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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.

A new seco-anthraquinone, crispuside A (1), and three new 3,4-dihydronaphthalen-1(2H)-ones, napthalenones A-C (2–4), were isolated from the roots of Rumex crispus L., along with 10 known anthraquinones (6–14) and naphthalenone (5). Their structures were fully determined by extensive spectroscopic analyses, including ECD, and X-ray crystallography in case of compound 5, whose absolute configuration was determined for the first time. The isolates 1, 6–14 were evaluated for their anti-inflammatory and anti-fungal activity against three skin fungi, e.g., Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum. Most of the isolates showed weak anti-fungal and anti-inflammatory activity. Only compound 9 exhibited obvious anti-fungal activity against E. floccosum (MIC50 = 2.467 ± 0.03 μM) and M. gypseum (MIC50 = 4.673 ± 0.077 μM), while the MIC50 values of the positive control terbinafine were 1.287 ± 0.012 and 0.077 ± 0.00258 μM, respectively. The results indicated that simple emodin type anthraquinone is more potential against skin fungi than its oxyglucosyl, C-glucosyl and glycosylated seco analogues. Graphical Abstract

Rumex L., a genus in Polygonaceae family with about 200 species, is growing widely around the world. Some Rumex species, called "sorrel" or "dock", have been used as food application and treatment of skin diseases and hemostasis after trauma by the local people of its growing areas for centuries. To date, 29 Rumex species have been studied to contain about 268 substances, including anthraquinones, flavonoids, naphthalenes, stilbenes, diterpene alkaloids, terpenes, lignans, and tannins. Crude extract of Rumex spp. and the pure isolates displayed various bioactivities, such as antibacterial, anti-inflammatory, antitumor, antioxidant, cardiovascular protection and antiaging activities. Rumex species have important potential to become a clinical medicinal source in future. This review covers research articles from 1900 to 2022, fetched from SciFinder, Web of Science, ResearchGate, CNKI and Google Scholar, using “Rumex” as a search term ("all fields") with no specific time frame set for the search. Thirty-five Rumex species were selected and summarized on their geographical distribution, edible parts, traditional uses, chemical research and pharmacological properties.

Terminalia Linn, a genus of mostly medium or large trees in the family Combretaceae with about 250 species in the world, is distributed mainly in southern Asia, Himalayas, Madagascar, Australia, and the tropical and subtropical regions of Africa. Many species are used widely in many traditional medicinal systems, e.g., traditional Chinese medicine, Tibetan medicine, and Indian Ayurvedic medicine practices. So far, about 39 species have been phytochemically studied, which led to the identification of 368 compounds, including terpenoids, tannins, flavonoids, phenylpropanoids, simple phenolics and so on. Some of the isolates showed various bioactivities, in vitro or in vivo, such as antitumor, anti HIV-1, antifungal, antimicrobial, antimalarial, antioxidant, diarrhea and analgesic. This review covers research articles from 1934 to 2018, retrieved from SciFinder, Wikipedia, Google Scholar, Chinese Knowledge Network and Baidu Scholar by using “Terminalia” as the search term (“all fields”) with no specific time frame setting for the search. Thirty-nine important medicinal and edible Terminalia species were selected and summarized on their geographical distribution, traditional uses, phytochemistry and related pharmacological activities.

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). Graphical Abstract Electronic supplementary material The online version of this article (10.1007/s13659-019-0211-4) contains supplementary material, which is available to authorized users.

The extensive chemical investigation on the branches and leaves of Terminalia chebula var. tomentella (Combretaceae) led to the isolation of two new lignan glucosides with a furofuran skeleton, termitomenins F (1) and G (2). In addition, 19 known compounds including five lignan glucosides (3–7), six hydrolyzable tannins (8–13) and eight simple phenolics (14–21) were also identified. Their structures were determined by comprehensive spectroscopic analyses. It is noted that 8 and 9 were C-glycosidic hydrolyzable tannins with one hexahydroxydiphenoyl and one gallagyl group linked to an open-chain glucosyl C-1/O-2/O-3 and O-4/O-6, respectively, which were rarely found in plants. Nine known compounds, 6–9, 13, and 18–21, were procured from the titled plant for the first time, while 3–5, 10–12 and 14–17 were also found in the fruits. Notably, the known hydrolyzable tannins 8–13 exhibited stronger α-glucosidase inhibitory activities with IC50 values ranging from 0.10 to 3.12 μM, than the positive control, quercetin (IC50 = 9.38 ± 0.33 μM). Graphic abstract

Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23S,26R-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 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-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, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β- d -xylopyranosyl-(1→3)-β- d -glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-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 (IC50 = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.

