(+)-lyoniresinol

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (+)-lyoniresinol
• 英文别名: lyoneresinol；(2R,3R)-(+)-lyoniresinol；(7'S,8'R,8R)-lyoniresinol；(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol
• 化学式: C₂₂H₂₈O₈
• 分子量: 420.46
• InChiKey: ZDVZKBOFCHOPLM-SUNYJGFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (+)-lyoniresinol 生成 lyoniresinol dimethyl ether
  参考文献：
  名称：

  Weinges,K., Chemische Berichte, 1961, vol. 94, p. 2522 - 2533

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-(8R,8'R,7'S)-lyoniresinol-9'-(6''-O-galloyl)-β-D-glucopyranoside 在 三氟乙酸 作用下， 反应 12.0h， 生成 (+)-lyoniresinol
  参考文献：
  名称：

  从苦木脂素的味道制导隔离无梗花栎及其葡萄酒标识

  摘要：

  Quercoresinosides A和B（1和2），两个新木脂素，是从一个分离烤无梗花栎心材提取物具有已知化合物一起，3-甲氧基-4-羟基苯酚1- ö -β- d - （6'- Ö -没食子酰基）吡喃葡萄糖苷（3）。提纯方案基于一种口味引导方法，该方法试图揭示从橡木释放到葡萄酒和烈酒中的新苦味化合物。使用HRMS和NMR数据确定化合物1和2是在相同位置带有葡糖基单元和没食子酰基单元的木脂素衍生物。这些化合物的水解显示，与（+）-和（-）-lyonyresinol标准品相比，通过手性LC-HRMS测定，它们可以通过各自的lyoreresinol genin的绝对构型来区分。感官分析是在上纯的化合物的非橡木酒进行1 - 3。这三个分子在2 mg / L时表现出苦味，对于化合物2和3尤其强烈。最后，LC-HRMS证实化合物的发生1 - 3 橡木酒和白兰地酒中的苦味，这支持了他们对橡木陈酿过程中苦味增加做出贡献的假设。

  DOI：

  10.1021/acs.jnatprod.6b00142

文献信息

• Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (−)-Lyoniresinol and Its Deuterated Analogues
  作者：Tuan Minh Luong、Lisa I. Pilkington、David Barker

  DOI：10.1021/acs.joc.1c03085

  日期：2022.3.18

  biological activities including anticancer, anti-inflammatory, antimicrobial, and others, these compounds have also been discovered in wines and spirits and shown to have gustatory effects in these alcoholic matrices. (+)-Lyoniresinol 1 is reported to impart a strong bitter taste while its enantiomer (−)-lyoniresnol 2 is tasteless. The first total asymmetric synthesis of both natural enantiomers (+)-1 and

  Lyoniresinol 及其衍生物是从大量植物物种中分离出来的木脂素。除了表现出一系列有趣的生物活性（包括抗癌、抗炎、抗菌等）外，这些化合物还在葡萄酒和烈酒中被发现，并显示出在这些酒精基质中具有味觉作用。据报道， (+)-Lyoniresinol 1具有强烈的苦味，而其对映体 (-)-lyoniresnol 2无味。天然对映异构体 (+)- 1和 (-)- 2及其氘代类似物 ( D 4 )-(+)- 3和 ( D 4 )-(-)- 4的首次完全不对称合成已经实现，确认了天然产物的结构和立体化学。合成的化合物可作为稳定同位素稀释分析的内标物，用于改进和优化现有的lyoniresinol定量方法。
• Three New Lignan Derivatives from<i>Lindera glauca</i>(<scp>Siebold</scp>et<scp>Zucc</scp>.)<scp>Blume</scp>
  作者：Won Se Suh、Ki Hyun Kim、Ho Kyung Kim、Sang Un Choi、Kang Ro Lee

  DOI：10.1002/hlca.201500002

  日期：2015.8

  Two new aryl‐tetralin lignan glycosides, linderanosides A and B (1 and 2, resp.), and a new dihydrobenzofuran neolignan glycoside, linderanoside C (3), together with five known lignan derivatives (4–8) were isolated from the trunk of Lindera glauca. The structures of these new compounds were determined through spectroscopic analyses, including extensive 2D‐NMR data and acid hydrolysis. The absolute

  两个新的芳基-四氢萘木脂素甙，linderanosides A和B（1和2，RESP），以及一个新的二氢苯并呋喃新木脂素糖苷，linderanoside C（3），加上5木脂素衍生物已知的（4 - 8）从主干分离的山胡椒。这些新化合物的结构通过光谱分析确定，包括广泛的2D NMR数据和酸水解。化合物的绝对构型通过圆二色性（CD）光谱研究得以阐明。化合物1 - 8使用磺基罗丹明评估了它们对A549（非小细胞肺腺癌），SK-OV-3（卵巢癌细胞），A498（人肾上皮细胞）和HCT-15（结肠癌细胞）人肿瘤细胞系的细胞毒性B体外测定。
• Chemical Evaluation of Betula Species in Japan. I. Constituents of Betula ermanii.
  作者：Hiroyuki FUCHINO、Tetsuya SATOH、Nobutoshi TANAKA

