Chemical constituents from Lagopsis supina (Steph.) Ik.-Gal. ex Knorr

Phytochemical investigation of the whole plants of Lagopsis supina (Steph.) Ik.-Gal. ex Knorr. led to the isolation of 18 compounds (1–18), including ten phenylethanoid glycosides (1–10), one phenylmethanoid glycoside (11), four megastigmane glycosides (12–15), and three monoterpenoid glycosides (16–18). Lagopsides A (1) and B (2) were identified as new phenylethanoid glycosides. This is the first report of compounds 7, 11, 12, 15, and 16 from the Labiatae family, while compounds 4–6, 8–10, 13–14, and 17–18 were isolated from the genus Lagopsis for the first time. The chemotaxonomic significance of these isolated compounds was summarized.     

Chemical constituents from the stem bark of Acer tegmentosum

A new phenolic glycoside, 4-hydroxyphenylethyl-1-O-β-D-[6′-O-(4-hydroxybenzoyl)]-glucopyranoside (1) was isolated from the stem bark of Acer tegmentosum, along with seven known phenolic compounds (2–8). The structure of compound 1 was determined by spectral analyses, including HR-ESI-MS, 1D and 2D NMR (COSY, HMQC and HMBC) experiments. Compounds 3 and 4 were found in the family Aceraceae for the first time.     

A new secoiridoid and a new xanthone glycoside from the whole plants of Lomatogonium rotatum

A new secoiridoid (1) and a new xanthone glycoside (2), together with fourteen known compounds (3−16) were isolated from the dried whole plants of Lomatogonium rotatum (L.) Fries ex Nym. The chemical structures were elucidated based on extensive spectroscopic experiments, including 1D and 2D NMR as well as HR-ESI-MS, and comparison with those reported in the literature. All the compounds were evaluated for anti-complementary activity against the alternative pathways. Compounds 12 and 16 exhibited anti-complementary activity.     

Norlignan glycosides from the leaves of Molineria latifolia

Two new norlignan glycosides, molinerioside D (5) and molinerioside E (9), were isolated from the methanol extract of fresh leaves of Molineria latifolia. Their structures were determined using spectroscopic evidence, such as 1D and 2D NMR and HR-ESI-MS studies. The structure of molinerioside D (5) was determined to be a norlignan glycoside with a C6-C5-C6 skeleton, while the structure of molinerioside E (9) was determined to be a glucosyl-fused norlignan derivative. In addition to the new compounds, twenty known compounds were found in the extract of M. latifolia fresh leaves.     

A new flavone glycoside from the leaves of Agastache rugosa (Fisch. & C.A.Mey.) Kuntze

Agastache rugosa (Fisch. & C.A.Mey.) Kuntze has been widely used as a food spice and a remedy for colds in Korea, China and Japan. In this study, one new flavone glycoside (1) along with six flavonoids (2–7), nine phenyl glycosides (8–16) and three megastigmane glycosides (17–19) were isolated from the leaves of A. rugosa. By extensive spectroscopic methods including 1D and 2D NMR, and MS data, the structure of the new compound (1) was elucidated as acacetin 7-O-β-(6″-(E)-crotonylglucopyranoside). From present investigation, compound 1 and 7–19 were isolated for the first time from the genus Agastache and 1, 16, 18 and 19 in the Lamiaceae family.     

Neolignan and monoterpene glycoside from the seeds of Pharbitis nil

Phytochemical investigation of an EtOH extract of Pharbitis nil seeds (Convolvulaceae) resulted in the isolation and identification of a new neolignan, 7R,8S-threo-dihydroxydehydrodiconiferyl alcohol (1), and a new monoterpene glycoside, (3Z,7S)-7-hydroxy-3,7-dimethyl-3,8-octadienyl-β-d-glucopyranoside (2), together with a known compound, ethyl α-l-arabinofuranoside (3). The chemical structures of these compounds were unambiguously determined using physical data, HR-ESI–MS and spectroscopic evidence, including 1D and 2D NMR experiments. The anti-inflammatory activities of the isolates were evaluated by estimating the inhibition of nitric oxide (NO) production. Compounds 1 and 2 reduced NO levels in lipopolysaccharide (LPS)-stimulated murine microglial BV-2 cells. In addition, compound 2 showed weak cytotoxicity against the HCT-15 cell line with an IC₅₀ value of 28.6 μM.     

