长寿花糖甙 | 54835-70-0

• 物质功能分类: 天然产物 - 倍半萜
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 长寿花糖甙
• 英文名称: (6S,9R)-roseoside
• 英文别名: (6S,7E,9R)-6,9-dihydroxy-megastigman-4,7-dien-3-one-9-O-β-D-glucopyranoside；(6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one-9-O-β-D-glucopyranoside；(6S,7E,9R)-6,9-dihydroxymegastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside；(6S,9R)-dihydroxymegastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside；vomifoliol-9-O-β-D-glucopyranoside；Roseoside；(4S)-4-hydroxy-3,5,5-trimethyl-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-1-enyl]cyclohex-2-en-1-one
• CAS: 54835-70-0
• 化学式: C₁₉H₃₀O₈
• 分子量: 386.442
• InChiKey: SWYRVCGNMNAFEK-MHXFFUGFSA-N

物化性质

• 沸点：
  595.9±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

安全信息

• 储存条件：
  储存条件：2-8℃，需干燥并密封保存。

制备方法与用途

玫瑰糖苷是一种从日本胡颓子叶中分离出来的化合物。

反应信息

• 作为反应物：
  描述：

  长寿花糖甙 在 β-glucosidase 作用下， 反应 48.0h， 以11 mg的产率得到吐叶醇
  参考文献：
  名称：

  Megastigmane glycosides from seeds of Trifoliumalexandrinum

  摘要：

  Five megastigmane glycosides have been isolated From the seeds of Trifolium alexandrinum L., of which two are known compounds, while three are new compounds showing the presence of apiofuranosyl-(1 --> 2)-glucopyranosyl residue as a sugar moiety. The structures of the isolated compounds were established on the basis of NMR and mass spectral data. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00603-7
• 作为产物：
  描述：

  (E,2R)-4-[(4R)-4-[tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethylcyclohexen-1-yl]but-3-en-2-ol 在 吡啶 、 甲醇 、 lithium hydroxide 、 sodium methylate 、 silver trifluoromethanesulfonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 氟化氢吡啶 、 间氯过氧苯甲酸 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 50.08h， 生成 长寿花糖甙
  参考文献：
  名称：

  Synthesis of Optically Active Vomifoliol and Roseoside Stereoisomers

  摘要：

  通过α-炔醇11a或11b有效地制备的α,β-炔酮10进行不对称转移氢化反应，成功合成了光学活性的vomifoliol立体异构体1—4及其葡萄糖苷，玫瑰苷立体异构体5—8。同时，还进行了这些立体异构体的HPLC分离。

  DOI：

  10.1248/cpb.53.541

文献信息

• Studies on the constituents of zizyphi fructus. V. Structures of glycosides of benzyl alcohol, vomifoliol and naringenin.
  作者：NOBUYUKI OKAMURA、AKIRA YAGI、ITSUO NISHIOKA

  DOI：10.1248/cpb.29.3507

  日期：——

  New glycosides, zizybeoside I (I) and II (II), zizyvoside I (IV) and II (V), and a mixture of 6, 8-di-C-glucosyl-2 (S)-naringenin and 6, 8-di-C-glucosyl-2 (R)-naringenin (compound A), together with vomifoliol and roseoside, were isolated from the ethanol extract of Zizyphi Fructus. On the basis of spectral and chemical evidence the structures of the new glycosides were determined as benzyl β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (I), benzyl β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside (II), vomifoliol 9-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (IV), vomifoliol 9-O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-β-glucopyranoside (V), 6, 8-di-C-glucosyl-2 (S)-naringenin (VII) and 6, 8-di-C-glucosyl-2 (R)-naringenin (VIII).

  新苷类，zizybeoside I (I) 和 II (II)，zizyvoside I (IV) 和 II (V)，以及 6, 8-di-C-glucosyl-2 (S)-naringenin 和 6, 8- 的混合物从枣子的乙醇提取物中分离出二-C-葡萄糖基-2(R)-柚皮素（化合物 A）以及伏米叶醇和玫瑰花苷。根据光谱和化学证据，新糖苷的结构被确定为苄基 β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃葡萄糖苷 (I)、苄基 β-D-吡喃葡萄糖基-(1→2) )-[β-D-吡喃葡萄糖基-(1→3)]-β-D-吡喃葡萄糖苷 (II)、vomifoliol 9-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷 (IV) , vomifoliol 9-O-β-吡喃葡萄糖基-(1→2)-[β-吡喃葡萄糖基-(1→3)]-β-吡喃葡萄糖苷 (V), 6, 8-二-C-葡萄糖基-2 (S)-柚皮素(VII)和6, 8-二-C-葡萄糖基-2(R)-柚皮素(VIII)。
• Characterization of Caffeoylglucoside Derivatives and Hypouricemic Activity of the Ethyl Acetate Fraction from <i>Aster glehni</i>
  作者：Min Jeoung Son、Changbae Jin、Yong Sup Lee、Jae Yeol Lee、Hyoung Ja Kim

