Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one
Dehydrocostus lactone
CAS: 477-43-0;74299-48-2
Molecular Formula: C15H18O2
Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one - Names and Identifiers
| Name | Dehydrocostus lactone |
| Synonyms | EPILIGULYL OXIDE DEHYDROCOSTUNOLIDE DEHYDROCOSTUSLACTONE dehydrocostuslactone Dehydrocostus lactone Costus lactone, dehydro- DEHYDROCOSTUS LACTONE hplc tris(methylene)-,(3aS,6aR,9aR,9bS)- Azuleno[4,5-b]furan-2(3H)-one,decahydro-3,6,9- Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one (3aS,6aR,9aR,9bS)-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3H)-one (3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one |
| CAS | 477-43-0 74299-48-2 |
| InChI | InChI=1/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1 |
| InChIKey | NETSQGRTUNRXEO-XUXIUFHCSA-N |
Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one - Physico-chemical Properties
| Molecular Formula | C15H18O2 |
| Molar Mass | 230.3 |
| Density | 1.09 |
| Melting Point | 57.0 to 61.0 °C |
| Boling Point | 140-143 °C(Press: 0.5 Torr) |
| Specific Rotation(α) | [α]/D -14.0±3.0°, c = 1 in chloroform |
| Flash Point | 161.2°C |
| Solubility | Soluble in ethyl acetate, acetone, DMSO and other solvents, insoluble in water. |
| Vapor Presure | 4.31E-06mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| Maximum wavelength(λmax) | ['206nm(MeOH)(lit.)'] |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.536 |
| MDL | MFCD00210277 |
| Physical and Chemical Properties | Soluble in ethyl acetate, acetone, DMSO and other solvents, insoluble in water. Derived from a plant belonging to the genus aucklandia of Compositae [Vladimiria souliei(Franch. )Ling] |
Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| HS Code | 29322090 |
Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one - Reference
| Reference Show more | 1. Wang Guiming, Yang Min, Lu, Yang, Fang et al. Study on the mechanism of dehydroxyholide intervention in human breast cancer MCF-7 cells [J]. Advances in modern biomedicine 2015 15(034):6601-6605. 2. Wang Min, Xu Min, Zhu, Ting-Heng et al. Specific inhibition of β-glucan synthesis in the cell wall of saccomyces cereviae by dehydrostolactone [J]. Food and Fermentation Industries 2013 39(10):29-34. 3. Peng, Zhang Xiao, et al. "Costatin and dehydrocostuslactone combination treatment inhibition cancer by induced cell cycle arrest and apoptosis through c-Myc/p53 and AKT/14-3-3 pathway." Scientific reports 7.1 (2017): 1-16.https:// doi.org/10.1038/sre 4. Kapinova, Andrew, et al. "Are plant-based functional foods better choice against cancer than single phytochemicals? A critical review of current breast cancer research." Biomedicine & Pharmacotherapy 96 (2017): 1465-1477.https://doi.org/10.1016/j.biopha.20 5. Peng, Z.-x., Wang, Y., Gu, X., Wen, Y.-y. and Yan, C. (2013) A platform for fast screening potential anti-breast cancer compounds in traditional Chinese medicines. Biomed. Chromatogr., 27: 1759-1766. https://doi.org/10.1002/bmc.2990 6. [IF=6.762] Caiping Tian et al."Multiplexed Thiol Reactivity Profiling for Target Discovery of Electrophilic Natural Products."Cell Chem Biol. 2017 Nov;24:1416 7. [IF=4.29] Peng Zhang-xiao et al."Metabolic transformation of breast cancer in a MCF-7 xenograft mouse model and inhibitory effect of volatile oil from Saussurea lappa Decne treatment."Metabolomics. 2015 Jun;11(3):636-656 8. [IF=4.011] Zhangxiao Peng et al."Costunolide and dehydrocostuslactone combination treatment inhibit breast cancer by inducing cell cycle arrest and apoptosis through c-Myc/p53 and AKT/14-3-3 pathway."Sci Rep-Uk. 2017 Jan;7(1):1-16 9. [IF=1.902] Zhang-xiao Peng et al."A platform for fast screening potential anti-breast cancer compounds in traditional Chinese medicines."Biomed Chromatogr. 2013 Dec;27(12):1759-1766 10. [IF=1.902] Zhangxiao Peng et al."Study on the pharmacokinetics and metabolism of costunolide and dehydrocostus lactone in rats by HPLC-UV and UPLC-Q-TOF/MS."Biomed Chromatogr. 2014 Oct;28(10):1325-1334 |
Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one - Reference Information
| costustum extract | deshydro-costustolide is a substance extracted from the roots of costustum, a plant of the genus Costustum of the Compositae family, which has relaxing smooth muscle and antispasmodic effects. The main components of costustaceae contain volatile oil and inulin. The volatile oil contains dehydro-wood lactone, etc. |
| Source plant | The main source is the root of the genus Asteraceae. [plant morphology] perennial herb with thick main root, up to 5cm in diameter. Stem erect, 1.5~2m high, unbranched, pubescent upper part. The basal leaves have long stalks with wing and pinnate lobes, and the leaves are very large and triangular; the base of the stems and leaves are wedge-shaped and extended into winged petioles or sessile, and the leaves are ovate or triangular-ovate, 30 ~ 50cm long and 10 ~ 30cm wide, with irregular serrations on the edges, short thorns on the tooth ends, short rough hairs on the surface, glabrous on the back or sparse short hairs on the veins. Head inflorescences solitary stem top or leaf axils, or 2~3 bundles, 3~4cm in diameter; involucre hemispherical, 2~2.5cm long, involucral bracts 7 layers, nearly leathery, ovate-lanceolate or narrowly lanceolate, glabrous or sparsely hairy; Trichose; Corolla tubular, about 15mm long, dark purple; Anther tail fasselate. Achenes oblong, ribbed; crest 2-layered, pale brown, feathery, outer layer shorter. The flower and fruit period is from May to October. [habitat distribution] should be planted in high mountain areas with an altitude of 2500~4000m, and cool plains and hills can also be planted. Native to India. China Shaanxi, Gansu, Hubei, Hunan, Guangdong, Guangxi, Sichuan, Yunnan, and Tibet are all cultivated. Figure 1 is the wood incense |
| extraction method | 1, solvent extraction method Xu Hui and others used orthogonal experimental method to investigate the various influencing factors of ethanol extraction of essential oil from wood, and analyzed the data through multi-index comprehensive score. Results The best extraction process was as follows: adding 8 times the volume fraction of 60% ethanol, heating and reflux extraction for 2 times, each extraction for 1h. This extraction process can effectively control the production process and fundamentally ensure the quality of the product. Hou Shuzhen et al. obtained the results on the basis of their experiments: the yield of volatile oil in the soup was the highest after soaking and decocting for about 20min. With the extension of decocting time, the content of volatile oil in the soup decreased, but it was not significant. The amount of extract decocted increases with the extension of decocting time. 2. Steam distillation After pulverizing the wood, use the volatile oil extractor to extract the volatile oil according to the "Chinese Pharmacopoeia" volatile oil determination method. The volatile oil is obtained after drying with anhydrous sodium sulfate, and the yield is 1.5%. The volatile oil is a pale yellow transparent oily liquid with a special strong fragrance. 3. carbon dioxide supercritical extraction method 20g of cotyledon was crushed and added into a 50mL supercritical CO2 extraction tank. The pressure is 15MPa, the temperature of the extraction tank is 50 ℃, and the temperature of the receiving tank is 30 ℃. Dynamic extraction for 50min to obtain yellow transparent oil with strong fragrance and oil yield of 2.4%. 4. Microwave irradiation-extraction method Hui Ruihua et al. used microwave irradiation-extraction method to extract the volatile substances of Radix Cotlewood. The content of the volatile oil of Radix Cotlewood was measured to be 4.5%. The gas chromatography-mass spectrometry (GCMS) method was used to separate and confirm 48 kinds of chemical components, accounting for more than 93.3% of the total volatile oil. The relative percentage content of each chemical component in volatile oil was obtained by using the peak area normalization method through the chemical workstation data processing system. The method is stable, reliable and reproducible. It is suitable for chemical composition analysis of volatile oil from traditional Chinese medicine. The wavelength of microwave is about 100~0.1cm, I .e. the frequency is 300~300GHz. Usually the frequency used for microwave extraction and chemical reactions is about 915MHz or 2450MHz, which is also called ultra-high electromagnetic wave. |
