Tie-Jun Ling

New triterpenoids and other constituents from a special microbial-fermented tea-Fuzhuan brick tea.

Fuzhuan brick tea, a special microbial-fermented tea prepared from the leaves of Camellia sinensis var. sinensis, is a traditional beverage used in China throughout history. Phytochemical investigation of this material led to the identification of three new triterpenoids, 3beta,6alpha,13beta-trihydroxyolean-7-one (1), 3beta-acetoxy-6alpha,13beta-dihydroxyolean-7-one (2), and 3beta-O-(8-hydroxyoctanoyl)-12-oleanene (3), together with 11 known compounds, friedelin (4), beta-amyrone (5), beta-amyrin (6), alpha-spinasterone (7), alpha-spinasterol (8), 22,23-dihydro-alpha-spinasterone (9), 22,23-dihydro-alpha-spinasterol (10), alpha-phytol (11), alpha-tocopherol (12), alpha-tocoquinone (13), and caffeine (14). The structures of 1-13 were determined by spectroscopic and chemical methods. Compounds 1 and 2 are the first two examples of triterpenoids possessing a 6-hydroxy-7-one function. All of the compounds, except 6, 8, 10, 11, and 14, were isolated from tea and Camellia spp. for the first time. The antibacterial activities of 1 were assessed against some enteric pathogenic microbes. Compound 1 showed no cytotoxic activity against A-549, Bel-7402, and HCT-8 cell lines.

Changes of major tea polyphenols and production of four new B-ring fission metabolites of catechins from post-fermented Jing-Wei Fu brick tea

HPLC analysis of samples from four major fermentation procedures of Jing-Wei Fu brick tea showed that the level of major tea catechins epigallocatechin gallate (EGCG) and epicatechin gallate (ECG) dropped increasingly to about 1/3 in the final product. Phytochemical study of the final product led to the discovery of four new B-ring fission metabolites of catechins (BRFCs) Fuzhuanin C-F (1-4) together with three known BRFCs (5-7), six known catechins (8-13), five simple phenols (14-18), seven flavones and flavone glycosides (19-25), two alkaloids (26, 27), three triterpenoids (28-30) and one steroid (31). The structures were elucidated by spectroscopic methods including 1D and 2D NMR, LC-HR-ESI-MS, IR, and CD spectra. Five compounds (16-18, 28, 29) were reported for the first time in tea. Possible pathways for the degradation of major tea catechins and the generation of BRFCs were also provided.

Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia.

Four phenolics, salviaplebeiaside (1), γ-tocopherol (2), chrysosplenol-D (4), and isovitexin (5), along with α-tocoquinone (3) and β-sitosterol (6) were isolated from the aerial parts of Vitex negundo var. cannabifolia. The isolation was performed using bio-assay tracking experiments. The structures of compounds 1-5 were established by spectroscopic means. The antibacterial activities of the compounds were assessed against Escherichia coli, Bacillus subtilis, Micrococcus tetragenus and Pseudomonas fluorescens. Chrysosplenol-D (4) exhibited activities against all the four spoilage microorganisms.

Novel triterpenoid saponins from residual seed cake of Camellia oleifera Abel. show anti-proliferative activity against tumor cells.

Four oleanane-type triterpenoid saponins were isolated from the seed cake of Camellia oleifera Abel.: camelliasaponin B1 and three new saponins, oleiferasaponin C1-C3 (1-3). Their structures were identified as 22-O-angeloyl-camelliagenin B 3-O-[β-d-galactopyranosyl-(1→2)]-[β-d-galactopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosiduronic acid methyl ester (1); 22-O-angeloyl-camelliagenin A 3-O-[β-d-galactopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→3)]-β-d-glucopyranosiduronic acid methyl ester (2); and 28-O-cinnamoyl-camelliagenin B 3-O-[β-d-galactopyranosylz-(1→2)] [β-d-galactopyranosyl(1→2)-α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosiduronic acid methyl ester (3) through 1D and 2D NMR, HR-ESI-MS, as well as GC-MS spectroscopic methods. The anti-proliferative activities of these four compounds were investigated on five human tumor cell lines (BEL-7402, BGC-823, MCF-7, HL-60 and KB). Compounds 1 and 2 and camelliasaponin B1 showed significant cytotoxic activities.

A New Saponin from Tea Seed Pomace (Camellia oleifera Abel) and Its Protective Effect on PC12 Cells

A new triterpenoid saponin, oleiferasaponin A1, was isolated from tea seed pomace (Camellia oleifera Abel). The structure of oleiferasaponin A1 was elucidated on the basis of chemical and physicochemical evidence and was found to be 22-O-cis-2-hexenoyl-A1-barrigenol 3-O-[β-D-galactopyranosyl(1→2)] [β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid. PC12 cells injured with H2O2 were used as the model to test the protective effects of oleiferasaponin A1. The results indicated that oleiferasaponin A1 can potentially prevent the H2O2-induced cell death of PC12 cells.

TMDB: a literature-curated database for small molecular compounds found from tea.

