印楝沙兰林 | 992-20-1

• 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: 印楝沙兰林
• 英文名称: salannin
• 英文别名: [(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-14-acetyloxy-6-(furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-12-yl] (E)-2-methylbut-2-enoate
• CAS: 992-20-1
• 化学式: C₃₄H₄₄O₉
• 分子量: 596.718
• InChiKey: CJHBVBNPNXOWBA-REXVOHEDSA-N

物化性质

• 熔点：
  167～170℃
• 沸点：
  631.9±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  5.560 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  9

制备方法与用途

生物活性

Salannin 是一种柠檬苦素，具有抗溃疡和杀精活性。此外，它对革兰氏阳性菌和阴性菌均有抗菌作用。

体内研究

Salannin 在不同剂量下表现出显著的保护活性。具体结果显示：

• 动物模型：Wistar 大鼠（体重 200-220 g），使用水杨酸诱导胃溃疡。
• 给药剂量：10、20 和 50 mg/kg，口服 (p.o.)。
• 结果：显著且剂量依赖性地抑制了水杨酸诱导的胃溃疡。

反应信息

• 作为反应物：
  描述：

  印楝沙兰林 在 苄基三甲基氢氧化铵 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以57%的产率得到2H,3H-环戊二烯并[b]呋喃并[2',3',4':4,5]萘并[2,3-d]呋喃-6-乙酸,8-(3-呋喃基)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-十二氢-3,5-二羟基-2a,5a,6a,7-四甲基-,甲基酯,(2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)-
  参考文献：
  名称：

  印度印za虫的昆虫拒食剂（第5部分）：印za素和一些相关柠檬苦素的化学修饰及其构效关系

  摘要：

  对强效昆虫拒食剂和生长破坏剂印za素（1）以及相关柠檬苦素3-tigloyl印za素（6）和塞兰宁（27）进行化学修饰已使人们能够探索这些化合物的生物活性。人们对拒食效应的结构依赖性作了一般性评论。

  DOI：

  10.1016/s0040-4020(01)81095-4

文献信息

• Structural flexibility in the biocatalyst-mediated functionalization of ring ‘A’ in salannin, a tetranortriterpene from Azadirachta indica
  作者：K. Madhava Madyastha、Krishnamachari Venkatakrishnan

  DOI：10.1039/b004260i

  日期：——

  Nocardia sp. quantitatively converts salannin 1 and 3-de-O-acetylsalannin 2 (C-seco limonoids) into 3-deacetoxy-1-de[(E)-2-methylbut-2-enoyloxy]salannin-1-en-3-one 10, a novel and potentially bioactive compound with an α,β-unsaturated ketone moiety in ring ‘A’. In order to establish the sequence of events involved in this transformation and the structural specificity of this bacterial system, several new derivatives of salannin 1 have been prepared. These studies have indicated that the transformation is initiated by deacetylation at C-3, followed by oxidation of the secondary hydroxy group to 3-keto, which appears to facilitate the elimination of the tigloyloxy/acetoxy group at C-1 with the formation of an olefinic linkage between C-1 and C-2. The organism very efficiently transforms some of the derivatives of salannin into their corresponding compounds possessing an enone system in ring ‘A’, an essential pre-requisite for various biological activities. Some of the C-seco limonoids prepared in the present study, viz. 10, 1,2-didehydro-1,3-dideoxy-3-oxosalannic acid 18, 3-deacetoxy-1-de[(E)-2-methylbut-2-enoyloxy]-20,21,22,23-tetrahydrosalannin-1-en-3-one 15 and 1,2-didehydro-1,3-dideoxy-3-oxosalannol 23 were hitherto not known. p

  诺卡氏菌（Nocardia sp.）能将丹宁1和3-de-O-乙酰基丹宁2（C-seco柠檬酸类）定量转化为3-deacetoxy-1-de[(E)-2-methylbut-2-enoyloxy]salannin-1-en-3-one 10，这是一种新型的、具有潜在生物活性的化合物，其δ,δ²-不饱和酮分子位于环§Aâ。为了确定这种转化所涉及的事件顺序以及这种细菌系统的结构特异性，我们制备了几种丹宁 1 的新衍生物。这些研究表明，这种转化是由 C-3 处的脱乙酰化开始的，随后仲羟基被氧化成 3-酮，这似乎促进了 C-1 处的惕格酰氧基/乙酰氧基的消除，并在 C-1 和 C-2 之间形成了烯烃连接。 该生物体能非常有效地将一些丹宁衍生物转化成相应的化合物，这些化合物在环§Aâ上拥有一个烯酮系统，这是各种生物活性的一个基本前提。本研究中制备的一些C-seco柠檬酸类化合物，即10、1,2-二脱氢-1,3-二脱氧-3-氧代丹宁酸18、3-脱乙酰氧基-1-脱[(E)-2-甲基丁-2-烯酰氧基]-20,21,22,23-四氢丹宁-1-烯-3-酮15和1,2-二脱氢-1,3-二脱氧-3-氧代丹宁醇23，迄今为止尚不为人所知。
• Melanogenesis-Inhibitory Activities of Isomeric C-<i>seco</i>Limonoids and Deesterified Limonoids
  作者：Toshihiro Akihisa、Maiko Horiuchi、Masahiro Matsumoto、Eri Ogihara、Kenta Ishii、Jie Zhang