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...

Panax, a genus of the Araliaceae family, is an important herbal group in traditional Chinese medicine (TCM). Nine species and three varieties are included in the genus of Panax, in which nearly all species have been used for medicinal purposes. Among them, Panax notoginseng (Burk) F. H. Chen, Panax ginseng C. A. Meyer and Panax quinquefolius L. are the most representative and valuable herbs world-wide, with a long history of cultivation. As the main bioactive chemical constituents, saponins with different aglycones are the major components in various Panax spp., and their pharmacological activities are mainly reflected in the effects on blood system, cardio- and cerebro-vascular systems, nervous system, metabolism, and immune regulation. Researchers of Kunming Institute of Botany (KIB), Chinese Academy of Sciences (CAS), have put many efforts into conducting the investigations on Panax species. Herein, we reviewed the research progress on Panax spp. in KIB, CAS, over the past few decades, from the aspects of history and origin, phytochemistry and pharmacological activities. Graphical Abstract

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 IC

Twelve indolyl diketopiperazines 1–12 were isolated from the mycelia culture of Aspergillus penicilliodes Speg., a dominant microorganism from the post fermentation process of ripe Pu-er tea. Their structures were elucidated by extensive spectroscopic methods. Among them, trypostatins C (1) and D (2) featuring with a rare methyl vinyl ketone side chain at C-2 are new compounds, while 3 and 4 were obtained for the first time from nature source. The isolates 3–12 did not show obvious cytotoxicities against five human cancer cell lines at a concentration of 40 μM. Electronic supplementary material The online version of this article (10.1007/s13659-018-0156-z) contains supplementary material, which is available to authorized users.

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 IC50 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 IC50 values ranging from 12.44 to 22.55 μM, as well as five human cancer cell lines with IC50 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.

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.

As one of the most extensively studied glycosaminoglycan lyases, heparinase I has been used in producing low or ultra-low molecular weight heparin. Its' important applications are to neutralize the heparin in human blood and analyze heparin structure in the clinic. However, the low productivity and activity of the enzyme have greatly hindered its applications. In this study, a novel Hep-I from Bacteroides cellulosilyticus (BcHep-I) was successfully cloned and heterologously expressed in E. coli BL21 (DE3) as a soluble protein. The molecular mass and isoelectric point (pI) of the enzyme are 44.42 kDa and 9.02, respectively. And the characterization of BcHep-I after purified with Ni-NTA affinity chromatography suggested that it is a mesophilic enzyme. BcHep-I can be activated by 1 mM Ca2+, Mg2+, and Mn2+, while severely inhibited by Zn2+, Co2+, and EDTA. The specific activity of the enzyme was 738.3 U·mg-1 which is the highest activity ever reported. The Km and Vmax were calculated as 0.17 mg·mL-1 and 740.58 U·mg-1, respectively. Besides, the half-life of 300 min at 30°C showed BcHep-I has practical applications. Homology modeling and substrate docking revealed that Gln15, Lys74, Arg76, Lys104, Arg149, Gln208, Tyr336, Tyr342, and Lys338 were mainly involved in the substrate binding of Hep-I, and 11 hydrogen bonds were formed between heparin and the enzyme. These results indicated that BcHep-I with high activity has great potential applications in the industrial production of heparin, especially in the clinic to neutralize heparin.

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 (IC50 = 3.87 ± 0.03 μM) and MCF-7 (IC50 = 9.231 ± 0.290 μM) cell lines, while the known lignan monodesmoside, 12, showed impressive cytotoxic efficacy (IC50 = 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 IC50 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.

