- Euscaphinin, a new ellagitannin dimer from Euscaphis japonica (Thunb.) Kanitz
-
A new ellagitannin dimer named euscaphinin was isolated from the leaves of Euscaphis japonica (Thunb.) Kanitz. The structure of this dimer was determined on the basis of spectroscopic and chemical evidence. The resulting structure indicated that it was pr
- Maeda, Hajime,Matsuo, Yosuke,Tanaka, Takashi,Kouno, Isao
-
-
Read Online
- A new trimeric hydrolyzable tannin, oenotherin T2, isolated from aerial parts of Oenothera tetraptera Cav.
-
A new hydrolyzable tannin, oenotherin T2, was isolated from the aerial parts of Oenothera tetraptera Cav., together with 15 known polyphenols compounds. The trimeric structure of oenotherin T2 was elucidated based on spectroscopic da
- Taniguchi, Shoko,Imayoshi, Yoko,Yoshida, Takashi,Hatano, Tsutomu
-
experimental part
p. 617 - 626
(2009/12/26)
-
- Phloroglucinol diglycosides accompanying hydrolyzable tannins from Kunzea ambigua
-
Six phloroglucinol diglucosides-kunzeaphlogins A-F (1-6) and a hydrolyzable tannin, kunzeatannin A (7)-were isolated along with 10 known polyphenols from the leaf extract of Kunzea ambigua. Structural elucidation of these compounds was based on spectroscopic analyses and chemical properties.
- Kasajima, Naoki,Ito, Hideyuki,Hatano, Tsutomu,Yoshida, Takashi
-
experimental part
p. 3080 - 3086
(2009/05/09)
-
- Two novel dicarboxylic acid derivatives and a new dimeric hydrolyzable tannin from walnuts
-
In addition to the 16 previously reported polyphenols including 3 new ellagitannins, 2 novel dicarboxylic acid derivatives, glansreginins A (1) and B (2), and a new dimeric hydrolyzable tannin, glansrin D (3), were isolated, together with 15 known compounds from walnuts, the seeds of Juglans regia. The structures of the new compounds were elucidated on the basis of 1D- and 2D-NMR analyses and chemical data. The antioxidant effect of these isolates was also evaluated by SOD-like and DPPH radical scavenging activities.
- Ito, Hideyuki,Okuda, Takahiro,Fukuda, Toshiyuki,Hatano, Tsutomu,Yoshida, Takashi
-
experimental part
p. 672 - 679
(2009/09/30)
-
- Structure and biogenesis of jolkinin, a highly oxygenated ellagitannin from Euphorbia jolkinii
-
A new ellagitannin, jolkinin (2), was isolated from the fresh whole plant of Euphorbia jolkinii, and its structure, including absolute configuration, was determined on the basis of spectroscopic and chemical evidence. A highly oxygenated acyl group with unique hexacyclic structure is attached to the 2,4-positions of 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-β-D- glucopyranose. The structural similarity to elaeocarpusin (4) suggests that jolkinin is produced by a condensation reaction between ascorbic acid and geraniin (1), the dominant ellagitannin in this plant, which contains a dehydrohexahydroxydiphenoyl group. A plausible mechanism for jolkinin formation is also proposed.
- Lee, Seung-Ho,Tanaka, Takashi,Nonaka, Gen-Ichiro,Nishioka, Itsuo
-
p. 1018 - 1022
(2007/10/03)
-
- Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica
-
Six new ellagitannins, phyllanemblinins A-F (1-6), were isolated from Phyllanthus emblica, along with 30 known tannins and related compounds. Their structures were determined by spectral and chemical methods. Phyllanemblinins A (1) and B (2) were confirme
- Zhang, Ying-Jun,Abe, Tomomi,Tanaka, Takashi,Yang, Chong-Ren,Kouno, Isao
-
p. 1527 - 1532
(2007/10/03)
-
- Three novel C-glycosidic ellagitannins, Rhoipteleanins H, I, and J, from Rhoiptelea chiliantha
-
Three novel C-glycosidic ellagitannins named rhoipteleanins H (1), I (2), and J (3) were isolated from the fruits and bark of Rhoiptelea chiliantha Diels et Hand.-Mazz. (Rhoipteleaceae), and the structures were elucidated on the basis of detailed spectroscopic analysis and chemical evidence. Rhoipteleanin H possesses a unique cyclopentenone carboxyl moiety, which is probably formed by oxidation and subsequent rearrangement of an aromatic ring of a usual C-glycosidic ellagitannin. Rhoipteleanin I is the first ellagitannin having a hydroxynaphthalene glucoside moiety. Rhoipteleanin J is a dimeric ellagitannin generated by dehydrative coupling between two molecules of a monomeric C-glycosidic ellagitannin and subsequent oxidation of an aromatic ring. From a chemotaxonomic viewpoint, presence of these characteristic ellagitannins in this plant provides a further support for the establishment of the order Rhoipteleales comprising Rhoipteleaceae as the only family.
