Resveratrol Oligomers and Their O-Glucosides from Cotylelobium lanceolatum

Ito, Tetsuro; Ali, Zulfıqar; Furusawa, Miyuki; Iliya, Ibrahim; Tanaka, Toŝhiyuki; Nakaya, Ken‐ichi; Murata, Jin; Darnaedi, Dedy; Iinuma, Munekazu

doi:10.1248/cpb.54.363

Cited by 7 publications

(13 citation statements)

References 16 publications

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“…In the majority of resveratrol tetramers, the structure can be attributed to the presence of the configurationally conserved dihydrobenzofuran motif, which is a crucial issue in explaining the absolute configuration of high-order ROs. The production of resveratrol tetramers proceeds in a similar fashion to the resveratrol trimers via the initial formation of two QMs, specifically 5B-5B bis-QM (33) (8-8′ coupling mode) and 5B-5E QM (34) (8-10′ [19], and cotylelophenol C (44) [42], respectively. This indicates the existence of a similar mechanism with corresponding QM intermediates between the resveratrol trimers and tetramers.…”

Section: Resveratrol Tetramersmentioning

confidence: 99%

“…Alternatively, the biosynthesis of 8-10′ tetramers can be explained by another primary intermediate, 34, which preferentially undergoes intramolecular 5-exo-trig cyclization through C 8b -C 7c isomerizing to 35 instead of 7-exo-trig cyclization as in 39, the latter of which would produce less types of frame skeletons than those from 33. The QM (35) and isomerized 5B-5E QM" (36) follow different cyclization pathways, resulting in the production of vaticanols B (42), C (43) [19] (vat diospyroidol [75]), and 44 [42]. In fact, 42, which is usually present with 43, is another abundant tetramer found in many DPs.…”

Section: Resveratrol Tetramersmentioning

confidence: 99%

“…Initial research goals mainly encompassed two topics: to define the structural diversity afforded by the condensation degree, varying skeletons, and isomerisms due to the number of asymmetric carbons found in this class of natural products; to gain insight into the research area of polyphenol (i.e., the chemistry of RO), which requires expanding the existing chemical library and accumulating spectroscopic details. In the last 2 decades, phytochemical studies have achieved the isolation and structural elucidation of roughly 200 ROs in species belonging to the following seven genus: Vatica (V. rassak [16][17][18][19], V. pauciflora [20,21], V. albiramis [22][23][24][25], and V. chinensis [25][26][27]), V. bantamensis [25], Vateria (V. indica) [28][29][30][31][32][33], Upuna (U. borneensis) [34][35][36][37][38][39][40][41], Cotylelobium, (C. lanceolatum) [42][43][44], Dipterocarpus (D. grandiflorus) [45,46], Shorea (S. hemsleyana [33,[47][48][49][50], S. uliginosa [33,[51][52][53]…”

Section: Introductionmentioning

confidence: 99%

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Resveratrol oligomer structure in Dipterocarpaceaeous plants

Ito

2020

J Nat Med

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Oligostilbenoids are a group of natural products derived from the oxidative coupling of C6–C2–C6 units found in some plant families. A structurally diverse chemical pool is produced after the successive regioselective and stereoselective oligomerization of resveratrol. This review describes the current status and knowledge of the structure of resveratrol oligomers (ROs) in Dipterocarpaceaeous plants (DPs). Beginning with the recently validated formation of ROs in DPs, each downstream conversion is described from the perspective of the resveratrol coupling mode. Particular emphasis is placed upon the regioselectivity of monomer- and dimer-derived radical–radical coupling processes, which are responsible for producing dimers, trimers, and tetramers with various cyclic frame skeletons, as well as related processes that result in highly condensed scaffolds, such as hexamers and octamers. Trimers in oxidized, dearomatized, and rearranged forms are also summarized, as well as the biogenic relationship between the compounds. Furthermore, emphasis is placed on the O- and C-glucosides of ROs, as well as on the hetero-coupled ROs. In addition, several stereoisomers that originate from asymmetric carbons and the stereochemistry with respect to the conformation due to the chiral axis are described. Besides, NMR spectroscopic properties such as coalescence and anisotropy are briefly described. Approaches to determine absolute configuration are also summarized.

