Pregnane glycosides from Solanum nigrum

Two new pregnane saponins, solanigroside A (1) and solanigroside B (2), along with two known compounds (3 and 4), were isolated from 60% ethanolic extract of the dried herb of Solanum nigrum L. The structures of 1 and 2 were elucidated as 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-xylopyranosyl-(1 → 3)-O-[α-l-arabinopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-O-β-d-galactopyranoside (1) and 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-glucopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-galactopyranoside (2), respectively, on the basis of extensive spectroscopic analysis as well as comparison with reported spectroscopic data of related compounds. This paper deals with the isolation and structural characterisation of pregnane glycosides from S. nigrum L.     

Two new alkyl glycosides from Clerodendranthus spicatus

Two new alkyl glycosides, 3-O-β-d-apifuranosyl-(1 → 6)-O-β-d-glucopyranosyl-(3S)-oct-1-en-3-ol (1, clerspide A) and 3-O-β-d-apifuranosyl-(1 → 6)-[β-d-xylopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(3S)-oct-1-en-3-ol (2, clerspide B), have been isolated from the whole plants of Clerodendranthus spicatus (Labiatae). Their structures were established on the basis of spectroscopic analyses and chemical method.     

New abietane-type diterpene glycosides from the roots of Tripterygium wilfordii

Two new abietane diterpene glycosides, wilfordosides A (1) and B (2), were isolated from the roots of Tripterygium wilfordii. The structures of compounds 1 and 2 were established using spectroscopic methods including extensive 1D and 2D NMR analysis, in combination with chemical reactions.     

Monoterpenoids from the whole herb of Veronicastrum axillare

Context: Veronicastrum axillare (Sieb. et Zucc.) Yamazaki (Scrophulariaceae) embraces varieties of bioactivities such as anti-inflammatory, anti-pyresis and detoxification activity, while little is known of the phytochemical components of this medicinal plant.

Objective: To isolate and identify bioactive constituents from the whole herb of V. axillare.

Materials and methods: Ethanol extract of the whole herb of V. axillare was subjected to successive column chromatography. Chemical structures of the compounds were elucidated by detailed spectroscopic analyses on the basis of NMR, IR and HR-MS data.

Results: A new monoterpenoid, axillacetal A (1) and a known analogue, tarumal (2), were isolated from the whole herb of V. axillare. The structure of tarumal (2) was also revised according to our NMR data.

Discussion and conclusion: This is the first report on the isolation and authentication of novel chemical constituents from V. axillare.     

Two new dimeric secoiridoid glycosides from the fruits of Ligustrum lucidum

Two new secoiridoid glycosides, ligusides A and B (1 and 2), as well as seven known compounds (3–9), were isolated from the fruits of Ligustrum lucidum. Their structures were elucidated on the basis of spectroscopic and chemical analysis.     

傣药小灯台中的吲哚生物碱

从傣药小灯台(Winchia catophylla A. DC.)中分到4个吲哚生物碱,经理化常数测定,光谱分析和化学转化,分别鉴定为echitamine chloride(Ⅰ),echitamidine(Ⅱ),N_B-demethyl-echitamine(Ⅲ)和22-O-acetyl-N_b--demethyl-echitamine(Ⅳ),其中Ⅳ为新的吲哚生物碱。     

Two new secoiridoid glycosides from Verbena officinalis

Two new secoiridoid glycosides, verbenoside A (1) and verbenoside B (2), have been isolated from the ethanol extract of the aerial parts of Verbena officinalis L. Their structures were elucidated on the basis of spectroscopic evidences, especially 1D, 2D NMR, and MS experiments.     

Two new coumarin glycosides from Herpetospermum caudigerum

Phytochemical investigation on the seeds of Herpetospermum caudigerum afforded two new coumarin glycosides A and B (1 and 2), together with a known compound herpetolide A (3). Their structures were determined by spectroscopic methods, including 2D NMR techniques. Compound 3 exhibited cytotoxicity against HepG2 cells with IC₅₀ value of 6.47 μg/ml. Compound 2 showed anti-hepatitis B virus activity with HBsAg secretion by 33.1% at 200 μg/ml.     

New xanthone glycosides from Securidaca inappendiculata

Three new xanthone glycosides, securixanside A ( 1 ), securixanside B ( 2 ), and securixanside C ( 3 ) were isolated from the stems of Securidaca inappendiculata . These compounds were characterized by spectrometric and chemical methods, including FABMS and one- and two-dimensional NMR experiments.     