- Jiang, Zhi-Hong,Tanaka, Takashi,Kouno, Isao
-
p. 425 - 429
(2007/10/03)
-
- Oligomeric hydrolysable tannins from Tibouchina multiflora
-
Two hydrolysable tannins, nobotanin O and nobotanin P, were isolated from the leaf extract of Tibouchina multiflora (Melastomataceae) and their dimeric and tetrameric structures elucidated on the basis of spectral data and chemical correlations with nobotanin B and K, respectively. Thirteen known hydrolysable tannins including nobotanins A, B, C and J, which are oligomers characteristic of the Melastomataceae, were also isolated.
- Yoshida, Takashi,Amakura, Yoshiaki,Yokura, Nami,Ito, Hideyuki,Isaza, Jose Hipolito,Ramirez, Stella,Pelaez, Diana P.,Renner, Sussane S.
-
p. 1661 - 1666
(2007/10/03)
-
- Dimeric and trimeric ellagitannins from Corylus heterophylla
-
Besides previously reported tannins and related polyphenots, additional two new hydrolysable tannins, heterophylliins F and G, were isolated from the leaf extract of Corylus heterophylla, and characterized by spectral and chemical evidence as dimeric and trimeric ellagitannins, respectively, in which monomeric units are linked to each other through a valoneoyl group.
- Jin, Zhe-Xiong,Ito, Hideyuki,Yoshida, Takashi
-
p. 333 - 338
(2007/10/03)
-
- Tannins and related compounds. CXXIV. Five new ellagitannins, platycaryanins A, B, C, and D, and platycariin, and a new complex tannin, strobilanin, from the fruits and bark of Platycarya strobilacea Sieb et Zucc., and biomimetic synthesis of C-glycosidic
-
Five new ellagitannins, platycaryanins A (27), B (26), C (30), and D (25), and platycariin (31), and a new complex tannin, strobilanin (32), have been isolated from the fruits and bark of Platycarya strobilacea SIEB, et ZUCC, (Juglandaceae), together with
- Tanaka,Kirihara,Nonaka,Nishioka
-
p. 1708 - 1716
(2007/10/02)
-
- Monoacetoxylation of Methylenedioxy Groups in Dimethyl 4,4'-Dimethoxy-2,3,2',3'-bismethylenedioxy-1,1'-biphenyl-6,6'-dicarboxylate with Lead Tetraacetate
-
The utility of lead tetraacetate as a reagent for the monoacetoxylation of a methylenedioxy group in dimethyl 4,4'-dimethoxy-2,3,2',3'-bismethylenedioxy-1,1'-biphenyl-6,6'-dicarboxylate (1a) is demonstrated.Mechanistic feature of the monoacetoxylation is descussed.
- Kimura, Masayuki,Matsuoka, Yoshiyuki,Hosaka, Kunio
-
p. 1989 - 1996
(2007/10/02)
-
- Tannins and related compounds. CXVII. Isolation and characterization of three new ellagitannins, lagerstannins A, B and C, having a gluconic acid core, from Lagerstroemia speciosa (L.) Pers
-
Lagerstannins A (6), B (11) and C (8), ellagitannins having a gluconic acid core, have been isolated from the fruits and leaves of Lagerstroemia speciosa (L.) Pers. (= L. flos-reginae Retz.) (Lythraceae). On the basis of chemical and spectroscopic evidence, their structures were established as 2,3;4,6-bis-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (6), 2,3,5-O-(S,R)-flavogallonyl-4,6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (11), and 5-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (8), respectively. Furthermore, the structure of an ellagitannin, punigluconin, previously isolated from the bark of Punica granatum L., was revised as 2,5-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (10), based on spectral re-examination.