| pharmacological action | 1. effect on digestive system: costustine 25% decoction (0.25g crude drug/mL) was given to rats at 10 mL/kg. as a result, the relative residual rate of pigment in the stomach of rats was significantly reduced and the propulsion ratio of small intestine was significantly increased, indicating that costustine can promote gastric emptying and intestinal propulsion. 10, 40g/kg of Muxiang decoction was injected into dogs with Hay's small stomach through the mouth. The results had no effect on gastric acid and serum gastrin concentration, but could promote the secretion of somatostatin. Muxiang can accelerate the emptying of barium by the stomach and promote the release of endogenous motilin. It has no effect on the basic gastric electrical rhythm of normal people. 2. The effect on the cardiovascular system: The wood and its extracts have a pressor effect, while the alkaloids, lactones, and lactone volatile oils contained in it have a hypotensive effect. Muxiang excites the cat heart with mild pressor response. Intravenous injection of water extract into anesthetized dogs has mild pressor effect. Intravenous injection of delactone volatile oil, total lactone, costule lactone, dihydrogen costule lactone, dehydro costule lactone or 12-methoxydihydrocostule lactone can reduce blood pressure in anesthetized dogs, and the antihypertensive effect lasts for at least 15min, and the effective time of delactone volatile oil can reach 1h. 12-methoxydihydrocoletholide has a strong effect. Neck spinal cord cut, vagus nerve cut on both sides, atropinization, ganglion blockers, antiepinephrine or antihistamines do not change the above antihypertensive response, indicating that its site of action is mainly peripheral, that is, It is related to cardiac inhibition and vasodilation. 3. Effect on the respiratory system: Using guinea pig isolated trachea and lung perfusion experiments, it shows that water extract, alcohol extract, volatile oil, total alkaloids, and total lactones contained in volatile oil The volatile oil has a antagonistic effect on the bronchoconstriction caused by histamine, acetylcholine and barium chloride. Intraperitoneal injection of total lactone or lactone volatile oil has a protective effect on inhaled lethal dose of histamine or acetylcholine aerosol in guinea pigs, which can prolong the incubation period of asthma and reduce mortality, indicating that it can directly expand bronchial smooth muscle, which is similar to papaverine. 4. Antibacterial effect: The concentration of volatile oil of 1 ∶ 3000 can inhibit the growth of Streptococcus, Staphylococcus aureus and Staphylococcus albicans, and has weak effect on Escherichia coli and Diphtheria; total alkaloids have no antibacterial effect. |
| identification | identification of wood fragrance cylindrical or semi-cylindrical, 5~10cm long and 5~50mm in diameter; The surface is yellowish brown to gray brown, most of the cork has been removed, with obvious longitudinal grooves and lateral root marks, and sometimes reticular wrinkles can be seen. The quality is hard, not easy to break, the section is not neat or slightly flat, the periphery and the center are grayish yellow, most of the rest are grayish brown to tan, the dark brown oil chamber dots are scattered everywhere, the formation layer is ring brown, with radial texture, and the center of the old root is more decayed. The aroma is rich and specific, and the taste is slightly bitter. The color is yellow and white, the quality is solid, and the aroma is strong. Microscopic identification of root cross section: the cork layer is 2~6 