Diverse neolignans and lignans from an aqueous extract of the Angelica sinensis root head.

Neolignans and lignans with diverse new chemical structures, including eleven pairs of separated chiral enantiomers [(+)-/(-)-1-(+)-/(-)-5, (+)-/(-)-8, (+)-/(-)-10, and (+)-/(-)-12-(+)-/(-)-15], two achiral compounds (6 and 9), and an unseparated racemate [(±)-11], together with a new natural product (7) and 21 known derivatives, were isolated from an aqueous extract of the Angelica sinensis root head (guitou). Among the chiral isolates, (+)-/(-)-13 and (+)-/(-)-15 were scalemic pairs with enantiomeric ratios of around 3:1 and 1.5:1, respectively, while others were enantiomeric equivalent pairs. This indicates that the diverse neolignans in A. sinensis are biosynthesized via different pathways with varying degrees of stereo-controlled manners.

Sulfonated alkaloids from an aqueous extract of Isatis indigotica roots.

Eleven new sulfonated alkaloids (1 - 11) having diverse structures were isolated from an aqueous extract of the Isatis indigotica root (ban lan gen). Their structures were determined by spectroscopic data analysis, chemical method, and theoretical calculation, of which (-)-4 was proved by single crystal X-ray diffraction.

Divanillyl sulfone suppresses NLRP3 inflammasome activation via inducing mitophagy to ameliorate chronic neuropathic pain in mice.

BACKGROUND: Chronic neuropathic pain is a frequent sequel to peripheral nerve injury and maladaptive nervous system function. Divanillyl sulfone (DS), a novel structural derivative of 4,4'-dihydroxydibenzyl sulfoxide from a traditional Chinese medicine Gastrodia elata with anti-nociceptive effects, significantly alleviated neuropathic pain following intrathecal injection. Here, we aimed to investigate the underlying mechanisms of DS against neuropathic pain. METHODS: A chronic constrictive injury (CCI) mouse model of neuropathic pain induced by sciatic nerve ligation was performed to evaluate the effect of DS by measuring the limb withdrawal using Von Frey filament test. Immunofluorescence staining was used to assess the cell localizations and expressions of Iba-1, ASC, NLRP3, and ROS, the formation of autolysosome. The levels of NLRP3-related proteins (caspase-1, NLRP3, and IL-1ß), mitophagy-related proteins (LC3, Beclin-1, and p62), and apoptosis-related proteins (Bcl-XL and Bax) were detected by Western blotting. The apoptosis of BV-2 cell and caspase activity were evaluated by flow cytometry. RESULTS: DS significantly alleviated the neuropathic pain by increasing the mechanical withdrawal threshold and inhibiting the activation of NLRP3 in CCI-induced model mice. Our findings indicated that DS promoted the mitophagy by increasing the LC3II and Beclin 1 and decreasing the levels of p62 protein in BV-2 cell. This is accompanied by the inhibition of NLRP3 activation, which was shown as inhibited the expression of NLRP3 in lysates as well as the secretion of mature caspase-1 p10 and IL-1ß p17 in supernatants in cultured BV-2 microglia. In addition, DS could promote mitophagy-induced improvement of dysfunctional mitochondria by clearing intracellular ROS and restoring mitochondrial membrane potential. CONCLUSION: Together, our findings demonstrated that DS ameliorate chronic neuropathic pain in mice by suppressing NLRP3 inflammasome activation induced by mitophagy in microglia. DS may be a promising therapeutic agent for chronic neuropathic pain.

Minor triterpenes from an aqueous extract of the hook-bearing stem of Uncaria rhynchophylla.

Six new triterpenes, uncarinic acids KP (1-6), along with 24 known analogues, were isolated as minor constituents of an aqueous decoction of the hook-bearing stems of Uncaria rhynchophylla (Gou-teng). By comprehensive spectroscopic data analysis, their structures were elucidated as derivatives of olean-12-en-28-oic acid and urs-12-en-28-oic acid with different oxidized forms at C-3, C-6, and/or C-23, respectively. Cell-based preliminary bioassay showed that the (E)-/(Z)-coumaroyloxy and (E)-/(Z)-feruloyloxy units at C-27 of olean-12-en-28-oic acid and urs-12-en-28-oic acid played roles in their bioactivities.[Formula: see text].

Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata.

