(1R,2S,6S,9S)-9-甲基-2-[(2S,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-3-氧杂双环[4.3.0]壬-4-烯-5-羧酸 | 22487-36-1

• 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
• 中文名称: (1R,2S,6S,9S)-9-甲基-2-[(2S,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-3-氧杂双环[4.3.0]壬-4-烯-5-羧酸
• 英文名称: bis-desoxy-dihydro-monotropein
• 英文别名: 7-deoxy-8-epi-loganic acid；8-epideoxyloganic acid；7-deoxyloganic acid；deoxyloganic acid；7-Desoxyloganin-saeure；(1S,4aS,7S,7aR)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• CAS: 22487-36-1
• 化学式: C₁₆H₂₄O₉
• 分子量: 360.361
• InChiKey: DSXFHNSGLYXPNG-YDYVGBNJSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  597.2±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,2S,6S,9S)-9-甲基-2-[(2S,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-3-氧杂双环[4.3.0]壬-4-烯-5-羧酸 在 4-二甲氨基吡啶 、 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 7-deoxyloganin 11-GABA amide
  参考文献：
  名称：

  Inoue, Kenichiro; Ono, Masami; Nakajima, Hirotoshi, Heterocycles, 1992, vol. 33, # 2, p. 673 - 695

  摘要：

  DOI：
• 作为产物：
  描述：

  7-Ketologanintetraacetat 在 sodium hydroxide 、 Raney Ni (W-2) 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 53.0h， 生成 (1R,2S,6S,9S)-9-甲基-2-[(2S,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-3-氧杂双环[4.3.0]壬-4-烯-5-羧酸
  参考文献：
  名称：

  Inoue, Kenichiro; Ono, Masami; Nakajima, Hirotoshi, Heterocycles, 1992, vol. 33, # 2, p. 673 - 695

  摘要：

  DOI：

文献信息

• Iridoid glucosides from Picconia excelsa
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/s0031-9422(97)00023-x

  日期：1997.6

  the iridoids of Picconia excelsa from Tenerife provided 17 iridoid glucosides together with verbascoside. Major constituents (> 0.5%) were loganin, ketologanin, oleoacteoside and the new picconioside 1-a bisiridoid consisting of loganin esterified with deoxyloganin. Minor constituents were secoxyloganin, 8- epi -kingiside, 8- epi -kingisidic, oleoside 11-methyl ester, excelsioside, ligstroside and loganic

  摘要 对来自特内里费岛的 Picconia excelsa 环烯醚萜的研究提供了 17 种环烯醚萜苷和毛蕊花苷。主要成分 (> 0.5%) 是马钱素、酮洛甘素、油苷和新的 picconioside 1-一种由用脱氧马钱素酯化的马钱素组成的双环戊二烯苷。次要成分是secoxyloganin、8-epi-kingiside、8-epi-kingisidic、油苷11-甲酯、excelsioside、ligstroside和loganic acid以及新化合物酮基酸、6β-hydroxy-7-epi-loganin和picconiosides II- V，后四种是马钱素和薄荷、叶酸、6-(Z)-叶酸或6,7-二氢叶酸的酯。其结构主要通过核磁共振谱进行阐明。
• NMR assignments and single-crystal X-ray diffraction analysis of deoxyloganic acid
  作者：Rong Wei Teng、De Zu Wang、Yun Shan Wu、Yang Lu、Qi Tai Zheng、Chong Ren Yang

  DOI：10.1002/mrc.1502

  日期：2005.1

  Morina nepalensis var. alba Hand.‐Mazz. and their structures were determined on the basis of spectroscopic evidence. The total assignments of 1H and 13C NMR spectra of 1 in solvents CD3OD, D2O and CDCl3 were reported, in addition to the single‐crystal X‐ray diffraction analysis of its tetraacetate 1a. All compounds were obtained from Morina genus for the first time. Copyright © 2004 John Wiley & Sons