In an effort to identify anti-viral and cytotoxic compounds from Phyllanthus spp., 14 highly oxygenated norbisabolane sesquiterpenoids, phyllaemblicins H1-H14, were isolated from the roots of Phyllanthus emblica Linn, along with phyllaemblicins B and C and glochicoccinoside D. Their structures were determined on the basis of detailed spectroscopic analysis and chemical methods. Determination of absolute configurations of these compounds was facilitated by theoretical calculations of electronic circular dichroism (ECD) spectra using time-dependent density functional theory (TDDFT) for the aglycone components, and pre-column derivative/chiral HPLC analysis for the monosaccharides. The known glochicoccinoside D displayed potent activity against influenza A virus strain H3N2 and hand, foot and mouth virus EV71, with IC50 values of 4.5 +/- 0.6 and 2.6 +/- 0.7 mu g/ml, respectively. Phyllaemblicin H1 showed moderate cytotoxicity against human cancer cell lines A-549 and SMMC-7721, with IC50 values of 4.7 +/- 0.7 and 9.9 +/- 1.3 mu M, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

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.

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 of Piper 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 compound 1 was 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.

“Long-Dan” and “Qin-Jiao” are two important TCM herbs since ancient times in China. In the Chinese Pharmacopoeia, the dried roots and rhizomes of four species from the genus Gentiana, e.g. Gentiana manshurica, G. scabra, G. triflora and G. rigescens, are recorded under the name of Gentianae Radix et Rhizoma (“Long-Dan” in Chinese), while the other four species from the same genus including G. macrophylla, G. crassicaulis, G. straminea and G. duhurica are recorded and used as the raw materials of Gentianae Macrophyllae Radix (“Qin-Jiao” in Chinese). On the basis of the establishment of a validated HPLC–UV method for quantifying simultaneously, five iridoid glycosides, e.g. loganic acid (1), swertiamarinin (2), gentiopicroside (3), sweroside (4) and 2′-(o,m-dihydroxybenzyl)sweroside (5) have been used successfully as chemical markers for the comparison of the species used as “Long-Dan”, “Qin-Jiao” and their adulterants in the present study. The results suggested that four iridoid glycosides 1–4 commonly existed in both “Long-Dan” and “Qin-Jiao”, while 2′-(o,m-dihydroxybenzyl)sweroside (5) also existed as one of the major components in “Dian-Long-Dan” species. Moreover, the contents of compounds 1–5 were various in different “Long-Dan” and “Qin-Jiao” species. Herein, we profiled and compared three “Long-Dan” species, four “Qin-Jiao” species and five adulterants by applying multivariate statistical techniques to their HPLC data sets to establish the differences and/or similarities. Electronic supplementary material The online version of this article (doi:10.1007/s13659-014-0039-x) contains supplementary material, which is available to authorized users.

A collection of 70 randomly selected three-year-old Panax notoginseng plants was analyzed to evaluate the germplasmic resources of cultivated notoginseng. The results obtained indicated that the individual plants of P. notoginseng were greatly diversified not only in saponin contents, but also in morphological features. It was further proven that, after hundreds years of cultivation, notoginseng has become a mixed farm cultivar with very large variations occurring. This high variance in saponin contents implies the possibility for breeding of this medicinal plant in order to obtain cultivars with higher saponin production. Statistic analysis of correlation between morphologic variation and chemical variation suggests that some morphological characters, such as root weight, plant height and peduncle length, can be correlated with saponin contents and can be used as important selective traits for selective breeding.

Three structurally interesting new diterpenoids, phyllanflexoids A-C(1-3), together with cleistanthol (4) were isolated from the roots of Phyllanthus flexuosus. Their structures with the absolute stereochemistry were elucidated on the basis of comprehensive spectroscopic analysis, computational method, and acidic hydrolysis in the case of 3. Compounds 1-3 were phenylacetylene-bearing tricyclic diterpenes and 3 was the first example of phenylacetylene-bearing 18-nor-diterpenoid glycoside. Compounds 1, 2, and 4 exhibited weak cytotoxicity against human esophagus cancer cell ECA109 with IC50 of 42.7, 21.4, and 24.5 mu M, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

A new 6/6/5/6-fused limonoid, phyllanthoid A (1), possessing both 19/30 and 19/29 oxygen bridges was isolated from Phyllanthus cochinchinensis (Euphorbiaceae), together with a new related limonoid, phyllanthoid B (2). Their structures were determined by spectroscopic analysis and single-crystal X-ray diffraction in the case of 1. Compound 1 displayed moderate antifeedant against the generalist plant-feeding insect Spodoptera exigua and cytotoxicity against the MCF-7 cell line.

