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Triterpene glycosides antifungal compounds of sea cucumber HolotoxinD-I and preparation method thereof

A technology of triterpenoid saponins and compounds, applied in the field of medicine, can solve problems such as no antifungal activity and the like

Inactive Publication Date: 2012-05-30
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triterpenoid saponins Holotoxin A, A have been isolated from this species of sea cucumber 1 , B, B 1 , C (Kitagawa I., Yamanaka H., Kobayashi M., et al. Saponin and Sapogenol. XV. Antifungal glycoside from these sea cucumber Stichopus japonicus Selenka. (2). Structures of Holotoxin A and Holotoxin B. Chem Phar Bull, 1976, 24 (2): 275; KitagawI.a, Yamanaka H., Kobayashi M., et al.Saponin and Sapogenol.XXVII.Revised structure of HolotoxinA and Holotoxin B, two antifungal oliligosides from the sea cucumber Stichopus japonicus Selenka.Chem Phar Bull, 1978 , 26(12): 3722; Maltser I.I, Stonik VA, Kalinovsky AI, et al.Triterpene glycosides from sea cucumber Stichopus japonicusSelenka.Comp.Biochem.Physiol.1984, 78B(2):421), but no relevant Holotoxin D~I isolated from Apostichopus japonicus and its antifungal activity reported

Method used

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  • Triterpene glycosides antifungal compounds of sea cucumber HolotoxinD-I and preparation method thereof
  • Triterpene glycosides antifungal compounds of sea cucumber HolotoxinD-I and preparation method thereof
  • Triterpene glycosides antifungal compounds of sea cucumber HolotoxinD-I and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Example 1 Preparation of Holotoxin D~I from Apostichopus japonicus

[0047] Grind 3.0kg of fresh freeze-dried imitation sea cucumber into powder, extract it in a 60% ethanol hot water bath with a weight ratio of 6 times, and recover the extract under reduced pressure to obtain a fluid extract, and suspend the fluid extract in water , pass through HP20 macroporous adsorption resin column, elute with pure water, 70% ethanol and 95% ethanol respectively, collect 70% ethanol eluate, recover to no alcohol smell, be 4 times of n-butanol extraction with weight ratio 3 Once, the extracts were combined, the recovered solvent was concentrated to dryness, and the total saponin extract of imitation sea cucumber was obtained, and the normal phase silica gel column chromatography was carried out, and the volume ratio of chloroform:methanol:water was 7:3:0.5 for solvent elution, According to the detection of thin layer chromatography, the fraction containing saponin is collected, and ...

Embodiment 2

[0048] Example 2 Preparation of Holotoxin D~I from Apostichopus japonicus

[0049] 4.5 kg of fresh freeze-dried imitation sea cucumber is crushed into powder, extracted in a hot water bath with 70% ethanol aqueous solution with a weight ratio of 5 times, and the extract is recovered under reduced pressure to obtain a fluid extract, and the fluid extract is suspended in In water, pass through a DA101 macroporous adsorption resin column, elute with pure water, 70% ethanol and 95% ethanol respectively, collect the 70% ethanol eluate, recover until it has no alcohol smell, and extract with n-butanol with a weight ratio of 4 times 3 times, the extracts were combined, the recovered solvent was concentrated to dryness, and the total saponin extract of imitation sea cucumber was obtained, and the normal phase silica gel column chromatography was carried out, and the volume ratio of chloroform:methanol:water was 6:4:0.8 for solvent elution , according to thin-layer chromatography detec...

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Abstract

The invention relates to the technical field of medicines, particularly to six triterpene glycosides antifungal compounds HolotoxinD-I separated from a sea cucumber. The chemical structural formula is as follow. An in vitro anifungal experiment shows that the compounds have obvious inhibitory effect on Candida ablbicans SC5314, Cryptococcus neoformans BLS108, Candida tropicalis, Trichophyton rubrum, Mircrosporum gypeseum and fuming Aspergillus. The invention can provide leading compounds for developing novel antifungal drug, and has a significant value on exploiting and using marine medical resources in China.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to novel triterpene saponin antifungal compounds Holotoxin D, E, F, G, H, I isolated from marine animal japonicus japonicus and a preparation method thereof. Background technique [0002] Apostichopus japonicus Selenka is a sea cucumber widely distributed in Shandong, Liaoning, Hebei, and northern Jiangsu coastal areas, belonging to the genus Apostichopus japonicus. Triterpenoid saponins Holotoxin A, A have been isolated from this species of sea cucumber 1 , B, B 1 , C (Kitagawa I., Yamanaka H., Kobayashi M., et al. Saponin and Sapogenol. XV. Antifungal glycoside from these sea cucumber Stichopus japonicus Selenka. (2). Structures of Holotoxin A and Holotoxin B. Chem Phar Bull, 1976, 24 (2): 275; KitagawI.a, Yamanaka H., Kobayashi M., et al.Saponin and Sapogenol.XXVII.Revised structure of HolotoxinA and Holotoxin B, two antifungal oliligosides from the sea cucumber Stichopus japoni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00C07J17/00C07J75/00A61K31/7048A61K31/704A61P31/10
Inventor 易杨华李玲王增蕾张文刘宝姝汤华张宏伟袁卫华
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY