brevifolin carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: brevifolin carboxylic acid
• 英文别名: Brevifolincarboxylic acid；7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylic acid
• 化学式: C₁₃H₈O₈
• 分子量: 292.202
• InChiKey: JFJWMFPFMLRLMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  brevifolin carboxylic acid 、 水 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Schmidt; Bernauer, Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 211,221

  摘要：

  DOI：
• 作为产物：
  描述：

  geraniin 在 盐酸 、 sodium benzenesulfonate 作用下， 以 乙腈 为溶剂， 反应 3.83h， 生成 brevifolin carboxylic acid
  参考文献：
  名称：

  Tannins and related compounds. C. Reaction of dehydrohexahydroxydiphenic acid esters with bases, and its application to the structure determination of pomegranate tannins, granatins A and B.

  摘要：

  一些脱氢六羟基二苯酸酯的新反应（例如，香商品（1））与碱的反应被展示出来。具体来说，用三乙胺或苯磺酸钠在乙腈中处理1，导致发生苯基酸类重排，生成短叶蓼酸衍生物（3）。另一方面，用吡啶处理1则得到了四羟基二苯并呋喃衍生物（8），而用水合氢氧化钠反应则断裂了碳-碳键，生成脱氢车前酸酯（10）。这些反应应用于石榴中的主要单宁成分——石榴单宁A和B，明确确立了它们的结构（分别为13和11）。

  DOI：

  10.1248/cpb.38.2424

文献信息

• Tannins and related compounds. XCV. Isolation and characterization of helioscopinins and helioscopins, four new hydrolyzable tannins from Euphorbia helioscopia L. (1).
  作者：Seung-Ho LEE、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.1518

  日期：——

  A chemical examination of polyphenols in Euphorbia helioscopia L. (Euphorbiaceae) has led to the isolation of four new hydrozable tannins named helioscopinins A (10) and B (9), and helioscopins A (11) and B (12), together with eight known tannins (1-8). On the basis of chemical and spectroscopic evidence, the structures of compounds 9-12 were established as 1, 6-(S)-hexahydroxydiphenoyl-3-O-galloyl-β-D-glucose, 1, 6-(S)-hexahydroxydiphenoyl-2, 4-(S)-dehydrohexahydroxydiphenoyl-3-O-galloyl-β-D-glucose, 1, 6-(S)-hexahydroxydiphenoyl-2, 4-(R)-elaeocarpusionoyl-3-O-galloyl-β-D-glucose and 1, 3, 6-tri-O-galloyl-2, 4-(R)-elaeocarpusinoyl-β-D-glucose, respectively.

  对大戟科植物日照大戟（Euphorbia helioscopia L.）中的多酚进行了化学分析，分离出四种新的水解鞣酸，分别命名为helioscopinins A (10) 和 B (9)，以及helioscopins A (11) 和 B (12)，同时还发现了八种已知的鞣酸（1-8）。根据化学和光谱证据，化合物9-12的结构被确认分别为：1, 6-(S)-六羟基二苯酰基-3-O-鞣酸基-β-D-葡萄糖，1, 6-(S)-六羟基二苯酰基-2, 4-(S)-脱氢六羟基二苯酰基-3-O-鞣酸基-β-D-葡萄糖，1, 6-(S)-六羟基二苯酰基-2, 4-(R)-油青果酸-3-O-鞣酸基-β-D-葡萄糖和1, 3, 6-三-O-鞣酸基-2, 4-(R)-油青果酸-β-D-葡萄糖。
• Tannins and Related Polyphenols of Euphorbiaceous Plants. IX. Hydrolyzable Tannins with 1C4 Glucose Core from Phyllanthus flexuosus MUELL. ARG.
  作者：Takashi YOSHIDA、Hideyuki ITOH、Shunyo MATSUNAGA、Reiko TANAKA、Takuo OKUDA

  DOI：10.1248/cpb.40.53

  日期：——

  Four new hydrolyzable tannins (phyllanthusiins A-D), a new polyphenol of related structure (phyllanthusiin E), and eight known polyphenols have been isolated from the leaves of Phyllanthus flexuosus. On the basis of the spectroscopic methods including 1H-13C long-range two-dimensional nuclear magnetic resonance techniques, phyllanthusiins A (9), B (12) and C(14), were characterized as oxidative metabolites of geraniin, each having a different new acyl group biogenetically formed via an oxidative cleavage of the dehydrohexahydroxydiphenoyl group, on the 1C4 glucopyranose core. Phyllanthusiin D (15) was determined to be a condensate of geraniin with acetone, and phyllanthusiin E (16), was an oxidized congener of ellagic acid.

