Minor alkaloids from an aqueous extract of the hook-bearing stem of .

Seven new monoterpene alkaloids (-), along with 16 known analogues, were isolated from an aqueous decoction of the hook-bearing stems of (Gou-teng). Their structures were determined by spectroscopic data analysis, single crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds and are stereoisomers belonging to a novel type of pseudoindoxyl monoterpene alkaloids, is the first monoterpene furoindole alkaloid from nature, and - are derivatives of the known monoterpene alkaloids featuring different structures.

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

Neolignans and lignans with diverse new chemical structures, including eleven pairs of separated chiral enantiomers [(+)-/(-)--(+)-/(-)-, (+)-/(-)-, (+)-/(-)-, and (+)-/(-)--(+)-/(-)-], two achiral compounds ( and ), and an unseparated racemate [(±)-], together with a new natural product () and 21 known derivatives, were isolated from an aqueous extract of the root head (guitou). Among the chiral isolates, (+)-/(-)- and (+)-/(-)- were scalemic pairs with enantiomeric ratios of around 3:1 and 1.5:1, respectively, while others were enantiomeric equivalent pairs.

Lignans and a neolignan from an aqueous extract of roots.

Four new lignans (-) and one new neolignan (), along with two known lignan derivatives ( and ), were isolated from an aqueous extract of the root (ban lan gen). Their structures were determined by spectroscopic data analysis, chemical method, and theoretical calculation, for which was proved by single-crystal X-ray diffraction. Compound exhibited antiviral activity against influenza virus A/Hanfang/359/95 (H3N2) with an IC value of 11.

Sulfonated alkaloids from an aqueous extract of roots.

Eleven new sulfonated alkaloids () 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 (-)- was proved by single crystal X-ray diffraction.

Minor monoterpene derivatives from an aqueous extract of the hook-bearing stem of .

Seven new minor monoterpene derivatives (), together with six known analogues, were isolated from an aqueous decoction of the hook-bearing stems of (Gou-teng). Their structures were determined by spectroscopic data analysis and electronic circular dichroism (ECD) calculations, of which was confirmed 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.

Denudatine-type diterpenoid alkaloids from an aqueous extract of the lateral root of .

Five new denudatine-type diterpenoid alkaloids (1-5), along with the known analogue aconicarmine (), were isolated from an aqueous decoction of the lateral roots of (fu-zi). Their structures were determined by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Compound is the first denudatine-type diterpenoid alcohol iminium alkaloid, which could be partially transformed into the aza acetal form in pyridine-.

Minor alkaloids from an aqueous extract of the hook-bearing stem of .

Seven new monoterpene alkaloids (-), along with 18 known analogues, were isolated from an aqueous decoction of the hook-bearing stems of (Gou-teng). Their structures were determined by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Compound is the first monoterpene 22-norindoloquinolizidine alkaloid with a ketene unit, while and are unusual indoloquinolizidine alkaloids having an oxazinane ring.

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

Six new triterpenes, uncarinic acids KP (), along with 24 known analogues, were isolated as minor constituents of an aqueous decoction of the hook-bearing stems of (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 ()-/()-coumaroyloxy and ()-/()-feruloyloxy units at C-27 of olean-12-en-28-oic acid and urs-12-en-28-oic acid played roles in their bioactivities.

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)-β-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 HO.

[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-β-D-glucopyranoside(1),(7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(2), (7S,8R)-urolignoside(3), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(4), saposide B(5), lanicepside A(6), matairesinol-4-O-β-D-glucopyranoside (7), tyraxjaponoside B(8), (+)-lyoniresinol-9'-O-β-D-glucopyranoside (9), alaschanisoside A (10), syringin (11), psoralenoside (12), isopsoralenoside (13), scopolin(14), 2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside (15), 3-hydroxy-4,5-dimethoxyphenyl-β-D-glucopyranoside (16), 2-(3,4-dihydroxyphenyl)ethyl-β-D-glucopyrnoside (17), 2-(4-dihydroxyphenyl)ethyl-β-D-glucopyranoside (18), (+)-catechin-7-O-β-D-glucopyranoside (19), 3'-O-methylepicatechin-7-O-β-D-glucopyranoside (20), kaempferitrin (21), quercetin-3-O-α-L-rhamnopyranside (22), kaempferol-3-O-β-D-glucopyranoside (23), kaempferol 3-O-β-D-glucopyranosyl(1→2)-O-β-D-galactopyr anoside-7-O-α-L-rhamnopyranoside (24), quercetin 3-O-α-L-rhamnopyranosyl(1→6)-O-β-D-glucopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranoside (25), staphylionoside D(26), vomifoliol 9-O-β-D-glucopyranoside (27), dihydrovomifoliol-O-β-D-glucopyranoside (28). Compounds 1-21 and 24-28 were obtained from this genus for the first time.

Diglycosidic indole alkaloid derivatives from an aqueous extract of Isatis indigotica roots.

Six new indole alkaloid diglycosides named isatigotindolediosides A-F (1-6), along with three known analogs (7-9), were isolated from an aqueous extract of the Isatis indigotica roots (ban lan gen). Their structures including the absolute configurations were determined by comprehensive spectroscopic data analysis, combined with enzyme or acid hydrolysis, and comparison of experimental circular dichroism (CD) and calculated electronic circular dichroism (ECD) spectra. In the preliminary assays, compounds 3, 5, and 8 showed antiviral activity against Coxsackie virus B3.

