Abstract

Three new iridoids, namely neonanin A (1), neonanin B (2) and neoretinin A (3), as well as twelve known compounds, 6-hydroxy-7-methyl-1-oxo-4-carbomethoxyoctahydrocyclopenta[c]pyran (4), 4-epi-alyxialactone (5), loganetin (6), loganin (7), phenylcoumaran-α′-aldehyde (8), cleomiscosin A (9), ficusal (10), balanophonin (11), vanillic acid (12), p-coumaric acid (13), cis,trans-abscisic acid (14), and trans,trans-abscisic acid (15) were isolated from the stems of Neonauclea reticulata (Havil.) Merr. These new structures were determined by the detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1–13 were evaluated using an in-vitro MTT cytotoxic assay for hepatocellular carcinoma (HCC) cells, and the preliminary results showed that ficusal (10), balanophonin (11), and p-coumaric acid (13) exhibited moderate cytotoxic activity, with EC50 values of 85.36 ± 4.36, 92.63 ± 1.41, and 29.18 ± 3.48 µg/mL against Hep3B cells, respectively.

Highlights

  • Neonauclea reticulate (Havil.) Merr. is a large evergreen tree, which is distributed over the Philippines and Taiwan

  • Alkaloids [2,3], anthraquinones [4], iridoids [5], triterpenes [6], and saponins [7] have been isolated from the plants of this genus in previous chemical investigations

  • The results show that the MeOH extract exhibits a dose-dependent cytotoxicity against the Hep3B cells

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Summary

Introduction

Neonauclea reticulate (Havil.) Merr. is a large evergreen tree, which is distributed over the Philippines and Taiwan. Of the forty species of the genus Neonauclea (Rubiaceae), this is the only species that can be found in Taiwan, located in the forests at low elevations of southern Taiwan, such as the Kaohsiung area, as well as Pingtung Mountain or Orchid Island [1]. Alkaloids [2,3], anthraquinones [4], iridoids [5], triterpenes [6], and saponins [7] have been isolated from the plants of this genus in previous chemical investigations. To the best of our knowledge, there have been no studies published that have investigated the chemical structure of N. reticulate. The only pharmacological study published mentions that the leaves of this plant could protect human skin fibroblast cells against the effects of ultraviolet B (UVB)

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