异落叶松脂素 | 548-29-8

• 物质功能分类: 天然产物 - 木脂素
• 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
• 中文名称: 异落叶松脂素
• 中文别名: (+)-异落叶松树脂醇
• 英文名称: (6R,7R,8S)-isolariciresinol
• 英文别名: (+)-Isolariciresinol；6R,7S,8S-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis-hydroxymethyl-3-methoxy-5,6,7,8-tetrahydro-naphthalen-2-ol；(7′S, 8′R, 8R)-isolariciresinol；(7S,8R,8'R)-(+)-cyclolariciresinol；(7'S,8'R,8R)-isolariciresinol；meso-secoisolariciresinol；Isolariciresinol, (+)-；(6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol
• CAS: 548-29-8
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: OGFXBIXJCWAUCH-KPHUOKFYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  584.1±50.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)
• 溶解度：
  丙酮：可溶，氯仿：可溶，二氯甲烷：可溶，DMSO：可溶，乙酸乙酯：可溶
• LogP：
  1.640 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异落叶松脂素 在 Et₃N*SO₃ 、 三氟甲磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以53%的产率得到4,4',9,9'-tetra-O-sulfoisolariciresinol, tetrasodium salt
  参考文献：
  名称：

  Study of sulfated derivatives of polyhydroxy compounds as inhibitors of blood coagulation

  摘要：

  天然多羟基化合物的过硫酸酯衍生物，如木脂素的分枝木脂素和异分枝木脂素、黄酮二氢槲皮素以及肌醇，已被合成。研究了这些化合物抑制血液凝固内源性途径（APTT测试）的能力，并在抗凝血酶（III）存在下降低凝血因子Xa活性的效果。

  DOI：

  10.1007/s11172-010-0067-6
• 作为产物：
  描述：

  (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 在 palladium on activated charcoal lithium aluminium tetrahydride 、 高氯酸 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 23.58h， 生成 异落叶松脂素
  参考文献：
  名称：

  The Syntheses of (R)-(+)-b-Vanillyl-g-butyrolactone and of Chiral Lignans Therefrom

  摘要：

  DOI：

  10.3987/r-1987-05-1169

文献信息

• Isolation and Characterization of the Lignans, Isolariciresinol and Pinoresinol, in Flaxseed Meal
  作者：Lucy P. Meagher、Gary R. Beecher、Vincent P. Flanagan、Betty W. Li

  DOI：10.1021/jf981359y

  日期：1999.8.1

  The isolation and characterization of the lignans, isolariciresinol, pinoresinol, secoisolariciresinol, and matairesinol, potent phytoestrogens, from flaxseed meal are described. This is the first report of isolariciresinol and pinoresinol being detected in a food. The extraction method selected combined the removal of the lignan glycosides from the plant matrix with an alcoholic solvent system, followed

  描述了从亚麻籽粕中分离和鉴定木脂素，异二十烷醇，松脂醇，癸二异西里烯醇和马来甾醇（有效植物雌激素）的方法。这是在食品中检测到异二十烷醇和松脂醇的首次报道。选择的提取方法结合了用醇溶剂系统从植物基质中去除木脂素苷，然后进行酸水解以释放糖苷配基。反相高效液相色谱-二极管阵列检测系统用于酸水解甲醇提取物中280 nm处木脂素的初步分离和检测。木质素三甲基甲硅烷基醚衍生物通过气相色谱/质谱法表征。异豆香脂树脂是亚麻籽中的主要木脂素。异二十烷醇，松脂醇，
• Lignans from the Roots of<i>Urtica dioica</i>and their Metabolites Bind to Human Sex Hormone Binding Globulin (SHBG)
  作者：Matthias Schöttner、Dietmar Ganßer、Gerhard Spiteller

  DOI：10.1055/s-2006-957756

  日期：1997.12

  Polar extracts of the stinging nettle (Urtica dioica L.) roots contain the lignans (+)-neoolivil, (-)-secoisolariciresinol, dehydrodiconiferyl alcohol, isolariciresinol, pinoresinol, and 3,4-divanillyltetrahydrofuran. These compounds were either isolated from Urtica roots, or obtained semisynthetically. Their affinity to human sex hormone binding globulin (SHBG) was tested in an in vitro assay. In addition, the main intestinal transformation products of plant lignans in humans, enterodiol and entero-lactone, together with enterofuran were checked for their activity. All lignans except (-)-pinoresinol developed a binding affinity to SHBG in the in vitro assay. The affinity of (-)-3,4-divanillyltetrahydrofuran was outstandingly high. These findings are discussed with respect to potential beneficial effects of plant lignans on benign prostatic hyperplasia (BPH).