[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.

20C, a bibenzyl compound isolated from Gastrodia elata, protects PC12 cells against rotenone-induced apoptosis via activation of the Nrf2/ARE/HO-1 signaling pathway.

Aim: Our preliminary study shows that a bibenzyl compound isolated from Gastrodia elata, 2-[4-hydroxy-3-(4-hydroxybenzyl)benzyl]-4-(4-hydroxybenzyl)phenol (designated 20C), protects PC12 cells against H2O2-induced injury. In this study we investigated whether 20C exerted neuroprotective action in a cell model of Parkinson's disease.

Methods: A cell model of Parkinson's disease was established in PC12 cells by exposure to rotenone (4 μmol/L) for 48 h.

[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-β-D-glucopyranosyl-（1’’’→2’’）-β-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.

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-β-D-boivinopyranosyl-3'-O-β-D-glucopyranoside (1) and chrysoeriol-6-C-β-D-boivinopyranosyl-4'-O-β-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.

[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-β-D-glucopyranosyl caffeate (9), (-)-dihydrophaseic acid 4'-O-β-D-glucopyranoside (10), ketologanin (11), 7α-morroniside (12), 7β-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.

[Terpenoids from Euphorbia micractina].

From an ethanol extract of Euphorbia micractina roots, sixteen terpenoids were isolated by a combination of various chromatographic techniques, including column chromatography over macroporous resin, silica gel, and Sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as loliolide myristate(1), 24-methylenetirucall-8-en-3β,11α-diol-7-one(2), loliolide(3), 3β-hydroxy- 5α,6α-epoxy-7-megastigmen-9-one(4), jolkinol A(5), jolkinol D(6), latilagascene F(7), helioscopinolide A(8), helioscopinolide B(9), 3-O-acetylhelioscopinolide B(10), helioscopinolide D(11), helioscopinolide E(12),(+)-11-acetoxyatis-16-en-3,14-dione(13), erythrodiol(14), uvaol(15) and betulin(16). All of the compounds were obtained from this plant for the first time, in which 1 and 2 are new compounds.

C14-polyacetylenol glycosides from the roots of Codonopsis pilosula.

Eight new C14-polyacetylenol glycosides, containing ene-diyne and ene-yn-ene chromophores named codonopilodiynosides H-M (1-6) and codonopiloenynenosides A and B (7 and 8), respectively, together with three known analogs lobetyolinin, pratialin B, and lobetyolin (9-11), were isolated from an aqueous extract of the roots of Codonopsis pilosula. Their structures were determined by spectroscopic and chemical methods including 2D NMR data analysis and enzymatic hydrolysis. The absolute configurations of aglycones in 1-10 were assigned by application of the methoxyphenylacetic acid (MPA) determination rule of Δδ(RS) values and/or the empirical rule of Mo2(OAc)4-induced circular dichroism for the vicinal diols, or by comparison of specific rotation values with those of reported compounds.

Antiviral glycosidic bisindole alkaloids from the roots of Isatis indigotica.

Seven new glycosidic bisindole alkaloids, isatindigobisindolosides A-G (1-7), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including absolute configurations were determined by spectroscopic and chemical methods, together with calculations of electronic circular dichroism (ECD) spectra based on the quantum-mechanical time-dependent density functional theory. In the NMR spectra of 1-3, it is found that integration of H-2 and intensity of C-2 are affected not only by a substitution group at C-2 but also by solvents.

4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata.

Seven new 4-hydroxybenzyl-substituted glutathione derivatives (2-8), together with a known analogue (1), were isolated from the aqueous extract of Gastrodia elata Blume rhizomes. Their structures were determined by using spectroscopic and chemical methods. The absolute configurations of 1-8 were assigned by using Marfey's method, combined with comparing the NMR and CD spectroscopic data of sulfoxide moieties in 3-6 with those of S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers (9-12) synthesized as authentic samples.

C₁₄-polyacetylene glucosides from Codonopsis pilosula.

Seven new C14-polyacetylene glucosides codonopilodiynosides A-G (1-7) were isolated from an aqueous extract of the Codonopsis pilosula roots. Their structures were determined by spectroscopic and chemical methods as (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranoside (1), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (2), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5,14-di-O-β-D-glucopyranoside (3), (-)-(5S,6E)-tetradeca-6-en-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranoside (4), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5-diol 5-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (5), (-)-(6S,4E,12E)-tetradeca-4,12-dien-8,10-diyn-1,6-diol 6-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (6), and (-)-(5S,6E)-tetradeca-6-en-1,5-epoxy-8,10-diyn-14-ol 14-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (7), respectively. The absolute configurations of 1-7 were assigned by enzymatic hydrolysis followed by isolation of glucose and aglycones (1a and 4a-7a), and subsequent comparison of specific rotation, TLC, and (1)H NMR data of the glucose with an authentic sugar sample and application of modified Mosher's method based on the MPA determination rule of Δδ(RS) values for 1a and 4a, and Δδ(S) values for 6a.

[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.

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.