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Section: Resveratrol Tetramersmentioning

confidence: 99%

Section: Resveratrol Tetramersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Resveratrol oligomer structure in Dipterocarpaceaeous plants

Ito

2020

J Nat Med

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“…[1][2][3][4][5][6][7] Fr. 7 (CHCl 3 -MeOH, 9 : 1) was further subjected to Sephadex LH-20 CC (MeOH) to give eight fractions (Fr.…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4][5][6][7] Further detailed examination of the acetone extract of stem yielded two new resveratrol tetramers, upunaphenols O (1) and P (2). The structure of isolates 1 and 2 were elucidated by means of 2D NMR techniques such as 1 H-1 H shift correlation spectroscopy (COSY), 13 C-1 H COSY, and 1 H-…”

mentioning

confidence: 99%

Two New Resveratrol Tetramers from Upuna borneensis

Ito

Abe

Ali

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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During the course of our research on the isolation and identification of bioactive polyphenols in Dipterocarpaceaeous plants, we have previously reported the structural variety of resveratrol oligomers in Upuna borneensis. [1][2][3][4][5][6][7] Further detailed examination of the acetone extract of stem yielded two new resveratrol tetramers, upunaphenols O (1) and P (2). The structure of isolates 1 and 2 were elucidated by means of 2D NMR techniques such as 1 H-1 H shift correlation spectroscopy (COSY), 13 C-1 H COSY, and 1 H- 13C heteronuclear multiple-bond correlation (HMBC), and the stereostructures were proposed by analysis of the nuclear Overhauser spectroscopy (NOESY) spectra. Results and DiscussionUpunaphenols (Fig. 1, Table 1) showed the presence of ortho-coupled aromatic protons assignable to three 4-hydroxylphenyl groups (rings A 1 , B 1 and D 1 ), a 4-oxygenated phenyl group (ring C 1 ), three sets of meta-coupled aromatic protons on a 1,2,3,5-tetrasubstituted benzene ring (rings A 2 , B 2 and C 2 ), and a 3,5-dihydroxyphenyl group (D 2 ). The NMR spectral data also disclosed the presence of two sets of aliphatic signals characteristic for 2,3-diaryldihydrobenzofuran moieties (H-7a/H-8a; H-7d/H-8d), 8) two coupled aliphatic methine protons (H-7b/H-8b), cis-coupled olefinic protons (H-7c/H8c), and nine phenolic hydroxyl groups (d H 7.97-8.64). Considering the molecular formula, the remaining three oxygens can be allocated to ether linkage. In the HMBC spectrum (Fig. 1), significant 3 J correlations were observed between H-7a/C-2a(6a), H-14a/C-8a, H-7b/C-2b(6b), H-14b/C8b, H-7c/C-2c(6c), H-8c/C-14c, H-7d/C-2d(6d), and H-8d/C10d(14d), indicating that rings A 1 , A 2 , B 1 , B 2 , C 1 , C 2 , D 1 , and D 2 are attached at C-7a, C-8a, C-7b, C-8b, C-7c, C-8c, C-7d, and C-8d, respectively. Further correlations observed between H-8a/C-11b, H-7b/C-11a, and H-8d/C-11c supported ; Japan: c Microbial Chemistry Research Center; Japan: d Botanical Gardens, Koishikawa, Graduate School of Science, University of Tokyo; Japan: and e Indonesian Institute of Sciences; Jalan Ir. H. Juanda 13, Bogor 16122, Indonesia. Received December 15, 2008; accepted February 16, 2009; published online February 25, 2009 Phytochemical investigation of an acetone extract of Upuna borneensis (Dipterocarpaceae) resulted in the isolation of two new resveratrol tetramers, upunaphenols O (1) and P (2). The structures were elucidated by spectroscopic analysis including NMR experiments.

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Bioactive stilbenes from plants

Zhou²,

Li³

2022

Studies in Natural Products Chemistry

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Resveratrol Oligomers and Their O-Glucosides from Cotylelobium lanceolatum

Cited by 7 publications

References 16 publications

Resveratrol oligomer structure in Dipterocarpaceaeous plants

Resveratrol oligomer structure in Dipterocarpaceaeous plants

Two New Resveratrol Tetramers from Upuna borneensis

Bioactive stilbenes from plants

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