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Nadoxane condensate and its preparation method and use

A technology of condensate and use, applied in the field of nadoxane-type sesquiterpene condensate

Active Publication Date: 2022-06-21
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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At present, there are no reports on these two structures and their functional activities

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  • Nadoxane condensate and its preparation method and use
  • Nadoxane condensate and its preparation method and use
  • Nadoxane condensate and its preparation method and use

Examples

Experimental program
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Embodiment 1

[0028] from Lemnalia Two new nardosinoids A (1) and B (2) were extracted and isolated from the genus soft coral, and their compound structures are as follows:

[0029] .

Embodiment 2

[0031] The preparation method of nadoxane condensate, the steps are as follows:

[0032] 1. Obtaining the crude extract: cut the frozen soft coral into pieces and freeze-dried, ultrasonically extract with acetone until colorless, recover acetone to dryness under reduced pressure, and repeat the extraction several times with a mixture of equal volumes of water and ether. , the ether extracts were combined and concentrated under reduced pressure to obtain crude extract;

[0033] 2. Separation and purification of compounds

[0034] (1) The above crude extract was separated by normal phase silica gel chromatography (200-300 mesh), and the petroleum ether-ethyl acetate solution with a volume ratio of (50:1) to (1:1) was used as the mobile phase to carry out gradient washing. According to the monitoring of thin-layer plate, the polarity of the fractions is arranged from small to large, and 5 components Fr.1~Fr.5 are collected and merged in sequence, and the elution gradient volume ...

Embodiment 3

[0040] Structure identification and NMR signal assignment of the compound:

[0041] Nardosinoid A (compound 1): colorless oily solid; [α]25 D=-42 ( c 0.1, MeOH); exact molecular weight m / z 493.3293 [M + Na] provided by positive ion high-resolution mass spectrometry (HRESIMS) quasi-molecular ion peak + (calculated as C 30 H 46 O 4 Na, 493.3294), giving the compound's formula C 30 H 46 O 4 , with 8 degrees of unsaturation. of the compound 1 H and 13 C NMR data see figure 1 and image 3 ,Table 1.

[0042] Nardosinoid B (compound 2): colorless oily solid; [α]25 D=-66 ( c 0.1, MeOH); exact molecular weight m / z 493.3286 [M + Na] provided by positive ion high-resolution mass spectrometry (HRESIMS) quasi-molecular ion peak + (calculated as C 30 H 46 O4 Na, 493.3294), giving the compound's formula C 30 H 46 O 4 , with 8 degrees of unsaturation. of the compound 1 H and 13 C NMR data see figure 2 and Figure 4 ,Table 1.

[0043] Table 1 Compounds 1 and 2 1 ...

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Abstract

The invention discloses a nadoxane condensate and its preparation method and application, which is characterized in that it is collected from the coast of the Xisha Islands in the South China Sea Lemnalia It is isolated from the secondary metabolites produced by soft corals, and the preparation method steps are as follows: extract the freeze-dried soft corals with acetone, then extract them with ether and water, combine the ether extracts and concentrate to obtain extracts; use the crude extracts Normal-phase silica gel chromatographic separation, using petroleum ether-ethyl acetate solution as the mobile phase for gradient elution, collecting components for reverse-phase medium-pressure column chromatography, using methanol-water solution as mobile phase for elution, collecting components with normal Phase silica gel chromatographic separation, using petroleum ether-ethyl acetate solution as the eluent for gradient elution, collected components were separated by reversed-phase semi-preparative high-performance liquid chromatography, and compound 1 and compound 2 were obtained. The advantage is that it has anti-subtilis spores Bacillus and Staphylococcus aureus and anti-inflammatory activity.

Description

technical field [0001] The invention relates to nadoxane-type sesquiterpene condensates, in particular to a kind of Lemnalia Nadoxane condensate extracted from genus coral and its preparation method and use. Background technique [0002] The beautiful appearance of marine soft corals makes them very attractive to predators, so these organisms must have effective self-protection methods in order to survive, which promotes the production of some characteristic metabolites. Therefore, soft corals are a rich source for the discovery of structurally diverse terpenoids with potential therapeutic applications. In recent years, the potential bioactive chemical constituents of many marine soft corals have been studied in oceans ranging from tropical to polar regions such as Taiwan and the South China Sea. [0003] Lemnalia soft coral ( Lemnalia sp.) belongs to Coelenterata (Coelenterata), Octocorallia (Octocorallia), Alcyonacea (Alcyonacea), and Nephtheidae (Nephtheidae) animals,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/92A61P31/04A61P29/00
CPCC07D307/92A61P31/04A61P29/00A61K35/614
Inventor 何山晏霞任露严小军
Owner NINGBO UNIV