- Tanaka,Tong,Xu,Ishimaru,Nonaka,Nishioka
-
p. 2975 - 2980
(2007/10/02)
-
- HIRSUNIN, AN ELLAGTANNIN WITH A DIARYLHEPTANOID MOIETY, FROM ALNUS HIRSUTA VAR. MICROPHYLLA
-
A novel ellagtannin, hirsunin, was isolated from the leaves of Alnus hirsuta var. microphylla and the structure which consist of diarylheptanoid glycoside (oregonin) and ellagtannin (praecoxin A) moieties connected through an ester linkage has been elucidated.Furthermore, the occurrence of the seven known hydrolysable tannins, pedunculagin, praecoxin A, 1,2,6- and 1,4,6-tri-O-galloyl-β-D-glucoses, 1-desgalloyleugeniin, 1-desgalloylrugosin F, and rugosin F, along with oregonin and gentisic acid 5-O-β-D-(6'-O-galloyl)-glucopyranoside has also been demonstrated. Key words: Alnus hirsuta var. microphylla; Betulaceae; hydrolysable tannin; ellagtannin; hirsunin; praecoxin A; diarylheptanoid; oregonin.
- Lee, Min-Won,Tanaka, Takashi,Nonaka, Gen-Ichiro,Nishioka, Itsuo
-
p. 967 - 970
(2007/10/02)
-
- Eucalbanins A, B and C. monomeric and dimeric hydrolyzable tannins from Eucalyptus alba Reinw.
-
Three new hydrolyzable tannins, eucalbanins A (5), B (8) and C (11), have been isolated from the fruit extract of Eucalyptus alba Reinw., and their structures were elucidated on the basis of spectral data and chemical correlation with known tannins. Quercetin-3-O-α-L-arabinopyranoside, (+)-catechin, procyanidin B-7, and nine known hydrolyzable tannins [casuarinin, casuariin, pedunculagin, tellimagrandin I (1), gemin D (2), cornusiin B (3),2,3-(S)-hexahydroxydiphenoyl-D-glucose, penta-O-galloyl-β-D-glucose and oenothein B (4)] have also been isolated.
- Yoshida,Maruyama,Nitta,Okuda
-
p. 1750 - 1754
(2007/10/02)
-
- Tannins and related polyphenols of euphorbiaceous plants. IX. Hydrolyzable tannins with 1C4 glucose core from Phyllanthus flexuosus Muell. Arg.
-
Four new hydrolyzable tannins (phyllanthusiins A-D), a new polyphenol of related structure (phyllanthusiin E), and eight known polyphenols have been isolated from the leaves of Phyllanthus flexuosus. On the basis of the spectroscopic methods including 1H-13C long-range two-dimensional nuclear magnetic resonance techniques, phyllanthusiins A (9), B (12) and C (14), were characterized as oxidative metabolites of geraniin, each having a different new acyl group biogenetically formed via an oxidative cleavage of the dehydrohexahydroxydiphenoyl group, on the 1C4 glucopyranose core. Phyllanthusiin D (15) was determined to be a condensate of geraniin with acetone, and phyllanthusiin E (16), was an oxidized congener of ellagic acid.
- Yoshida,Itoh,Matsunaga,Tanaka,Okuda
-
-
- Tannins of Euphorbiaceous plants. X. Antidesmin A, a new dimeric hydrolyzable tannin from Antidesma pentandrum var. barbatum
-
A new hydrolyzable tannin, antidesmin A (4), was isolated along with carpinusin (1) and geraniin (2) from dried leaves of Antidesma pentandrum MERR. var. barbatum MERR., and its dimeric structure, composed of davidiin (3) and geraniin (2), has been elucidated by spectral and chemical methods.
- Yoshida,Namba,Lu,Yang,Yen,Okuda
-
p. 338 - 342
(2007/10/02)
-
- Woodfordin D and oenothein A, trimeric hydrolyzable tannins of macro-ring structure with antitumor activity
-
Two new antitumor trimeric hydrolyzable tannins, woodfordin D (5) and oenothein A (13), were isolated from the dried flowers of Woodfordia fruticosa, and their macrocyclic structures, which have a novel constituent unit (woodfordinoyl group) connecting the monomers, have been elucidated on the basis of spectral and chemical evidence. Oenothein A (13) was also isolated from the leaves of Oenothera biennis.
- Yoshida,Chou,Matsuda,Yasuhara,Yazaki,Hatano,Nitta,Okuda
-
p. 1157 - 1162
(2007/10/02)
-
- Tannins and related compounds. CIX. Isolation of alienanins A and B, novel C,C-linked ellagitannin dimers from Quercus aliena Blume
-
Two novel hydrolyzable tannins, alienanins A (5) and B (13), have been isolated from the leaves of Quercus aliena Blume (Fagaceae), and their structures were elucidated on the basis of chemical and spectroscopic evidence to be dimeric C-glycosidic ellagitannins in which the hexahydroxydiphenoyl ester group is linked to the C-glycosidic C-1 atom through a carbon to carbon linkage. In addition, the structure elucidation of the monomeric C-glycosidic ellagitannin, epipunicacortein A (1), is also described briefly.
