(+)-terrecyclic acid A | 93219-11-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-terrecyclic acid A
• 英文别名: (-)-Terrecyclic acid A；terrecyclic acid A；(1R,5S,6S,9S)-11,11-dimethyl-2-methylidene-3-oxotricyclo[4.3.2.01,5]undecane-9-carboxylic acid
• CAS: 93219-11-5
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: SMAWCSOVJJHIOI-DDIVZENXSA-N

物化性质

• 沸点：
  413.4±24.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-terrecyclic acid A 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 5(6)-dihydroterrecyclic acid A
  参考文献：
  名称：

  Structure of a new antibiotic, terrecyclol, from Aspergillus terreus Thom.

  摘要：

  确定土曲霉荆棘 14 号新倍半萜抗生素 terrecyclol（I）的结构为 I，其抗菌活性与土曲霉荆棘 14 号的主要抗菌产物 terrecyclic acid A（II）一样高。

  DOI：

  10.1271/bbb1961.48.117
• 作为产物：
  描述：

  methyl 2-[(1R)-2,2-dimethyl-4-oxocyclopentyl]acetate 在 吡啶 、 盐酸 、 磷酸 、 potassium tert-butylate 、 四氯化钛 、 lithium thiopropiolate 、 对甲苯磺酸 、 对甲苯磺酰氯 、 sodium iodide 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 、 苯 为溶剂， 反应 24.92h， 生成 (+)-terrecyclic acid A
  参考文献：
  名称：

  （-）-环酸A的合成。环酸A和四氢萘酮的绝对构型

  摘要：

  由（+）-富琴酮（1）合成（-）-四环酸A（15）。建立了环酸A和四氢萘酮的绝对构型。

  DOI：

  10.1016/0040-4039(84)80119-7

文献信息

• Studies on the biosynthesis of terrecyclic acid A II confirmation of the cyclization mechanism and hydrogen shifts using [2-2H3]acetate and [213C2H3]acetate
  作者：Akira Hirota、Masahira Nakagawa、Heiichi Sakai、Akira Isogai、Kazuo Furihata、Haruo Seto

  DOI：10.1016/s0040-4039(00)89266-7

  日期：1985.1

  Feeding experiments with [2-3H3]acetate and [2-13C2H3]acetate in Aspergillus terreus Thom No. 14 indicated that the hydrogen at C-2 in terrecyclic acid A is incorporated without migration from the precursor acetic acid; the results favour our group's earlier speculation for the cyclization to the tricyclic skeleton in the biosynthetic scheme.

  在土曲霉Thom No. 14中用[2- 3 H 3 ]乙酸盐和[2- 13 C 2 H 3 ]乙酸盐进料的实验表明，环戊酸A中C-2处的氢没有从前体乙酸中迁移出; 这一结果有利于我们小组早先推测在生物合成方案中环化成三环骨架。
• Structure of a new antibiotic, terrecyclol, from Aspergillus terreus Thom.
  作者：Masahira NAKAGAWA、Heiichi SAKAI、Akira ISOGAI、Akira HIROTA

  DOI：10.1271/bbb1961.48.117

  日期：——

  The structure of a new sesquiterpene antibiotic, terrecyclol (I), from Aspergillus terreus Thorn No. 14 was determined to be I. The antimicrobial activity ofI is as high as that ofterrecyclic acid A (II), which is a main antimicrobial product of Asp. terreus No. 14.

  确定土曲霉荆棘 14 号新倍半萜抗生素 terrecyclol（I）的结构为 I，其抗菌活性与土曲霉荆棘 14 号的主要抗菌产物 terrecyclic acid A（II）一样高。
• Nakagawa, Masahira; Sakai, Heiichi; Isogai, Akira, Agricultural and Biological Chemistry, 1984, vol. 48, # 9, p. 2279 - 2284
  作者：Nakagawa, Masahira、Sakai, Heiichi、Isogai, Akira、Hirota, Akira

  DOI：——

  日期：——
• Synthesis of (−)-terrecyclic acid A. Absolute configuration of terrecyclic acid A and quadrone
  作者：Kenji Kon、Kenji Ito、Sachihiko Isoe

  DOI：10.1016/0040-4039(84)80119-7

  日期：——

  (−)-Terrecyclic acid A (15) was synthesized from (+)-fenchone (1). The absolute configuration of terrecyclic acid A and quadrone was established.

  由（+）-富琴酮（1）合成（-）-四环酸A（15）。建立了环酸A和四氢萘酮的绝对构型。
• Cytotoxic Constituents of <i>Aspergillus </i><i>t</i><i>erreus</i> from the Rhizosphere of <i>Opuntia </i><i>v</i><i>ersicolor</i> of the Sonoran Desert
  作者：E. M. Kithsiri Wijeratne、Thomas J. Turbyville、Zhongge Zhang、Donna Bigelow、Leland S. Pierson、Hans D. VanEtten、Luke Whitesell、Louise M. Canfield、A. A. Leslie Gunatilaka

  DOI：10.1021/np030266u

  日期：2003.12.1

  A novel cyclopentenedione, asterredione (1), two new terrecyclic acid A derivatives, (+)-5(6)-dihydro-6-methoxyterrecyclic acid A (2) and (+)-5(6)-dihydro-6-hydroxyterrecyclic acid A (3), and five known compounds, (+)-terrecyclic acid A (4), (-)-quadrone (5), betulinan A (6), asterriquinone D (7), and asterriquinone C-1 (8), were isolated from Aspergillus terreus occurring in the rhizosphere of Opuntia versicolor, using bioassay-guided fractionation. Acid-catalyzed reaction of 2 under mild conditions afforded 4, whereas under harsh conditions 2 yielded 5 and (-)-isoquadrone (9). Catalytic hydrogenation and methylation of 4 afforded 5(6)-dihydro-terrecyclic acid A (10) and (+)-terrecyclic acid A methyl ester (11), respectively. The structures of 1-11 were elucidated by spectroscopic methods. All compounds were evaluated for cytotoxicity in a panel of three sentinel cancer cell lines, NCI-H460 (non-small cell lung cancer), MCF-7 (breast cancer), and SF-268 (CNS glioma), and were found to be moderately active. Cell cycle analysis of 2, 4, and 5 using the NCI-H460 cell line indicated that 4 is capable of disrupting the cell cycle through an apparent arrest to progression at the G(1) and G(2)/M phases in this p53 competent cell line. A pathway for the biosynthetic origin of asterredione (1) from asterriquinone D (7) is proposed.