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Erschienen in: Journal of Natural Medicines 4/2009

01.10.2009 | Original Paper

Lignan and neolignan glucosides, and tachioside 2′-O-4″-O-methylgallate from the leaves of Glochidion rubrum

verfasst von: Wen-Hu Cai, Katsuyoshi Matsunami, Hideaki Otsuka, Takakazu Shinzato, Yoshio Takeda

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2009

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Abstract

Thirteen compounds (113) were isolated from a MeOH extract of leaves of Glochidion rubrum. The structures of four new compounds were elucidated to be (−)-isolariciresinol 2a-O-β-d-glucopyranoside (1), (7R,8S)- and (7R,8R)-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan 7-O-β-d-glucopyranosides (2 and 3, respectively), and tachioside 2′-O-4″-O-methylgallate (4) on detailed inspection of one- and two-dimensional NMR spectral data.
Literatur
1.
Zurück zum Zitat Otsuka H, Kotani K, Bando M, Kido M, Takeda Y (1998) A novel dimeric butenolide, glochidiolide, from the leaves of Glochidion acuminatum. Chem Pharm Bull 46:1180–1182 Otsuka H, Kotani K, Bando M, Kido M, Takeda Y (1998) A novel dimeric butenolide, glochidiolide, from the leaves of Glochidion acuminatum. Chem Pharm Bull 46:1180–1182
2.
Zurück zum Zitat Takeda Y, Mima C, Masuda T, Hirata E, Takushi A, Otsuka H (1998) Glochidioboside, a glucoside of (7S,8R)-dihydrodehydrodiconiferyl alcohol from leaves of Glochidion obovatum. Phytochemistry 49:2137–2139CrossRef Takeda Y, Mima C, Masuda T, Hirata E, Takushi A, Otsuka H (1998) Glochidioboside, a glucoside of (7S,8R)-dihydrodehydrodiconiferyl alcohol from leaves of Glochidion obovatum. Phytochemistry 49:2137–2139CrossRef
3.
Zurück zum Zitat Otsuka H, Hirata E, Shinzato T, Takushi A, Takeda Y, Bando M, Kido M (2000) Glochidionolactones A–F: butenolide glucosides from leaves of Glochidion zeylanicum (Gaertn) A Juss. Chem Pharm Bull 48:547–551PubMed Otsuka H, Hirata E, Shinzato T, Takushi A, Takeda Y, Bando M, Kido M (2000) Glochidionolactones A–F: butenolide glucosides from leaves of Glochidion zeylanicum (Gaertn) A Juss. Chem Pharm Bull 48:547–551PubMed
4.
Zurück zum Zitat Otsuka H, Hirata E, Shinzato T, Takeda Y (2000) Isolation of lignan glucosides and neolignan sulfate from the leaves of Glochidion zeylanicum (Gaertn) A Juss. Chem Pharm Bull 48:1084–1086PubMed Otsuka H, Hirata E, Shinzato T, Takeda Y (2000) Isolation of lignan glucosides and neolignan sulfate from the leaves of Glochidion zeylanicum (Gaertn) A Juss. Chem Pharm Bull 48:1084–1086PubMed
5.
Zurück zum Zitat Otsuka H, Hirata E, Shinzato T, Takeda Y (2001) Glochiflavanosides A–D: flavanol glucosides from the leaves of Glochidion zeylanicum (Gaerten) A Juss. Chem Pharm Bull 49:921–923PubMedCrossRef Otsuka H, Hirata E, Shinzato T, Takeda Y (2001) Glochiflavanosides A–D: flavanol glucosides from the leaves of Glochidion zeylanicum (Gaerten) A Juss. Chem Pharm Bull 49:921–923PubMedCrossRef
6.
Zurück zum Zitat Otsuka H, Kijima K, Hirata E, Shinzato T, Bando M, Takeda Y (2003) Glochidionionosides A–D: megastigmane glucosides from leaves of Glochidion zeylanicum (Gaertn) A Juss. Chem Phram Bull 51:286–290CrossRef Otsuka H, Kijima K, Hirata E, Shinzato T, Bando M, Takeda Y (2003) Glochidionionosides A–D: megastigmane glucosides from leaves of Glochidion zeylanicum (Gaertn) A Juss. Chem Phram Bull 51:286–290CrossRef
7.
Zurück zum Zitat Otsuka H, Takeda Y, Hirata E, Shinzato T, Bando M (2004) Glochidiolide, isoglochidiolide, acuminaionoside, and glochidacuminosides A–D from the leaves of Glochidion acuminatum Muell. Chem Pharm Bull 52:591–596PubMedCrossRef Otsuka H, Takeda Y, Hirata E, Shinzato T, Bando M (2004) Glochidiolide, isoglochidiolide, acuminaionoside, and glochidacuminosides A–D from the leaves of Glochidion acuminatum Muell. Chem Pharm Bull 52:591–596PubMedCrossRef
8.
Zurück zum Zitat Hatusima S (1975) Flora of Ryukyus, added and corrected. The Biological Society of Okinawa, Naha, Japan, p 372 Hatusima S (1975) Flora of Ryukyus, added and corrected. The Biological Society of Okinawa, Naha, Japan, p 372