From an aqueous extract of "tian ma" (the steamed and dried rhizomes of Gastrodia elata), ten new compounds gastrodibenzins A-D (1-4) and gastrotribenzins A-F (5-10), along with known analogues (11-20), having structure features coupling between two and three p-hydroxybenzyl-derived units via carbon- and/or ether-bonds, were isolated and characterized by spectroscopic data analysis. Meanwhile, the new compounds 5a, 6a, 8a, 22, and 23, as well as the known derivatives 13a, 14a, 15, 17-21, 24, 25, and p-hydroxybenzyl aldehyde were isolated and identified from a refluxed aqueous solution of p-hydroxybenzyl alcohol. Methylation of 5a and 6a in methanol and ethylation of 6a, 8a, 13a, and 14a in ethanol produced 5 and 6 and 7, 8, 13, and 14, respectively. using ultra-performance liquid chromatography high-resolution electrospray ionization mass spectrometry (UPLC-HRESIMS) analysis of the refluxed solutions of p-hydroxybenzyl alcohol and the refluxed extracts of the fresh G. elata rhizome and "tian ma" extracts indicated consistent production and variation of the dimeric and trimeric derivatives of p-hydroxybenzyl alcohol upon extracting solvents and refluxing time. In various assays, the dimeric and trimeric derivatives showed more potent activities than p-hydroxybenzyl alcohol itself and gastrodin, which are the main known active constituents of "tian ma". These results revealed for the first time that the more effective dimers and trimers can be produced through condensation of the co-occurring p-hydroxybenzyl alcohol during processing and decocting of the G. elata rhizomes, demonstrating insights into medicinal chemistry behind application protocols of traditional Chinese medicines.

Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root.

From an aqueous decoction of the traditional Chinese medicine "ban lan gen" (the Isatis indigotica root), an antiviral natural product CI - 39 was isolated as an NNRTI (non-nucleoside reverse transcriptase inhibitor) (EC50 = 3.40 µM). Its novel structure was determined as methyl (1-methoxy-1H-indol-3-yl)acetamidobenzoate by spectroscopic data and confirmed by single crystal X-ray diffraction. Through synthesis and structure-activity relationship (SAR) investigation of CI - 39 and 57 new derivatives (24 with EC50 values of 0.06-8.55 µM), two optimized derivatives 10f and 10i (EC50: 0.06 µM and 0.06 µM) having activity comparable to that of NVP (EC50 = 0.03 µM) were obtained. Further evaluation verified that 10f and 10i were RT DNA polymerase inhibitors and exhibited better activities and drug resistance folds compared to NVP against seven NNRTI-resistant strains carrying different mutations. Especially, 10i (EC50 = 0.43 µM) was more active to the L100I/K103N double-mutant strain as compared to both NVP (EC50 = 0.76 µM) and EFV (EC50 = 1.08 µM). The molecular docking demonstrated a possible binding pattern between 10i and RT and revealed activity mechanism of 10i against the NNRTI-resistant strains.

Two folate-derived analogues from an aqueous decoction of Uncaria rhynchophylla.

Two new folate-derived analogues, named uncarophyllofolic acids A (1) and B (2), respectively, were isolated from the Uncaria rhynchophylla hook bearing stem (Gouteng in Chinese). The distinct stereochemical structures of 1 and 2 were determined by spectroscopic data analysis in combination with acidic hydrolysis and Marfey's derivatization, along with comparison of their specific rotation and Cotton effect (CE) data with those of the biogenetically related known derivatives as well as theoretical calculations of electronic circular dichroism (ECD) spectra. A plausible biosynthetic pathway of 1 and 2, associating to folate metabolism and the previously reported orychophragines A-C from Orychophragmus violaceus, is discussed.

Gastrodin Derivatives from Gastrodia elata.

Nine new gastrodin derivatives, including seven p-hydroxybenzyl-modified gastrodin ethers (1-7), 6'-O-acetylgastrodin (8), and 4-[α-D-glucopyranosyl-(1 →6)-ß-D-glucopyranosyloxy]benzyl alcohol (9), together with seven known derivatives, were isolated from an aqueous extract of Gastrodia elata ("tian ma") rhizomes. Their structures were determined by spectroscopic and chemical methods as well as single crystal X-ray diffraction. Compounds 1-4, 7, 10, and 11 were also isolated from a reaction mixture by refluxing gastrodin and p-hydroxybenzyl alcohol in H2O. As both gastrodin and p-hydroxybenzyl alcohol exist in the plant, the reaction results provide evidence for the production and increase/decrease of potential effective/toxic components when "tian ma" is decocted solely or together with ingredients in Chinese traditional medicine formulations, though the isolates were inactive in the preliminarily cell-based assays at concentrations of 10 µM. Moreover, using ultra-performance liquid chromatography high-resolution electrospray ionization mass spectrometry (UPLC-HRESIMS), 4, 7, 10, and 11, as well as component variations, were detectable in the freshly prepared extracts of different types of samples, including the freeze-dried fresh G. elata rhizomes.