Three new acylated flavonoid C-glycosides, 6‴-(-)-phaseoylspinosin (1), 6‴-(3″″,4″″,5″″-trimethoxyl)-(E)-cinnamoylspinosin (2), and 6‴-(4″″-O-β-D-gluco-pyranosyl)-benzoylspinosin (3), were isolated from the seeds of Ziziphus mauritiana (Rhamnaceae). A further 19 known compounds including eight spinosin analogues (4–11) were also isolated. Their structures were elucidated by means of spectroscopic analysis and chemical method. Among spinosin derivatives 1, 2, 4, 7, 8, and triterpenoid saponin 14, jujuboside A (14) displayed moderate acetylcholinesterase (AchE) inhibitory activity with an inhibition value of 46.2% at a concentration of 1 µM. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0028-5 and is accessible for authorized users.

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).

A detailed chemical investigation of the red resins from Dracaena cochinchinensis (Chinese dragon’s blood) yielded five new flavonoid oligomers, named cochinchinenins D-H (1–5), together with a known biflavonoid, cinnabarone (6), and a mixture of two known biflavonoids, socotrin-4′-ol (7) and homoisosocotrin-4′-ol (8). Of these new compounds, 1–3 were biflavonoids and 4 and 5 were triflavonoids. Their structures were determined on the basis of spectroscopic analysis. The isolated compounds were tested for cytotoxicity (Cdc25), antibacterial (PEPT) and antifungal (YNG) activities. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0020-5 and is accessible for authorized users.

Three new phenolic compounds, eucalmaidin F (1), (3S)-5-guaiacyl-3-hydroxypentanoic acid (2), and 8-beta-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone (3), were isolated from the branches of E. maideni, together with 30 known compounds, including four phenylpropanoids, three lignans, four phloroglucinol glucosides, five dihydroflavonoids, seven simple phenolic compounds, six terpenoids, and glycerol. The new structures were established by spectroscopic studies (MS, and 1D- and 2D-NMR), chemical degradation, and modified Mosher's method. Compounds 3, guaiacylglycerol, 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one, caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid, (7'S,8R,8'R)-lyoniresinol, (+)-lyoresinol 3a-O-a-L-rhamnopyranoside, garcimangosone, phlorocetophenone 2'-glucopyranoside, (+)-taxifolin 3a-O-a-L-rhamnopyranoside, (+)-aromadendrin, (+)-taxifolin, resveratrol, piceatannol, 3,4,5-trihydroxyphenol. Tachiaside, gallic acid, macrocapals A und G, and oleuropeic acid were evaluated for their cytotoxicities against five human cancer cell lines. Resveratrol, piceatannol, gallic acid, and macrocapal G exhibited moderate inhibitory effects on human myeloid heukemia HL-60 cell, with IC50 values of 22.05, 22.05, 7.75, and 31.93 mu M, respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC-7721 cell, with an IC50 value of 26.75 mu M.

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.

Four new dammarane-type triterpenoid saponins, namely notoginsenosides SFt1-SFt4 (1–4) were isolated from the steamed leaves of Panax notoginseng (Burk.) F. H. Chen (Araliaceae), together with 17 known saponins. Their structures were established on the basis of detailed spectroscopic analyses and acidic hydrolysis. The known ginsenosides Rk2 and Rh3 were obtained from P. notoginseng for the first time. All of these new saponins showed no in vitro cytotoxicity against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-7, and SW480). Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-011-0036-2 and is accessible for authorized users.

Phytochemical investigation of the rhizomes of Panax japonicus C. A. Meyer (Araliaceae) resulted in the isolation of two new dammarane-type triterpenoid saponins, yesanchinoside R1 (1) and yesanchinoside R2 (2), together with one new natural product, 6'''-O-acetylginsenoside Re (3). In addition, 25 known compounds, including 23 triterpenoid saponins, 426, beta-sitosterol 3-O-beta-D-glucopyranoside (27), and ecdysterone (28), were also identified. The known saponins 12, 15, and 1822 were reported for the first time from the title plant. Their structures were elucidated on the basis of detailed spectroscopic analyses, including 1D- and 2D-NMR techniques, as well as acidic hydrolysis.

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.

