Name | dictamnine |
Synonyms | dictamine DICTAMNINE dictamnine Dectamine) Dictamine (Dictamnine 3-b)quinoline,4-methoxy-furo( 4-Methoxyfuro[2,3-b]quinoline furo[2,3-b]quinoline, 4-methoxy- Dictamnine 4-Methoxyfuro[2,3-b]quinoline |
CAS | 484-29-7 |
InChI | InChI=1/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3 |
Molecular Formula | C12H9NO2 |
Molar Mass | 199.21 |
Density | 1.1919 (rough estimate) |
Melting Point | 133° |
Boling Point | 336.72°C (rough estimate) |
Flash Point | 161.4°C |
Solubility | Soluble in hot ethanol and chloroform, slightly soluble in ether, hardly soluble in water |
Vapor Presure | 0.000142mmHg at 25°C |
Appearance | White crystal |
Color | Light Beige |
pKa | 7.24±0.40(Predicted) |
Storage Condition | Inert atmosphere,Room Temperature |
Refractive Index | 1.5880 (estimate) |
MDL | MFCD00221742 |
Physical and Chemical Properties | Soluble in hot ethanol and chloroform, slightly soluble in ether, difficult to dissolve in water from the Rutaceae plant White fresh (Dictamnus dasynchronous Turcz.) root |
Reference Show more | 1. Shen Jinhua, Han Shuhui, Shi shunbo. Relaxant effect and mechanism of White fresh alkali on tracheal smooth muscle [J]. Journal of South-Central University for Nationalities: Natural Science Edition, 2020, 39(1):24-28. 2. Duan, Qiannan, et al. "Viral effect of Chinese herb prescription JieZe-1 on attachment and expenditure of VK2/E6E7 with herpes simplex viruses type 2." Journal of ethnopharmacology 249 (2020): 112405.https://doi.org/10.1016/j.jep.2019.112405 3. [IF=3.69] Qianni Duan et al."Antiviral effect of Chinese herbal prescription JieZe-1 on adhesion and penetration of VK2/E6E7 with herpes simplex viruses type 2."J Ethnopharmacol. 2020 Mar;249:112405 |
Alkaloid | White fresh alkali is a natural product of alkaloids with a variety of biological activities, which can be isolated from a variety of plants (mainly from white fresh peel), It can also be obtained by artificial synthesis. It has antibacterial and therapeutic effects on skin eczema and skin itching. |
plant source | 1. main source-white fresh peel: rutaceae (Rutaceae) plant white fresh Dictamnus dasycarpus Turcz. Root bark. Cortex Dictamni is also known as moss skin, northern fresh skin, and smelly root skin. It is mainly produced in Liaoning, Hebei, Sichuan, Jiangsu and other places. Dig in spring and autumn, wash the soil, remove the fibrous roots and coarse skin, cut longitudinally when fresh, remove the wood core, and dry it. White fresh alkali (dictamnine) is one of the main components of white fresh skin, the content in white fresh skin is about 0.1%. The main chemical components of white fresh: the above-ground part contains psoralen, pepper toxin, scopolamine, and quercetin; the root contains white fresh alkali, Yinji alkali, white sharp alkali, fenugreek, choline, white fresh alcohol, Qinpi Kone, togenone, limonin, β-sitosterol, campesterol, saponins, etc. Figure 1 is a picture of fresh white plants. 2. Other sources: Bamboo leaf pepper Zanthoxylum planispinum Sieb. et Zucc. Root Songfengcao Boenninghausenia albiflora(Hook.)Meissn. Above ground part Japanese pine wind grass B.albiflora Meissn.var.japonica S.Suzuki root Ailanthus zanthoxylum bungeanum Zanthoxylum ailanthoides Sieb. et Zucc. Root Fagara mayu Engler bark Flinderia pimonteliana F.Muell. Bark Anoti Zanthoxylum bungeanum Zanthoxylum arnottianum Maxim. Stem Ducari Zanthoxylum bungeanum Zanthoxylum decaryi H.Perr. Stem bark Helietta longifoliata Britton bark. |
separation and extraction | 1. preparation of crude extract from white fresh skin: accurately weigh 50g of medicinal material powder, use 85% ethanol solution as extraction solvent, solid-liquid ratio of 1: 20, reflux extraction at 80 ℃ for 2 times, extraction time of 1h, combine filtrate and concentrate to dry under reduced pressure by rotary evaporator, dry in vacuum dryer and store. 2. preparation of white fresh alkali monomer: high-speed countercurrent chromatography separation and high performance liquid chromatography detection, white fresh alkali monomer. The separation conditions of high-speed countercurrent chromatography are as follows: the solvent system is n-hexane-ethyl acetate-ethanol-water (1 ∶ 1 ∶ 1 ∶ 1), the upper phase is used as stationary phase, the lower phase is used as mobile phase, the detection wavelength is 228nm, the flow rate is 1.3mL?min-1, the rotating speed is 1200r?min-1, and the running time is 180min. Column temperature 25 ℃, mobile phase methanol-water (58 ∶ 42), flow rate 0.8mL?min-1, injection volume 10 μL; The detection wavelength is 228nm. |
