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Diterpenoid compound derived from Lemnalia bournei as well as preparation method and application of diterpenoid compound

A technology for diterpenoids and soft corals, which is applied in the field of diterpenoids and their preparations derived from the soft corals of Polan scaly, and can solve problems such as drugs that have not yet been seen

Active Publication Date: 2021-09-17
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports on the chemical structure and antibacterial activity of these compounds, so there are no related drugs on the market.

Method used

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  • Diterpenoid compound derived from Lemnalia bournei as well as preparation method and application of diterpenoid compound
  • Diterpenoid compound derived from Lemnalia bournei as well as preparation method and application of diterpenoid compound
  • Diterpenoid compound derived from Lemnalia bournei as well as preparation method and application of diterpenoid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] From Xisha in the South China Sea Lemnalia Diterpenoids extracted from soft corals: biofloranate A−D (1−4), euplexaurene D (5) and cneorubin K (6), the chemical structure is as follows:

[0040] .

Embodiment 2

[0042] From Xisha in the South China Sea Lemnalia A preparation method for obtaining six kinds of diterpenoids by extracting and separating from soft corals, the specific steps are as follows:

[0043] 1. Frozen Nanhai Xisha Lemnalia Soft coral (wet weight 1.9 Kg) was cut into small pieces and freeze-dried (dry weight 480 g), then extracted five times with a mixture of equal volumes of dichloromethane and methanol under ultrasound, and concentrated under reduced pressure to obtain the extract 33.8 g, then extracted four times with a mixture of equal volumes of ether and water, combined the ether extracts, and concentrated under reduced pressure to obtain 25.5 g of crude extract;

[0044] 2. Dissolve the above crude extract with 20-30mL of dichloromethane first, then perform Sephadex column chromatography, using petroleum ether / dichloromethane / methanol solution with a volume ratio of 2:1:1 as the eluent The fractions were collected tube by tube, arranged according to the mole...

Embodiment 3

[0053] Compound structure identification and NMR signal assignment:

[0054] Diterpenoid 1 (Biofloranate A ): colorless oil; [α]25 D﹢34 ( c 0.1, MeOH); HRESIMS m / z 357.2400 [M + Na] + (calcd for C 21 h 34 o 3 , 357. 2508), the compound's 1 H and 13 For CNMR data see figure 1 and figure 2 , Table 1 and Table 2.

[0055] Diterpenoid 2 (Biofloranate B ): colorless oil; [α]25 D﹢33 ( c 0.1, MeOH); HRESIMS m / z 357.2395 [M + Na] + (calcd for C 21 h 34 o 3 , 357. 2508), the compound's 1 H and 13 For CNMR data see image 3 and Figure 4 , Table 1 and Table 2.

[0056] Diterpenoid 3 (Biofloranate C): colorless oil; [α]25 D-105 ( c 0.1, MeOH); HRESIMS m / z 355.2251 [M + Na] + (calcd for C 21 h 32 o 3 , 355. 2351), the compound's 1 H and 13 For CNMR data see Figure 5 and Figure 6 , Table 1 and Table 2.

[0057] Diterpenoid 4 (Biofloranate D): colorless oil; [α]25 D﹢30 ( c 0.1, MeOH); HRESIMS m / z 355.2251 [M + Na] + (calcd for C 20 h 34 O, 316. 261...

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Abstract

The invention discloses a diterpenoid compound derived from Lemnalia bournei and a preparation method and application thereof, the diterpenoid compound is obtained by separating the secondary metabolite generated by Lemnalia bournei of Xisha. The preparation method comprises the following steps: 1) concentrating a frozen soft coral borenz extracting solution and then extracting to obtain an extract; (2) carrying out sephadex column chromatography separation on the crude extract, carrying out isocratic elution by taking a mixed solvent of petroleum ether, dichloromethane and methanol as a mobile phase, and collecting nine fractions in total; (3) performing normal-phase reduced-pressure column chromatography on the second fraction, and collecting the fraction by taking a mixed solution of petroleum ether and ethyl acetate as a mobile phase and a mixed solution of acetonitrile and water as a mobile phase; (4) respectively carrying out reversed-phase reduced-pressure column chromatography on the second fraction, the fifth fraction and the sixth fraction, and collecting respective corresponding fractions; (5) subjecting corresponding fractions to preparative high-performance liquid phase separation and purification, and acquiring six novel diterpenoid compounds. The invention has the advantage that the compounds No. 1-4 and 6 have an inhibiting effect on staphylococcus aureus and bacillus subtilis.

Description

technical field [0001] The invention relates to a diterpene compound, in particular to a diterpene compound derived from the Bolan scale soft coral and a preparation method and use thereof. Background technique [0002] The South China Sea is located in the tropics and subtropics, with vast sea areas and rich marine biological resources. It is one of the sea areas with the most extensive coral distribution in the world. Since the 1980s, researchers have studied the chemical composition of various corals collected in the South China Sea. At present, many compounds with novel structures have been isolated, such as steroids, terpenes, and alkaloids. in, Lemnalia Soft corals have structurally diverse new terpenoids, mainly including sesquiterpenoids and diterpene glycosides with good biological activity. [0003] During our exploration of the biologically active secondary metabolites of marine soft corals, a soft coral was collected by scuba diving in the waters of the Paracel...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/48C07C67/56C07C33/14C07C29/74C07C29/76C07C35/37A61P31/04
CPCC07C69/732C07C67/48C07C67/56C07C33/14C07C29/74C07C29/76C07C35/37A61P31/04C07C2602/28C07C2603/34C07C2603/62
Inventor 晏霞欧阳翰何山严小军
Owner NINGBO UNIV