Chemical constituents from Cistanche sinensis (Orobanchaceae)

Phytochemical investigation of 70% aqueous EtOH extract of Cistanche sinensis led to the isolation of fifteen compounds (1–15), including nine phenylethanoid glycosides (PhGs, 1–9), five iridoid glycosides (10–14), and one lignan glycoside (15). Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. Among the isolated compounds, 1 was identified as a new compound, three compounds (9, 14, and 15) were firstly reported from the genus Cistanche, and seven compounds (2–6, 11, and 12) were isolated from C. sinensis for the first time. PhGs with a 6′-O-rhamnosyl moiety such as cistansinenside B (1), poliumoside (7), and 2′-O-acetylpoliumoside (9) could serve as chemotaxonomic markers to differentiate C. sinensis from other species of Cistanche.     

Tyrosinase inhibitory activity of three new glycosides from Breynia fruticosa

Two new flavanone glycoside derivatives and one new sulfur-containing spiroacetal glycoside, (2R, 3R)-3-acetyl-7-methoxy-(−)-epicatechin 5-O-(6-isobutanoyl)-β-d-glucopyranoside (1), (2R, 3R)-3-acetyl-7-methoxy-(−)-epicatechin 5-O-[6-(2-methylbutanoyl)]-β-d-glucopyranoside (2) and 4-[(carboxymethyl)thio]-5′-hydroxy-phyllaemblic acid O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside ester (3), along with twelve known flavonoids and one known sulfur-containing spiroacetal glycoside, were isolated from Breynia fruticosa. Their structures were elucidated by the use of extensive spectroscopic methods (UV, IR, HR-ESI-MS, 1D and 2D NMR, and CD). The in vitro inhibition of tyrosinase activity by all of these compounds was also evaluated, and we concluded that the flavanol-containing 5-O- and 7-O-sugar moieties possessed more potent effects than the other compounds examined herein.     

Chemical constituents from leaves of Cinnamomum subavenium

A new eudesmane sesquiterpene glycoside, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-15-carboxaldehyde-6-O-β-d-Glucopyranoside (1), together with eleven known compounds (2–12) were isolated from the leaves of Cinnamomum subavenium Miq. Their structures were elucidated by a combination of spectroscopic data analysis and comparison with literature data. All compounds were isolated from C. subavenium for the first time. The chemotaxonomic significance of the isolated compounds was summarized.     

A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity

A new secoiridoid glycoside, isopatrinioside (1) and a new sesquiterpenoid glycoside, valeriananoid F (2), together with nine known compounds, were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was an unusual monocyclic iridoid glycoside ring-opened between C-1 and C-2 produced by the cleavage of the pyran ring. Of the eleven isolates, compounds 1 and 4 exhibited moderate neuroprotective effects against CoCl₂-induced neuronal cell death in PC12 cells.     

Coixlachryside A: A new lignan glycoside from the roots of Coix lachryma-jobi L. var. ma-yuen Stapf.

A new lignan glycoside, 1-[3,6-(4,4⿲-dihydroxy-3,3⿲-dimethoxy-δ-truxinyl)-β-fructofuranosyl]-α-glucopyranoside (1), named coixlachryside A, together with nine known simple phenolic compounds (3⿿11) were isolated from the roots of Coix lachryma-jobi var. ma-yuen using various chromatographic methods. Their chemical structures were determined based on the spectroscopic data interpretation, particularly circular dichroism (CD), 1D and 2D NMR data including HSQC and HMBC.     

Four new glycosides from the seeds of Cassia obtusifolia

Four new glycosides, including one anthraquinone glycoside (1), one naphthalene glycoside (2), and two naphthopyrone glycosides (3–4), with 10 known compounds (5–14) were isolated from the seeds of Cassia obtusifolia L. The new structures were determined by spectroscopic analysis and chemical transformations.     

Phytochemical study of Capraria biflora L. aerial parts (Scrophulariaceae) from Martinique island (French West Indies)

Aerial parts of Capraria biflora L. were collected in Martinique (French West Indies) and extracted by methanol. Two original chlorinated iridoids, 3-hydroxymyopochlorin (1) and 5-hydroxyglutinoside (2) were isolated by CPC (centrifugal partition chromatography) and characterized from the extract together with five known iridoid glycosides (3–7), two flavonoid glucuronides (8–9) and the phenylethanoid glycoside verbascoside (10). The structure of these compounds together with their relative configuration was established by spectroscopic data including in particular 1D and 2D NMR experiments (HSQC, HMBC, NOESY) and HRESIMS. Preliminary antibacterial evaluation of 1, 2 and 3 against a panel of Gram-positive and Gram-negative strains has been performed.     