  7-脱氧木酸 (1)、柑橘 C (2)、3,4-二羟基苯甲酸 (3) 和 (E)-咖啡酸 (4) 从 Morina nepalensis var. 的乙醇提取物的水溶性部分中分离出来。alba Hand.-Mazz。并且它们的结构是根据光谱证据确定的。除了其四乙酸酯 1a 的单晶 X 射线衍射分析外，还报告了 1 在溶剂 CD3OD、D2O 和 CDCl3 中的 1H 和 13C NMR 光谱的总归属。所有化合物均为首次从桑属植物中获得。版权所有 © 2004 John Wiley & Sons, Ltd.
• Crotasteroiridocin: A New Steroiridoid from Crotalaria emarginella and its anti-Inflammatory Activity
  作者：Bahar Ahmed、Tawfeq A. Al-Howiriny、Jaber S. Mossa

  DOI：10.1515/znb-2006-0521

  日期：2006.5.1

  The aerial parts of Crotalaria emarginella Vatke (Leguminosae) have afforded a new steroidiridoid, characterized as 1’-hydroxy-isoiridomyrmecinyl- 1’-O-β -3-O-α-stigmast-5-ene, designated as crotasteroiridocin (1), which shows a unique combination of iridoid and sterol units, found very rarely in nature. Furthermore, a rare iridoid glucoside namely, bis-desoxy-dihydro-monotropein (2) has also been isolated from the aerial parts of the plant. The structures of the isolated products were elucidated on the basis of spectral and chemical studies. The anti-inflammatory activity has also been screened, wherein compounds 1 and 2 have shown 25.92% and 28.39% activity respectively, with respect to phenyl butazone against carrageenan employing the rat paw method.

  Crotalaria emarginella Vatke（豆科）的地上部分提供了一种新的类固醇萜苷，被描述为1'-羟基-异鼠李素基-1'-O-β-3-O-α-甾醇-5-烯，命名为crotasteroiridocin（1），它显示了在自然界中很少见到的萜苷和甾醇单元的独特组合。此外，还从该植物的地上部分分离出一种罕见的萜苷葡萄糖苷，即双去氧去氢单萜苷（2）。通过光谱和化学研究，阐明了所分离产物的结构。还筛选了其抗炎活性，其中化合物1和2分别显示了25.92％和28.39％的活性，相对于苯丁酸钠，采用大鼠爪法对卡拉胶进行检测。
• Catalytic Site Constraints in the P450s Mediating Loganic Acid (7DLH) and Secologanic Acid Synthesis (SLAS) in <i>Camptotheca</i>
  作者：Priya Rao、Mark A. Yaroslavsky、Justin C. Miller、Mary A. Schuler

  DOI：10.1021/acs.biochem.3c00126

  日期：2023.9.19

  Terpene indole alkaloids (TIAs) are plant-derived natural products synthesized in low levels in medicinal plants such as Catharanthus roseus and Camptotheca acuminata. TIA pathways species utilize several CYP72A subfamily members to form loganic acid from 7-deoxyloganic acid (a simple hydroxylation) as well as secologanin and secologanic acid from loganin and loganic acid (a C–C bond scission). Divergences

  萜烯吲哚生物碱 (TIA) 是在长春花和喜树等药用植物中低含量合成的植物源性天然产物。TIA 途径物种利用多个 CYP72A 亚家族成员从 7-脱氧马钱酸（简单羟基化）形成马钱酸，以及从马钱素和马钱酸（C-C 键断裂）形成赛洛甘宁和赛洛甘酸。这些 P450 特异性的差异使得喜树酸合酶 (SLAS) 成为能够执行这两种反应的双功能酶。相比之下，长春花7-脱氧龙酸羟化酶 (7DLH) 和 secologanin 合酶 (SLS) 仍然是单功能酶，能够单氧化或 C-C 键断裂。我们的体外重构现已证明喜树还含有单功能 7DLH，仅能够羟基化 7-脱氧龙果酸。旨在评估对喜树7DLH (CYP72A729) 的严格特异性和 SLAS (CYP72A564) 的广泛特异性重要的残基的诱变已鉴定出几个残基，其中相互转换显着影响其活性：7DLH 中的 Lys128His 增加 7-脱氧木香酸的羟基化，His132Lys
• AN ESTERASE THAT IS CAPABLE OF CONVERTING IRIDOIDS AND SECO-IRIDOIDS
  申请人：N-Zyme BioTec GmbH

