- Triterpene glycosides from the bark of Robinia pseudo-acacia L. I
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From the bark of Robinia pseudo-acacia L., five new triterpene glycosides, robiniosides A-D (3, 5-7) and compound III (4), were isolated and their structures were elucidated as 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranosyl 3β,22β-dihydroxyolean-12-en-29-oic acid (3), 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 2)-β-D-glucuronopyranosyl 3β,22β,24-trihydroxyolean-12-en-29-oic acid (4), whose sapogenol was unambiguously characterized and designated as oxytrogenin, 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranosyl oxytrogenin (5), 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 2)-β-D-glucuronopyranosyl oxytrogenin 22-O-α-L-rhamnopyranoside (6), 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranosyl oxytrogenin 22-O-α-L-rhamnopyranoside (7), respectively, together with two known triterpene glycosides, kaikasaponin III (1) and 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 2)-β-D-glucuronopyranosyl 3β,22β-dihydroxyolean-12-en-29-oic acid (2).
- Cui,Kinjo,Nohara
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- Hepatoprotective and hepatotoxic activities of sophoradiol analogs on rat primary liver cell cultures
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As a part of our studies of hepatoprotective drugs, we prepared kaikasaponin I (2), sophoradiol monoglucuronide (SoMG, 3) and sophoradiol (4) from kaikasaponin III (1). We examined the hepatoprotective effects of these analogs, using immunologically-induced liver injury in primary cultured rat hepatocytes and found that compound I was more effective than soyasaponin I (1a) while 2 was more effective than 1. On the other hand, 3 was less effective than 2 at 30 - 200 μM. Further, compound 3 was strongly cytotoxic at 500 μM while 4 exhibited hepatoprotective activity at the same dose, although less potent. When the cytotoxicity toward hepatocytes of these analogs was tested, only 3 was cytotoxic at doses of 200 and 500 μM. This is the first example of an oleanene glucuronide (OG) which is cytotoxic toward hepatocytes. Compound 3 exhibited hepatoprotective activity at 200 μM, while it was also cytotoxic at the same dose without antiserum. Therefore, the hepatoprotective activity of OG represents a balance between a hepatoprotective action and its cytotoxicity toward hepatocytes.
- Kinjo,Ikeda,Okawa,Udayama,Hirakawa,Shii,Nohara
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- Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model
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To shed light on the structure-activity relationship, various soyasapogenol B derivatives were synthesized and evaluated for preventive effects on liver injury in the concanavalin A (Con A)-induced hepatitis model in mice. Con A injection into mice induces some pathophysiology of human liver disease such as autoimmune or viral hepatitis. Two hydroxyl groups on the A ring of soyasapogenol B are required for amelioration of liver damage. Modification of the C-22 hydroxyl moiety with an acyloxy or alkyloxy group, or removal of the hydroxyl group, resulted in a greatly enhanced percentage of alleviation. Among the series of soyasapogenol B derivatives examined, six compounds exhibited preventive effects on liver damage.
- Sasaki, Kazue,Minowa, Nobuto,Kuzuhara, Hiroyuki,Nishiyama, Shoji
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p. 4900 - 4911
(2007/10/03)
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- Synthesis and hepatoprotective effects of soyasapogenol B derivatives
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Derivatives of soyasapogenol B (1), which is the aglycon moiety of soyasaponins from soybean, were synthesized and evaluated for their hepatoprotective effects in vitro.
- Sasaki, Kazue,Minowa, Nobuto,Kuzuhara, Hiroyuki,Nishiyama, Shoji,Omoto, Shoji
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- Studies on the Constituents of the Bark of Dalbergia hupeana
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Two new triterpenoid glycosides, 3-O-α-L-rhamnopyranosyl-(1-2)-β-D-galactopyranosyl-(1-2)-β-D-glucuronopyranosiduronic acids (2 and 3) of 3β,22β-dihydroxyolean-12-en-29-oic acid and 3β,21β,22β-trihydroxyolean-12-en-29-oic acid, along with a known glycoside, kaikasaponin III (1), were isolated from the bark of Dalbergia hupeana HANCE.Their structures were determined by chemical and spectral methods.
- Yahara, Shoji,Emura, Seiko,Feng, Huiming,Nohara, Toshihiro
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p. 2136 - 2138
(2007/10/02)
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- Saponin and Sapogenol. XLI. Reinvestigation of the Structures of Soyasapogenols A, B, and E, Oleanene-Sapogenols from Soybean. Structures of Soyasaponins I, II, and III
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A full account of the structure revision of soyasapogenols is presented.The structures of soyasapogenols A, B, and E have been confirmed to be expressed as 3β,21β,22β,24-tetrahydroxyolean-12-ene (1), 3β,22β,24-trihydroxyolean-12-ene (2), and 3β,24-dihydroxyolean-12-en-22-one (5), respectively, rather than the previously reported 3β,21α,22α,24-tetrahydroxyolean-12-ene (1'), 3β,21α,24-trihydroxyolean-12-ene (2'), and 3β,24-dihydroxyolean-12-en-21-one (5').In consequence, the structures of soyasaponins I, II, and III are formulated as 3-O-2)-β-D-galactopyranosyl(1->2)-β-D-glucuronopyranosyl>soyasapogenol B (8), 3-O-2)-α-L-arabinopyranosyl(1->2)-β-D-glucuronopyranosyl>soyasapogenol B (9), and 3-O-2)-β-D-glucuronopyranosyl>soyasapogenol B (10), respectively.Keywords - soybean; Glycine max; oleanene-sapogenol; soyasapogenol A; soyasapogenol B; soyasapogenol E; soyasaponin I; soyasaponin II; soyasaponin III; bioactive triterpene oligoglycoside
- Kitagawa, Isao,Wang, Hui Kang,Taniyama, Toshio,Yoshikawa, Masayuki
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p. 153 - 161
(2007/10/02)
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- REVISED STRUCTURES OF SOYASAPOGENOLS A, B, AND E, OLEANENE-SAPOGENOLS FROM SOYBEAN. STRUCTURES OF SOYASAPONINS I, II, AND III
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The structures of soyasapogenols A, B, and E, three of five hitherto isolated sapogenols of soybean (Glycine max Merrill), were re-investigated.Based on the chemical and X-ray analyses, it has been shown that the structures of soyasapogenols A, B, and E should be partly revised respectively from 1', 2', and 3' to 1, 2, and 3 and consequently the structures of soyasaponins I, II, and III are expressed as 6, 7, and 8.KEYWORDS - soybean; Glycine max; oleanene-sapogenol; triterpene-oligoglycoside; soyasapogenols; soyasaponins; photolysis; X-ray analysis
- Kitagawa, Isao,Yoshikawa, Masayuki,Wang, Hui Kang,Saito, Masayuki,Tosirisuk, Veeraphan,et al.
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p. 2294 - 2297
(2007/10/02)
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