content determination | determination method of white fresh alkali content in white fresh skin: sample was refluxed with methanol for 60 min, the extract was evaporated to dry, and the volume was fixed in a 25mL volumetric flask. HPLC method was used to determine the content of white fresh alkali in white fresh skin. C18 chromatographic column was used, acetonitrile-water (37 ∶ 63) was used as mobile phase, detection wavelength was 228 nm, flow rate was 1 mL min-1, and column temperature was 40 ℃. |
pharmacological effects | 1. efficacy of white fresh skin white fresh skin was first published in shennong's herbal classics and listed as a middle grade. Materia Medica has been collected in all dynasties. Both are wild. Li Shizhen said: Fresh, the spirit of the sheep, this grass root is white, there is mutton, hence the name. Chinese medicine is less commonly used. Bitter taste, cold in nature. Return to spleen, stomach and bladder meridian. It has the effects of clearing away heat and dampness, dispelling wind and detoxification. Clinical application:(1) for rubella, eczema, scabies. (2) for rheumatic fever arthralgia, joint redness, swelling, heat and pain. (3) for damp-heat jaundice. Spleen and stomach deficiency and cold syndrome should be taken carefully. 2. Modern pharmacological applications (1) Antibacterial: In vitro tests of Cortex Dinca have different degrees of inhibition of various skin pathogenic fungi such as Trichophyton pansy, Trichophyton concentric, and Trichophyton Schlan's. Leucine directly or indirectly affects the normal synthesis of fungal cell genetic material and cannot complete the normal cell cycle, thereby inhibiting fungal growth and even leading to death. Leucine can form an adduct with the pyrimidine bases in the double helix structure of DNA. This property is similar to the psoriasis treatment drug 8-methoxypsoralen, so it may become a psoriasis treatment drug. (2) immune and anti-inflammatory effects: white skin has obvious inhibitory effect on contact dermatitis caused by hapten Picryl chloride and plantar reaction caused by granular antigen sheep red blood cell (SRBC). Water extract has inhibitory effect on cellular immunity and humoral immunity. The main inhibitory effect on delayed allergy is the effect phase, and the anti-inflammatory effect is one of its mechanisms. (3) cardiotonic effect: small dose can increase myocardial tension, and increase cardiac output per stroke and output per minute. (4) antihypertensive effect: leucine is a calcium antagonist, which can inhibit extracellular calcium influx, relax smooth muscle and relax blood vessels, and reduce blood pressure. (5) hepatotoxicity: higher concentration of leucine (≥ 100 μmo?lL-1) has potential hepatotoxicity, and cell membrane damage and mitochondrial damage may be one of its mechanisms of hepatotoxicity. In recent years, traditional Chinese medicine compound containing white fresh skin, such as Qingdai pills, Xiaoyin tablets, Keyin pills, vitiligo capsules, Shiduqing capsules and Zhixue capsules, etc., have caused different degrees of liver injury. (6) other: anti-cancer, anti-tuberculosis, anti-hypoxia, anti-fatigue, antipyretic, mutagenic and insect anti-feeding, etc. |
clinical application | (pulmonary tuberculosis empyema) after routine chest puncture and discharge of pus, the pus cavity is first flushed with normal saline, then 50-100ml of sterilized leachate of white white peel is injected, and the drainage tube is closed. After 8 hours of retention, negative pressure suction is carried out to suck out the liquid medicine and pus. Once a day or every other day. At the same time, take white fresh skin powder 2g each time, 3 times a day. A total of 25 cases were treated, and 13 cases were cured, 10 cases were markedly effective, 1 case was effective, and 1 case was ineffective. The total effective rate was 96%. |
synthesis method | the content of white fresh alkali in plants is low, which can be obtained by artificial synthesis. Using aniline as the starting material, it is synthesized by 5 steps of substitution, ring closure, methylation, reduction and elimination. The total yield is 17%. Figure 2 is a reaction roadmap for the synthetic white fresh alkali. |
leucine derivatives | there are many alkaloids with similar structures to leucine in nature. their common feature is that they all have the skeleton structure of furanand [2,3-b] quinoline, such as γ-fagarine, evolitrine and pteliene. Figure 3 is a natural source of white alkali analog. |
use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has antibacterial and therapeutic effects on skin eczema and skin itching. |