Hippophae rhamnoides L.: A Comprehensive Review on the Botany, Traditional Uses, Phytonutrients, Health Benefits, Quality Markers, and Applications.

Hippophae rhamnoides L. (sea buckthorn), consumed as a food and health supplement worldwide, has rich nutritional and medicinal properties. Different parts of H. rhamnoides L. were used in traditional Chinese medicines for relieving cough, aiding digestion, invigorating blood circulation, and alleviating pain since ancient times. Phytochemical studies revealed a wide variety of phytonutrients, including nutritional components (proteins, minerals, vitamins, etc.) and functional components like flavonoids (1-99), lignans (100-143), volatile oils (144-207), tannins (208-230), terpenoids (231-260), steroids (261-270), organic acids (271-297), and alkaloids (298-305). The pharmacological studies revealed that some crude extracts or compounds of H. rhamnoides L. demonstrated various health benefits, such as anti-inflammatory, antioxidant, hepatoprotective, anticardiovascular disease, anticancer, hypoglycemic, hypolipidemic, neuroprotective, antibacterial activities, and their effective doses and experimental models were summarized and analyzed in this paper. The quality markers (Q-markers) of H. rhamnoides L. were predicted and analyzed based on protobotanical phylogeny, traditional medicinal properties, expanded efficacy, pharmacokinetics and metabolism, and component testability. The applications of H. rhamnoides L. in juice, wine, oil, ferment, and yogurt were also summarized and future prospects were examined in this review. However, the mechanism and structure-activity relationship of some active compounds are not clear, and quality control and potential toxicity are worth further study in the future.

New compounds from the stems of Fissistigma acuminatissimum Merr. and their in vitro anti-inflammatory activity.

Three new compounds, 4,5,6,7-tetramethoxy-3-benzoylbenzofuran (1), 4-hydroxy-3,5,6-trimethoxydihydrochalcone-2-O-ß-D-glucopyranoside (2) and 2-hydroxy-3,4,5,6-tetramethoxyphenylethyl benzoate (3) along with five known flavonoids were isolated from the dichloromethane fraction of the stems of Fissistigma acuminatissimum Merr.'s ethanol extracts. The compounds were obtained by chromatographic methods and the structure elucidation was completed primarily on the basis of spectroscopic analyses, all of these compounds were isolated from F. acuminatissimum for the first time. All the fractions and compounds were evaluated for their anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated tumor necrosis factor α (TNF-α) production in RAW264.7 cells in vitro. The dichloromethane fraction showed the most potent inhibition(38.2%) at 60 µg/mL, compound 1 (70.2%) and 3 (65.2%) showed significant inhibition at 10 µM.

α-Pyrones with glucose uptake-stimulatory activity from the twigs of Cryptocarya wrayi.

Five new α-pyrones, cryptowratones A-E (1-5), and five known congeners (6-10), together with four other known compounds 11-14 were isolated from the twigs of Cryptocarya wrayi. The structures of the new compounds were elucidated on the basis of extensive spectroscopic data analysis and ECD calculations. All α-pyrones except 6 were evaluated for their stimulatory effects on glucose uptake in vitro with CHO-K1/GLUT4 cells. The positive control insulin displayed an approximate 42 ± 0.14% promotion on glucose uptake at 25 µM, compared with the CHO-K1/GLUT4 group. Compounds 1a/2a, 2, 3, and 10 showed a more significant stimulation of glucose uptake than insulin (25 µM) by 36 ± 0.08%, 27 ± 0.12%, 28 ± 0.12%, and 25 ± 0.12% at 1.5 µM, respectively. Immunofluorescence assays indicated the glucose uptake-stimulatory activity of α-pyrones might be correlated with increased GLUT4 translocation.

Melanoxylonin A-G, neoflavonoids from the heartwood of Dalbergia melanoxylon and their cardioprotective effects.

Seven undescribed neoflavonoids, named melanoxylonins A-G, were isolated from the heartwood of Dalbergia melanoxylon, and all the non-toxic isolates were evaluated for their cardioprotective effect against ischemia/reoxygenation (I/R) injury in H9c2 cells. Of these, melanoxylonin A-D containing the 8-OH group showed better potent cardioprotective effects than the other four congeners. Molecular docking studies confirmed the capacity of melanoxylonin D to interact with the myeloperoxidase (MPO) protein. These results indicated that the potential cardioprotective effects of melanoxylonin D in H9c2 cells with I/R injury may be imparted through suppression of MPO. These results may provide a new medicinal usage of D. melanoxylon.

