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Resveratrol Oligomers from the Stem Bark of Vatica mangachapoi

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Vatica, a genus comprising about 65 species, belongs to the largest subfamily Dipterocarpoideae in the family Dipterocarpaceae, most of which are tall, hardy, and evergreen trees primarily distributed throughout Southeast… Click to show full abstract

Vatica, a genus comprising about 65 species, belongs to the largest subfamily Dipterocarpoideae in the family Dipterocarpaceae, most of which are tall, hardy, and evergreen trees primarily distributed throughout Southeast Asia, especially in Indonesia and Malaysia [1], south and east India, and Sri Lanka. This genus is well documented to be a rich source of biologically active resveratrol oligomers. As a phytoestrogen, resveratrol and its oligomers have recently attracted attentions because of their multifunctional bioactivities that may account for its possible cardioprotective action, including smooth muscle cell proliferation and platelet aggregration [2], chemoprevention of cancers [3], activation of human SIRT1 [4], and anti HIV effect [5]. Because of its pharmacological functions, resveratrol and its oligomers are now gaining scientific attention as a longevity promoter. Vatica mangachapoi, a large and rather rare species, occurs only in Hainan Island in China and is used as a disinfection, against hepatitis, and in the extraction of borneol. Although Vatica species have been reported to possess a diversity of polyphenols and biological activities, there have been rare reports of phytochemical investigations or biological activity of this plant [6]. In an attempt to screen the biologically active fractions and compounds from tropical medicinal plants [7], a preliminary screening of successive petroleum ether, EtOAc, and H2O extracts of the stem bark of V. mangachapoi for antioxidant activities was made to measure their free-radical-scavenging effects using the DPPH free radical method [8, 9]. The EtOAc and H2O extracts showed good antioxidant capacity, with IC50 values of 54.4 and 32.7 μM, respectively. Further chemical investigations of the EtOAc extract led to the isolation of 15 resveratrol oligomers, including parviflorol (1) [10], diptoindonesin D (2) [11], eight resveratrol dimers vaticahainol (3) [6], vitisinol G (4) [12], malibatol A (5) [13], vaticahainol C (6) [6], ampelopsin A (7) [14], balanocarpol (8) [10], ampelopsin F (9) [15], and isoampelopsin (10) [16], two resveratrol tetramers vaticaffinol (11) [17] and isohopeaphenol A (12) [18], two resveratrol dimers O-glucosides cordifoloside B (13) [19] and vatalbinoside D (14) [20], and one resveratrol trimer O-glucoside paucifloroside B (15) [21]. These compounds were characterized by spectral data and comparison with those reported in the literature. The three resveratrol oligomers O-glucosides (13–15) were firstly isolated from Shorea cordifolia [19], V. albiramis [20], and V. pauciflora [21], respectively, and recently from V. mangachapoi, which was the second time that these resveratrols were isolated from a natural source. It is also the first report of resveratrol oligomer O-glucosides isolated from V. mangachapoi. Thus, resveratrol oligomers (1–15) isolated from Vatica species could be chemotaxonomic markers for the Vatica genus. The stem bark of V. mangachapoi was collected in Changjiang County, Hainan Province, P. R. China in July 2011. It was identified by Ass. Prof. Zhong Qiong-xin. The voucher specimen has been deposited at the Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, Hainan Normal University, Haikou, Hainan, P. R. China. The air-dried powder of the stem bark of V. mangachapoi (10.0 kg) was exhaustively extracted three times with 85% EtOH–H2O at room temperature to afford a crude extract (1.2 kg). The extract was suspended in H2O and then partitioned successively with petroleum ether and EtOAc.

Keywords: resveratrol; resveratrol oligomers; stem bark; mangachapoi; vatica

Journal Title: Chemistry of Natural Compounds
Year Published: 2018

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