lambertellin | 28980-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: lambertellin
• 英文别名: 9-hydroxy-3-methylbenzo[g]chromene-2,5,10-trione
• CAS: 28980-51-0
• 化学式: C₁₄H₈O₅
• 分子量: 256.215
• InChiKey: WOEURUGFOVZZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  lambertellol A 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到lambertellin
  参考文献：
  名称：

  Lambertellols A and B, Novel 3,4-Dihydronaphthalen-1(2H)-ones with Spiro-butenolide Produced by Lambertella sp.1346

  摘要：

  [GRAPHICS]Lambertella sp. 1346 was found to produce lambertellols A (1) and B (2) carrying a novel dihydronaphthalen-1(2H)-ones with spiro-1-furan-2(5'H)-one. The spiro-lactone ring moiety of both 1 and 2 were easily migrated to afford lambertellin, a known metabolite of Lambertella corni-maris. The absolute stereochemistry of these compounds was established on the basis of CD spectrum after chemical derivatization.

  DOI：

  10.1021/ol035889d

文献信息

• Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones
  作者：Saroj R. De、Sujit K. Ghorai、Dipakranjan Mal

  DOI：10.1021/jo801961w

  日期：2009.2.20

  of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37).

  环氧醌（例如24）易于通过简化的Dowd氧化反应从喹诺醇（例如27）一步组装而成，经过重排后生成吡喃并萘醌（例如28）和它们的环收缩同系物（例如29）在450℃和0.01Torr下进行快速真空热解。已经证明该重排对于兰伯特林的区域特异性合成是有用的（3）。类似地，被掩蔽的叠氮基叠氮环戊酮9重新排列为2-吡啶酮（37）。
• Stimulation of the Biosynthesis of the Antibiotics Lambertellols by the Mycoparasitic Fungus<i>Lambertella corni-maris</i>under the Acidic Conditions Produced by Its Host Fungus<i>in Vitro</i>
  作者：Takanori MURAKAMI、Noboru TAKADA、Yukio HARADA、Toshikatsu OKUNO、Masaru HASHIMOTO

  DOI：10.1271/bbb.60667

  日期：2007.5.23

  The filamentous fungus, Lambertella corni-maris (L. corni-maris), a mycoparasite on Monilinia fructigena, produces the antibiotics, lambertellols A (1), B (2), and lambertellin (3), in a substantial amounts under acidic conditions, whereas these antibiotics were hardly detected when the fungus was cultured on a potato-sucrose (PS) medium without added acids. Our investigations also revealed that the host, M. fructigena, changed its surroundings into acidic conditions, suggesting that the acidic conditions acted as kairomones that stimulated the production of 1–3.

  玉米蓝伯菌（Lambertella corni-maris，L. corni-maris）是果蝇莫尼林菌（Monilinia fructigena）的一种寄生真菌，在酸性条件下会产生大量抗生素--蓝伯醇 A（1）、B（2）和蓝伯醇（3），而在不添加酸的马铃薯蔗糖（PS）培养基上培养该真菌时几乎检测不到这些抗生素。我们的研究还发现，宿主果蝇菌将其周围环境变为酸性条件，这表明酸性条件是刺激产生 1-3 的空气激素。
• Lambertellin system, the mechanism for fungal replacement of Monilinia fructigena with Lambertella corni-maris without competitive inhibition on agar media
  作者：Akane Hirose、Shinji Kudo、Takanori Murakami、Kazuaki Tanaka、Yukio Harada、Masaru Hashimoto

  DOI：10.1016/j.bmc.2014.02.051

  日期：2014.4

  The `Lambertellin system' was disclosed which rationally explains the fungal replacement (mycoparasitism) of Monilinia fructigena (M. f., the host) with Lambertella corni-maris (L. corni-maris, the parasite) without competitive inhibition in the simultaneous incubations on agar media. The `Lambertellin system' involves; (a) L. corni-maris secretes nontoxic lambertellols (1, 2) as the diffusible precursors of the authentic responsible substance 3 regardless of existence of the host M. f.; (b) In the absence of the host, the environment around the parasite is kept under neutral condition, and both 1 and 2 are readily transformed into 3; (c) Lambertellin (3) inhibits not only the host but also the parasite. The parasite degrades 3 for detoxification; and (d) Upon the host M. f. approaching closely to the area where the parasite inhabits, the environment around the parasite becomes acidic to stabilize 1 and 2, which gives them a chance to diffuse into the host area. Then these are gradually transformed into 3 to inhibit the host without damaging the parasite. This mechanism also accords with the progress of `Natsu-Nenju' disease on apple fruits, which is known to be a mysterious phyto-disease because of two unique stages of its lifecycle, anamorphic (asexual) and teleomorphic (sexual). The `Lambertellin system' would be categorized as a novel class of alleropathies. (C) 2014 Elsevier Ltd. All rights reserved.
• Lambertellols A and B, Novel 3,4-Dihydronaphthalen-1(2<i>H</i>)-ones with Spiro-butenolide Produced by <i>Lambertella </i>sp.1346
  作者：Takanori Murakami、Yoshifumi Morikawa、Masaru Hashimoto、Toshikatsu Okuno、Yukio Harada

  DOI：10.1021/ol035889d

  日期：2004.1.1

  [GRAPHICS]Lambertella sp. 1346 was found to produce lambertellols A (1) and B (2) carrying a novel dihydronaphthalen-1(2H)-ones with spiro-1-furan-2(5'H)-one. The spiro-lactone ring moiety of both 1 and 2 were easily migrated to afford lambertellin, a known metabolite of Lambertella corni-maris. The absolute stereochemistry of these compounds was established on the basis of CD spectrum after chemical derivatization.