Eighteen phenolic compounds, including eight flavonoids, five hydrolysable tannins, two lignans and three simple phenolic compounds were isolated on the leaves of Syzygium forrestii (Myrtaceae). Of them, nine compounds are new for the genus Syzygium , while three are new for the family Myrtaceae. The existence of acetylated glycosidic flavonoids in the genus Syzygium is firstly reported. Several flavonoid glycosides and hydrolysable tannins could be served as the chemotaxonomic markers of the genus Syzygium .

Ripe Pu-er tea, a special microbial postfermented tea originated from Yunnan Province, China, since ancient times, is made from green Pu-er tea prepared from the leaves of Camellia sinensis var. assamica (Theaceae). Chemical investigation on thearubigin (n-BuOH-soluble) fraction of the commercial ripe Pu-er tea, led to the identification of four new flavan-3-ol derivatives, 8-carboxymethyl-(+)-catechin (1), 8-carboxymethyl-(+)-catechin methyl ester (2), 6-carboxymethyl-(+)-catechin (3), and 6-carboxyl-(-)-gallocatechin (4), together with 18 known compounds, including other three flavan-3-ol derivatives (5-7), 10 flavonoid glycosides (8-17), two hydrolyzable tannins (18 and 19), two quinic acid derivatives (20-21), and a purine alkaloid (22). Flavonoid glycosides 8-11 are reported from tea plants for the first time. The thearubigin fraction of ripe Pu-er tea was qualitatively analyzed by HPLC, and gallic acid was found to be the major component. Compounds 4, 6-17, 21 and 22 were tested for their acute activities on insulin sensitivity in differentiated 3T3-L1 adipocytes, but none of them showed significant bioactivity at a concentration of 10 mu M.

During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1–G8 (1–8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6–G8 (6–8) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 6–9 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 ± 0.97 and 5.68 ± 1.75 μM towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.

Two new highly oxygenated limonoids, flexuosoids A (1) and B (2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D-F (3-5), were isolated from the roots of Phyllanthus flexuosus, in addition to three known lignans, phyllanthusmin C, arabelline, and (+)-diasyringaresinol. Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1 and 2, two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1, C-2, C-3, C-7, C-11, C-17, and C-30, represent the second example of limonoids in the Euphorbiaceae family. Most of the isolates were tested for their antifeedant, anti-herpes simplex virus 1, and cytotoxic activities. The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm (Spodoptera exigua) with EC50 values of 25.1 and 17.3 μg/cm(2), respectively. In addition, both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, along with the known lignan glycoside, phyllanthusmin C, with the IC50 values of 11.5 (1), 8.5 (2), and 7.8 (phyllanthusmin C) μM, respectively.Two new highly oxygenated limonoids, flexuosoids A (1) and B (2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D-F (3-5), were isolated from the roots of Phyllanthus flexuosus, along with three known lignans. Flexuosoids A (1) and B (2) showed promising antifeedant activity against the beet army worm (Spodoptera exigua) with EC50 values of 25.1 and 17.3 μg/cm(2), respectively. In addition, both of them and the known lignan glycoside, phyllanthusmin C, displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, with the IC50 values of 11.5, 8.5, and 7.8 μM, respectively.

6′-O-Caffeoylarbutin, an arbutin derivative, is a naturally occurring glucoside of hydroquinone from Vaccinium 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.

A novel C-C-coupled dimer derivative of bergenin was produced by the biotransformation of cultured mycelia of white rot fungus Pleurotus ostreatus. Its structure was elucidated by detailed spectroscopic analysis.

“Long-Dan” is an important traditional Chinese medicinal (TCM) herb used widely for the treatment of inflammation, hepatitis, rheumatism, cholecystitis, and tuberculosis. In the Chinese Pharmacopoeia, the roots and rhizomes of four species from the genus Gentiana (Gentianaceae) are recorded as the original materials of “Long-Dan”, called Gentianae Radix et Rhizoma. The species included G. manshurica, G. scabra, G. triflora and G. rigescens, which are distributed in different areas of China. Though iridoid and secoiridoid glucosides were reported as the main constituents in “Long-Dan”, these four different species also resulted in different minor components, which may related to their pharmacological activities. Herein, we summarized the herbal textual study, distribution, chemical constituents, biological investigation and quality control of the recorded “Long-Dan” origins in Chinese Pharmacopoeia during the period 1960 to 2011.