rows of cork cells. The phloem is broad and the sieve tube group is obvious; the phloem fibers are several to a dozen bundles. The cambium intermittently forms a ring. The xylem catheter bundle is radially bifurcated, and the catheter 2 exists in multiple groups or individually; the wood fiber is small, and the catheter is adjacent to each other; the near-center wood fiber bundle is arranged in 3~4 rings. This product is scattered with most large split oil chambers, oval or round in shape, 29~254 μm in diameter, 6~11 secreting cells around, containing volatile oil droplets; Parenchyma cells are full of inulin. Powder: brown, with a strong aroma, slightly sweet taste, bitter after. (1) The powder is observed with a Si's liquid device, and colorless and irregular inulin clumps can be seen; with chloral hydrate liquid device (not heated), inulin is fan-shaped, with radial lines, and it gradually melts after long-term storage. (2) The wood fiber is mostly bundled, long fusiform, oblique or fine tip at the end, 16~24 μm in diameter, 4~5 μm in wall thickness, fine holes, transverse cracks or herringbone or cross-shaped. (3) the reticulated catheter has a rim hole and a ladder tube diameter of 32~90 μ m, and the catheter molecules are generally very short, some are only 64 μ m long; The reticulated holes are slit-shaped and dense. ④ Light yellow fragments can sometimes be seen in the oil chamber, containing volatile oil droplets. ⑤ Some parenchyma cells contain small calcium oxalate square crystals or volatile oil droplets. Physical and chemical identification: 100g of sample powder is taken, volatile oil is extracted in a volatile oil extractor, 0.1ml of volatile oil is added with 1ml of petroleum ether to dissolve, and is placed on a silica gel G-CMCNa-fluorescein (5g:0.5% 15ml:1mg) plate, petroleum ether (30-60C)-ethyl acetate-benzene (14:3:3) is used as developing agent, and isomethylenolide is used as control. The spreading distance is 18cm, and the lactone spots are all blue fluorescent under the ultraviolet light lamp (254nm), and the color is developed with 5% vanillin-concentrated sulfuric acid, with 5 spots. |
| character characteristics | 1. medicinal materials: cylindrical or semi-cylindrical, slightly curved, slightly twisted, slightly similar to chicken leg bone, 5~25cm long and 0.5~1.5cm in diameter. The surface is yellowish brown or dark brown, with longitudinal wrinkles or longitudinal grooves, and protruding lateral root marks or occasionally branched at the lower part. The quality is hard, easy to break, the cross section is slightly flat, yellowish brown, and there is an obvious brown ring, brown oil spots can be seen on the skin, and the wood is often biased to one side, showing chrysanthemum heart. The air is special, the taste is slightly bitter, slightly pungent, and the sticky teeth are chewed. 2. processed products: yuexi wood fragrance slices: round-like flakes with a diameter of 0.5~1.5cm and a thickness of 1.5~3mm. the cut surface is yellowish brown or yellowish brown, with an obvious brown ring. brown oil spots can be seen on the skin part, and the wood part is often biased to one side, showing chrysanthemum heart. The periphery is yellowish brown, dark brown or grayish brown, with longitudinal wrinkles. The air is special, the taste is slightly bitter, pungent, and the sticky teeth are chewed. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has a strong choleretic effect, and has a good antispasmodic effect on bronchial smooth muscle and small intestinal smooth muscle. The antispasmodic effect is muscular, similar to papaverine and weaker. |
Last Update：2024-04-09 15:16:50
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Product Name: Dehydrocostus lactone Visit Supplier Webpage Request for quotationCAS: 477-43-0
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Dehydrocostus Lactone Visit Supplier Webpage Request for quotationCAS: 477-43-0
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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