  刺荨麻（Urtica dioica L.）根的极性萃取物中含有木脂素（+）-neoolivil、（-）-secoisolariciresinol、dehydrodiconiferyl alcohol、isariciresinol、pinoresinol 和 3,4-divanillyltetrahydrofuran。这些化合物或从荨麻根中分离出来，或通过半合成方法获得。在体外试验中测试了它们与人类性激素结合球蛋白（SHBG）的亲和力。此外，还检测了植物木酚素在人体肠道中的主要转化产物肠二醇和肠内酯以及肠呋喃的活性。在体外试验中，除 (-)-pinoresinol 外，所有木酚素都与 SHBG 具有结合亲和力。(-)-3,4-divanillyltetrahydrofuran 的亲和力非常高。这些研究结果讨论了植物木酚素对良性前列腺增生症（BPH）的潜在有益作用。
• Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities
  作者：Mana Sampei、Midori A. Arai、Masami Ishibashi

  DOI：10.1007/s11418-018-1198-6

  日期：2018.6

  pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization

  木质素广泛分布于植物中，并表现出显着的药理作用，包括抗肿瘤和抗氧化活性。在这里，我们描述了schizandriside（1）的总合成，该化合物以前是通过使用1,1-二苯基-2-picylhydrazyl自由基清除试验监测抗氧化活性而从Saraca asoca分离得到的。从串联迈克尔-醛醇缩合反应开始，木脂素骨架是通过6个步骤合成的，包括环化步骤。为了确定1的立体化学，我们从乙醇17合成了天然产物（±）-异lariciresinol（18）。光谱数据的比较显示出良好的一致性。使用四种不同的糖基供体研究糖基化。只有使用三氟甲磺酸银和1,1,3,3-四甲基脲的Koenigs–Knorr条件才提供糖基化产物。使用反相高效液相色谱进行脱保护和纯化，得到了schizandriside（1）和其非对映异构体saracoside（2）。合成1，2和18显示出抗氧化活性与IC 50 分别= 34.4，28.8，53
• Isolation and Structure of Some Constituents of the Australian Medicinal Plant Tinospora smilacina ('Snakevine')
  作者：Natasha L. Hungerford、Donald P. A. Sands、William Kitching

  DOI：10.1071/c98034

  日期：——

  The structures of a number of compounds isolated from the stems of Tinospora smilacina (known as ‘snakevine’) have been determined. The known clerodane-type compound columbin is a major component, and two new minor compounds incorporate a heavily oxygenated tetrahydrofuran ring in place of the furan ring of columbin. The lignan isolariciresinol is also shown to be a minor component, along with dihydrosyringenin. The traditional medicinal use of the vine, particularly in countering snake venom, may be associated primarily with the presence of columbin.

  从蛇床子（Tinospora smilacina，又称 "蛇藤"）茎中分离出的一些化合物的结构 Tinospora smilacina（又名 "蛇藤"）茎中分离出的多种化合物的结构。 的结构已经确定。已知的clerodane型化合物columbin是其主要成分。 两种新的次要化合物在茎中含有一个含氧较高的四氢呋喃环。 的呋喃环。木质素 也是一种次要成分。 二氢瑞香素。藤本植物的传统药用价值，尤其是在抗蛇毒方面 藤本植物的传统药用价值，尤其是在对抗蛇毒方面，可能主要与其中的 秋兰宾。
• Synthetic transformation of hydroxymatairesinol from Norway spruce (Picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol
  作者：Patrik Eklund、Reijo Sillanpää、Rainer Sjöholm

  DOI：10.1039/b202493d

  日期：——

  We have developed a method for the transformation of hydroxymatairesinol to optically pure (+)-lariciresinol and (+)-cyclolariciresinol via the hitherto unreported lignan 7-hydroxysecoisolariciresinol. The two naturally occurring isomers of hydroxymatairesinol were reduced with LiAlH4 to a mixture of two epimers of 7-hydroxysecoisolariciresinol, which were further selectively transformed to (+)-lariciresinol and (+)-cyclolariciresinol by an acid catalysed intramolecular cyclisation reaction. The structure of the major isomer of 7-hydroxysecoisolariciresinol was confirmed by X-ray crystallography and thereby also the absolute configurations of the two isomers of hydroxymatairesinol were unambiguously proven. Optical purities were determined by chiral HPLC-MS/MS and optical rotation measurements.

  我们开发了一种方法，通过迄今未报道过的木质素 7-羟基secoisolariciresinol，将羟基马泰松脂醇转化为光学纯度为(+)-落叶松脂醇和(+)-环落叶松脂醇。用 LiAlH4 将两种天然存在的羟基马脱脂木脂素异构体还原为 7-hydroxysecoisolariciresinol 的两种表聚体混合物，再通过酸催化的分子内环化反应，将其选择性地转化为 (+)-lariciresinol 和 (+)-cyclolariciresinol 。7-hydroxysecoisolariciresinol 主要异构体的结构通过 X 射线晶体学得到了证实，从而也明确地证明了羟基马来松脂醇两种异构体的绝对构型。光学纯度是通过手性 HPLC-MS/MS 和光学旋转测量确定的。