CN105935054B - Use of triterpenes for improving algal bloom - Google Patents
Use of triterpenes for improving algal bloom Download PDFInfo
- Publication number
- CN105935054B CN105935054B CN201510479078.0A CN201510479078A CN105935054B CN 105935054 B CN105935054 B CN 105935054B CN 201510479078 A CN201510479078 A CN 201510479078A CN 105935054 B CN105935054 B CN 105935054B
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- CN
- China
- Prior art keywords
- triterpene compound
- acid
- poisons
- freshwater
- algal tufa
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 150000003648 triterpenes Chemical class 0.000 title description 4
- 239000005422 algal bloom Substances 0.000 title description 2
- 239000013505 freshwater Substances 0.000 claims abstract description 18
- ONFPYGOMAADWAT-OXUZYLMNSA-N Dehydroeburicoic acid Chemical compound CC1(C)[C@@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H]([C@@H](CCC(=C)C(C)C)C(O)=O)CC[C@@]4(C)C3=CC[C@H]21 ONFPYGOMAADWAT-OXUZYLMNSA-N 0.000 claims description 38
- -1 triterpene compound Chemical class 0.000 claims description 38
- ONFPYGOMAADWAT-UHFFFAOYSA-N Dehydroeburicolic acid Natural products CC1(C)C(O)CCC2(C)C3=CCC4(C)C(C(CCC(=C)C(C)C)C(O)=O)CCC4(C)C3=CCC21 ONFPYGOMAADWAT-UHFFFAOYSA-N 0.000 claims description 19
- DVXFDXIVWQWLIU-UHFFFAOYSA-N dehydroeburiconic acid Natural products CC1(C)C(=O)CCC2(C)C3=CCC4(C)C(C(CCC(=C)C(C)C)C(O)=O)CCC4(C)C3=CCC21 DVXFDXIVWQWLIU-UHFFFAOYSA-N 0.000 claims description 19
- LIVBXKAVLWBDCR-FRRGXQJJSA-N dehydrosulphurenic acid Natural products [H][C@@]1(C[C@H](O)[C@@]2(C)C3=CC[C@]4([H])[C@]([H])(CC[C@H](O)C4(C)C)C3=CC[C@]12C)[C@@H](CCC(=C)C(C)C)C(O)=O LIVBXKAVLWBDCR-FRRGXQJJSA-N 0.000 claims description 17
- 239000002574 poison Substances 0.000 claims description 13
- 231100000614 poison Toxicity 0.000 claims description 13
- 230000003463 hyperproliferative effect Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 abstract description 4
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000000605 extraction Methods 0.000 description 7
- 241001486992 Taiwanofungus camphoratus Species 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000004255 ion exchange chromatography Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 241000195493 Cryptophyta Species 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003894 drinking water pollution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- CDMXXXZRZWQJQE-UHFFFAOYSA-N acetic acid;2-methylprop-2-enoic acid Chemical compound CC(O)=O.CC(=C)C(O)=O CDMXXXZRZWQJQE-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000012851 eutrophication Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AVRGPVXXZLTCBB-UHFFFAOYSA-N methane oxalonitrile Chemical compound N#CC#N.C AVRGPVXXZLTCBB-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000008239 natural water Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002098 selective ion monitoring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Use of a triterpenoid for ameliorating algal blooms, the triterpenoid being administered to a body of fresh water to inhibit hyperproliferation of algal cells in the body of fresh water; wherein the triterpenoid is selected from dehydro-poric acid or dehydrothiochromic acid.
Description
Technical field
The present invention relates to a kind of purposes of triterpene compound, especially in regard to a kind of triterpene compound improving algae
The purposes of magnificent phenomenon.
Background technology
Algal tufa phenomenon (algal bloom) is also known as body eutrophication, is that nitrogen and phosphorus content is excessively high in poisons in freshwater, exceeds
Environmental carrying capacity and self-purification capacity, the phenomenon that causing algae excessive to be proliferated, are likely to result in the pollution of drinking water source, and strong to human body
Health causes damages.