Gallic acid activates hippocampal BDNF-Akt-mTOR signaling in chronic mild stress.

Gallic acid (3,4,5-trihydroxybenzoic acid) is a naturally occurring polyphenolic compound. Previous study has shown that gallic acid possessed significant antidepressant-like activity in mice, which was partly mediated by increasing serotonin and catecholamine levels. The main aim of the present study is to investigate the possible effects of gallic acid on brain-derived neurotrophic factor (BDNF) signaling activation. Mice were exposed to chronic mild stress (CMS) and orally administrated with gallic acid for four weeks. The behavioral results showed that gallic acid not only reversed the decreased sucrose preference, but also attenuated the increased immobility time. In addition, gallic acid promoted both the BDNF and p-TrkB levels in the hippocampus induced by CMS. Moreover, the results also demonstrated that the inactivated Akt-mTOR signaling pathway, as well as its downstream effectors induced by CMS was activated again by gallic acid. Last, immunofluorescence detection indicated that gallic acid reversed the newborn neurons inhibition in the dentate gyrus by CMS. In conclusion, these results show that the activation of the hippocampal BDNF-Akt-mTOR signaling is involved in the antidepressant-like effects of gallic acid.

[Two new compounds from Smilax glaucochina].

A new sesquiterpenes named glaucochinarol A (1) and a new phenylpropane glycoside named glcacochinaside A (2), together with six known ones, including trichothecolone (3), ß-D-(6-O-trans-feruloyl)fructofuranosyl-α-D-O-glucopyranoisde (4), 3,4,5-trimethoxyphenyl-ß-D-glucopyranoside (5), (4R)-p-menth-1-ene-7,8-diol-7-O-ß-D-glucopyranoside (6), naringenin (7), and emodin-8-O-ß-glucoside (8) were isolated from smilax glaucochina warb. Their structures were elucidated on the basis of NMR, MS and published data. Compounds 3-8 were isolated from the species for this first time.

Distinguishing Smilax glabra and Smilax china rhizomes by flow-injection mass spectrometry combined with principal component analysis.

Flow-injection mass spectrometry (FIMS) coupled with a chemometric method is proposed in this study to profile and distinguish between rhizomes of Smilax glabra (S. glabra) and Smilax china (S. china). The proposed method employed an electrospray-time-of-flight MS. The MS fingerprints were analyzed using principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) with the aid of SIMCA software. Findings showed that the two kinds of samples perfectly fell into their own classes. Further predictive study showed desirable predictability and the tested samples were successfully and reliably identified. The study demonstrated that the proposed method could serve as a powerful tool for distinguishing between S. glabra and S. china.

Six new furostanol glycosides from Smilax glauco-china and their cytotoxic activity.

Six new steroidal saponins, namely glauco-chinaosides A-F, and one known compound were isolated from the tubers of Smilax glauco-china. Their structures were elucidated by a combination of spectroscopic analysis and hydrolysis followed by spectral and chromatographic analysis. Compounds 1-7 were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, and Lovo). Compounds 1, 2, and 5 exhibited cytotoxic activity against SGC-7901, with IC50 values of 2.7, 11.5, and 6.8 µM, respectively.

Chemical composition and antioxidant activities of essential oils from different parts of the oregano.

This research was undertaken in order to characterize the chemical compositions and evaluate the antioxidant activities of essential oils obtained from different parts of the Origanum vulgare L. It is a medicinal plant used in traditional Chinese medicine for the treatment of heat stroke, fever, vomiting, acute gastroenteritis, and respiratory disorders. The chemical compositions of the three essential oils from different parts of the oregano (leaves-flowers, stems, and roots) were identified by gas chromatography-mass spectrometry (GC-MS). The antioxidant activity of each essential oil was assessed using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay and reducing the power test. Among the essential oils from different parts of the oregano, the leaf-flower oils have the best antioxidant activities, whereas the stem oils are the worst. The results of the DPPH free radical scavenging assay showed that the half maximal inhibitory concentration (IC50) values of the essential oils were (0.332±0.040) mg/ml (leaves-flowers), (0.357±0.031) mg/ml (roots), and (0.501±0.029) mg/ml (stems), respectively. Interestingly, the results of reducing the power test also revealed that when the concentration exceeded 1.25 mg/ml, the leaf-flower oils had the highest reducing power; however, the stem oils were the lowest.