- Nonaka,Sakai,Mihashi,Nishioka
-
p. 884 - 888
(2007/10/02)
-
- Structures of Alnusiin and Bicornin, New Hydrolyzable Tannins Having a Monolactonized Tergalloyl Group
-
From the fruit extract of Alnus sieboldiana, a new hydrolyzable tannin, alnusiin (1), was isolated together with five known tannins: tellimagrandin I (6), pedunculagin (7), casuarinin (9), casuariin (10) and 2,3-O-(S)-hexahydroxydiphenoyl-D-glucose (11).The structure (1) of alnisiin in which a monolactonized tergalloyl group, a rare component unit, bonds to the glucose residue, was elucidated based on spectral analyses including 1H-13C long-range shift correlation spectroscopy, and chemical methods.Another new hydrolyzable tannin with a related structure, bicornin (21), and six known galloylglucoses as well as six ellagitannins (including oligomers), were isolated from Trapa bicornis fruits and their structures were characterized. Keywords Alnus sieboldiana; Betulaceae; tannin; hydrolyzable tannin; alnusiin; Trapa bicornis; Trapaceae; bicornin
- Yoshida, Takashi,Yazaki, Kazufumi,Memon, Muhammad Usman,Maruyama, Izumi,Kurokawa, Kenji,et al.
-
p. 2655 - 2660
(2007/10/02)
-
- Tannins and Related Compounds. LXXIX. Isolation and Characterization of Novel Dimeric and Trimeric Hydrolyzable Tannins, Nuphrins C, D, E and F, from Nuphar japonicum DC.
-
Four novel dimeric and trimeric hydrolyzable tannins, nupharins C (1), D, (13), E (15) and F (16), which possess a less favorable α-D-glucopyranose core with an atropisomeric (R)- or (S)-hexahydrodiphenoyl group at the 3,6-position, have been isolated from the rhizomes of Nuphar japonicum DC. (Nymphaeaceae).The structures of these compounds were established on the basis of spectroscopic and chemical evidence.Keywords - Nuphar japonicum; Nymphaeaceae; nupharin C-F; dimeric ellagitannin; trimeric ellagitannin; dehydrodigallic acid; α-D-glucose; R-, S-hexahydrodiphenoic acid; atropisomerism; diastereomer
- Ishimatsu, Makoto,Tanaka, Takashi,Nonaka, Gen-ichiro,Nishioka, Itsuo,Nishizawa, Makoto,Yamagishi, Takashi
-
p. 1735 - 1743
(2007/10/02)
-
- Tannins and Related Compounds. LXXVI. Isolation and Characterization of Cercidinins A and B and Cuspinin, Unusual 2,3-(R)-Hexahydroxydiphenoyl Glucoses from Cercidiphyllum japanicum and Castanopsis cuspidata var. sieboldii
-
Cercidinins A (1) and B (2) and cuspinin (3), unusual ellagitannins having an R-hexahydroxydiphenoyl ester group at the glucose 2,3-positions, have been isolated from the bark of Cercidiphyllum japonicum (Cercidiphyllaceae) and the leaves of Castanopsis cuspidata var. sieboldii (Fagaceae).On the basis of chemical and spectroscopic evidence, their structures were established as 1,4,6-tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-β-D-glucose (1), 4,6-di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-D-glucose (2) and 1-O-galloyl-2,3-(R);4,6-(S)-hexahydroxydiphenoyl-β-D-glucose (3).The co-occurrence of 3 with the atropisomeric S-hexahydroxydiphenoyl derivative suggests the non-specificity of the enzyme which converts gallic acid to hexahydroxydiphenoic acid.Keywords: Cercidiphyllum japonicum; Cercidiphyllaceae; Castanopsis cuspidata var. sieboldii; Fagaceae; cercidinin A; cercidinin B; cuspinin; ellagitannin; 2,3-(R)-hexahydroxydiphenoyl glucose; atropisomerism
- Nonaka, Gen-ichiro,Ishimatsu, Makoto,Ageta, Masayuki,Nishioka, Itsuo
-
-
- Tannins and Related Compounds. LXXV. Isolation and Characterization of Novel Diastereoisomeric Ellagitannins, Nupharins A and B, and Their Homologues from Nuphar japonicum DC.
