fasciculol C | 65694-19-1

• 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
• 英文名称: fasciculol C
• 英文别名: (2R,3R,5R,10S,12S,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R,5R)-1,5,6-trihydroxy-6-methylheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-2,3,12-triol
• CAS: 65694-19-1
• 化学式: C₃₀H₅₂O₆
• 分子量: 508.739
• InChiKey: YRXIDKUVBPMNRA-YTOKZNHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  fasciculol C 、 4-溴苯甲酰氯 以 氘代吡啶 为溶剂， 反应 48.0h， 以18 mg的产率得到fasciculol C 2,3,21-tri-p-bromobenzoate
  参考文献：
  名称：

  Calmodulin inhibitors from the bitter mushroom Naematoloma fasciculare (Fr.) KARST. (Strophariaceae) and absolute configuration of fasciculols.

  摘要：

  苦毒蘑菇Naematoloma fasciculare (Fr.) KARST.（毒伞科）中发现了钙调素抑制剂。通过液滴逆流色谱法分离出活性化合物fasciculols B、C和F，并根据各种物理和光谱数据进行了鉴定。通过将二苯甲酸酯手性方法应用于fasciculol C的4-溴苯甲酸酯衍生物，可以确定C-2和C-3位置的绝对构型分别为（R）和（S）。

  DOI：

  10.1248/cpb.33.3821
• 作为产物：
  描述：

  crustulinol 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以50 mg的产率得到fasciculol C
  参考文献：
  名称：

  香菇Hebeloma spoliatum中三种有毒代谢物的分离，鉴定和药理研究。

  摘要：

  从蘑菇中分离出三种代谢物，暂定为HS-A，-B和-C，这是对小鼠的致命毒性原理。HS-A被鉴定为3-乙酰基-2-（3'-羟基-3'-甲基）戊二烯基硬脂醇，作为细胞毒性原理，它已从硬壳bel和菜豆中分离出来。HS-B和-C推导为3,21-二乙酰基-2-（3'-羟基-3'-甲基）戊二烯基硬脂醇和3-乙酰基-2-（3'-羟基-3'-甲基）戊二氢基硬脂醇，分别从其化学和光谱数据 以100 mg / kg的剂量腹膜内给予HS-A，-B和-C导致小鼠四肢瘫痪后死亡。该化合物引起小鼠乙酰胆碱氯化物或氯化钡处理后收缩的小肠松弛。

  DOI：

  10.1248/cpb.40.869

文献信息

• Isolation of the 3′R and 3′S diastereomers of fasciculic acid C from the Australian mushroom Hypholoma australianum
  作者：Joshua B. Hayton、Benjamin T. Ward、Ali R. Elnaas、Matthew Zunk、Darren C. Holland、Tom W. May、Tanja M. Voser、Arjuna Abitbol、Oren Cooper、Joe Tiralongo、I. Darren Grice、Anthony R. Carroll、Evelin Tiralongo

  DOI：10.1016/j.tetlet.2021.153294

  日期：2021.8

  including the new diastereomers (3′R)-fasciculic acid C (1) and (3′S)-fasciculic acid C (2), the triterpenes (3–5), the sesquiterpenes (6–7) and the diketopiperazines (8–9) were isolated from the Australian mushroom Hypholoma australianum. Several lanostane triterpenes have been isolated from the genus Hypholoma previously contain a 3-hydroxy-3-methylglutaric acid or a 3-hydroxy-3-methylglutaryl-glycine side

  九种化合物，包括新的非对映异构体 (3' R )-束状酸 C ( 1 ) 和 (3' S )-束状酸 C ( 2 )、三萜 ( 3 – 5 )、倍半萜 ( 6 – 7 ) 和二酮哌嗪( 8 – 9 ) 是从澳大利亚蘑菇Hypholoma australianum中分离出来的。先前已从Hypholoma属中分离出几种羊毛脂烷三萜，它们含有 3-羟基-3-甲基戊二酸或 3-羟基-3-甲基戊二酰基-甘氨酸侧链。只有Hypholoma衍生的三萜具有S-这两条侧链的构型之前已经分离出来。化合物1是从Hypholoma 中分离出的三萜的第一个例子，其侧链具有R构型。
• Lanostane Triterpenoids from the Mushroom <i>Naematoloma fasciculare</i>
  作者：Ki Hyun Kim、Eunjung Moon、Sang Un Choi、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1021/np300801x

