Tannins of theaceous plants. II. Camelliins A and B, two new dimeric hydrolyzable tannins from flower buds of Camellia japonica L. and Camellia sasanqua Thunb.

Yoshida, Takashi; Chou, Tong; Maruyama, Yasuhiko; Okuda, Takuo

doi:10.1248/cpb.38.2681

Cited by 29 publications

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“…While the NMR spectrum of synthetic 2 was identical to that of the authentic chart, significant differences were observed regarding the sign of optical rotation. 23) This discrepancy was likely due to impurities in the natural sample, as evidenced by unidentified peaks in the authentic NMR chart.…”

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Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

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“…The NMR spectrum and the optical rotation of synthetic 2 matched those of the reported data. 23) 9 SCHEME 7. Synthesis of 2 and 3.…”

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Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

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“…14) From the 1-butanol-soluble fraction, we have isolated new acylated oleanane-type triterpene saponins termed sasanquasaponins I (1), II (2) . 15) In addition, we examined the inhibitory effects of sasanquasaponins (1)(2)(3)(4)(5) and 6 on the release of b-hexosaminidase from RBL-2H3 cells. In this paper, we describe the isolation and structure elucidaMedicinal Flowers.…”

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“…XXXI. September 14, 2010 tion of the new saponins (1)(2)(3)(4)(5) and the inhibitory effects of the saponin constituents on the release of b-hexosaminidase from RBL-2H3 cells.…”

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“…Furthermore, comparison of the 1 H-and 13 C-NMR data for 2 and 3 with those for 1a revealed an acylation shift around the 22-postion of the A 1 -barrigenol part. Consequently, the chemical structures of sasanquasaponins II (2) and III (3) were characterized to be as shown. The proton and carbon signals in the 1 H-and 13 C-NMR spectra of 4 was also similar to those of 2, except for the signals due to the 22-and 28-positions.…”

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Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I-V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua

et al. 2010

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A Theaceae plant, Camellia (C.) sasanqua THUNB. (Japanese name "sazanka"), which is native to Japan, has been widely cultivated as an ornamental plant in Japanese garden. The flower buds of this plant are used for the similar purpose to those of C. japonica (Japanese name "tsubaki"), which has been used for the treatment of blood vomiting and bleeding due to internal and external injury, and also as antiinflamatory, tonic, and stomachic in Japanese folk medicine. As chemical constituents of this medicinal flower, several hydrolyzable tannins, 2) acylated anthocyanins, 3) and purin alkaloids 4) were reported. However, the pharmacological activities of the flower buds of this plant have not yet characterized. Recently, we have reported the isolation and structure elucidation of triterpene saponins from the flower buds of C. japonica L. (camelliosides A-D), 5,6) C. sinensis L. (chakasaponins I-VI, floratheasaponins A-J), [7][8][9][10][11][12] and C. oleifera ABEL (yuchasaponins A-D).13) Furthermore, those saponins were found to exhibit antiallergic, antidiabetic, antiobestic, gastroprotective, and platelet aggregation activities, etc. 5-13)As a continuation of our studies on bioactive constituents of the flower buds of Camellia species, we found that the methanolic extract and its 1-butanol-soluble fraction from the flower buds of C. sasanqua inhibited an immediate allergic reaction by monitoring the release of b-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. 14) From the 1-butanol-soluble fraction, we have isolated new acylated oleanane-type triterpene saponins termed sasanquasaponins I (1), II (2), III (3), IV (4), and V (5), together with a known saponin, primulagenin15) In addition, we examined the inhibitory effects of sasanquasaponins (1-5) and 6 on the release of b-hexosaminidase from RBL-2H3 cells. In this paper, we describe the isolation and structure elucidaMedicinal Flowers. XXXI. Yamashina-ku, Kyoto 607-8412, Japan: and b Pharmaceutical Research and Technology Institute, Kinki University; 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan. Received August 9, 2010; accepted September 13, 2010; published online September 14, 2010 The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia sasanqua THUNB. were found to show inhibitory activities on the release of b-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. From the 1-butanol-soluble fraction, five new acylated oleanane-type triterpene saponins, sasanquasaponins I-V, were isolated together with a known saponin and their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, sasanquasaponins I-III, with an acyl group at the 22-position of the aglycon part showed the inhibitory effects on the release of b-hexosaminidase and some structure-activity relationships were reported.

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Chemistry and function of vegetable polyphenols with high molecular weights

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Structure and function of polypehnols with high molecular weights (tannins) were briefly reviewed to better understand the significance of polyphenol-rich foods and beverages. In a survey of bioactive ellagiannins with a macrocyclic structure and/or a gluconic acid core, some new oligomeric ellagitannins (eucarpanins and elaeagnatins) have been found in species of Myrtaceae and Elaeagnaceae, and their structures were elucidated by spectroscopic and chemical methods. Cytotoxic activity against human oral tumor cell lines and antibacterial activity against Helicobacter pylori have been evaluated for the ellagitannins obtained from both plants, and related compounds. The macrocyclic dimers, oentothein B, camelliin B and woodfordin C showed a remarkable cytotoxicity against human oral squamous cell carcinoma, but not against normal cells. These active tannins induced apoptosis of tumor cells. A potent antibacterial activity against Helicobacter pylori was exhibited by monomeric ellagitannins such as tellimagrandin I and stricitinin.

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Tannins of theaceous plants. II. Camelliins A and B, two new dimeric hydrolyzable tannins from flower buds of Camellia japonica L. and Camellia sasanqua Thunb.

Cited by 29 publications

References 0 publications

Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I-V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua

Chemistry and function of vegetable polyphenols with high molecular weights

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