-
The diastereoisomeric ellagitannins, nupharins A (1) and B (11), and related compouns (8, 10, and 15), have been isolated from the rhizomes of Nuphar japonicum DC. (Nymphaeaceae).On the basis of physicochemical evidence, their structures were characterized as 1,2,4-tri-O-galloyl- (1) and 1,2-di-O-galloyl-3,6-(S)-hexahydroxydiphenoyl-α-D-glucopyranoses (8), 2-O-galloyl-3,6-(S)-hexahydroxydiphenoyl-D-glucose (10), and 1,2,4-tri-O-galloyl- (11) and 1,2-di-O-galloyl-(R)-hexahydroxydiphenoyl-α-D-glucopyranoses (15).Keywords - Nuphar japonicum; Nymphaeaceae; diastereoisomer; ellagitannin; R-, S-hexahydroxydiphenoic acid; atropisomerism; nupharin A; nupharin B; α-D-glucose
- Ishimatsu, Makoto,Tanaka, Takashi,Nonaka, Gen-ichiro,Nishioka, Ituso,Nishizawa, Makoto,Yamagishi, Takashi
-
p. 129 - 134
(2007/10/02)
-
- Tannins of cornaceous plants. I. Cornusiins A, B and C, dimeric monomeric and trimeric hydrolyzable tannins from Cornus officinalis, and orientation of valoneoyl group in related tannins.
-
Cornusiin A (1), cornusiin B (2) and cornusiin C (3), new dimeric, monomeric and trimeric hydrolyzable tannins, were isolated from the fruits of Cornus officinalis (Cornaceae). Their structures, including the orientation of the valoneoyl group in 1 and 3, were established on the basis of chemical and spectroscopic data. 2,3-Di-O-galloyl-D-glucose (7), 1,2,3-tri-O-galloyl-beta-D-glucose, 1,2,6-tri-O-galloyl-beta-D-glucose, 1,2,3,6-tetra-O-galloyl-beta-D-glucose, gemin D (5), isoterchebin, tellimagrandin I (6) and tellimagrandin II were also isolated from the fruits. The orientation of the valoneoyl group in camptothin A (14) and that in camptothin B (15), which had been isolated from Camptotheca acuminata (Nyssaceae), were also determined based on that in 1.
- Hatano,Ogawa,Kira,Yasuhara,Okuda
-
p. 2083 - 2090
(2007/10/02)
-
- Tannins and Related Compounds. LXXXV. Structures of Novel C-Glycosidic Ellagitannins, Grandinin and Pterocarinins A and B
-
The structures of three hydrolyzable tannins, i,e,, grandinin (3) (isolated from various species of Myrtaceae, Fagaceae and Lythraceae), pterocarinin A (4) (from Pterocarya steroptera C.DC. and Eucalyptus viminalis LABILL.) and pterocarinin B (6) (from P. stenoptera), have been established on the basis of chemical and spectroscopic evidence as novel C-glycosidic ellagitannins in which a C5-polyalcohol unit with lyxose-type configuration is linked through a carbon-carbon bond to the C-1 position of the C-glycosyl mioety.Successful biomimetic synthesis of 3 and 4 suggest that the C5-polyalcohol unit is biosynthetically derived from L-ascorbic acid.
- Nonaka, Gen-ichiro,Ishimaru, Kanji,Azuma, Ryutaro,Ishimatsu, Makoto,Nishioka, Itsuo
-
p. 2071 - 2077
(2007/10/02)
-
- Alnusnins A and B from the leaves of Alnus sieboldiana
-
Two new ellagitannins, alnusnins A and B, have been isolated from the leaves of Alnus sieboldiana (Betulaceae) and characterized as 1-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-4,6-(S)-tergalloyl-β-d-glucose and 2,3-(S)-hexahydroxydiphenoyl-4,6-(S)-tergalloyl-d-glucose, respectively, by chemical and spectral evidence. The occurrence of eight known tannins, 1,2,6-tri-O-galloyl-β-d-glucose, strictinin, casuarinin, stachyurin, pedunculagin, 1(β)-O-galloylpedunculagin and stenophyllanin A, and two flavonoids, pinocembrin and quercetin 3-O-β-d-glucuronide, has also been demonstrated.
- Ishimatsu, Makoto,Tanaka, Takashi,Nonaka, Gen-ichiro,Nishioka, Itsuo
-
p. 3179 - 3184
(2007/10/02)
-
- Tannins and related compounds. LXXXIV. Isolation and characterization of five new hydrolyzable tannins from the bark of Mallotus japonicus.
