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<p><i>Pistacia chinensis</i> (Anacardiaceae) is a deciduous tree widely distributed in East Asia. Despite its long-standing use for ornamental, timber, and medicinal purposes, its secondary-metabolite profile remains only partially characterized. In this study, branches of <i>P. chinensis</i> were extracted with methanol, and the ethyl acetate-soluble fraction was subjected to repeated chromatographic separation, yielding five previously undescribed chalcone-containing biflavonoids, pistaciaphenols A–E (<b>1</b>–<b>5</b>), along with the known biflavonoid pauferrol B (<b>6</b>) and two flavanones, (2<i>S</i>,3<i>S</i>)-aromadendrin (<b>7</b>) and (2<i>S</i>,3<i>S</i>)-taxifolin (<b>8</b>). Comprehensive spectroscopic analyses, including 1D and 2D NMR (HMQC, HMBC, and double quantum filtered COSY) and high-resolution electrospray ionization mass spectrometry, established the structures of <b>1</b>–<b>5</b> as dimers composed of either isoliquiritigenin- or dihydroisoliquiritigenin-derived units linked to flavanone or flavone counterparts. Pistaciaphenols A (<b>1</b>) and C (<b>3</b>) possessed a liquiritigenin-derived flavanone moiety, whereas pistaciaphenol B (<b>2</b>) contained a flavone unit. Pistaciaphenols D (<b>4</b>) and E (<b>5</b>) featured a rare spiro-structure, a structural motif previously reported only from several <i>Daphne</i> species. The absolute configurations of <b>1</b> and <b>3</b> (2′′<i>R</i>,3′′<i>S</i>) were determined via analysis of electronic circular dichroism (ECD) spectra in conjunction with empirical correlations reported for C-3-substituted flavanones. For <b>4</b> and <b>5</b>, GIAO-based <sup>13</sup>C NMR chemical-shift calculations with DP4 + and CP3 analysis, together with experimental and time-dependent DFT-calculated ECD data, established <b>4</b> as 2′′<i>R</i>,3′′<i>R</i> and supported assignment of <b>5</b> as most plausibly 2′′<i>R</i>,3′′<i>S</i>. These findings expand the structural diversity of chalcone-based biflavonoids in Anacardiaceae and provide new scaffolds for future biological evaluation.</p> Graphical abstract <p></p>

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Pistaciaphenols A–E: novel chalcone-based biflavonoids from the branches of Pistacia chinensis

  • 期刊论文

  • 发表日期：

    2026年4月21日

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  • Tomoki Mizoguchi,
  • Naohito Abe,
  • Satoshi Endo,
  • Satoshi Okubo,
  • Takao Yamaura,
  • Masayoshi Oyama,
  • Ken-ichi Nakashima

摘要

Pistacia chinensis (Anacardiaceae) is a deciduous tree widely distributed in East Asia. Despite its long-standing use for ornamental, timber, and medicinal purposes, its secondary-metabolite profile remains only partially characterized. In this study, branches of P. chinensis were extracted with methanol, and the ethyl acetate-soluble fraction was subjected to repeated chromatographic separation, yielding five previously undescribed chalcone-containing biflavonoids, pistaciaphenols A–E (1–5), along with the known biflavonoid pauferrol B (6) and two flavanones, (2S,3S)-aromadendrin (7) and (2S,3S)-taxifolin (8). Comprehensive spectroscopic analyses, including 1D and 2D NMR (HMQC, HMBC, and double quantum filtered COSY) and high-resolution electrospray ionization mass spectrometry, established the structures of 1–5 as dimers composed of either isoliquiritigenin- or dihydroisoliquiritigenin-derived units linked to flavanone or flavone counterparts. Pistaciaphenols A (1) and C (3) possessed a liquiritigenin-derived flavanone moiety, whereas pistaciaphenol B (2) contained a flavone unit. Pistaciaphenols D (4) and E (5) featured a rare spiro-structure, a structural motif previously reported only from several Daphne species. The absolute configurations of 1 and 3 (2′′R,3′′S) were determined via analysis of electronic circular dichroism (ECD) spectra in conjunction with empirical correlations reported for C-3-substituted flavanones. For 4 and 5, GIAO-based 13C NMR chemical-shift calculations with DP4 + and CP3 analysis, together with experimental and time-dependent DFT-calculated ECD data, established 4 as 2′′R,3′′R and supported assignment of 5 as most plausibly 2′′R,3′′S. These findings expand the structural diversity of chalcone-based biflavonoids in Anacardiaceae and provide new scaffolds for future biological evaluation.

Graphical abstract