  从蛇菰（Phyllanthus flexuosus）的叶子中分离出了四种新的可水解单宁（Phyllanthusiins A-D）、一种相关结构的新型多酚（Phyllanthusiin E）以及八种已知多酚。根据包括1H-13C长程二维核磁共振技术在内的光谱学方法，Phyllanthusiins A（9）、B（12）和C（14）被鉴定为-geraniin的氧化代谢产物，每种都具有不同的新酰基，通过对去氢六羟基二苯酰基（dehydrohexahydroxydiphenoyl）基团的氧化裂解，在1C4葡萄糖吡喃核心上生成。Phyllanthusiin D（15）被确定为geraniin与丙酮的缩合物，而Phyllanthusiin E（16）则是鞣酸的氧化同类物。
• Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants
  作者：Yun-Qiu Li、Masako Kitaoka、Juri Takayoshi、Ya-Feng Wang、Yosuke Matsuo、Yoshinori Saito、Yong-Lin Huang、Dian-Peng Li、Gen-ichiro Nonaka、Zhi-Hong Jiang、Takashi Tanaka

  DOI：10.3390/molecules26020337

  日期：——

  The aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From Persicaria chinensis, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-O-galloyl-4,6-(S)-dehydrohexahydroxydiphenoyl-d-glucose. Interestingly, acid hydrolysis of this compound afforded ellagic acid, despite the absence of a hexahydroxydiphenoyl group. From the rhizome of Polygonum runcinatum var. sinense, a large amount of granatin A, along with minor ellagitannins, helioscpoinin A, davicratinic acids B and C, and a new ellagitannin called polygonanin A, were isolated. Based on 2D nuclear magnetic resonance (NMR) spectroscopic examination, the structure of polygonanin A was determined to be 1,6-(S)-hexahydroxydiphenoyl-2,4-hydroxychebuloyl-β-d-glucopyranose. These are the second and third hydrolyzable tannins isolated from Polygonaceous plants. In addition, oligomeric proanthocyanidins of Persicaria capitatum and P. chinensis were characterized by thiol degradation. These results suggested that some Polygonaceous plants are the source of hydrolyzable tannins not only proanthocyanidins.

  本研究的目的是表征蓼科植物中的可水解单宁，因为之前只有少数植物被报道含有椰子酸单宁。从中国蓼（Persicaria chinensis）中分离出一种新的可水解单宁，称为persicarianin，并被确定为3-O-没食子酸基-4,6-(S)-去氢六羟基二苯乙酰-D-葡萄糖。有趣的是，尽管缺少一个六羟基二苯乙酰基团，但对该化合物进行酸水解后得到了酚酸。从中国蓼的根茎中分离出了大量的石榴酸A，以及少量的椰子酸单宁、helioscpoinin A、davicratinic 酸B和C，以及一种新的椰子酸单宁称为polygonanin A。根据二维核磁共振（NMR）光谱检查，确定了polygonanin A的结构为1,6-(S)-六羟基二苯乙酰基-2,4-羟基chebuloyl-β-D-葡萄糖苷。这些是从蓼科植物中分离出的第二和第三种可水解单宁。此外，通过巯基降解法表征了中国蓼和Persicaria capitatum中的寡聚原花青素。这些结果表明，一些蓼科植物不仅是原花青素的来源，还是可水解单宁的来源。
• トリプターゼ活性阻害剤およびその利用
  申请人：一丸ファルコス株式会社

  公开号：JP2011057596A

  公开（公告）日：2011-03-24

  【課題】安全なトリプターゼ活性阻害剤とそれを配合した、掻痒、しわ、肌荒れ、全身アナフィラキシー、喘息、間質性肺疾患、間質性膀胱炎、アトピー、疼痛、歯肉炎、慢性間接リウマチ、関節炎、歯周病、花粉症等の疾患の治療又は予防のための外用剤、服用剤、飲食品を提供する。【解決手段】加水分解型タンニンであるコリラギン Corilagin，ブレビホリンカルボン酸 Brevifolincarboxylic acid，ゲラニイン Geraniinのうちの１種以上を有効成分として含有するトリプターゼ活性阻害剤、及びこれらトリプターゼ活性阻害剤を配合して外用剤、服用剤または飲食品組成物とする。 【選択図】なし

  目的] 提供安全的色氨酸酶活性抑制剂和含有它们的外用制剂、剂型和食品，用于治疗或 预防瘙痒、皱纹、皮肤粗糙、全身过敏性休克、哮喘、间质性肺病、间质性膀胱炎、过敏症、 疼痛、牙龈炎、慢性间接风湿病、关节炎、牙周病和花粉病等疾病。解决方案]一种胰蛋白酶活性抑制剂，其有效成分包括一种或多种水解型单宁酸 corilagin 珊瑚苷、Brevifolin 羧酸、Geraniin，并将这些胰蛋白酶活性抑制剂混入外用制剂、剂型或食品/饮料组合物中。 无。
• Anti-inflammatory isocoumarins from the bark of <i>Fraxinus chinensis</i> subsp. <i>rhynchophylla</i>
  作者：Beom Zoo Lee、Chan-Sik Kim、Soon-Kyu Jeong、Sulhae Lee、Ik Soo Lee、KwangWon Hong

  DOI：10.1080/14786419.2020.1715401

  日期：2021.11.17

  A new isocoumarin (1) named fraxicoumarin was isolated from the bark of Fraxinus chinensis subsp. rhynchophylla along with three known compounds (2-4). The structure of the new compound was established by extensive spectroscopic studies and chemical evidence. The anti-inflammatory effects of the isolated compounds (1-4) on lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells were evaluated in vitro. Of the compounds tested, compounds 1 and 3 inhibited LPS-induced nitric oxide (NO) production in RAW 264.7 cells. Consistent with these findings, they also suppressed LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein level in RAW 264.7 cells.