Antioxidant lignoids from leaves of Ribes nigrum

• Published in: Phytochemistry (Oxford) Vol. 95; pp. 333 - 340
• Main Authors: Sasaki, Tatsunori, Li, Wei, Zaike, Shinnosuke, Asada, Yoshihisa, Li, Qin, Ma, Fenghua, Zhang, Qingbo, Koike, Kazuo
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.11.2013; Elsevier
• Subjects: Antioxidant activity; Antioxidants; Antioxidants - chemistry; Antioxidants - isolation & purification; Antioxidants - pharmacology; Biochemistry & Molecular Biology; Biphenyl Compounds; Biphenyl Compounds - metabolism; chemical analysis; chemistry; Dilignan; free radical scavengers; Furans; Furans - chemistry; Furans - isolation & purification; Furans - pharmacology; Grossulariaceae; isolation & purification; leaves; Life Sciences & Biomedicine; Lignan; Lignans; Lignans - chemistry; Lignans - isolation & purification; Lignans - pharmacology; metabolism; Molecular Structure; pharmacology; Picrates; Picrates - metabolism; Plant Extracts; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Leaves; Plant Leaves - chemistry; Plant Sciences; Ribes; Ribes - chemistry; Ribes nigrum; Science & Technology; Sesquilignan; spectroscopy; Structure-Activity Relationship; superoxide anion; Superoxides; Superoxides - metabolism; Ribes nigrum; Lignan; Grossulariaceae; Sesquilignan; Antioxidant activity; Dilignan; PRODELPHINIDINS; ASCORBIC-ACID; CONSTITUENTS
• ISSN: 0031-9422; 1873-3700; 1873-3700
• DOI: 10.1016/j.phytochem.2013.07.022

7,7′-Epoxylignans, tetrahydrofuran-type sesquilignans and spirocyclic dilignans were isolated from leaves of Ribes nigrum. Ribesin D and ribesin G showed potent superoxide anion scavenging activity. •Eight lignoids were isolated from Ribes nigrumleaves.•First report of 7,7′-epoxylignans, sesquilignans and dilignans in Grossulariaceae.•Six lignoids and a flavonol showed potent superoxide anion scavenging activity.•The structure–activity relationship was discussed. Phytochemical investigation of the leaves of Ribes nigrum resulted in the isolation of fourteen compounds, including four 7,7′-epoxylignans, three tetrahydrofuran-type sesquilignans, and a spirocyclic dilignan. Their structures were elucidated by extensive spectroscopic analyses and by chemical transformations. The isolated compounds were evaluated for their antioxidant activities using superoxide anion scavenging assay and DPPH free radical scavenging assay. Ribesin D and ribesin G showed the most potent superoxide anion scavenging activity with EC50 values of 1.24 and 1.12μM, respectively, and the structure–activity relationship was discussed.