桑皮苷A | 102841-42-9

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 桑皮苷A
• 英文名称: mulberroside A
• 英文别名: trans-mulberroside A；(2S,3R,4S,5S,6R)-2-[3-hydroxy-4-[(E)-2-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 102841-42-9
• 化学式: C₂₆H₃₂O₁₄
• 分子量: 568.532
• InChiKey: HPSWAEGGWLOOKT-VUNDNAJOSA-N

物化性质

• 熔点：
  235-236o C
• 沸点：
  954.7±65.0 °C(Predicted)
• 密度：
  1.654
• 闪点：
  531℃
• 溶解度：
  DMSO（轻微，超声处理），甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  239
• 氢给体数：
  10
• 氢受体数：
  14

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Mulberroside A是从桑白皮根的乙醇提取物中分离出的一种成分，具有抗酪氨酸酶和抗氧化活性，并被广泛用作化妆品中的活性成分。Mulberroside A能够降低TNF-α、IL-1β 和 IL-6 的表达并抑制 NALP3、caspase-1 和 NF-κB 的激活以及 ERK、JNK 和 p38 的磷酸化。

靶点

Target	Value
TNF-α	()
IL-1β	()
IL-6	()
NALP3	()
Caspase-1	()

体内研究

Mulberroside A (10, 20, 和 40 mg/kg) 能够减少高尿酸小鼠的血清尿酸水平并增加尿酸排泄和尿酸排泄分数。实验结果显示：

动物模型	雄性昆明小鼠（20±2 g）
剂量	5, 10, 20, 和 40 mg/kg；每千克体重给药体积为10 mL
给药方式	于上午9点口服开始
结果	10、20和40 mg/kg剂量显著增加了24小时内的尿酸排泄量，导致尿酸排泄分数（FEUA）明显升高，并且最高剂量完全逆转了高尿酸小鼠的FEUA变化至正常水平。

化学性质

Mulberroside A是一种白色结晶粉末，可溶于甲醇、乙醇和DMSO等有机溶剂，来源于桑白皮。

用途

Mulberroside A具有镇咳平喘、抑制酪氨酸酶活性以及抗氧化等多种作用，适用于含量测定/鉴定/药理实验等。

反应信息

• 作为反应物：
  描述：

  桑皮苷A 在 crude β-glucosidase extract from Leuconostoc paramesenteroides PR 作用下， 以 aq. phosphate buffer 为溶剂， 反应 2.0h， 生成 氧化白藜芦醇
  参考文献：
  名称：

  Enhancement of the Tyrosinase Inhibitory Activity of Mori Cortex Radicis Extract by Biotransformation UsingLeuconostoc paramesenteroidesPR

  摘要：

  Mori Cortex Radicis (MCR), the root bark of Morus alba L., consists of various phytochemicals and exhibits a strong inhibitory effect on tyrosinase. To enhance the tyrosinase inhibitory activity of MCR extract without further purification of bioactive compounds, whole MCR extract was biotransformed with crude enzyme extract from a selected lactic acid bacterium, Leuconostoc paramesenteroides PR (LP). Mulberroside A (MA), a major stilbene glucoside of MCR, contains two beta-glucosyl residues at the C3 and C4' positions of oxyresveratrol (OXY). The crude enzyme of LP hydrolyzed the two glycosidic bonds of MA effectively, and 97.1% of MA was biotransformed into OXY within 2 h. Commercial almond beta-glucosidase hydrolyzed only one site of the two glycosidic bonds of MA, and 68.7% of MA was biotransformed to OXY-glucoside. The tyrosinase inhibitory activity of the crude extract of MCR was increased approximately 6.5-fold by biotransformation using LP, and the IC50 value of the transformed MCR was 3.7 mu g/mL.

  DOI：

  10.1271/bbb.111002

文献信息

• Sequential glucosylation determined by NMR in the biosynthesis of mulberroside D, a cis-oxyresveratrol diglucoside, in Morus alba L. cell cultures
  作者：Y. Hano、K. Goi、T. Nomura、S. Ueda

  DOI：10.1007/pl00000597

  日期：1997.3

  Three new diglucosides, mulberrosides D, E, and F, were isolated from Morus albu cell cultures and their structures were established by spectroscopy. In the biosynthesis of mulberroside D, a cinnamoylpolyketide-derived cis-oxyresveratrol diglucoside in the cell cultures, the different ratio of C-13-enrichment between two glucose moieties of mulberroside D, revealed by administering [U-C-13(6)]-D-glucose and [1,3-C-13(2)]glycerol to the cell cultures, suggested that two glucosylation steps in the biosynthesis of the glucoside occur with different time courses.
• [EN] COMPOSITION COMPRISING A MORUS ALBA EXTRACT, AND ITS COSMETIC USES<br/>[FR] COMPOSITION COMPRENANT UN EXTRAIT DE MORUS ALBA ET SES UTILISATIONS COSMÉTIQUES
  申请人：OREAL

  公开号：WO2020201432A1

  公开（公告）日：2020-10-08

  The present invention relates to a composition comprising, in a physiologically acceptable medium, at least mulberroside A and mulberroside E. It also relates to cosmetic uses of said composition, especially for depigmenting, lightening and/or bleaching keratin materials, in particular the skin.