Zhejiang Hongyuan Pharmaceutical Co., Ltd.

In this phytochemical investigation, a total of 16 previously undescribed and 27 known diterpene-related compounds were isolated from the endangered Chinese endemic conifer Podocarpus annamiensis. Podoannamiacids A (1) and B (2) represent the first examples of a new chemical class of diterpene-phenylpropanoid hybrids characterized by a unique 7'-phenyl-7',8'-dihydrobenzofuran unit. This structure is hypothesized to be biogenetically derived through the formation of newly generated C-12-C-8' and C-13-O-C-7' bonds via a free radical coupling reaction between a totarane unit and a phenylpropanoid moiety. The remaining previously undescribed compounds are structurally diverse diterpenoid monomers, including totarane-type compounds 3-9. Notably, annamiacids C (3) and D (4) feature a rare dihydro-pyrane fragment, while annamiacids E (5) and F (6) contain a dihydro-furan and a β,γ-unsaturated-γ-lactone motif, respectively. Compounds 10-14 are classified as abietane-type diterpenes, whereas compounds 15 and 16 are categorized as sempervirane-type and podocarpane-type diterpenes, respectively. Their chemical structures were elucidated using spectroscopic data analysis, GIAO NMR calculations combined with DP4+ probability analyses, electronic circular dichroism calculations, and single-crystal X-ray diffraction analysis. Liquiditerpenoic acid A (30) exhibited inhibitory activity against ATP-citrate lyase (ACL) with an IC₅₀ value of 5.0 μM. Similarly, 18-hydroxysempervirol (40) inhibited acetyl-CoA carboxylase 1 (ACC1) with an IC₅₀ value of 14.41 μM. Additionally, rakanmakilactone I (43) demonstrated anti-neuroinflammatory effects in BV-2 cells, reducing NO release by 21.4 % at a concentration of 20 μM. The above findings, along with previously reported totarane-O-abietane (44) and abietane-O-abietane dissymmetric bis-diterpenes (45), further expand the understanding of the structural diversity and medicinal potential of this endangered conifer, offering a promising strategy for its sustainable utilization and conversation. This approach not only positions the species as a potential source for treating metabolic diseases but also encourages the further protection of these fragile plant resources.

A new method for preparing alkylated (iso)quinolines with substituted (iso)quinolines and alkanes as substrates, PIFA as an oxidant, and Rose bengal as a photosensitizer under 50 W light irradiation is proposed. Diverse structures were shown to be tolerated under optimal conditions, and a series of alkylated products were obtained in the desired yields. Compared with previous reactions using aldehydes and carboxylic acids as carbon sources, this method uses simple alkanes as carbon sources, offering good chemical stability and high atom economy.

Rhizoma Paridis (RP) is a traditional Chinese herb used for the treatment of tumors, detoxification and hemostasia. Studies show the main components of RP are Polyphyllin I (PPI), polyphyllin VI (PPVI), and polyphyllin VII (PPVII). However, the pharmaco-mechanisms of these compounds are not clear.

By used 1H nuclear magnetic resonance (1H-NMR) based metabolomics approach to identify the Anticancer effects of PPI, PPVI and PPVII in HepG2 cells.

1H nuclear magnetic resonance (1H-NMR) based metabolomics approach was applied to investigate the toxicological effect of PPI, PPVI, PPVII on HepG2 cells. Multivariate statistical analysis was employed to examine the metabolic changes and abnormal metabolic pathways, including Principal Component Analysis (PCA), Partial Least Squares Discriminant Analysis (PLS-DA), and orthogonal PLS-DA (OPLS-DA).

The results showed that the effects of metabolic phenotypes were affected separately by PPI, PPVI, and PPVII. The metabolic phenotypes were also changed over time. The characteristic metabolites were varied by affecting different polyphylins, which were identified by the reconstructed OPLSDA loading plots. According to the characteristic metabolites, the mainly disturbed metabolic pathways were found, such as alanine, aspartate and glutamate metabolism, pyruvate metabolism, glycine, serine, and threonine metabolism.

The current work could allow us to understand the therapeutic effect of RP in metabolism. It also indicated that RP would be a promising candidate for liver cancer treatment.