  DOI：10.1002/cbdv.201600100

  日期：2016.10

  evaluation of all these limonoids for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), five structurally modified limonoids, 3-deacetyl-28-oxosalannin (6a), 9, 17-epi-17-hydroxynimbocinol (14), 17-epi-17-hydroxy-15-methoxynimbocinol (15), and 7-deacetyl-17-epinimolicinol (18), in addition to a natural limonoid, 1, exhibited potent

  用BF3·Et2O和碘离子结合处理八种C-seco柠檬苦素，包括六种丹兰素型1-6，和二种宁宾型7和8，结合使用BF3·Et2O和碘离子，得到异构化的C-seco衍生物，即分别为6个异异单宁和1a-6a，以及2个异异单宁和7a和8a。对Ohchinin（1）进一步进行LiAlH4还原，得到脱酯的三羟基柠檬苦素类化合物，宁比丁醇（9）。此外，从印za子种子提取物的中性部分中获得了十种柠檬苦素，包括七个印za素酮型（10-16）和三个葛菌素素型（17-19），它们在分子中均不具有酯官能度。碱水解。在上述化合物中，有12种化合物（即1a-4a，6a，9、13-16、18和19）是新化合物，在广泛的光谱分析和与文献数据比较的基础上阐明了它们的结构。在评估所有这些柠檬苦素类化合物对α-黑素细胞刺激激素（α-MSH）诱导的B16黑色素瘤细胞中黑色素生成的抑制活性后，得到了五个结构修饰的柠檬苦素类化合物
• Biocatalyst mediated functionalization of salannin, an insecticidal limonoid
  作者：Saikat Haldar、Swati P. Kolet、Devdutta S. Dandekar、Balaji S. Kale、Rajesh G. Gonnade、Hirekodathakallu V. Thulasiram

  DOI：10.1039/c4ra04652h

  日期：——

  Novel and efficient modification was achieved on the furan moiety of salannin by fungi mediated biocatalysis.

  通过真菌介导的生物催化作用，对萨兰宁分子中的呋喃基团进行了新颖高效的修饰。
• Ethylenediamine: an effective reagent for deacetylation of natural products
  作者：Ramasamy Mohankumar、Kaliappan Ilango、Vichangal Pridiuldi Santhanakrishnan、Viswanathan Radhakrishnan、Srinivasan Narasimhan

  DOI：10.1080/10286020.2010.507545

  日期：2010.10

  The use of ethylenediamine in methanol is described for the selective cleavage of the acetate group in nimbin (1) to 6-deacetyl nimbin (1a) under microwave irradiation. This method enables to deacetylate without affecting other functional groups such as ,-unsaturated ketone, ester, ether, etc. in certain tetranortriterpenoids and other acetate-containing natural compounds.
• Photooxidation of Nimbin and Salannin, Tetranortriterpenoids from the Neem Tree (Azadirachta indica)
  作者：Andrew P. Jarvis、Shaun Johnson、E. David Morgan、Monique S. J. Simmonds、Wally M. Blaney

  DOI：10.1023/a:1022523329255

  日期：1997.12

  Nimbin and salannin, major triterpenoids accompanying azadirachtin in extracts of neem (Azadirachta indica) seeds, were photooxidized by UV light in the presence of oxygen to more polar, unstable intermediates that rearranged on silica gel to two final products in which the furan ring had been oxidized to isomeric hydroxybutenolides. The isomeric hydroxybutenolides were also readily formed when a crude extract of triterpenoids from neem seeds was irradiated, and both isomers of salannin have been isolated from seeds. Photooxidation of nimbin and salannin proceeded much faster than that of azadirachtin. All photoproducts showed some biological activity against Spodoptera littoralis, Locusta migratoria, and Schistocerca gregaria. Isonimbinolide was as potent as azadirachtin at inhibiting feeding in all three species, and it also inhibited the growth of S. littoralis. Isosalanninolide showed potent antifeedant and growth inhibitory activity against S. littoralis.