-
A chemical examination of the bark of Mallotus japonicus (Thunb.) Mueller-Arg. (Euphorbiaceae) has led to the isolation of five new hydrolyzable tannins (16-20), together with fourteen known tannins (1-14). On the basis of chemical and spectroscopic evidence, the structures of compounds 16 and 17 were established as 1,2-di-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-beta-D-glucose and 1-O-digalloyl-3,6-(R)-hexahydroxydiphenoyl-beta-D-glucose, respectively, while compounds 18 (mallojaponin) and 19 (mallonin) were shown to be 1-O-galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-bet a-D-glucose and 1-O-galloyl-2,4-elaeocarpusinoyl-beta-D-glucose. Compound 20 (mallotusinin) was characterized as a novel ellagitannin which possesses a unique 1,1'-(3,3',4,4'-tetrahydroxy)dibenzofurandicarboxyl group. On the other hand, examination of the leaves revealed the presence of hydrolyzable tannins (8-10, 12-15) all containing a beta-D-glucopyranose core with 1C4-conformation. Furthermore, the orientation of the valoneayl group in mallotinic acid (13) and mallotusinic acid (14), which had remained unclarified, was determined on the basis of 1H-13C shift correlation spectral analysis and chemical correlations.
- Saijo,Nonaka,Nishioka
-
p. 2063 - 2070
(2007/10/02)
-
- Tannins and Related Compounds. LXVII. Isolation and Characterization of Castanopsinins A-H, Novel Ellagitannins Containing a Triterpenoid Glycoside Core, from Castanopsis cuspidata var. sieboldii NAKAI. (3)
-
A new class of ellagitannins, castanopsinins A-H (1, 6, 25, 27, 32, 42, 47 and 51), containing a triterpenoid glycoside core, have been isolated from the leaves of Castanopsis cuspidata var. sieboldii NAKAI (Fagaceae).On the basis of spectroscopic and chemical data these compounds have been characterized as 3,23-(R)- (1), 24-O-galloyl-3,23-(R)- (6), 2,3-(R)- (25), 3,23-(S)- (27), 3,24-(S)- (32), 24-O-galloyl-3,23-(S)- (42), 3'-O-galloyl-23,24-(R)- (47) and 24,3'-di-O-galloyl-3,23-(R)-hexahydroxydiphenoyl (51) 2α,3β,23,24-tetrahydroxyolean(urs)-12-en-28-oic acid 28-O-β-D-glucopyranosides.In addition, separation of structural isomers consisting of a mixture of oleanane- and ursane-type triterpenoids was successfully achieved.Keywords - Castanopsis cuspidata var. sieboldii; Fagaceae; castanopsinin A-H; ellagitannin; triterpenoid 28-O-β-D-glucopyranoside; 2α,3β,23,24-tetrahydroxyolean(urs)-12-en-28-oic acid; castanopsigenin A, B; (R)- and (S)-hexahydroxydiphenic acid; atropisomerism.
- Ageta,Masayuki,Nonaka, Gen-Ichiro,Nishioka, Itsuo
-
p. 1646 - 1663
(2007/10/02)
-
- GUAVINS A, C AND D, COMPLEX TANNINS FROM PSIDIUM GUAJAVA
-
Three new tannins named guavins A (1), C(2) and D(3), were isolated from the leaves of Psidium guajava and their structures, each consisting of a hydrolyzable tannin part and a flavan unit, were established.KEYWORDS - guavin A; guavin C; guavin D; complex tannin; hydrolyzable tannin; C-glucosidic tannin; ellagitannin; condensed tannin; Psidium guajava; Myrtaceae
- Okuda, Takuo,Yoshida, Takashi,Hatano, Tsutumo,Yazaki, Kazufumi,Ikegami, Yukihiko,Shingu, Tetsuro
-
p. 443 - 446
(2007/10/02)
-
- Tannins and Related Compounds. LI. Elucidation of the Stereochemistry of the Triphenoyl Moiety in Castalagin and Vescalagin, and Isolation of 1-O-Galloyl Castalagin from Eugenia grandis
-
The chirality of the nonahydroxytriphenoyl group in castalagin (1) and vescalagin (2) was determined to be in the S,S-series on the basis of circular dichroism analysis.In addition, a new ellagitannin (4) has been isolated from the leaves of Eugenia grandis (Myrtaceae), and the structure was established to be 1-O-galloyl castalagin on the basis of chemical and spectroscopic evidence. Keywords --- castalagin; vescalagin; C-glycosidic ellagitannin; atropisomerism; absolute stereochemistry; nonahydroxytriphenoyl group; flavogallonic acid; Eugenia grandis; 1-O-galloyl castalagin
- Nonaka,Gen-Ichiro,Ishimaru, Kanji,Watanabe, Michiyo,Nishioka, Itsuo,Yamauchi, Tatsuo,Wan, Alfred S. C.