  DOI：10.1248/cpb.43.1937

  日期：——

  The constituents of Betula ermanii CHAM. in Japan were identified as follws. Fresh leaves : 20(S), 24(R)-epoxydammmaran-3β, 11α, 25-triol (1), 3-O-β-D-glucopyranoside of 1 (2), 2'-acetate of 2 (3), 11, 2'-diacetate of 2 (4), dammar-24-en-3β-, 11α-20(S)-triol (5), 3-O-β-D-2-O-acetylglucopyranoside of 5 (6). Outer bark : betulin (7), betulin 3-caffeate (8), oleanolic acid (9). Inner bark : (+)-lyoniresinol 3α-O-α-L-rhamnopyranoside (10), (-)-lyoniresinol 3α-O-β-D-xylopyranoside (11), 9, 9'di-O-feruloyl-(-)-secoisolariciresinol (12), acerogenin E (13), 3, 4, 5-trimethoxyphenol β-D-apiofuranosyl(1→6)-β-D-glucopyranoside (14), 4-(4-hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (15), (+)-catechine 7-O-β-D-xylopyranoside (16), lupeol (17), monogynol A (18). Root outer bark : lupeol caffeate (19), betulin 3-caffeate (8), oleanolic acid caffeate (20), dammarendiol II 3-caffeate (21). Compounds 2, 3, 4, 6, 19 and 21 are new.

  日本桦木（Betula ermanii CHAM.）的成分鉴定如下。鲜叶：20(S)，24(R)-epoxydammmaran-3β，11α，25-triol (1)，3-O-β-D-吡喃葡萄糖苷 1 (2)，2 的 2'-acetate (3)，11，2'-diacetate of 2 (4)，dammar-24-en-3β-，11α-20(S)-triol (5)，3-O-β-D-2-O-acetylglucopyranoside of 5 (6)。外树皮：白桦脂素（7）、白桦脂素 3-咖啡酸酯（8）、齐墩果酸（9）。内树皮 ：(+)-lyoniresinol 3α-O-α-L-rhamnopyranoside (10)，(-)-lyoniresinol 3α-O-β-D-xylopyranoside (11)，9, 9'di-O-feruloyl-(-)-secoisolariciresinol (12)，acerogenin E (13)，3, 4、5-trimethoxyphenolβ-D-apiofuranosyl(1→6)-β-D-glucopyranoside(14)、4-(4-羟基苯基)-2-丁醇 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside(15)、(+)-儿茶素 7-O-β-D-xylopyranoside(16)、羽扇豆醇 (17)、单炔醇 A (18)。根外树皮：羽扇豆醇咖啡酸酯（19）、白桦林 3-咖啡酸酯（8）、齐墩果酸咖啡酸酯（20）、达玛姻二醇 II 3-咖啡酸酯（21）。化合物 2、3、4、6、19 和 21 是新化合物。
• A New Lignan Glycoside and Phenylethanoid Glycosides from Strobilanthes cusia BREMEK
  作者：Tomonori Tanaka、Tsuyoshi Ikeda、Miho Kaku、Xing-Hua Zhu、Masafumi Okawa、Kazumi Yokomizo、Masaru Uyeda、Toshihiro Nohara

  DOI：10.1248/cpb.52.1242

  日期：——

  The root of Strobilanthes cusia BREMEK. (Acanthaceae), popularly known as Da-Ching-Yeh, has been commonly used in traditional Chinese medicine. It is used to treat influenza, epidemic cerebrospinal meningitis, encephalitis B, viral pneumonia, mumps, and severe acute respiratory syndrome (SARS). In this study, we found a new lignan glycoside (6) and two new phenylethanoid glycosides (7, 8) together with five known compounds as chemical constituents of Strobilanthes cusia root. Some samples were examined for anti-herpes simplex virus type-1 (HSV-1) activity. Among the tested samples, lupeol showed anti-HSV-1 activity (EC50: 11.7 μM) and showed 100% inhibition of virus plaque formation at 58.7 μM.

  马鞭草（Strobilanthes cusia BREMEK.，Acanthaceae）根在中国传统医学中广泛使用，俗称大青叶。它可用于治疗流行性感冒、流行性脑脊髓膜炎、乙型脑炎、病毒性肺炎、腮腺炎和严重急性呼吸综合征（SARS）。在这项研究中，我们发现了马鞭草根中新的木脂素苷（6）和两个新的苯乙基苷（7、8）以及五个已知的化合物。一些样品被检测了抗单纯疱疹病毒1型（HSV-1）活性。在测试的样品中，羽扇豆醇显示出抗HSV-1活性（EC50：11.7 μM），并在58.7 μM时显示出100%的病毒斑形成抑制。
• Phenolic constituents from the twigs of Betula schmidtii collected in Goesan, Korea
  作者：Kyoung Jin Park、Joon Min Cha、Lalita Subedi、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1016/j.phytochem.2019.112085

  日期：2019.11

  Six undescribed phenolic derivatives along with thirty two known compounds were isolated from the twigs of Betula schmidtii. The chemical structures were characterized through extensive spectroscopic analysis and chemical methods. All known compounds were first isolated in this plant. The anti-inflammatory effect of the isolates was tested by measuring nitric oxide production in lipopolysaccharide-activated BV-2 cells. Isotachioside, 4-allyl-2-hydrophenyl 1-O-beta-D-apiosyl-(1 (R) 6)-beta-D-glucopyranoside, genistein 5-O-beta-D-glucoside, and prunetinoside showed a slight potency to lower the NO production against LPS-activated microglia with IC50 values of 23.9, 25.3, 28.8, and 34.0 mu M, respectively.