Comparison of empirical therapy with cefoperazone/sulbactam or a carbapenem for bloodstream infections due to ESBL-producing Enterobacteriaceae.

Objectives: Carbapenems are widely recommended for the treatment of infections caused by ESBL producers however, non-carbapenem ß-lactams such as ß-lactam/ß-lactamase inhibitor combinations (BLBLIs) deserve consideration for the treatment of ESBL infections. Cefoperazone/sulbactam is one of the most commonly used BLBLIs in China; however, few outcome studies have been reported. In this study, we evaluated and compared the clinical efficacy of cefoperazone/sulbactam with that of a carbapenem in the treatment of bloodstream infections (BSIs) caused by ESBL-producing Enterobacteriaceae. Methods: Patients with monomicrobial ESBL-producing Enterobacteriaceae BSIs empirically treated with cefoperazone/sulbactam or a carbapenem were included. Outcomes of interest were clinical response and 14 day mortality. To make a comparison of the efficacy of cefoperazone/sulbactam and a carbapenem more accurate, propensity score analysis was performed. Results: No statistically significant differences in success rates or 14 day mortality were found between the cefoperazone/sulbactam (n = 17) and carbapenem (n = 46) groups. In the propensity score analysis with 17 case-control pairs, the success rate in the cefoperazone/sulbactam group (70.6%, 12/17) was lower than that in the carbapenem group (94.1%, 16/17), but the difference was not significant (P = 0.175). Sepsis-related mortality and 14 day mortality rates did not significantly differ either (P = 1.000 for both). In the cefoperazone/sulbactam group, 66.7% (2/3) of the patients with a Pitt bacteraemia score ≥5 died within 14 days, whereas none (0/14) of the patients with a Pitt bacteraemia score <5 died within 14 days (P = 0.022). Conclusions: This study showed that cefoperazone/sulbactam had a lower success rate and a higher 14 day mortality rate compared with carbapenems, although the differences were not statistically significant because of the small patient numbers. Further evaluation of cefoperazone/sulbactam is needed.

[Water soluble constituents from the twigs of Litsea cubeba].

Twenty five known aromatic glycosides (1-25) and three known sesquiterpene glycosides (26-28) have been isolated from the twigs of Litsea cubeba by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis (MS, IR, 1D and 2D NMR) as (7S,8R)-dehydrodiconiferyl alcohol 4,9'-di-O-ß-D-glucopyranoside(1),(7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside(2), (7S,8R)-urolignoside(3), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside(4), saposide B(5), lanicepside A(6), matairesinol-4-O-ß-D-glucopyranoside (7), tyraxjaponoside B(8), (+)-lyoniresinol-9'-O-ß-D-glucopyranoside (9), alaschanisoside A (10), syringin (11), psoralenoside (12), isopsoralenoside (13), scopolin(14), 2,6-dimethoxy-4-hydroxyphenol-1-O-ß-D-glucopyranoside (15), 3-hydroxy-4,5-dimethoxyphenyl-ß-D-glucopyranoside (16), 2-(3,4-dihydroxyphenyl)ethyl-ß-D-glucopyrnoside (17), 2-(4-dihydroxyphenyl)ethyl-ß-D-glucopyranoside (18), (+)-catechin-7-O-ß-D-glucopyranoside (19), 3'-O-methylepicatechin-7-O-ß-D-glucopyranoside (20), kaempferitrin (21), quercetin-3-O-α-L-rhamnopyranside (22), kaempferol-3-O-ß-D-glucopyranoside (23), kaempferol 3-O-ß-D-glucopyranosyl(1→2)-O-ß-D-galactopyr anoside-7-O-α-L-rhamnopyranoside (24), quercetin 3-O-α-L-rhamnopyranosyl(1→6)-O-ß-D-glucopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→2)-O-ß-D-glucopyranoside (25), staphylionoside D(26), vomifoliol 9-O-ß-D-glucopyranoside (27), dihydrovomifoliol-O-ß-D-glucopyranoside (28). Compounds 1-21 and 24-28 were obtained from this genus for the first time.

New Anti-HBV C-Boivinopyranosyl Flavones from Alternanthera philoxeroides.