BackgroundTea is one of the most consumed beverages worldwide. The healthy effects of tea are attributed to a wealthy of different chemical components from tea. Thousands of studies on the chemical constituents of tea had been reported. However, data from these individual reports have not been collected into a single database. The lack of a curated database of related information limits research in this field, and thus a cohesive database system should necessarily be constructed for data deposit and further application.DescriptionThe Tea Metabolome database (TMDB), a manually curated and web-accessible database, was developed to provide detailed, searchable descriptions of small molecular compounds found in Camellia spp. esp. in the plant Camellia sinensis and compounds in its manufactured products (different kinds of tea infusion). TMDB is currently the most complete and comprehensive curated collection of tea compounds data in the world. It contains records for more than 1393 constituents found in tea with information gathered from 364 published books, journal articles, and electronic databases. It also contains experimental 1H NMR and 13C NMR data collected from the purified reference compounds or collected from other database resources such as HMDB. TMDB interface allows users to retrieve tea compounds entries by keyword search using compound name, formula, occurrence, and CAS register number. Each entry in the TMDB contains an average of 24 separate data fields including its original plant species, compound structure, formula, molecular weight, name, CAS registry number, compound types, compound uses including healthy benefits, reference literatures, NMR, MS data, and the corresponding ID from databases such as HMDB and Pubmed. Users can also contribute novel regulatory entries by using a web-based submission page. The TMDB database is freely accessible from the URL of http://pcsb.ahau.edu.cn:8080/TCDB/index.jsp. The TMDB is designed to address the broad needs of tea biochemists, natural products chemists, nutritionists, and members of tea related research community.ConclusionThe TMDB database provides a solid platform for collection, standardization, and searching of compounds information found in tea. As such this database will be a comprehensive repository for tea biochemistry and tea health research community.

Fuzhuanins A and B: the B-ring fission lactones of flavan-3-ols from Fuzhuan brick-tea.

Fuzhuan brick-tea is a special dark tea prepared from the leaves of Camellia sinensis var. sinensis. Its production involves a fungal fermentation stage, which forms the unique flavors and functions by a series of biochemical reactions. Our phytochemical research of the material led to the isolation of two new B-ring fission lactones of flavan-3-ols, fuzhuanins A (1) and B (2). In addition, three other flavan-3-ol derivatives (3-5), three flavone C-glycosides (6-8), eight flavonoid O-glycosides (10-17), five simple phenolics (19-23), two norisoprenoid glycosides (24, 25), two sesquiterpenoids (26, 27), and theobromine (28), as well as two flavonoid anions (9 and 18), were also identified. The structures of these compounds were determined by spectroscopic methods. Compounds 4, 19, 20, 22-24, 26, and 27 were reported for the first time in Camellia spp. and tea. Furthermore, HPLC analysis method was performed to compare the chemical constituents of the before/after fungal fermentation Fuzhuan brick-teas. Compound 1 was indicated as one of the major characteristic constituents generated in the fungal fermentation process. The IC50 value of the antiproliferative activity of 2 on HeLa cells was assayed as 4.48 μM. None of the isolated compounds showed any inhibition activity against the enteric pathogenic microbes at 800 μg/mL by the hole plate diffusion method.

A New Norisoprenoid and Other Compounds from Fuzhuan Brick Tea

Fuzhuan brick tea, a kind of dark tea consumed mainly in the border regions of Southwestern and Northwestern China since the 1860s, is produced from the leaves of Camellia sinensis var. sinensis by microbial fermentation. From this special fermented tea, a new norisoprenoid, 3R,9R-oxido-5-megastigmene, was isolated, together with α-linolenic acid, strictin, isovitexin, astragalin, (+)-catechin, (−)-epicatechin, (−)-epicatechin gallate, (+)-gallocatechin, (−)-epigallocatechin, (−)-epigallocatechin gallate and gallic acid. The structures of the compounds were identified by spectroscopic means. The new compound didn’t show any inhibition activity against the tested enteric pathogenic microorganisms at a concentration of 800 μg/mL by the hole plate diffusion method.

Novel acetylcholinesterase inhibitors from Zijuan tea and biosynthetic pathway of caffeoylated catechin in tea plant

Zijuan tea is a special cultivar of Yunnan broad-leaf tea (Camellia sinensis var. assamica) with purple buds, leaves, and stems. Phytochemical study on this tea led to the discovery of three hydroxycinnamoylated catechins (HCCs) (1-3), seven other catechins (4-10), three proanthocyanidins (11-13), five flavones and flavone glycosides (14-18), two alkaloids (19, 20), one steroid (21), and one phenylpropanoid glycoside (22). The isolation and structural elucidation of the caffeoylated catechin (1) by means of spectroscopic techniques were described. We also provide the first evidence that 1 is synthesized via a two-step pathway in tea plant. The three HCCs (1-3) were investigated on their bioactivity through molecular modeling simulation and biochemical experiments. Our results show that they bind acetylcholinesterase (AChE) tightly and have strong AChE inhibitory activity with IC50 value at 2.49, 11.41, 62.26μM, respectively.

A new anti-proliferative acylated flavonol glycoside from Fuzhuan brick-tea

Abstract Fuzhuan brick-tea (FBT) is unique for a fungal fermentation stage in its manufacture process and is classified in dark tea. A new acylated flavonol glycoside, kaempferol 3-O-[E-p-coumaroyl-(→2)][α-l-arabinopyranosyl-(1→3)][α-l-rhamnopyranosyl(1→6)]-β-d-glucopyranoside, which was trivially named as camellikaempferoside A (1), was isolated from FBT along with camelliquercetiside C (2). Their structures were unambiguously elucidated by combination of spectroscopic and chemical methods. Compound 1 showed anti-proliferative activity against MCF-7 and MDA–MB-231 cells with IC50 values of 7.83 and 19.16 μM, respectively.