Eugenol-based meroterpenoids with neural differentiation activity from Eugenia caryophyllata.

Phytochemical investigation of Eugenia caryophyllata buds led to the discovery of nine previously undescribed eugenol-based meroterpenoids, named eugenianols A-I (1-9). Among them, compound 1 is the first reported meroterpenoid featuring a eugenol moiety fused with a sesquiterpenoid unit via two C-C bonds, forming an unprecedented tricyclo[9.4.

Antiviral C-geranylated flavonoids from Artocarpus communis.

Ten C-geranylated flavonoids, along with three known analogues, were isolated from the leaves of Artocarpus communis. The chemical structures of these compounds were unambiguously determined via comprehensive spectroscopic analysis, single-crystal X-ray diffraction experiments, and quantum chemical electronic circular dichroism calculations. Structurally, artocarones A-I (1-9) represent a group of unusual, highly modified C-geranylated flavonoids, in which the geranyl chain is cyclised with the ortho-hydroxy group of flavonoids to form various heterocyclic scaffolds.

Anti-inflammatory naphthoquinone-monoterpene adducts and neolignans from Eugenia caryophyllata.

A phytochemical investigation on the buds of edible medicinal plant, Eugenia carvophyllata, led to the discovery of seven new compounds, caryophones A-G (1-7), along with two biogenetically-related known ones, 2-methoxy-7-methyl-1,4-naphthalenedione (8) and eugenol (9). Compounds 1-3 represent the first examples of C-5-C-1' connected naphthoquinone-monoterpene adducts with a new carbon skeleton. Compounds 4-7 are a class of novel neolignans with unusual linkage patterns, in which the C-9 position of one phenylpropene unit coupled with the aromatic core of another phenylpropene unit.

Tautomeric cinnamoylphloroglucinol-monoterpene adducts from and their antiviral activities.

Guided by H NMR spectroscopic experiments using the characteristic enol proton signals as probes, three pairs of new tautomeric cinnamoylphloroglucinol-monoterpene adducts (-) were isolated from the buds of . Their structures with absolute configurations were established by spectroscopic analysis, modified Mosher's method, and quantum chemical electronic circular dichroism calculation. Compounds - represent a novel class of cinnamoylphloroglucinol-monoterpene adducts featuring an unusual C-4-C-1' linkage between 2,2,4-trimethyl-cinnamyl--triketone and modified linear monoterpenoid motifs.

Cleistocaltones A and B, Antiviral Phloroglucinol-Terpenoid Adducts from .

Two novel phloroglucinol-terpenoid adducts ( and ), featuring a rare 2,2,4-trimethyl-cinnamyl-β-triketone unit, were isolated from the buds of . Their structures with absolute configurations were established by spectroscopic analyses, single-crystal X-ray diffraction, and quantum chemical calculations. Structurally, compound represents a new carbon skeleton possessing a densely functionalized tricyclo[11.

Wenyang Huoxue Jiedu formula inhibits thin-cap fibroatheroma plaque formation via the VEGF/VEGFR signaling pathway.

Ethnopharmacological Relevance: For many years, Guangzhou University of Chinese Medicine has been successfully using the empirical Wenyang Huoxue Jiedu formula (WHJF) to treat coronary heart disease. Modern theories of acute coronary syndrome mainly focus on rupture of thin-cap fibroatheromas (TCFAs), which is closely related to the release of vascular endothelial growth factor and its receptor (VEGF/VEGFR).

Aim Of Study: We investigated the effects of WHJF on the formation of TCFA plaques and the potential mechanism (VEGF/VEGFR signaling pathway).