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Eleven flavonoids including one new flavonol glycoside, quercetin-3-O-(2-α-L-rhamnopyranosyl)-β-D-glucuronopyranosyl methyl ester (1), were isolated for the first time from the fruits of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Their structures were determined by extensive spectroscopic data. The known flavonoids, quercetin-3-O-β-D-glucuronide methyl ester (3), quercetin-3-O-(2''-α-L-rhamnopyranosyl-6''-O-α-L-rhamno pyranosyl)-β-D-glucopyranoside (5), myricetin (9), and 6-methoxy-naringenin (11) were isolated for the first time from the genus Phyllanthus. Flavonoids 4, 6 and 9 (IC50 = 6.01, 6.32, and 7.84 μM, respectively) showed stronger α-glucosidase inhibitory activities than the positive control, acarbose (IC50 = 306.45 μM). The fruits of P. acidus might be further developed as an anti-diabetic food supplement. [ABSTRACT FROM AUTHOR]

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]

A novel highly oxygenated norbisabolane sesquiterpene, namely phyllanthacidoid U (1), along with nine known sesquiterpenes (2–10) was isolated from the roots and stems of Phyllanthus acidus (L.) Skeels (Phyllanthaceae), collected from Xishuangbanna, Yunnan province, China. Their structures were elucidated by means of extensive spectroscopic analysis and by comparison of their data with reported values in literatures. Instead of the C-13 ester O-glycosyl found mostly in the titled plant growing in Thailand, compound 1 possessed a rare N-β-glucosamine-2-N-acetate moiety linked directly to the carbonyl at C-13 through an amido bond. Moreover, the acyl group at C-10 in 1 was (Z)-2-(2-hydroxyethyl)-pent-2-enedioyl group, instead of benzoic or p-hydroxybenzoic moieties found commonly in the reported norbisabolane sesquiterpenes. The known sesquiterpene 5 displayed stronger anti hepatitis B virus (HBV) activity with IC50 values of 1.69 ± 0.22 and 2.79 ± 0.69 μM towards HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively. [ABSTRACT FROM AUTHOR]

The fresh leaves of Metapanax delavayi (Araliaceae) have been used as a common wild vegetable for salad and soup, and also herbal tea by the local people living in its growing areas of Yunnan province, China. Detailed chemical investigation led to the identification of a new triterpenoid saponin, 3-O-α-L-arabinopyranosyl-28-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-3β-hydroxyolean-12-ene-28,29-dioic acid (1) from the fresh leaves, together with 11 known compounds, including six triterpenoid saponins (2–7), two caffeoylquinic acid derivatives (8–9), and three flavonoid glycosides (10–12). Their structures were determined on the basis of spectroscopic analysis and acidic hydrolysis. Compounds 3–5 and 8–12 were isolated from M. delavayi for the first time. Moreover, the known saponins 3-O-β-D-xylopyranosyl-3β-hydroxyolean-12-ene-28,29-dioic acid (3) and yiyeliangwanoside IV (5) exhibited protective effects on HepG2 cells damaged by the alcohol intakes, at a concentration of 1.0 µg/mL. The results indicated M. delavayi is an ideal dietary vegetable and herbal tea with potential hepatoprotective activity. [ABSTRACT FROM AUTHOR]

Dasiphora fruticosa L. (Rosaceae), also known as Potentilla fruticosa L. (syn.), is a hardy deciduous shrub widely distributed in the north temperate regions of the world. Three methylene bisflavan-3-ols (1-3), together with a procyanidin dimer, (-)-afzelechin-(4α→8)-(-)-afzelechin (4) were isolated for the first time from the branches and leaves of the titled plant, in addition to 11 known compounds (5-15). Their structures were elucidated by means of extensive spectroscopic analysis and by comparison with data reported in the literatures. Methylene 6,8-bis(7-O-glucosyl) catechin (1) was determined to be a new dimeric flavan-3-ol glycoside through a methylene linkage between C-8 and C-8 of two units. At a concentration of 128 μg/mL, the known compounds 9 – 13 exhibited antibacterial activities on Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa. Compound 12 also showed certain glucose uptake stimulating activity. [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]

Further phytochemical investigation of the steaming treated roots of Panax notoginseng (Araliaceae) led to the identification of two new dammarane-type triterpenoid saponins, notoginsenoside SP20 (1) and SP21 (2). In addition, a pair of new phenolic glycosides (3a and 3b) was also isolated together with two known compounds. Their structures were elucidated by HRESIMS, 1D- and 2D-NMR spectra. Compounds 1 and 2 showed no in vitro cytotoxicity against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-9 and SW480). [ABSTRACT FROM AUTHOR]

Fifty-eight phenolic compounds isolated from Phyllanthus emblica were screened and compared for their in vitro and in vivo antioxidant properties, as well as hyaluronidase (HAase) inhibitory activities. Among them, 20 compounds showed to be promising antioxidants due to the stronger scavenging activity in both DPPH radical and Danio rerio reactive oxygen species assays, while nine compounds were potential HAase inhibitors with 100-fold stronger activities than that of the positive control, DSCG. The structure activity relationship was discussed. [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]

A new methylene-bridged dimeric flavonol glycoside, methylenebisnicotiflorin (1), was isolated from ripe Pu-er tea, along with 10 known flavonoids (2–11) and seven known phenolic compounds (12–18). The structure elucidation was based on spectroscopic analysis. Among them, 1,3-dihydroxyphenyl-2-O-sulfate (13), 2,3,4-trihydroxybenzoic acid (16) and 3,3′,4,4′-tetrahydroxybiphenyl (18) are reported from tea plants for the first time. [ABSTRACT FROM PUBLISHER]

Fifteen known compounds including four triterpenoids (1–4), one sterol (5), one diketopiperazine alkaloid (6) and nine phenolics (7–15) were isolated from the stems ofPiper wallichii. Their structures were elucidated by means of spectroscopic analysis, and acidic hydrolysis in case of the 2-oxo-3β,19α,23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (1). The structure of compound1was fully assigned by 1D and 2D NMR experiments for the first time. All isolates were tested for their antibacterial, antifungal, anti-inflammatory and antiplatelet aggregation bioactivities. [ABSTRACT FROM PUBLISHER]

Arbutin (1), chlorogenic acid (2) and 6′-O-caffeoylarbutin (3) are three major components in Vaccinium dunalianum Wight with various promising bioactivities. A reliable, reproducible and accurate method for simultaneous and quantitative determination of 1–3 is developed by RP-HPLC analysis. This method should be appropriate for the quality assurance of unprocessed and processed materials of V. dunalianum. The contents of 1–3 in different parts of V. dunalianum from different origins were analysed. The content of 3 was much higher than those of 1 and 2, accounting for up to 31.76% in the dried leaf buds. Moreover, the leaf buds, flower buds and leaves showed a tendency towards higher contents of 1–3 than the other plant parts. [ABSTRACT FROM AUTHOR]

6′-O-Caffeoylarbutin, an arbutin derivative, is a naturally occurring glucoside of hydroquinone fromVaccinium dunalianum. On anti-melanogenic effect assay, 6′-O-caffeoylarbutin expressed a stronger anti-melanin activity in a dose-dependent manner with about a two-fold more than that of arbutin, but with less toxicity about a two-fold lower than that of arbutin. In addition, melanin synthesis could be fully recovered after the removal of 6′-O-caffeoylarbutin. The result suggested that 6′-O-caffeoylarbutin could be a candidate natural product to serve as a skin-whitening ingredient with the merits of potent melanin inhibition, less toxicity and reversible melanin synthesis after stopping use. [ABSTRACT FROM PUBLISHER]