Two Novel Trimeric Resveratrol Derivatives fromCotylelobium lanceolatum

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

doi:10.1002/cbdv.200590091

Cited by 18 publications

(14 citation statements)

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“…The other ROEs H-3b(5b) (1A)/H-3e(5e) (1B) and H-3d(5d) (1A)/H-8f (1B) indicated the relationship between 1A and 1B as shown in Fig. 2 and confirmed the lack 15) and grandiphenol D. 16) Compound 1 can be considered to be a condensed product of resveratrol tetramer (1A: vaticanol B) and resveratrol dimer (1B). As previously discussed, vaticanol B, one of the major constituents, functions as a blocking unit in the biogenesis of highly condensed resveratrol oligomers as elucidated by structures of vaticanol J (heptamer), 12) upunoside A (pentamer), 17) and pauciflorol D (heptamer), 18) and can be applicable to the biosynthetic pathway of 1.…”

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Resveratrol Derivatives from Vatica albiramis

et al. 2011

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Resveratrol Derivatives from Vatica albiramis

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“…14) As discussed in previous articles, the behavior of some protons in stilbene oligomers is very complicated. 3,4,[22][23][24][25] Therefore, further spectroscopic evidence in connection with steric factors are required for the accurate determination of the configuration in stilbene oligomers such as 1 and related compounds.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleDipterocarpaceaeous plants have been known to have an abundance of stilbene oligomers that have a blocking unit of resveratrol. The woody plant Vateria indica LINN. (Dipterocarpaceae) is distributed in India and Sri Lanka, and the resin has been used as a traditional medicine for sore throat, chronic bronchitis, rheumatism, and diarrhea.1) The stem of the genus Vateria is known to produce biologically active compounds such as oligostilbenoids and monoterpenes. [2][3][4][5][6] Our previous study demonstrated that the leaves also contain stilbene derivatives in high quantity. 6) Recently, the bioactivities of stilbenoids isolated from Dipterocarpaceaeous plants have been reported to have antimicrobial activites, 7,8) antitumor activities, [9][10][11] and regulation of endoplasmic reticulum stress. H COSY, and heteronuclear multiple bond connectivity (HMBC). Stereostructures were proposed by analysis of nuclear Overhauser effect spectroscopy (NOESY), differential rotating frame Overhauser enhancement (ROE), and ROESY spectra, as well as high-resolution (HR) FAB-MS and electrospray ionization (ESI)-MS analysis and circular dichroism (CD) spectroscopic properties. Vateriaphenol F (1) has a unique C 2 -symmetric structure. Results and DiscussionVateriaphenol F (1) and vaterioside A (2) were purified from an acetone extract of V. indica by open column chromatography on DMS, octadecyl silica (ODS), Silica gel, and Sephadex LH-20, as well as HPLC. Vaterioside B (4) was purified from MeOH extract by repeated chromatography.Vateriaphenol F (1) ([a] D 25 Ϫ136°), obtained as a pale-yellow solid, showed positive reaction to Gibbs reagent. The structure is composed of four resveratrol units (A-D; resveratrol A unit: i.e., between rings A 1 and A 2 via carbons C-7a and C-8a). A detailed elucidation was carried out as follows. The molecular formula was assigned to C 56 H 44 O 13 by HR-ESI-MS that showed a pseudomolecular ion [MϩNa] ϩ at m/z 947.2670, indicating 35 degrees of unsaturation. In the 1 H-and 13 C-NMR spectra at rt, some signals due to ring A 2 were broadened in various solvents. In the 1 H-NMR spectrum in acetone-d 6 at Ϫ30°C, the signals due to Pharmacognosy, Gifu Pharmaceutical University; 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan: b Institute of Microbial Chemistry, Tokyo; 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan: and c Survey of Medicinal Plant Unit, Central Council for Research in Ayurveda and Siddha; Tirunelveli-627002, Tamil Nadu, India. Received June 23, 2010; accepted July 15, 2010; published online July 16, 2010 Comprehensive re-investigation of the chemical constituents in the leaves of Vateria indica (Dipterocarpaceae) resulted in the isolation of a novel resveratrol dimeric dimer having a C 2 -symmetric structure, vateriaphenol F (1), and two new O-glucosides of resveratrol oligomers, vateriosides A (2) (resveratrol dimer) and B (4) (resveratrol tetramer), along with a new natural compound (3) and 33 known compounds including 26 resveratrol derivatives. The absolu...

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“…Stilbene trimer without dihydrofuran ring is rarely found in this genus [46]. The constituents from this group are vaticanol G (40) isolated from V. rassak [47], V. pauciflora [30,31] and V. umbonata [39] as well as its glycoside known as vaticaside D (41) isolated from V. rassak [47] and V. pauciflora [31].…”

Section: Stilbene Trimermentioning

confidence: 99%

Oligostilbenoids from Vatica Species and Bioactivities

Kamarozaman

Rajab²,

Latip³

2014

Recent Trends in Physics of Material Science and Technology

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Reactive species (RS) which are generated from the pollution, deep fried and spicy foods, leakage of electrons from mitochondrial electron transport chains etc. may result in an oxidative damage in the body. The oxidative damage may lead to various diseases such as Alzheimer, atherosclerosis and cancer. In order to prevent such diseases, antioxidants play important roles in reducing the powerful oxidizing agents. Vatica species that belongs to the family of Dipterocarpaceae has been widely known to contain abundant source of oligostilbenoids which demonstrated interesting result in biological activities such as anticancer and antioxidant. This may lead to a development of drugs as well as natural antioxidants. In this chapter, we are highlighting the oligostilbenoids isolated from Vatica species from various researcher as well as the biological activities.

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Two Novel Trimeric Resveratrol Derivatives fromCotylelobium lanceolatum

Cited by 18 publications

References 18 publications

Resveratrol Derivatives from Vatica albiramis

Resveratrol Derivatives from Vatica albiramis

Chemical Constituents in the Leaves of Vateria indica

Oligostilbenoids from Vatica Species and Bioactivities

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