-
p. 217 - 220
(2007/10/02)
-
- SCYLLO-QUERCITOL GALLATES AND HEXAHYDROXYDIPHENOATES FROM QUERCUS STENOPHYLLA
-
Key Word Index - Quercus stenophylla; Fagaceae; scyllo-quercitol; gallotannin; ellagitannin; gallic acid; hexahydroxydiphenic acid.A series of gallotannins and ellagitannins based on a scyllo-quercitol core have been isolated from the bark of Quercus stenophylla.On the basis of chemical and spectroscopic evidence, the structures of the gallotannins have been established as 2-O-, 1,2-di-O-, 1,2,3-tri-O-, 1,2,3,4-tetra-O- and 1,2,3,4,5-penta-O-galloyl-scyllo-quercitols, and the ellagitannins as 1,5-di-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-scyllo-quercitol and 1,4-(or 4,5)-di-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-scyllo-quercitol.
- Nishimura, Hiroaki,Nonaka, Gen-Ichiro,Nishioka, Itsuo
-
p. 2599 - 2604
(2007/10/02)
-
- Tannins of Coriaria japonica A. GRAY. II. Coriariins C, D, E and F, New Dimeric and Monomeric Hydrolyzable Tannins
-
Three new dimeric hydrolyzable tannins, named coriariins C (3), D (4), and E (5), and a new monomeric tannin, coriariin F (6), have been isolated from the leaves of Coriaria japonica A.GRAY along with rugosin B (7), gemin D (8) and strictinin, and the structures of the new tannins have been established upon the basis of chemical and spectroscopic evidence.Keywords-tannin; ellagitannin; dimeric hydrolyzable tannin; Coriariaceae; Rosaceae; Coriaria japonica; coriariin C; coriariin D; coriariin E; coriariin F
- Hatano, Tsutomu,Hattori, Shin,Okuda, Takuo
-
p. 4533 - 4539
(2007/10/02)
-
- Tannins and Related Compounds. XLII. Isolation and Characterization of Four New Hydrolyzable Tannins, Terflavins A and B, Tergallagin and Tercatain from the Leaves of Terminalia catappa L.
-
A chemical examination of the leaves of Terminalia catappa L. (Combretaceae) has led to the isolation and characterization of four new hydrolyzable tannins named terflavins A (1) and B (2), tergallagin (3) and tercatain (4), together with eight known tannins: punicalin (5), punicalagin (6), chebulagic acid (7), geraniin (8), granatin B (9), l-desgalloyleugeniin (10), corilagin (11) and 2,3--D-glucose (12).Terflavins A (1) and B (2) posses novel structures in which a flavogallonyl (triphenyl) ester group is single bonded to the glucopyranose ring, and are presumed to be biosynthetic precursors of punicalagin (6) and punicalin (5), respectively, while tergallagin (3), which contains a gallagyl (tetraphenyl) group and a unique tergalloyl ester group attached to the glucose moiety, seems to be formed biosynthetically from punicalagin (6).Keyword - Terminalia Cattapa; Combretaceae; terflavin A; terflavin B; tercatain; hydrolyzable tannin; tergallic acid; flavogallonic acid; biosynthesis
- Tanaka, Takashi,Nonaka, Gen-Ichiro,Nishioka, Itsuo
-
p. 1039 - 1049
(2007/10/02)
-
- Tannins and Related Compounds. Part 37.1 Isolation and Structure Elucidation of Elaeocarpusin, a Novel Ellagitannin from Elaeocarpus sylvestris var. Ellipticus
-
A new hydrolysable tannin, elaeocarpusin, isolated from the leaves of Elaeocarpus sylvestris var.Ellipticus, has been characterized on the basis of chemical, spectroscopic, and X-ray analyses to be a novel ellagitannin in which a unique acid ester group probably derived by a condensation of a hexahydroxydiphenoyl group and dehydroascorbic acid is attached to the 2,4-positions of 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucopyranose (corilagin).This structural feature suggest the possibility of the participation of dehydroascorbic acid as a co-enzyme in oxidative metabolism of the hexahydroxydiphenoyl group to the corresponding dehydro group.
