Stilbenoids Isolated from Stem Bark of Shorea hemsleyana.

Abstract

Two new stilbene glucosides [(+)-alpha-viniferin 13b-O-beta-glucopyranoside and resveratrol 12-C-beta-glucopyranoside] and two new resveratrol oligomers, hemsleyanols A and B, were isolated from the bark of Shorea hemsleyana along with four known resveratrol oligomers. The structures of the isolates, including the relative configurations, were established by spectroscopic data involving long-range coupling and nuclear Overhauser effect experiments.

Hopeafuran and a C-Glucosyl Resveratrol Isolated from Stem Wood of Hopea utilis.

“…4) Dipterocarpaceaous plants generally contain stilbene derivatives, which consist of a resveratrol (E-3,5,4Ј-trihydroxystilbene) unit and are sometimes substituted with a glycosyl moiety. 5,6) We previously reported the isolation and structure elucidation of resveratrol oligomers in this family (Hopea, 7) Vatica, 8,9) and Shorea 10,11) ) and their distinctive cytotoxicity was disclosed.…”

Occurrence of C-Glucoside of Resveratrol Oligomers in Hopea parviflora

“…The presence of a C-b-glucopyranosyl moiety was supported by NMR spectral data which showed six carbon signals (d C 78.6, 73.7, 79.3, 69.9, 80.7, 60.9) and an anomeric proton [d H 4.86 (d, Jϭ9.6 Hz)]. 4,9,11,13) These results indicated that the aglycone of 1 has the composition C 70 H 52 O 16 corresponding to five Res units (Res A-E; resveratrol A unit: i.e., between rings A 1 and A 2 via carbons C-7a and C-8a), which indicated that the aglycone has 44 degrees of unsaturation. The significant 3 J HMBC correlations [H-7a/C-2a(6a), H-8a/C14a, H-7b/C-2b(6b), H-7c/C-2c(6c), H-8c/C-14c, H-7d/C2d(6d), H-8d/C-10d(14d), H-7e/C-2e(6e), and H-8e/C-14e] demonstrated the C-C bonds C-1a-C-7a, C-8a-C-9a, C1b-C-7b, C-1c-C-7c, C-8c-C-9c, C-1d-C-7d, C-8d-C-9d, C-le-C-7e, and C-8e-C-9e, which showed the presence of four Res units (Res A, C-E) and a phenyl ethane moiety (ring B 1 -C-7b-C-8b).…”

“…Our previous phytochemical study demonstrated that the structural diversity is due to the oligomerization degree of the blocking unit of resveratrol, which generates a skeletal variation and complicated stereostructures, and the production of O-and C-glucosides. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] The genus Hopea belongs to Shoreae, one of the two major tribes of the subfamily Dipterocarpoideae, with about 102 species distributed throughout southeast Asia, especially in Indonesia and Malaysia, southern China, southern and eastern India, and Sri Lanka. 15) During this decade, this genus has been well documented to be a good source of biologically active stilbenoids.…”

Modern Applied Science, Vol. 3, No. 4, April 2009, all in one file

“…These plants are mainly growth in tropical areas. The chemical research on these plants has long been done (Dai et al, 1998;Ito et al, 2000;Noviany et al, 2002;Saraswathy, et al, 1992;Sultanbawa et al, 1987;Zheng et al, 1994), but for such big family plants, the chemistry of Dipterocarpaceae is relatively less known. This is because the initial research on Dipterocarpaceae was mainly focused on chemical compounds of their resins such as terpenoid, sesquiterpen and triterpen.…”