A novel phloroglucinol and two new phenolic glycosides from Psidium littorale.

One novel phloroglucinol, psidosone A (1), and two new phenolic glycosides, psidoside A (2), and psidoside B (3), together with nine known phenol compounds (4-12), were isolated from the fruits of Psidium littorale Raddi. Their structures were elucidated using data obtained from MS, 1H and 13C NMR spectra, and correlation experiments (HMQC and HMBC), as well as by comparison with published data.

[Flavonoids from leaves of Psidum littorale].

We investigated the chemical constituents of the leaves of Psidum littorale, which include 16 flavonoids, including seven flavonols, six flavonoid glycosides and three flavonones. The compounds were isolated by silica gel column chromatography. Their structures were elucidated on the basis of spectral analysis and by comparison with published data. Seven flavonols were kaempferol (1), isorhamnetin (2), myricetin- 3,7,3'-trimethyl ether(3), laricitrin (4), quercetin (5), myricetin (6) and quercein-3,4'-dimethyl ether (7), six flavonoid glycosides were guaijaverin (8), hyperoside (9), 5,4'-dyhydroxy-3,7,5'-methoxyflavone-3'-O-ß-D- glucoside (10), laricitrin-3-O-xyloside (11), myricetin-3-O-α-L-rhamnopyranoside (12) and myricetin-3-O-ß-D- xyloside (13). Three flavonones were 4'-O-methyldihydroquercetin (14), dihydroapigenin (15) and ampelopsin 4'-O-ß-D-glucopyranoside (16). Compound 10 is a new chemical, compounds 2-4, 7, 10-16 were first isolated from this plant. (1)H NMR and (13)C NMR data of compound 11 were not reported in literature.

[Studies on chemical constituents of rhizomes of Smilax trinervula].

The chemical constituents were separated and purified from the 70% ethanol extract of Smilax trinervulaby various chromatographic methods including silica gel, Sephadex LH-20, MCI and preparative HPLC. Their structures were obtained and identified by analysis of the spectroscopic data. Compounds 1-11 were separated from this genus for the first time. Compound 12 was obtained from S. trinervula for the first time.

Research progress of bioactivity of steroidal saponins in recent ten years.

Steroidal saponins have a wide range of pharmacological effects and biological activities, such as anti-tumor, antifungal, hypoglycemic, immune regulation, insecticides, etc. In the last ten years, some new structures of steroidal saponins compounds were found from natural plants, they have some new and different activities. In order to accelerate the research on the drug innovation of steroidal saponins, we summarized the new progress of the research on such compounds.

[Quality control of Maca (Lepidium meyenii)].

To control the quality of Maca, the quality standard was established in this study. According to the methods recorded in the Appendix of Chinese Pharmacopoeia (2010 Edition), the water, extract, total ash, acid insoluble substance, and heavy metals inspections in Lepidium meyenii were carried out. N-benzyl-9Z, 12Z-octadecadienamide in L. meyenii was identified by TLC, and it was determined by HPLC. The results showed that the N-benzyl-9Z, 12Z-octadecadienamide identification of TLC was a strong mark and specificity. In content determination experiment, the linearity of N-benzyl-9Z, 12Z-octadecadienamide was in the range of 0.01-2 microg (r = 0.9998), and the average recovery (n=9) was 99.27% (RSD 2.0%). The methods were simple, accurate, with good reproducibility. It is suitable for quality control L. meyenii.

A new alkaloid from the fruit of Nandina domestica Thunb.

A new steroidal alkaloid, (20S,22R,24R)-24-ethyl-3-oxocholest-4-en-22-amino, named as nandsterine (1), together with 10 known alkaloids, palmatine (2), O-methylbulbocapnine (3), nantenine (4), dehydronantenine (5), glaucine (6), didehydroglaucine (7), dehydrocorydaline (8), jatrorrhizine (9), magnoflorine (10) and berberine (11), was isolated from the fruit of Nandina domestica Thunb. Their structures were elucidated by using spectroscopic methods as well as by comparing with the published data. Compound 1 was a new class of steroidal alkaloid isolated from the family Berberidaceae, meanwhile compounds 2, 3, 6-8 and 10 were obtained from N. domestica for the first time. Compound 1 exhibited cytotoxicity against HL-60 cells (human leukaemia) with IC50 values of 52.1 µM.

[Study on Megastigmane Glycosides and Lignan Constituents from Leaves of Psidium littorale].