- Tanaka, Takashi,Nonaka, Gen-ichiro,Nishioka, Itsuo,Miyahara, Kazumoto,Kawasaki, Toshio
-
p. 369 - 376
(2007/10/02)
-
- PUNICAFOLIN, AN ELLAGITANNIN FROM THE LEAVES OF PUNICA GRANATUM
-
A new ellagitannin, punicafolin has been isolated from the leaves of Punica granatum and characterized by physicochemical data and spectral evidence as 1,2,4-tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-β-D-glucose.The occurrence in the leaves of the known tannins, granatins A and B, corilagin, strictinin, 1,2,4,6-tetra-O-galloyl-β-D-glucose and 1,2,3,4,6-penta-O-galloyl-β-D-glucose has also been demonstrated.Key Word Index -Punica granatum; Punicaceae; pomegranate; punicafolin; ellagitannin; gallotannin.
- Tanaka, Takashi,Nonaka, Gen-Ichiro,Nishioka, Itsuo
-
p. 2075 - 2078
(2007/10/02)
-
- Tannins of Casuarina and Stachyurus Species. Part 1. Structures of Pendunculagin, Casuarictin, Strictinin, Casuarinin, Casuariin, and Stachyurin
-
Three novel C-glucosidic ellagitannins, casuarinin, casauriin, and stachyurin, and two additional new ellagitannins, casuarictin and strictinin, were isolated from the leaves of Casuarina stricta, and their structures elucidated on the basis of chemical and spectral evidence.Pedunculagin and tellimagrandin I were also isolated, and the structure having (S)-4,4',5,5',6,6'-hexahydroxydiphenoyl groups was established for pedunculagin.These seven ellagitannins isolated from C. stricta have been found also in Stachyurus praecox.
- Okuda, Takuo,Yoshida, Takashi,Ashida, Mariko,Yazaki, Kazufumi
-
p. 1765 - 1772
(2007/10/02)
-
- Structure of Gemin A, a new Dimeric Ellagitannin having α- and β-Glucose Cores
-
A dimeric ellagitannin, gemin A (1), has been isolated from Geum japonicum Thunb., and its structure, which contains α- and β-glucose cores, has been elucidated.
- Yoshida, Takashi,Okuda, Takuo,Memon, M. Usman,Shingu, Tetsuro
-
p. 351 - 353
(2007/10/02)
-
- Tannins and Related Compounds. Part 3. A New Phenolic Acid, Sanguisorbic Acid Dilactone, and Three New Ellagitannins, Sanguiins H-1, H-2, and H-3, from Sanguisorba officinalis
-
A new phenolic acid, sanguisorbic acid dilactone, and three new ellagitannins, sanguiins H-1, H-2, and H-3, have been isolated from the underground parts of Sanguisorba officinalis L. (Rosaceae).On the basis of chemical and spectroscopic evidence, sanguisorbic acid dilactone has been shown to possess a trimeric gallic acid structure and to be a structural isomer of valoneaic acid dilactone.Similarly, sanguiins H-1 and H-2 have been characterized as 1,6-digalloyl-2,3-(4,4',5,5',6,6'-hexahydroxydiphenoyl)glucose and 1-galloyl-2,4-(4,4',5,5',6,6'-hexahydroxydiphenoyl)-3,6-sanguisorboylglucose, respectively.Sanguiin H-3 has been shown mainly by spectroscopic data and analyses of partial hydrolysates to have a novel dimeric structure containing 2,3-(hexahydroxydiphenoyl)glucose and sanguiin H-2 moieties.
- Nonaka, Gen-ichiro,Tanaka, Takashi,Nishioka, Itsuo
-
p. 1067 - 1074
(2007/10/02)
-
- RUGOSIN A, B, C AND PRAECOXIN A, TANNINS HAVING A VALONEOYL GROUP
-
New hydrolyzable tannins, rugosin A (1), B (2), C (3) from Rosa rugosa, and 3 and praecoxin A (7) from Stachyurus praecox, were isolated, and their structures, including the valoneoyl group, were elucidated.Keywords - Rosa rugosa; Rosaceae; Stachyurus praecox; Stachyuraceae; tannin; valoneoyl group; rugosin A; rugosin B; rugosin C; praecoxin A
- Okuda, Takuo,Hatano, Tsutomu,Yazaki, Kazufumi,Ogawa, Noboru
-
p. 4230 - 4233
(2007/10/02)
-
- Agrimoniin and Potentillin, an Ellagitannin Dimer and Monomer having an α-Glucose Core
-
Potentillin (3), which has an α-glucosyl linkage, and its dimer, agrimoniin (1) have been isolated from Agrimonia pilosa Ledeb. and Potentilla kleiniana Wight et Arnott., and their structures elucidated.
- Okuda, Takuo,Yoshida, Takashi,Kuwahara, Masaaki,Memon, M. Usman,Shingu, Tetsuro
-
p. 163 - 164
(2007/10/02)
-