  公开号：EP3409766A1

  公开（公告）日：2018-12-05

  The present invention relates to a polypeptide having esterase activity selected from the group consisting of (a) a polypeptide comprising the amino acid sequence of SEQ ID NO: 7; (b) a polypeptide that is at least 60 % identical to the amino acid sequence of SEQ ID NO: 7 and which is characterized by having an esterase activity; (c) a polypeptide encoded by a nucleic acid molecule which is at least 60 % identical to the nucleic acid sequence of SEQ ID NO: 5 or 6 wherein said polypeptide is characterized by having an esterase activity; (d) a polypeptide encoded by the nucleic acid molecule of SEQ ID NO: 5 or 6; and (e) a polypeptide encoded by the complementary sequence of a nucleic acid molecule that is able to hybridize with the nucleic acid molecule of SEQ ID NO: 5 or 6. Further, the present invention relates to a polypeptide having esterase activity selected from the group consisting of SEQ ID NO: 24 and 37 (as encoded by nuleic acid molecule of SEQ ID NO: 22 or 23 and SEQ ID NO: 35 and 36). The present invention also relates to a method for the production of oleacein, oleocanthal, or decarboxymethyl elenolic acid dialdehyde (DEDA) comprising the use of the esterase of the present invention. to an organism, preferably a plant cell, genetically engineered with a nucleic acid molecule encoding a polypeptide characterized by having an esterase activity or the vector of the present invention. The present invention also relates to a method for the production of oleacein, oleocanthal, and/or decarboxymethyl elenolic acid dialdehyde (DEDA) comprising the use of the esterase of the present invention.

  本发明涉及一种具有酯酶活性的多肽，该多肽选自由以下组成的组 (a) 包含 SEQ ID NO: 7 的氨基酸序列的多肽；(b) 与 SEQ ID NO: 7 的氨基酸序列至少 60% 相同的多肽，其特征在于具有酯酶活性；(c) 由核酸分子编码的多肽，该核酸分子与 SEQ ID NO: 5 或 6 的核酸序列至少 60% 相同，其中所述多肽的特征在于具有酯酶活性；(d) 由 SEQ ID NO: 5 或 6 的核酸分子编码的多肽；以及(e) 由 SEQ ID NO: 6 的核酸分子编码的多肽：5或6的核酸分子编码的多肽，其中所述多肽的特征在于具有酯酶活性；(d)由SEQ ID NO：5或6的核酸分子编码的多肽；以及(e)由能够与SEQ ID NO：5或6的核酸分子杂交的核酸分子的互补序列编码的多肽。此外，本发明涉及一种具有酯酶活性的多肽，该多肽选自 SEQ ID NO: 24 和 37（由 SEQ ID NO: 22 或 23 和 SEQ ID NO: 35 和 36 的核酸分子编码）组成的组。本发明还涉及一种生产油菜素、油菜醛或脱羧甲基烯醇酸二醛（DEDA）的方法，包括使用本发明的酯酶。本发明涉及一种生物体，最好是植物细胞，其基因工程中含有编码具有酯酶活性的多肽的核酸分子或本发明的载体。本发明还涉及一种生产油菜素、油菜醛和/或脱羧甲基烯醇酸二醛（DEDA）的方法，包括使用本发明的酯酶。

表征谱图