayed cytotoxic potential against HL-60 (IC 50 = 2.00 μM) and MCF-7 (IC 50 = 3.55 μM) cells, and anti-inflammatory activity (IC 50 = 6.47 μM). [Display omitted] [ABSTRACT FROM AUTHOR]

• New compounds, Carissaedulosides A–J, were isolated from C. edulis. • Comprising apiosylated phenolics (A–F), coumarin-secoiridoid (G), & lignans (H–J). • Three compounds displayed significant cytotoxic effects. • The known cardenolide induced apoptosis in SW480 and HL-60 cells. Ten previously undescribed glycosides, carissaedulosides A–J (1 – 10) referring to six apiosylated phenylpropanoids (1 – 6), one coumarin-secoiridoid hybrid (7), and three furofuran lignans (8 – 10) were isolated from the root barks of Carissa edulis , together with 13 known analogues (11 – 23). Their structures were elucidated by spectroscopic analysis, ECD computational methods, and chemical derivations for configurations of sugar moieties. The new lignan bisdesmoside, 10 , exhibited significant cytotoxicity against A549 (IC 50 = 3.87 ± 0.03 μM) and MCF-7 (IC 50 = 9.231 ± 0.290 μM) cell lines, while the known lignan monodesmoside, 12 , showed impressive cytotoxic efficacy (IC 50 = 5.68 ± 0.180 μM) against only MCF-7 cell line. It is noted that a known cardenolide, 11 , displayed strong cytotoxic potency against HL-60, A549, MCF-7 and SW480 cell lines with IC 50 values ranging from 0.023 to 0.137 μM. Moreover, compound 11 induced dose-dependent apoptosis on SW480 cell, but not explicit dose-dependent apoptosis on HL-60 cells. [ABSTRACT FROM AUTHOR]