OBJECTIVE: To study the chemical constituents of the leaves of Psidium littorale. METHODS: The constituents were isolated with silica gel column chromatography and the structures of these compounds were elucidated on the basis of spectral analysis. RESULTS: Four megastigmane glycosides and three lignans were isolated and their structures were identified as Bridelionoside B(1), Euodinoside E(2), (3S,5R,6R,7E,9S)-Megastignan-7-ene-3,5,6,9-tetrol 9-O-ß-D-glucopyranoside (3), Bridelionoside C(4), (--)-Isolaricires-inol 3-α-O-ß-D-glucopyranoside (5), (--)-5'-methoxy-Isolariciresinol 3-α-O-ß-D-glucopyranoside (6) and dihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside(7). CONCLUSION: Compounds 1-7 are isolated from this plant for the first time. The results have provided the scientific basis for further exploitation of Psidium littoratle.

[Study on the diterpenoids of Tripterygium wilfordii by electrospray ionization tandem and electron impact mass spectrometry].

OBJECTIVE: To study the diterpenoids of Tripterygium wilfordii by electrospray ionization tandem (ESI) and electron impact (EI) mass spectrometry and establish the methods for quickly and on line identification of these diterpenoids. METHODS: The diterpenoids were analyzed by ESI-MS and EI-MS under positive ion model. RESULTS: In ESI-Trap-MS (+) model, the quasi-molecular ions [M + H] + of the diterpenoids took place bond cleavage and generally lost neutral molecules such as H2O, CH2CHCH3, CO and CH2CO, then generated characteristic fragment ion series (m/z 197, 183, 169). In ESI-TOF-MS (+) model, the quasi-molecular ions [M + H] + of the diterpenoids took place bond cleavage and generally lost neutral molecules such as H2O, CO, then generated characteristic fragment ion series (m/z 277, 185, 93). In EI-MS model, the molecular ions of the diterpenoids took place bond cleavage and generally lost neutral molecules such as H2O, CO, CH4, and isopropyl radical, then generated characteristic fragment ion series (m/z 149, 105, 91, 71, 55, 43). CONCLUSION: The ESI-MS and EI-MS characteristics of diterpenoids of Tripterygium wilfordii are reported for the first time. Based on these characteristics, the methods for quickly and on line identification of diterpenoids are established.

A new triterpenoid from Verbena officinalis L.

To investigate the chemical constituents of Verbena officinalis L., five triterpenoid constituents were isolated and elucidated as 3α,19,23-trihydroxyurs-12-en-28-oic acid, namely, 4-epi-barbinervic acid (1), 2α,3ß-dihydroxyurs-12-en-28-oic acid (2), 3α,24-dihydroxyurs-12-en- 28-oic acid (3), 3α,24-dihydroxy-olean-12-en-28-oic acid (4), ursolic acid (5), using spectroscopic methods and comparing with published data. Compounds 2 and 4 were obtained from V. officinalis for the first time, and compound 1 is a new triterpenoid compound, which exhibits significantly higher antitumor activity against human hepatoma cell line Bel 7402 in vitro than the blank control.

Steroidal saponins and pregnane glycosides from Smilax microphylla.

Six steroidal saponins and two pregnane glycosides were isolated from the BuOH subfraction of 70% EtOH extract of Smilax microphylla C.H.Wright, among them two were new compounds (1 and 7). Pregnane glycosides were firstly isolated from the genus Smilax (Smilacaceae). Structures of the new compounds were determined on the basis of HR-ESI-MS, 1D and 2D NMR spectroscopic analysis.

One new diphenylmethane glycoside from the leaves of Psidium guajava L.

To investigate the chemical constituents of Psidium guajava L, the EtOH/H(2)O extract of the fresh leaves was subjected to various chromatography. One diphenylmethane, one benzophenone, and eight flavonoids were isolated and elucidated as 2,6-dihydroxy-3-formaldehyde-5-methyl-4-O-(6″-O-galloyl-ß-D-glucopyranosyl)-diphenylmethane (1), 2,6-dihydroxy-3,5-dimethyl-4-O-(6″-O-galloyl-ß-D-glucopyranosyl)-benzophenone (2), kaempferol (3), quercetin (4), quercitrin (5), isoquercitrin (6), guaijaverin (7), avicularin (8), hyperoside (9), reynoutrin (10) by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS spectrometry as well as by comparison with published data. Compounds 5 and 10 are obtained from P. guajava for the first time, and compound 1 is a new diphenylmethane compound.