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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: 2010-03-17
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] The fresh freeze-dried imitation sea cucumber 3.0kg was pulverized into powder, and extracted with a 60% ethanol hot water bath with a weight ratio of 6 times. The extract was recovered under reduced pressure to obtain a liquid extract. The liquid extract was suspended in In water, pass through HP20 macroporous adsorption resin column, eluting with pure water, 70% ethanol and 95% ethanol respectively, collect 70% ethanol eluate, recover to no alcohol smell, and extract with 4 times the weight ratio of n-butanol Three times, the extracts were combined, the solvent was recovered and concentrated to dryness to obtain the total saponins extract of sea cucumber, which was then subjected to normal phase silica gel column chromatography and eluted with a solvent with a volume ratio of chloroform:methanol:water of 7:3:0.5 According to thin-layer chromatography detection, collect the saponins-containing fra...

Embodiment 2

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

[0049] 4.5 kg of fresh freeze-dried imitation sea cucumber was pulverized into powder, and extracted with a 70% ethanol aqueous solution with a weight ratio of 5 times in a hot water bath. The extract was recovered under reduced pressure to obtain a liquid extract, and the liquid extract was suspended in In water, pass through DA101 macroporous adsorption resin column, eluting with pure water, 70% ethanol and 95% ethanol respectively, collect 70% ethanol eluate, recover to no alcohol smell, and extract with 4 times the weight ratio of n-butanol Three times, the extracts were combined, the solvent was recovered and concentrated to dryness to obtain the total saponins extract of sea cucumber, which was then subjected to normal phase silica gel column chromatography and eluted with a solvent with a volume ratio of chloroform: methanol: water of 6:4:0.8 According to thin-layer chromatography detection, collec...

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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 isas follows on the right. 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 is a novel triterpene saponin antifungal compound Holotoxin D, E, F, G, H, I isolated from marine animal imitation sea cucumber and a preparation method thereof. Background technique [0002] Apostichopus japonicus Selenka (Apostichopus japonicus Selenka) is a sea cucumber species widely distributed along the coasts of Shandong, Liaoning, Hebei and northern Jiangsu, belonging to the genus Apostichopus japonicus. Triterpene saponin compounds HolotoxinA and A have been isolated from this sea cucumber animal 1 , B, B 1 , C (Kitagawa I., Yamanaka H., Kobayashi M., et al. Saponin and Sapogenol. XV. Antifungal glycoside from thesea 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 oliglycosides fro...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J17/00C07J75/00A61K31/7048A61K31/704A61P31/10
Inventor 易杨华王增蕾李玲张文刘宝姝汤华张宏伟袁卫华
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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