11-deoxo-6-oxo-5α,6-dihydrojervine | 19773-24-1

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 11-deoxo-6-oxo-5α,6-dihydrojervine
• 英文别名: peimisine；peimisin；(23R)-17,23-epoxy-3β-hydroxy-(5α)-veratr-12-en-6-one；(23R)-17,23-epoxy-3β-hydroxy-5α-veratr-12-en-6-one；(23R)-17,23-Epoxy-3β-hydroxy-5α-veratr-12-en-6-on；(3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,4a,6,6a,6b,7,8,11,11a-dodecahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-5-one
• CAS: 19773-24-1
• 化学式: C₂₇H₄₁NO₃
• 分子量: 427.627
• InChiKey: KYELXPJVGNZIGC-GKFGJCLESA-N

物化性质

• 熔点：
  270℃
• 沸点：
  573.0±50.0 °C(Predicted)
• 密度：
  1.17
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

生物活性

生物碱 — 贝母辛 (Peimisine) 是一种甾体生物碱，是贝母中的主要生物活性成分，具有多种毒理和药理作用。

化学性质

它是一种白色结晶粉末，能够溶于三氯甲烷、乙醚和甲醇。该物质来源于贝母（Fritillary）。

用途

贝母辛 具有镇咳和抗溃疡的作用，并可用于含量测定、鉴定及药理实验等场合。

药理作用：

贝母辛通过作用于M受体并拮抗内钙释放，从而舒张气管平滑肌，实现平喘的效果。

反应信息

• 作为反应物：
  描述：

  11-deoxo-6-oxo-5α,6-dihydrojervine 在 铂 氢气 作用下， 以 乙醇 为溶剂， 生成 (3S,3'R,3a'S,4aS,5R,6aR,6bS,6'S,7a'R,9R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4a,4',5,5',6,6a,6b,6',7,7',7a',8,11,11a,11b-icosahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridine]-3,5-diol
  参考文献：
  名称：

  Structure and configuration of peimisine

  摘要：

  DOI：

  10.1007/bf00573056
• 作为产物：
  描述：

  peimisine-3-O-β-D-glucopyranoside 在 β-glucosidase 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 生成 葡萄糖 、 11-deoxo-6-oxo-5α,6-dihydrojervine
  参考文献：
  名称：

  贝母的鳞茎中的类固醇生物碱。

  摘要：

  两个新的甾体生物碱peimisine -3- ö -β- d吡喃葡萄糖苷（1）和puqiedinone -3- ö -β- d吡喃葡萄糖苷（3）中，用三个已知化合物peimisine（一起2），puqiedinone（4），和从川贝母的鳞茎中分离出puqiedine（5）并进行鉴定。通过光谱和化学方法充分阐明了它们的结构。化合物1对鱼藤酮诱导的PC12细胞系的神经毒性显示出中等的保护作用。

  DOI：

  10.1080/10286020.2011.619980

文献信息

• Kitajima, Junichi; Noda, Naoki; Ida, Yoshiteru, Heterocycles, 1981, vol. 15, # 2, p. 791 - 796
  作者：Kitajima, Junichi、Noda, Naoki、Ida, Yoshiteru、Miyahara, Kazumoto、Kwasaki, Toshio

  DOI：——

  日期：——
• Alkaloids ofPetilium eduardi
  作者：R. Shakirov、R. N. Nuriddinov、S. Yu. Yunusov

  DOI：10.1007/bf00568298

  日期：1965.11
• Study the mechanism of peimisine derivatives on NF‐κB inflammation pathway on mice with acute lung injury induced by lipopolysaccharide
  作者：Xin Jin、Xu Gao、Meng Lan、Chun‐nan Li、Jia‐ming Sun、Hui Zhang

  DOI：10.1111/cbdd.14013

  日期：2022.5

  AbstractPeimisine is one of the alkaloids in Fritillariae ussuriensis Bulbus, which has anti‐acute lung injury effect. In order to obtain compounds with superior bio‐activity, 14 new derivatives were obtained from peimisine, and the better activity compounds were screened by MTT method. It was found that boc‐leucine mono peimisine ester monoamide (compound G, 25 μg/ml) had increased cell survival rate and reduced the TNF‐α, IL‐1β, IL‐6, and iNOS levels in RAW 264.7 by lipopolysaccharide (LPS)‐stimulated. In vivo, LPS (10 mg/kg) was given intraperitoneally to establish ALI model, and compound G (2.5 or 10 mg/kg) was injected into mice as the experimental group. The results showed that after the compound G (10 mg/kg) treatment, the Wet / Dry ratio of the lung was reduced, and the expression of TNF‐α, IL‐1β, IL‐6 and iNOS was inhibited. Meanwhile, compound G (10 mg/kg) could increase the content of IκB protein and reduce the content of p65 protein in lung tissue by Western blot analysis, which may play an anti‐acute lung injury role by inhibiting the activity of NF‐κB signaling pathway. In conclusion, compound G could attenuate LPS‐induced ALI in mice and it may become a new approach to treat ALI.
• COMPOSITION FOR TREATING SKIN PIGMENTATION AND RELATED METHODS
  申请人：Access Business Group International LLC

  公开号：US20180311142A1

  公开（公告）日：2018-11-01

  A composition for treating skin pigmentation, a method of forming the composition, and a method of treating skin pigmentation are disclosed. The composition comprises at least one pharmaceutically acceptable additive. The composition further comprises at least one melanin production inhibitor, which may be a depigmentation agent. The melanin production inhibitor is present in an amount effective to inhibit melanin production in human skin cells of a subject that is administered the composition. The melanin production inhibitor is selected from the group consisting of cyclovirobuxine D, lipoic acid, nuciferine, peimisine, oleuropein, Rhodiola algida extract, Rhodiola kirilowii (Regel) Maxim extract, Glycyrrhizae Radix et Rhizoma extract, Cirsii japonici herba extract, Platycladi semen extract, Synotis erythropappa extract, Astragali complanati semen extract, Plantaginis semen extract, Lycopi herba extract, Euryales semen extract, Cuscutae semen extract, Amomi fructus extract, Tara seed extract, Platycladi cacumen extract, Eucommiae cortex extract, Dioscoreae rhizoma extract, Cirsii herba extract, and combinations thereof.
• Steroidal alkaloids from the bulbs of<i>Fritillaria unibracteata</i>
  作者：Qing-Jian Zhang、Zhong-Fei Zheng、De-Quan Yu

  DOI：10.1080/10286020.2011.619980

  日期：2011.12

  Two new steroidal alkaloids peimisine-3-O-β-d-glucopyranoside (1) and puqiedinone-3-O-β-d-glucopyranoside (3), together with three known compounds peimisine (2), puqiedinone (4), and puqiedine (5), were isolated and characterized from the bulbs of Fritillaria unibracteata. Their structures were fully elucidated by spectroscopic and chemical methods. Compound 1 showed moderate protection effect on neurotoxicity

  两个新的甾体生物碱peimisine -3- ö -β- d吡喃葡萄糖苷（1）和puqiedinone -3- ö -β- d吡喃葡萄糖苷（3）中，用三个已知化合物peimisine（一起2），puqiedinone（4），和从川贝母的鳞茎中分离出puqiedine（5）并进行鉴定。通过光谱和化学方法充分阐明了它们的结构。化合物1对鱼藤酮诱导的PC12细胞系的神经毒性显示出中等的保护作用。