C-boivinopyranosyl flavones have rarely been isolated from nature. In the search for anti-HBV (hepatitis b virus) constituents of Alternanthera philoxeroides, two new compounds, luteolin-6-C-ß-D-boivinopyranosyl-3'-O-ß-D-glucopyranoside (1) and chrysoeriol-6-C-ß-D-boivinopyranosyl-4'-O-ß-D-glucopyranoside (2), along with three known C-boivinopyranosyl flavones (compounds 3-5) were isolated. Their structures were determined by spectroscopic analyses including 1D and 2D NMR, HR-ESI-MS, IR spectra. Compounds 1, 2 and 3 showed significant anti-HBV activities through specifically inhibiting the secretion of HBsAg in HepG2.2.15.

[Lignanoids from an aqueous extract of the roots of Codonopsis pilosula].

Sixteen lignanoids were isolated from an aqueous extract of the commonly used Chinese traditional medicine Dangshen, the dried roots of Codonopsis pilosula, by using a combination of various chromatographic techniques, including silica gel, macroporous adsorbent resin, MCI resin, sephadex LH-20, and reversed phase semi-preparative HPLC. On the basis of spectral data analysis, their structures were elucidated and identified as（-）-（7R,7'R,8R,8'S）-4,4'-dihydroxy-3,3',5,5',7-pentamethoxy-2,7'-cyclolignane（1）,（-）-（7R,8S）- dihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranosyl-（1'''→2''）-ß-D-glucopyranoside（2）,（-）-（7R,8S）- dihydrodehydrodiconiferyl alcohol（3）,（+）-（7S,8R）-dehydrodiconiferyl alcohol（4）,（+）-balanophonin（5）,（+）- demethoxypinoresinol（6）,（+）-pinoresinol（7）,（+）-epipinoresinol（8）,（-）-syringaresinol（9）,（-）-medioresinol（10）,（-）-lariciresinol（11）,（-）-secoisolariciresinol（12）,（-）-ent-isolariciresinol（13）,（+）-（7S,8S）-3-methoxy-3',7- expoxy-8,4'-neolignan-4,9,9'-triol（14）,（+）-（7S,8R）-3',4-dihydroxy-3-methoxy-8,4'-neolignan（15）, and（-）-（7R,8R）-3',4-dihydroxy-3-methoxy-8,4'-neolignan（16）. All these compounds were isolated from C. pilosula for the first time, while compound 1 is a new natural product of 2,7'-cyclolignan and 2 is a new 4',7-epoxy- 8,3'-neolignan diglucoside. Compound 12 showed activity against Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation with an inhibition ratio of（63.4 ± 8.3） % at 1×10(-5) mol·L(-1).

[Chemical constituents from ethyl acetate exaction of root of Paeonia lactiflora].

Two new phenylpropanoids(1 and 2), together with thirteen known compounds(3-15), have been isolated from the root of Paeonia lactiflora by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis(MS,IR,1D and 2D NMR)as(+)-(7R,8R)-1-guaiacyl-1,2-propanediolacetonide(1),(-)-(7R,8S)-1-guaiacyl-1,2-propanediolacetonide(2),O-senecioyllomatin(3),O-angeloyllomatin(4),(+)-cis-3'-senecioyloxy-4'-angeloyloxy-3',4'-dihydroseselin(5),columbianadin(6), benzyl 2,5-dihydroxybenzoate(7),3,6-dimethyl-5-hydroxyBenzo-furan(8),(S)-evofolin-A(9),2,3-dihydroxy-4-methoxyacetophenone(10), 2,5-dihydroxy-4-methoxyacetophenone(11), 2,5-dihydroxy-4-methyl acetophenone(12),ethyl 4-hydroxybenzoate(13), vanillic acid(14),and 4-hydroxy-3-methoxybenzaldehyde(15).Compounds 1 and 2 were new compounds,and compounds 3-9 were obtained from the genus Paeonia for the first time.

Emergence of tigecycline- and carbapenem-nonsusceptible Klebsiella pneumoniae ST11 clone in patients without exposure to tigecycline.