  日期：2013.5.24

  In our continuing search for structurally interesting and bioactive metabolites from Korean wild mushrooms, bioassay-guided fractionation and a chemical investigation of the MeOH extracts of the fruiting bodies of the mushroom Naematoloma fasciculare resulted in the isolation of four new lanostane triterpenoids (1-4), together with 11 known compounds (5-15). The structures of 1-5 were determined by a combination of ID and 2D NMR and HRMS. The absolute configuration of the 3-hydroxy-3-methylglutaryl group as a side chain in 1 and 2 was determined by the alkaline methanolysis method. The full NMR data assignment of the known compound fasciculol G (S) is reported for the first time. Compounds 1-15 were tested for their antiproliferative activities against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) and evaluated for their inhibitory effects on nitric oxide production in a lipopolysaccharide-activated murine microglial cell line.
• Isolation, Identification and Pharmacological Studies on Three Toxic Metabolites from a Mushroom, Hebeloma spoliatum.
  作者：Haruhiro FUJIMOTO、Yasuhiro TAKANO、Mikio YAMAZAKI

  DOI：10.1248/cpb.40.869

  日期：——

  Three metabolites, tentatively named HS-A, -B and -C, were isolated from a mushroom, Hebeloma spoliatum, as the fatal toxic principles to mice. HS-A was identified as 3-acetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol, which has been isolated from Hebeloma crustuliniforme and H. sinapizans as a cytotoxic principle. HS-B and -C were deduced to be 3,21-diacetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol

  从蘑菇中分离出三种代谢物，暂定为HS-A，-B和-C，这是对小鼠的致命毒性原理。HS-A被鉴定为3-乙酰基-2-（3'-羟基-3'-甲基）戊二烯基硬脂醇，作为细胞毒性原理，它已从硬壳bel和菜豆中分离出来。HS-B和-C推导为3,21-二乙酰基-2-（3'-羟基-3'-甲基）戊二烯基硬脂醇和3-乙酰基-2-（3'-羟基-3'-甲基）戊二氢基硬脂醇，分别从其化学和光谱数据 以100 mg / kg的剂量腹膜内给予HS-A，-B和-C导致小鼠四肢瘫痪后死亡。该化合物引起小鼠乙酰胆碱氯化物或氯化钡处理后收缩的小肠松弛。
• Calmodulin inhibitors from the bitter mushroom Naematoloma fasciculare (Fr.) KARST. (Strophariaceae) and absolute configuration of fasciculols.
  作者：ISAO KUBO、AKIKO MATSUMOTO、MUTSUO KOZUKA、WILLIAM F. WOOD

  DOI：10.1248/cpb.33.3821

  日期：——

  Calmodulin inhibitors were found in the bitter poisonous mushroom Naematoloma fasciculare (Fr.) KARST. (Strophariaceae). The active compounds, fasciculols B, C, and F, were isolated by droplet counter-current chromatography and identified on the basis of various physical and spectral data. Application of the dibenzoate chirality method to a p-bromobenzoate derivative of fasciculol C allowed the absolute configurations at the C-2 and C-3 positions to be determined as (R) and (S), respectively.

  苦毒蘑菇Naematoloma fasciculare (Fr.) KARST.（毒伞科）中发现了钙调素抑制剂。通过液滴逆流色谱法分离出活性化合物fasciculols B、C和F，并根据各种物理和光谱数据进行了鉴定。通过将二苯甲酸酯手性方法应用于fasciculol C的4-溴苯甲酸酯衍生物，可以确定C-2和C-3位置的绝对构型分别为（R）和（S）。