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Two new compounds named 4,4′-bis(β-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, ten known compounds (3–12) were also identified, including a flavonoid glycoside (3), seven steroids (4–10), a nucleoside (11), and a phenylpropanoid glycoside (12) were found. Notably, compounds 3–6 were isolated from this plant for the first time. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of these compounds showed strong antioxidant activity, and compound 1 demonstrated the most potent reduction of ferric ions (Fe3+) with an IC50 value of 0.59 ± 0.18 mg/mL. Compounds 2 and 3 exhibited the highest scavenging activity against superoxide anion radicals (O2−·) with an IC50 value of 0.02 ± 0.01 mg/mL. Additionally, compound 3 displayed substantial scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with IC50 values of 0.21 ± 0.17 mg/mL and 0.02 ± 0.01 mg/mL, respectively. The discovery of these two new compounds is a reference for identifying Allii Macrostemonis Bulbus quality markers. Moreover, their exceptional antioxidant activity offers a promising avenue for uncovering novel natural antioxidants. [ABSTRACT FROM AUTHOR]

Ten phenolic constituents, including three new macrocyclic glycosides (1–3), a new phenolic glycoside (5), a new biphenyl glycoside (6), and five known compounds (4, 7–10), were isolated from a 70% MeOH extract of the leaves of Heliciopsis terminalis by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-guided molecular networking. The chemical structures of new compounds 1–3, 5 and 6 were established based on comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS techniques. All isolated compounds (1–10) were evaluated for their stimulation of glucose uptake in differentiated 3T3-L1 adipocytes using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) as a fluorescent glucose analog. Compounds 3, 6 and 8 showed stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells. Among them, compounds 3 and 6 activated the AMPK signaling pathway in differentiated C2C12 myoblasts. [ABSTRACT FROM AUTHOR]

Two new compounds named 4,4′-bis(β-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, ten known compounds (3–12) were also identified, including a flavonoid glycoside (3), seven steroids (4–10), a nucleoside (11), and a phenylpropanoid glycoside (12) were found. Notably, compounds 3–6 were isolated from this plant for the first time. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of these compounds showed strong antioxidant activity, and compound 1 demonstrated the most potent reduction of ferric ions (Fe3+) with an IC50 value of 0.59 ± 0.18 mg/mL. Compounds 2 and 3 exhibited the highest scavenging activity against superoxide anion radicals (O2−·) with an IC50 value of 0.02 ± 0.01 mg/mL. Additionally, compound 3 displayed substantial scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with IC50 values of 0.21 ± 0.17 mg/mL and 0.02 ± 0.01 mg/mL, respectively. The discovery of these two new compounds is a reference for identifying Allii Macrostemonis Bulbus quality markers. Moreover, their exceptional antioxidant activity offers a promising avenue for uncovering novel natural antioxidants.

Ten phenolic constituents, including three new macrocyclic glycosides (1–3), a new phenolic glycoside (5), a new biphenyl glycoside (6), and five known compounds (4, 7–10), were isolated from a 70% MeOH extract of the leaves of Heliciopsis terminalis by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-guided molecular networking. The chemical structures of new compounds 1–3, 5 and 6 were established based on comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS techniques. All isolated compounds (1–10) were evaluated for their stimulation of glucose uptake in differentiated 3T3-L1 adipocytes using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) as a fluorescent glucose analog. Compounds 3, 6 and 8 showed stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells. Among them, compounds 3 and 6 activated the AMPK signaling pathway in differentiated C2C12 myoblasts.

Fortuneanoside F (1), a new biphenyl glycoside, together with two known phenyl glycosides: phenylmethyl O-β-D-glucopyranoside (2) and 2-phenylethyl O-β-D-glucopyranoside (3), was isolated from the fruit of Pyracantha fortuneana (Maxim.) Li. Its chemical structure was elucidated to be 4-hydroxy-3,5-dimethoxy-(1,1'-biphenyl)-2-O-β-D-glucoside on the basis of spectroscopic analysis and chemical methods. Compounds 1-3 showed mild inhibitory activity against tyrosinase. [ABSTRACT FROM AUTHOR]

Two novel sulfur-containing dibenzofurans, sorbusins A (1) and B (2), two unprecedented biphenyl glycosides, 2′-hydroxyaucuparin 2′- O - ɑ -L-rhamnoside (3) and noraucuparin 5- O - ɑ -L-rhamnoside (4), and four known analogues (5 – 8), were isolated from Sorbus pohuashanensis suspension cell induced by yeast extract. Their structures were elucidated based on spectroscopic analyses and quantum calculation of 13C NMR data. Structurally, compound 1 possessed a rare naturally occurring benzothiazole moiety and represents the first example of thiazole fused dibenzofuran. A plausible biosynthetic pathway for the sulfur-containing dibenzofurans is proposed. These dibenzofuran and biphenyl phytoalexins were evaluated for their antimicrobial activities against pathogenic fungi and drug-resistant bacteria. Compound 7 exhibited significant antibacterial activity against methicinllin-resistant Staphylococcus aureus with an MIC value of 3.13 μg/mL. [Display omitted] • Sulfur-containing dibenzofurans were isolated from Sorbus pohuashanensis suspension cell. • The quantum calculation of 13C NMR data was applied for structure elucidation. • This is the first example of naturally occurring thiazole fused dibenzofuran. • A plausible biosynthetic pathway for the sulfur-containing dibenzofurans is proposed. • The dibenzofuran and biphenyl phytoalexins were evaluated for their antifungal and antibacterial activities. [ABSTRACT FROM AUTHOR]