(-)-3,3'-bisdemethylpinoresinol | 340167-81-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (-)-3,3'-bisdemethylpinoresinol
• 英文别名: (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane；(+)-Sesamin dicatechol；4-[(3S,3aR,6S,6aR)-3-(3,4-dihydroxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]benzene-1,2-diol
• CAS: 340167-81-9
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: OQSOTSIYXPYTRE-YDOWWZDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  重氮甲烷 、 (-)-3,3'-bisdemethylpinoresinol 以 甲醇 为溶剂， 反应 24.0h， 以11 mg的产率得到松脂素二甲醚
  参考文献：
  名称：

  来自Joannesiaprinceps种子的倍半木脂素和其他成分

  摘要：

  除了已知的新木脂素 americanol A、isoamericanol A 和 isoamericanin A 外，从巴西 Joannesia 的种子的甲醇提取物中分离出 3,3'-双去甲基松脂素和六种新的倍半木脂素，这些新木脂素被发现是主要成分。开发了一种从光谱上区分美洲醇和异美洲醇类型化合物的方法。

  DOI：

  10.1016/s0031-9422(02)00357-6
• 作为产物：
  描述：

  (+)-Pinoresinol 在 Eubacterium sp. ARC-2 、 general anaerobic medium 作用下， 反应 132.0h， 以8 mg的产率得到(-)-3,3'-bisdemethylpinoresinol
  参考文献：
  名称：

  Further Studies on a Human Intestinal Bacterium Ruminococcus sp. END-1 for Transformation of Plant Lignans to Mammalian Lignans

  摘要：

  A human intestinal bacterium Ruminococcus (R.) sp. END-1 capable of oxidizing (-)-enterodiol to (-)-enterolactone, enantioselectively, was further investigated from the perspective of transformation of plant lignans to mammalian lignans; A cell-free extract of the bacterium transformed (-)-enterodiol to (-)-enterolactone through an intermediate, enterolactol. The bacterium showed not only oxidation but also demethylation and deglucosylation activities for plant lignans. Arctiin and secoisolariciresinol diglucoside were converted to (-)-dihydroxyenterolactone and (+)-dihydroxyenterodiol, respectively. Moreover, by coincubation with Eggerthella sp. SDG-2, the bacterium transformed arctiin and secoisolariciresinol diglucoside to (-)-enterolactone and (+)-enterodiol, respectively.

  DOI：

  10.1021/jf900902p

文献信息

• Furofuran lignans as a new series of antidiabetic agents exerting α-glucosidase inhibition and radical scarvenging: Semisynthesis, kinetic study and molecular modeling
  作者：Wisuttaya Worawalai、Titiruetai Doungwichitrkul、Warin Rangubpit、Panyakorn Taweechat、Pornthep Sompornpisut、Preecha Phuwapraisirisan

  DOI：10.1016/j.bioorg.2019.03.077

  日期：2019.6

  A new series of furofuran lignans containing catechol moiety were prepared from the reactions between lignans and a variety of phenolics. All 22 products obtained were evaluated against three different α-glucosidases (maltase, sucrase and Baker's yeast glucosidase) and DPPH radical. Of furofuran lignans evaluated, β-14, having two catechol moieties and one acetoxy group, was the most potent inhibitor

  从木脂素和各种酚类之间的反应制备了一系列含有邻苯二酚部分的呋喃呋喃木脂素。针对三种不同的α-葡糖苷酶（麦芽糖酶，蔗糖酶和贝克酵母葡糖苷酶）和DPPH自由基对获得的所有22种产品进行了评估。在评估的呋喃呋喃木脂素中，具有两个邻苯二酚部分和一个乙酰氧基的β-14是最有效的针对贝克酵母，麦芽糖酶和蔗糖酶的抑制剂，IC50值分别为5.3、25.7和12.9 µM。令人感兴趣的是，它对贝克酵母的抑制能力是标准药物阿卡波糖的28倍，其DPPH自由基清除能力（SC50 11.2 µM）是商业抗氧化剂BHT的130倍。随后对β-14抑制作用的潜在机制的研究表明，它阻断了Baker' 酵母和蔗糖酶通过混合抑制作用发挥功能，同时对麦芽糖酶产生非竞争性抑制作用。最强效的呋喃呋喃木脂素（4，α-8b，α-14和β-14）与大鼠肠麦芽糖酶在结合位点的同源性的分子动力学模拟显示，邻苯二酚，乙酰氧基和醌部分的氢键相互作
• Discovery of a sesamin-metabolizing microorganism and a new enzyme
  作者：Takuto Kumano、Etsuko Fujiki、Yoshiteru Hashimoto、Michihiko Kobayashi

  DOI：10.1073/pnas.1605050113

  日期：2016.8.9

  Lignans, including sesamin, are produced by a wide variety of plants, but the microbial degradation of lignan has not been identified biochemically. Here, we show that Sinomonas sp. no. 22 can catabolize sesamin as a sole-carbon source. We identified the sesamin-converting enzyme, SesA, from strain Sinomonas sp. no. 22. SesA catalyzed methylene group transfer from sesamin to tetrahydrofolate (THF). The resulting 5,10-CH ₂ -THF might find use as a C1-donor for bioprocesses. SesA gene homologs were found in the genomes of both Gram-positive and Gram-negative bacteria, suggesting that sesamin (lignan) utilization is a widespread, but still unrecognized, function in environments where lignans are produced and degraded.

  木脂素，包括芝麻素，由许多植物产生，但木脂素的微生物降解尚未在生化上得到确定。在这里，我们展示了Sinomonas sp. no. 22可以将芝麻素作为唯一的碳源进行分解。我们从Sinomonas sp. no. 22菌株中鉴定了芝麻素转化酶SesA。 SesA催化芝麻素向四氢叶酸（THF）的亚甲基基团转移。由此产生的5,10-CH₂-THF可能作为C1供体用于生物过程。在革兰氏阳性和阴性菌的基因组中发现了SesA基因同源物，这表明芝麻素（木脂素）利用是在产生和降解木脂素的环境中普遍存在但尚未被认识的功能。

• First Chemical Synthesis of Antioxidative Metabolites of Sesamin
  作者：Hidehito Urata、Yuka Nishioka、Takafumi Tobashi、Yasuo Matsumura、Namino Tomimori、Yoshiko Ono、Yoshinobu Kiso、Shun-ichi Wada

  DOI：10.1248/cpb.56.1611

  日期：——

  The first chemical synthesis of two metabolites ((1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-1) and (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-2)) of sesamin was achieved by a simple two-step approach from sesamin. The approach consists of acetoxylation of the methylenedioxy moiety(ies) with lead(IV) tetraacetate

  两种代谢物（（1R，2S，5R，6S）-6-（3,4-二羟基苯基）-2-（3,4-亚甲基二氧苯基）-3,7-二氧杂双环[3,3,0]的第一化学合成辛烷（SC-1）和（1R，2S，5R，6S）-2,6-双（3,4-二羟基苯基）-3,7-二氧杂双环[3,3,0]辛烷（SC-2））芝麻素是通过芝麻素的简单两步方法获得的。该方法包括用四乙酸铅（IV）对亚甲基二氧基部分进行乙酰氧基化，并将所得的半原酸酯酸水解为SC-1和SC-2。