A new flavonoid glycoside from the leaves of Homonoia riparia

One new flavonol glycoside, myricetin 3-O-(6″-3,4-dihydroxybenzoyl)-β-glucopyranoside (1) and 13 known compounds (2 − 14) were isolated from the leaves of Homonoia riparia. Their structures were elucidated by spectroscopic methods. Among them, compounds 1–12 were obtained from the genus Homonoia for the first time. Compounds 4, 5, 8 and 11 were isolated for the first time in Euphorbiaceae family from present investigation.     

Cytotoxic oligophenols from the rhizome of Wikstroemia indica

A new tricoumarin glycoside, triumbelletin-7-O-β-d-glucoside (1) and a new biflavonoid, wikstroflavone A (2), together with two known compounds, wikstaiwanone A (3) and wikstaiwanone B (4), were isolated from the rhizome of Wikstroemia indica. The structures of new compounds were elucidated by extensive spectroscopic techniques (UV, IR, HRESIMS, 1D, 2D NMR and CD), in combination with quantum chemical calculations of ¹³C NMR and ECD spectra. All isolates were tested for their antineoplastic activities against cancer-derived cell lines HCT116, SW480, U87 and T98G. Compounds 2–4 exhibited moderate cytotoxic activities to the four cell lines. The flow cytometry assay and western blot analysis revealed that the cytotoxic effects were possibly attributed to the induced apoptotic cell death.     

Two new hemiterpene glycosides and one new phenolic glycoside from the roots of Securidaca inappendiculata Hassk

Two new hemiterpene glycosides, named as securiterpenoside B (1), and securiterpenoside C (2), and one new phenolic glycoside, named as securiphenoside A (3) were isolated from the roots of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of 1D and 2D NMR data and HRESIMS and comparisons with published data. Moreover, compounds 1–3 were evaluated for cytotoxicities against A549 (Lewis lung cancer), Hela (human cervical cancer) and MCF-7 (human breast cancer) cell lines.     

Structure–activity relationship of lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-γ

Phytochemical investigation resulted in the isolation of three new lupane-triterpene glycosides acankoreosides M–O (1, 2 and 8) together with eight known lupane-triterpene glycosides (3–7, 9–11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-γ were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells.     

Acylated flavonol glycosides and δ-truxinate derivative from the aerial parts of Lysimachia clethroides

Phytochemical investigation of the aerial parts of Lysimachia clethroides led to the isolation of a new acylated flavonol glycoside (1) and a new δ-truxinate derivative (2), together with three known acylated flavonol glycosides. The structures of the new compounds were determined by spectroscopic methods and chemical evidence as quercetin-3-O-β-d-(6-O-Z-p-coumaroyl)glucopyranoside (1) and monomethyl 3,3′,4,4′-tetrahydroxy-δ-truxinate (2), respectively. All of the isolates were evaluated for their in vitro inhibitory activity against aldose reductase.     

Megastigmane and 7,9′-dinorlignan glycosides from the tubers of Stephania kaweesakii

Two isomers of megastigmane glycosides, (6R, 9S)-blumenol C 9-O-gentibioside (2) and (6S, 9S)-blumenol C 9-O-gentiobioside (3), and a new 7,9′-dinorlignan glycoside, stepdonorlignoside (4) were isolated from the tubers of Stephania kaweesakii. The structure determinations were considered based on the physical data and spectroscopic evidence. The absolute configurations of two megastigmanes were determined for the first time. Additionally, ten known compounds were isolated: (6R, 9S)-blumenol C 9-O-β-D-glucopyranoside, (+)-isolariciresinol 3a-O-β-D-glucopyranoside, salidroside, N-trans-caffeoyltyramine, (R)-isococlaurine, (R)-isococlaurine 4′-O-β-glucopyranoside, (−)-oblongine, (+)-magnocurarine, fordianoside, and (−)-cyclanoline.     

A novel neolignan glycoside from Aquilaria sinensis

Phytochemical investigation of Aquilaria sinensis afforded one novel neolignan glycoside (1) and fourteen known compounds (2–15). Their structures were elucidated by spectroscopic methods. Among them, compounds 1–3, 5 and 7–9 were obtained from the genus Aquilaria for the first time. The profile of chromone glycosides and iriflophenone glycosides may have chemotaxonomic significance within this genus.