Trimer Stilbenoids from Shorea materialis Ridl. (Dipterocarpaceae)

Shorea, a genus in the family of Dipterocarpaceae, is a notable source of oligostilbenoids with various degrees of polymerisation, including monomers, dimers, trimers and tetramers which possess significant biological actions. Shorea materialis, also known as Balau Pasir, grows primarily in swampy habitats in Pahang, Perak, Terengganu's coast and Johor. In continuing to discover active constituents with therapeutic potential from Shorea, a phytochemical study on the stem bark of Shorea materialis was conducted. The stem bark of S. materalis was dried and ground into powder (1 kg). The powder was macerated in acetone at room temperature for 24 hours to yield crude acetone extract (117 g). Using the eluent of n-hexane:ethyl acetate by vacuum liquid chromatography, eight fractions were produced from the fractionation of the crude extract. Fraction 5 (26 g) was fractionated twice, followed by purification using column chromatography (CC) with the eluent chloroform:methanol, which yielded compounds 1 (8 mg) and 2 (4 mg). Compound 3 (5 mg) was obtained from fraction 6 (568 mg) using CC with the same solvent system. The spectroscopic analyses and literature data revealed that the pure compounds are trimer stilbenoids, known as (+)-alpha-viniferin (1), hopeanolin (2) and davidiol A (3) ([Fig. 1]). These compounds have been reported from other species for their antiproliferative, antioxidant and antibacterial properties. Notably, this is the first report of these chemical constituents in this species.

Fig. 1 Structure of compounds 1-3.

Funding We appreciate the funding provided by University Teknologi MARA [600-UITMSEL (PI. 5/4) (127/2022)].

 

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Conflict of Interest

The authors declare no conflict of interest.

Publication History

Article published online:
16 November 2023