BACKGROUND/PURPOSE: Currently, tigecycline-nonsusceptible Klebsiella pneumoniae (TNSKP) is mainly reported to emerge following clinical use of tigecycline and is usually polyclonal. This study aimed to characterize TNSKP isolated from patients without prior tigecycline use. METHODS: Twenty-six TNSKP clinical isolates were collected, and carbapenemase and 16S rRNA methylase genes were identified by polymerase chain reaction and sequencing. Molecular typing was conducted by pulsed-field gel electrophoresis (PFGE) and multilocus sequence typing (MLST). Clinical data of patients in the carbapenem-susceptible TNSKP group and the tigecycline- and carbapenem-nonsusceptible K. pneumoniae (TCNSKP) group were compared. RESULTS: Of the 26 TNSKP isolates, eight contained both blaKPC-2 and 16S rRNA methylase genes. In the remaining 18 TNSKP isolates, no carbapenemase gene was detected, and only three had the 16S rRNA methylase gene. Among the 26 isolates, 24 distinct pulsotypes and 19 sequence types (STs) were identified by PFGE and MLST, respectively. Six of the eight TCNSKP were ST11, whereas the remaining 18 TNSKP isolates were assigned to 17 different STs. No patient received tigecycline prior to the isolation of TNSKP. By comparison, intensive care unit exposure, mechanical ventilation, prior ß-lactam/ß-lactamase use, and longer hospitalization were more common for the TCNSKP group than for the carbapenem-susceptible TNSKP group. CONCLUSION: TNSKP can occur without tigecycline use, and TCNSKP ST11 is predominant among them. Further, this report proposes potential risk factors for the occurrence of carbapenem-nonsusceptibility in TNSKP.

Shifts in the Antibiotic Susceptibility, Serogroups, and Clonal Complexes of Neisseria meningitidis in Shanghai, China: A Time Trend Analysis of the Pre-Quinolone and Quinolone Eras.

BACKGROUND: Fluoroquinolones have been used broadly since the end of the 1980s and have been recommended for Neisseria meningitidis prophylaxis since 2005 in China. The aim of this study was to determine whether and how N. meningitidis antimicrobial susceptibility, serogroup prevalence, and clonal complex (CC) prevalence shifted in association with the introduction and expanding use of quinolones in Shanghai, a region with a traditionally high incidence of invasive disease due to N. meningitidis. METHODS AND FINDINGS: A total of 374 N. meningitidis isolates collected by the Shanghai Municipal Center for Disease Control and Prevention between 1965 and 2013 were studied. Shifts in the serogroups and CCs were observed, from predominantly serogroup A CC5 (84%) in 1965-1973 to serogroup A CC1 (58%) in 1974-1985, then to serogroup C or B CC4821 (62%) in 2005-2013. The rates of ciprofloxacin nonsusceptibility in N. meningitidis disease isolates increased from 0% in 1965-1985 to 84% (31/37) in 2005-2013 (p < 0.001). Among the ciprofloxacin-nonsusceptible isolates, 87% (27/31) were assigned to either CC4821 (n = 20) or CC5 (n = 7). The two predominant ciprofloxacin-resistant clones were designated ChinaCC4821-R1-C/B and ChinaCC5-R14-A. The ChinaCC4821-R1-C/B clone acquired ciprofloxacin resistance by a point mutation, and was present in 52% (16/31) of the ciprofloxacin-nonsusceptible disease isolates. The ChinaCC5-R14-A clone acquired ciprofloxacin resistance by horizontal gene transfer, and was found in 23% (7/31) of the ciprofloxacin-nonsusceptible disease isolates. The ciprofloxacin nonsusceptibility rate was 47% (7/15) among isolates from asymptomatic carriers, and nonsusceptibility was associated with diverse multi-locus sequence typing profiles and pulsed-field gel electrophoresis patterns. As detected after 2005, ciprofloxacin-nonsusceptible strains were shared between some of the patients and their close contacts. A limitation of this study is that isolates from 1986-2004 were not available and that only a small sample of convenience isolates from 1965-1985 were available. CONCLUSIONS: The increasing prevalence of ciprofloxacin resistance since 2005 in Shanghai was associated with the spread of hypervirulent lineages CC4821 and CC5. Two resistant meningococcal clones ChinaCC4821-R1-C/B and ChinaCC5-R14-A have emerged in Shanghai during the quinolone era. Ciprofloxacin should be utilized with caution for the chemoprophylaxis of N. meningitidis in China.

[Aporphine alkaloids from Litsea greenmaniana].

A new aporphine alkaloid (1), together with five known analogues (2-6), has been isolated from the branch of Litsea greenmaniana by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis ( MS, IR, 1D and 2D NMR) as 2,9-dihydroxy-1,10-dimethoxy-4,5-dihydro-7-oxoaporphine (1), laurotetanine (2), N-methyllaurotetanine (3), isodomesticine (4), isocorydine (5), and norisocorydine (6). Compound 1 was a new compound, and compounds 2-6 were obtained from this plant for the first time.