New xanthone glycosides from Securidaca inappendiculata

Three new xanthone glycosides, securixanside A ( 1 ), securixanside B ( 2 ), and securixanside C ( 3 ) were isolated from the stems of Securidaca inappendiculata . These compounds were characterized by spectrometric and chemical methods, including FABMS and one- and two-dimensional NMR experiments.     

Two new caffeyol glycosides from Forsythia suspensa

Two new caffeoyl glycosides of phenethyl alcohol, suspensaside A (1) and suspensaside B (2), were isolated from the fruits of Forsythia suspensa. Also obtained in this investigation were two known compounds forsythiaside (3) and suspensaside (4). The structures of compounds 1 and 2 were established by 1D and 2D NMR techniques and chemical methods.     

New antioxidant phenylethanol glycosides from Torenia concolor

Two new phenylethanol glycosides, phenylethyl-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranoside (torenoside A, 1) and 2′-O-3,4-dihydroxy-β-phenylethoxy-O-α-l-rhamnopyranosyl-(1″ → 3′)-(4′-O-caffeoyl)-β-d-glucopyranoside (torenoside B, 2), along with the 17 known compounds (3–19) were isolated from Torenia concolor. Those structures were established on the basis of spectroscopic analysis including NMR spectroscopic techniques (¹³C, ¹H, ¹H–¹H COSY, HMQC, HMBC, TOCSY, and NOESY). Moreover, phenylethanol glycosides 3–6 exhibited significant antioxidant activities in DPPH radical scavenging assay.     

Two new flavonoid glycosides from Artemisia frigida Willd.

An investigation of the n-BuOH-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new flavonoid glycosides, named friginoside A and friginoside B. Their structures were characterized as 5,7-dihydroxy-3′,4′,5′-trimethoxy flavone 7-O-β-d-glucuronide (1) and 5,7-dihydroxy-3′,4′,5′-trimethoxyflavone 7-O-β-d-glucuronyl-(1 → 2)O-β-d-glucuronide (2) on the basis of 1D and 2D NMR spectral analysis.     

Pregnane glycosides from the stems of Marsdenia tenacissima

Four new pregnane glycosides, named marstenacissides A (1), B (2), C (3), and D (4), have been isolated from the stems of Marsdenia tenacissima. Their structures were established on the basis of chemical and spectral methods.     

Pregnane glycosides from the stems of Marsdenia tenacissima

Four new pregnane glycosides, named marstenacissides A (1), B (2), C (3), and D (4), have been isolated from the stems of Marsdenia tenacissima. Their structures were established on the basis of chemical and spectral methods.     

Two new norbisabolane sesquiterpenoid glycosides from Glochidion coccineum

Two new norbisabolane sesquiterpenoid glycosides, glochicoccinosides A (1) and B (2), together with two known compounds, have been isolated from the rhizomes of Glochidion coccineum. Their structures were elucidated by the combination of 1D NMR, 2D NMR, and MS spectral analysis, as well as chemical evidence. Cytotoxic activities and the antioxidant effect of these compounds were evaluated, but none of them showed activity.     

New lignan glycosides from Cupressus duclouxian (Cupessaceae)

From the branches and leaves of Cupressus duclouxiana two new lignan glycosides named cupressoside A (1) and cupressoside B (2), together with matairesinoside (3), dihydrodehydrodiconiferyl alcohol (4), dihydrodehydrodiconiferyl alcohol-9-O-α-l-rhamnopyranoside (5), dihydrodehydrodiconiferyl alcohol-4-O-α-l-rhamnopyranoside (6), ( ? )-isolariciresinol (7) and ( ? )-isolariciresinol-9-O-β-d-xylopyranoside (8), were isolated. The structures of these compounds were determined on the basis of their HR-FAB-MS, IR, UV, ¹H and ¹³C NMR (DEPT), and 2D NMR (HMQC, HMBC, COSY, NOESY) spectral data.     

Two new sesquiterpene lactone glycosides from Artemisia frigida Willd.

The investigation of EtOAc-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new sesquiterpene lactone glycosides, named as artemofriginoside A and artemofriginoside B. Their structures were characterized as 3β-(β-d-glucopyranosyloxy)-8β-(p-hydroxyphenylacetyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (1) and β-(β-d-glucopyranosyloxy)-8β-(2-hydroxy-3-methylbutanoyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (2), on the basis of 1D and 2D NMR spectral analysis.     

Neolignan and lignan glycosides from branch bark of Davidia involucrata

Two new neolignan glycosides, davidioside A (1) and davidioside B (2), have been isolated along with six known compounds from the branch bark of Davidia involucrata. Identification of their structures was achieved by 1D and 2D NMR experiments, including ¹H-¹H COSY, NOESY, HMQC, and HMBC methods as well as FAB mass spectral data.