  DOI：10.1002/bkcs.10095

  日期：2015.2

  In the search for xanthine oxidase (XOD) inhibitors as anti‐gout agents from natural products, various chromatographic separations of the ethyl acetate‐soluble fraction of Aster glehni (AGEF) led to the isolation of five new caffeoylglucoside derivatives, namely 6′‐O‐caffeoyl‐(6S,9R)‐roseoside (1), 6′‐O‐caffeoylampelopsisionoside (2), 6′‐O‐caffeoylsonchuinoside C (3), 6′‐O‐caffeoyldihydrosyringin (4), and (2E)‐2‐methyl‐but‐2‐ene‐1,4‐diol‐6′‐O‐caffeoyl‐1‐O‐β‐glucopyranoside (glehnoside, 5), together with 13 known compounds. The absolute stereochemistry of the 6′‐O‐caffeoylsonchuinoside C (3) was established with the help of spectroscopic analyses, enzymatic hydrolysis, and Mosher's method, as well as in comparison with literature data. All isolated substances were determined for their inhibitory activities on uric acid production by the xanthine/XOD system. Among them, 4,5‐O‐dicaffeoylquinic acid methyl ester (12) showed the most potent inhibitory activity with an IC₅₀ value of 2.6 ± 0.1 μM, which was comparable to that of allopurinol used as a positive control. Furthermore, hypouricemic effects of AGEF were assessed by measuring serum uric acid levels 3 h after potassium oxonate treatment (250 mg/kg, i.p.) to induce hyperuricemia in rats. When preadministered orally once a day at doses of 50, 100, and 300 mg/kg for 7 days, AGEF reduced the potassium oxonate‐induced elevated serum uric acid level by 15.4, 39.8, and 32.3%, respectively. The results suggest that AGEF has the potential to be a new source of agents for the prevention and/or treatment of hyperuricemia and gout.

  在从天然产物中寻找黄嘌呤氧化酶（XOD）抑制剂作为抗痛风药物的过程中，对Aster glehni（AGEF）的乙酸乙酯可溶性馏分进行了各种色谱分离，分离出了5种新的咖啡酰葡萄糖苷衍生物，即6′-O-咖啡酰-（6S、9R)-roseoside (1)、6′-O-咖啡酰灯盏花苷 (2)、6′-O-咖啡酰松果菊苷 C (3)、6′-O-咖啡酰二氢紫丁香苷 (4)、和(2E)-2-甲基-丁-2-烯-1,4-二醇-6′-O-咖啡酰-1-O-β-吡喃葡萄糖苷（glehnoside，5），以及 13 种已知化合物。通过光谱分析、酶水解和莫舍尔法，以及与文献数据的比较，确定了 6′-O-咖啡酰松弛苷 C（3）的绝对立体化学性质。所有分离出的物质都被测定了对黄嘌呤/XOD 系统产生尿酸的抑制活性。其中，4,5-O-二咖啡酰奎宁酸甲酯（12）的抑制活性最强，IC50 值为 2.6 ± 0.1 μM，与作为阳性对照的别嘌醇的抑制活性相当。此外，在氧化钾（250 毫克/千克，静脉注射）诱导大鼠高尿酸血症后 3 小时，通过测量血清尿酸水平来评估 AGEF 的降尿酸作用。每天口服一次，剂量分别为 50、100 和 300 毫克/千克，连服 7 天后，AGEF 可使草酸钾引起的血清尿酸水平升高分别降低 15.4%、39.8% 和 32.3%。这些结果表明，AGEF 有可能成为预防和/或治疗高尿酸血症和痛风的新药源。
• Glycosidically Bound Norisoprenoids from Vitis vinifera cv. Riesling Leaves
  作者：George K. Skouroumounis、Peter Winterhalter

  DOI：10.1021/jf00041a004

  日期：1994.5

  HRGC and HRGC-MS identifications of glycosidically bound Riesling leaf constituents were achieved after extraction with MeOH, Amberlite XAD-2 adsorption, and subsequent enzymatic hydrolysis of the glycoconjugates. Among the enzymatically liberated aglycons 23 bound C-13 norisoprenoids were identified. With the aid of multilayer coil countercurrent chromatography (MLCCC) five major C-13 glycosides were purified, and their structures were elucidated by high-field NMR, i.e., the beta-D-glucopyranosides of vomifoliol, 4,5-dihydrovomifoliol, 3-hydroxy-5,6-epoxy-beta-ionone, grasshopper ketone, and 3-oxo-megastigman-9-ol. The latter glucoside with a saturated megastigmane skeleton is reported here for the first time. In addition, the P-D-glucopyranosides of benzyl alcohol and raspberry ketone have been isolated.
• Iridoid and other constituents of Canthium subcordatum
  作者：Hans Achenbach、Reiner Waibel、Bernd Raffelsberger、Ivan Addae-Mensah

  DOI：10.1016/s0031-9422(00)98538-8

  日期：——
• A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells
  作者：Arata Yajima、Yutaka Oono、Ryusuke Nakagawa、Tomoo Nukada、Goro Yabuta

  DOI：10.1016/j.bmc.2008.11.002

  日期：2009.1

  Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers. (c) 2008 Elsevier Ltd. All rights reserved.