Zheng Zhao's research works

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Cnidimonins A–C, Three Types of Hybrid Dimer from Cnidium monnieri : Structural Elucidation and Semisynthesis

Article

August 2017

39 Reads

19 Citations

Organic Letters

[...]

Three pairs of racemic dimers, (±)-cnidimonins A–C (1–3), were isolated from the fruits of Cnidium monnieri. They represent novel hybrid-dimerization patterns of coumarin skeleton with structurally diverse units (flavonol, benzofuran, and chromone) via an unprecedented terminal chiral carbon of prenyl. The absolute configurations of the enantiomers were determined by electronic circular dichroism (ECD). To investigate their bioactivities in depth, (±)-cnidimonins A–C (1–3) were synthesized. The racemic mixture (±)-1 exhibited stronger antiviral activity against HSV-1 (IC50: 1.23 μM) than its corresponding optically pure enantiomers.

... Thus, the choice to make up a drug of either the racemate or a single enantiomer must take into consideration many clinical assessments, as mixture of enantiomers can induce synergistic, additive, reduced or negative effects. For example, the natural racemate cnidimonin A (28) (IC 50 = 1.23 μM) has a greater antiviral potency than its single enantiomers (IC 50 ≥ 3.7 μM) 81 , and gaudichaudianic acid (52) (IC 50 = 55.8 μM) has a much increased trypanocidal activity than its single enantiomers (IC 50 > 176.0 μM) 159 . ...
Reference:
Demystifying racemic natural products in the homochiral world

Cnidimonins A–C, Three Types of Hybrid Dimer from Cnidium monnieri : Structural Elucidation and Semisynthesis

Citing Article
August 2017

Organic Letters

[...]

Zheng Zhao's scientific contributions

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