[Studies on chemical constituents of aqueous extract of Lonicera japonica flower buds].

From an aqueous extract of Lonicera japonica flower buds, sixteen compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as 6'-O-acetylvogeloside (1), 6'-O-acetylsecoxyloganin (2), dichlorogelignate (3), guanosinyl-(3' --> 5')-adenosine monophosphate(GpA,4) , 5'-O-methyladenosine (5), 2'-O-methyladenosine (6), adenosine (7), syringin (8), methyl 4-O-ß-D-glucopyranosyl caffeate (9), (-)-dihydrophaseic acid 4'-O-ß-D-glucopyranoside (10), ketologanin (11), 7α-morroniside (12), 7ß-morroniside (13), kingiside (14), cryptochlorogenic acid methyl ester (15), and 6-hydroxymethyl-3-pyridinol (16). All the compounds were obtained from this plant for the first time, compounds 1 and 2 are new compounds, 3 and 5 are new natural products, and 4 is the first example of dinucleoside monophosphate isolated from a plant extract.

Aromatic acid derivatives from the lateral roots of Aconitum carmichaelii.

Seven new aromatic acid derivatives (1-7), together with five known analogs, were isolated from the lateral roots of Aconitum carmichaelii. Structures of the new compounds were determined by spectroscopic and chemical methods as 4-methyl ( - )-(R)-hydroxyeucomate (1), 4-butyl ( - )-(R)-hydroxyeucomate (2), 4-butyl-1-methyl (+)-(R)-2-O-(4'-hydroxy-3'-methoxybenzoyl)malate (3), 1-butyl-4-methyl (+)-(R)-2-O-(4'-hydroxy-3'-methoxybenzoyl)malate (4), dimethyl (+)-(R)-2-O-(4'-hydroxy-3'-methoxybenzoyl)malate (5), dimethyl (+)-(R)-2-O-(4'-hydroxybenzoyl)malate (6), and methyl ( ± )-3-(4'-hydroxy-3'-methoxyphenyl)-3-sulfopropionate (7), respectively. Compounds 1 and 2 are 2-benzylmalates (eucomate derivatives), 3-6 belong to 2-O-benzoylmalates, and 7 is a rare phenylpropionate containing a sulfonic acid group. The absolute configurations of eucomate derivatives were confirmed by X-ray crystallographic analysis of 4-methyl eucomate (11).

[Chemical constituents from Litsea greenmaniana].

A new compound (1), together with ten known compounds (2-11), have been isolated from the branch of Litsea greenmaniana by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis as N-trans-3, 4-methylenecinnamoyl-3-methoxytyramine (1), N-trans-feruloyltyramine (2), N-cis-feruloyltyramine (3), (+)-sesamin (4), (+)-pinoresinol(5), cinnamophilin (6), dihydrodehydrodiconiferyl alcohol (7), benzoic acid (8), 4-hydroxy ethylbenzoate (9), p-hydroxybenzaldehyde(10), and 4-hydroxy-3-methoxy-benzyl alcohol (11). Compound 1 was a new compound, and compounds 2-11 were obtained from this plant for the first time.

[Chemical constituents from aqueous extract of Gastrodia elata].

Two new compounds (1 and 2), together with twenty-one known compounds (3-23), were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic data analysis as 4-hydroxy-3-(4-hydroxybenzyl) benzyl methyl ether (1), 4-( methoxymethyl) phenyl-1-O-beta-D-glucopyranoside (2), hibicutaiwanin (3), 4-(4-hydroxybenzyl)-2-methoxyphenol (4), 4,4'-methylenebis(2-methoxyphenol) (5), L-phenyllactic acid (6) ,4-hydroxy-3-methoxybenzyl ethol ether (7), p-hydroxylbenzyl alcohol (8), p-hydroxylbenzyl methyl ether (9), p-hydroxylbenzyl ethyl ether (10), p-hydroxybenzaldehyde (11), p-hydroxybenzoic acid (12), p-hydroxybenzoic acid (13), gastrodin (14), 4-(ethoxymethyl) phenyl-1-O-beta-D-glucopyranoside (15), 4-(beta-D-glucopyranosyloxy) benzaldehyde (16), p-methylphenyl-1-O-beta-D-glucopyranoside (17 ), methyl-O-beta-D-glucopyranoside (18), 5-hydroxymethl-furan aldehyde (19), parishin (20), parishin B (21), parishin C (22), and diosgenin (23). The 13C-NMR data of compound 4 was first reported.