Oligostilbenoids in stem bark of Vatica rassak

Tanaka, Toŝhiyuki; Ito, Testuro; Nakaya, Ken‐ichi; Iinuma, Munekazu; Riswan, Seodarsono

doi:10.1016/s0031-9422(00)00026-1

Cited by 102 publications

(86 citation statements)

References 8 publications

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“…If this conjecture is adopted, the absolute structure of 1 is determined. However, the configuration of carbons on two 3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl groups of grandiphenol B (38) 14,17) is opposite, which requires clarification with spectroscopic evidence. The absolute configuration of 1 was assigned based on the CD spectroscopic evidence [ Fig.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

“…However, two 3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-benzofuranyl groups in the diaryltetrahydrofuran ring of 1 would bring about additional effects on the Cotton curve, requiring exact understanding of which substituents are further associated with the curve in the region 220-250 nm. Grandiphenols A (19) and B (38) are stereoisomers of 1, 14) the relative configurations of which were determined in our previous study; 7a-R, 8a-R, 7b-R, 8b-R, 7c-S, 8c-R, 7d-R, and 8d-R for 19 and 7a-R, 8a-R, 7b-R, 8b-R, 7c-R, 8c-S, 7d-S, and 8d-S for 38. When the CD curves of 1 and 19 are compared, a difference is observed in intensity of the negative Cotton effects at 238 nm [19: De Ϫ50.0 (cϭ10.1 mM, MeOH)], which indicated that the configurational difference of C-7b contributes to the results because 19 is an epimer of 1 of C-7b.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

“…30) 2-b-glucopyranosyloxyphenanthrene-4,6-diol (9), 31) paucifloroside A (11), 23) cis-(Ϫ)-eviniferin (12), 32) upunoside D (13), 33) balanocarpol (14), 34) melanoxylin A (15), 35) malibatol (16), 36) (Ϫ)-ampelopsin F (17), 37) pauciflorol B (18), 23) vaticanol C (20), 38) hemsleyanols C (21) and D (22), 39) pauciflorol C (23), 23) vateriaphenol B (24), 4) nepalensinol G (25), 40) stenophyllol A (26), 41) vaticanol B (27), 38) vaticasides B (28) and C (29), 42) and upunaphenol F (30). 43) The other known compounds were identified to be flavonols [kaempferol 3-O-rhamnoside (31), 44) kaempferol 3-O-rhamnopyranosyl-(1→2)-rhamnopyranoside (32), and quercitrin (33) 45) ], diterpenes [columbin (34) 46) and palmarin (35) 47) ], bergenin (36), 11) and syringin (37).…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

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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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Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

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Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…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.…”

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confidence: 99%

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

Tanaka

Ito

Ido

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Among those already investigated, great attention has been paid to polyphenols because of their antioxidant and possible antitumor properties [1], including α-and γ-mangostin from the mangosteen pericarp [2][3][4] and resveratrol. Resveratrol, a chemo preventive and therapeutic polyphenol found in grape skin and dipterocarpaceous plants [5], is one of the most famous phytochemical compounds currently under investigation. Several studies have shown that resveratrol actually possesses multiple biological activities ranging from anti-tumor functions [6] to prevention of heart disease [7].…”

Section: Editorialmentioning

confidence: 99%

A Novel Resveratrol Tetramer Vaticanol C from Stem Bark Acts as an Antimetastatic Action in a Mouse Mammary Cancer Model

Shibata¹

2015

Altern Integr Med

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EditorialPlants and plant extracts have been traditionally used in Ayuvedic and Chinese medicine for many centuries. A large number of natural products appear to have strong therapeutic effects and the discovery of new plants with potential biological activities is a passionate endeavor for many concerned with natural medicinal. Among those already investigated, great attention has been paid to polyphenols because of their antioxidant and possible antitumor properties [1], including α-and γ-mangostin from the mangosteen pericarp [2-4] and resveratrol. Resveratrol, a chemo preventive and therapeutic polyphenol found in grape skin and dipterocarpaceous plants [5], is one of the most famous phytochemical compounds currently under investigation. Several studies have shown that resveratrol actually possesses multiple biological activities ranging from anti-tumor functions [6] to prevention of heart disease [7].Isolated from the stem bark of Vatica rassak in Dipterocarpacea, the resveratrol tetramer vaticanol C has shown induction of apoptotic cell death and suppression of cell proliferation in various human cancer cells [8], suggesting anti-tumoral effects. We recently demonstrated anti-metastatic effects of vaticanol C [9] in a mouse metastatic mammary cancer model carrying a p53 mutation, a model which demonstrates a metastatic spectrum similar to that seen in human breast cancers [4,10]. Here, we introduced the summary of the results on anti-metastatic abilities of vaticanol C in vitro and in vivo experiments [9].Vaticanol C induced in vitro apoptosis, as evaluated by morphological changes, nucleosomal DNA fragmentation, and elevated activities of caspases (which are executional factors of apoptosis); similarly, apoptosis was significantly increased in vivo in mammary tumor cells exposed to 200 ppm dietary vaticanol C. Although tumor growth was similar between the control and vaticanol C-treated groups, the multiplicities of lymph node and lung metastasis were significantly reduced only in animals receiving the highest dose (200 ppm) of vaticanol C; overall metastasis to any organ also decreased, but not to a statistically significant degree over control. Cell proliferation rates tended to decrease in mammary tumors with exposure to vaticanol C in a dose-dependent manner but, again, the decrease was not statistically significant. Breast cancer is one of the most lethal cancers in humans, and death is largely due to metastasis, usually to lungs, lymph node, liver, and bone. Since lymph node involvement is the most important prognostic factor in breast cancer patients, the anti-metastatic activity of vaticanol C may be of clinical significance.Angiogenesis in mammary tumors tended to be lower in vaticanol C-treated groups. Furthermore, the numbers of dilated lymphatic vessels having intraluminal cancer cells (an indication of lymphatic invasion) in mammary tumors were significantly decreased with administration of vaticanol C, indicating a reduction in tumor cell migration -at least, by the lymphatic route. The most...

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Oligostilbenoids in stem bark of Vatica rassak

Cited by 102 publications

References 8 publications

Chemical Constituents in the Leaves of Vateria indica

Chemical Constituents in the Leaves of Vateria indica

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

A Novel Resveratrol Tetramer Vaticanol C from Stem Bark Acts as an Antimetastatic Action in a Mouse Mammary Cancer Model

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