9.
Zurück zum Zitat Achenbach A, Lowel M, Waibel R, Gupta M, Solis P (1992) New lignan glucosides from Stemmadenia minima. Planta Med 58:270–272PubMedCrossRef Achenbach A, Lowel M, Waibel R, Gupta M, Solis P (1992) New lignan glucosides from Stemmadenia minima. Planta Med 58:270–272PubMedCrossRef
10.
Zurück zum Zitat Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1987) Studies on the glycosides of Epimedium grandiflorum Morr var, thunbergianum (Miq) Nakai II. Chem Pharm Bull 35:3713–3719 Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1987) Studies on the glycosides of Epimedium grandiflorum Morr var, thunbergianum (Miq) Nakai II. Chem Pharm Bull 35:3713–3719
11.
Zurück zum Zitat Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1988) Studies on the glycosides of Epimedium grandiflorum Morr var, thunbergianum (Miq) Nakai III. Chem Pharm Bull 36:2475–2484 Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1988) Studies on the glycosides of Epimedium grandiflorum Morr var, thunbergianum (Miq) Nakai III. Chem Pharm Bull 36:2475–2484
12.
Zurück zum Zitat Yoshikawa M, Shimada H, Saka M, Yoshimizu S, Yamahara J, Matsuda H (1997) Medicinal foodstuffs. V Moroheiya (1): absolute stereostructure of corchoionosides A, B and C, histamine release inhibitor from the leaves of Vietnamese Corchorus olitorius L (Tiliaceae). Chem Pharm Bull 45:464–469PubMed Yoshikawa M, Shimada H, Saka M, Yoshimizu S, Yamahara J, Matsuda H (1997) Medicinal foodstuffs. V Moroheiya (1): absolute stereostructure of corchoionosides A, B and C, histamine release inhibitor from the leaves of Vietnamese Corchorus olitorius L (Tiliaceae). Chem Pharm Bull 45:464–469PubMed
13.
Zurück zum Zitat Murthy YLN, Jairaj MA (1988) Crystalline constituents of Fluggea microcarpa Blume. J Ind Chem Soc 65:738–749 Murthy YLN, Jairaj MA (1988) Crystalline constituents of Fluggea microcarpa Blume. J Ind Chem Soc 65:738–749
14.
Zurück zum Zitat Braga ACH, Zacchino S, Badano H, Sierra MG, Rúveda EA (1984) 13C NMR spectral and conformational analysis of 8-O-4’ neolignans. Phytochemistry 23:2025–2028CrossRef Braga ACH, Zacchino S, Badano H, Sierra MG, Rúveda EA (1984) 13C NMR spectral and conformational analysis of 8-O-4’ neolignans. Phytochemistry 23:2025–2028CrossRef
15.
Zurück zum Zitat Huo C, Liang H, Zhao Y, Wang B, Zhang Q (2008) Neolignan glycosides from Symplocos caudate. Phytochemistry 69:788–795PubMedCrossRef Huo C, Liang H, Zhao Y, Wang B, Zhang Q (2008) Neolignan glycosides from Symplocos caudate. Phytochemistry 69:788–795PubMedCrossRef
16.
Zurück zum Zitat Inoshiri S, Sasaki M, Kohda H, Otsuka H, Yamasaki K (1987) Aromatic glycosides from Berchemia racemosa. Phytochemistry 26:2811–2814CrossRef Inoshiri S, Sasaki M, Kohda H, Otsuka H, Yamasaki K (1987) Aromatic glycosides from Berchemia racemosa. Phytochemistry 26:2811–2814CrossRef
17.
Zurück zum Zitat Asakawa Y, Toyota M, Harrison L (1985) Phytochemistry isotachin A and isotachin B, two sulphur-containing acrylates from the liverwort Isotachis japonica. Phytochemistry 24:1505–1508 Asakawa Y, Toyota M, Harrison L (1985) Phytochemistry isotachin A and isotachin B, two sulphur-containing acrylates from the liverwort Isotachis japonica. Phytochemistry 24:1505–1508
18.
Zurück zum Zitat Zhong X-N, Otsuka H, Ide T, Hirata E, Takeda Y (1999) Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii. Phytochemistry 52:923–927CrossRef Zhong X-N, Otsuka H, Ide T, Hirata E, Takeda Y (1999) Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii. Phytochemistry 52:923–927CrossRef
Metadaten
Titel
Lignan and neolignan glucosides, and tachioside 2′-O-4″-O-methylgallate from the leaves of Glochidion rubrum
verfasst von
Wen-Hu Cai
Katsuyoshi Matsunami
Hideaki Otsuka
Takakazu Shinzato
Yoshio Takeda
Publikationsdatum
01.10.2009
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 4/2009
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-009-0344-6

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