Invention content
The present invention provides a kind of triterpene compound to improve the purposes of algal tufa phenomenon, using triterpene compound as using
To inhibit the active constituent person of frustule hyper-proliferative.
To improve the purposes of algal tufa phenomenon, which throws light in one triterpene compound of the present invention
Water water body, to inhibit the hyper-proliferative of frustule in the poisons in freshwater；Wherein, the triterpene compound be selected from dehydroeburicoic acid or
Dehydrosulphurenic acid.
Triterpene compound of the present invention is improving the purposes of algal tufa phenomenon, wherein the triterpene compound is
Dehydroeburicoic acid, and with monthly, the administering dosage of 30~500 μ g/mL administers the poisons in freshwater every time.
Triterpene compound of the present invention is improving the purposes of algal tufa phenomenon, wherein the triterpene compound is
Dehydrosulphurenic acid, and with monthly, the administering dosage of 30~500 μ g/mL administers the poisons in freshwater every time.
The triterpene compound of the present invention is to improve the purposes of algal tufa phenomenon, by using the triterpene compound as use
To inhibit the active constituent of frustule hyper-proliferative, to prevent the risk of drinking water pollution problem caused by algal tufa phenomenon, reach dimension
The effect of protecting health.
Description of the drawings
Fig. 1 a：For the chemical structural formula of triterpene compound dehydroeburicoic acid.
Fig. 1 b：For the chemical structural formula of triterpene compound dehydrosulphurenic acid.
Fig. 2 a：For total ion chromatography result of triterpene compound.
Fig. 2 b：For the selective ion chromatography result of triterpene compound.
Fig. 3 a：Influence (the Trendline formula for being triterpene compound dehydroeburicoic acid to frustule survival rate：Y=
84.041*e^ (- 0.0052947x), R2=0.95112).
Fig. 3 b：Influence (the Trendline formula for being triterpene compound dehydrosulphurenic acid to frustule survival rate：y
=74.777*e^ (- 0.0071371x), R2=0.88586).
Specific implementation mode
For above-mentioned and other purposes, feature and the advantage of the present invention can be clearer and more comprehensible, the present invention cited below particularly compared with
Good embodiment, and coordinate institute's accompanying drawings, it is described in detail below：
" poisons in freshwater " of the present invention refers to various water accumulation places, can be rivers and creeks, lake, pond, mountain stream etc.
Natural water also includes the artificial waters such as reservoir and bay.
The triterpene compound of the present invention, can throw in a poisons in freshwater, to inhibit the mistake of frustule in the poisons in freshwater
Degree proliferation, wherein the triterpene compound can be dehydroeburicoic acid (dehydroeburicoic acid, chemical structural formula
System is as shown in Figure 1a), dehydrosulphurenic acid (dehydrosulfurenic acid, chemical structural formula such as Fig. 1 b institutes
Show).Aforementioned triterpene compound can be through artificial synthesized synthesis compound, or be extraction from the medium-height grass plant such as Antrodia camphorata
The native compound of medicinal material is not limited in this.
It is worth noting that, the administering dosage and frequency of use of the triterpene compound can be according to the formation of algal tufa phenomenon
Whether and it is different.Such as：It, can be by the triterpene compound when not yet forming algal tufa phenomenon in the poisons in freshwater
To prevent the poisons in freshwater algal tufa phenomenon occurs for administering, at this point, the frequency of use of the triterpene compound can be every month 1
It is secondary, and it can be 30~200 μ g/mL (dehydroeburicoic acid, dehydrosulphurenic acid) to administer dosage；Or in the fresh water
After having formed algal tufa phenomenon in water body, then it can promote the frustule of hyper-proliferative by the administering of the triterpene compound
Death, to reach the algal tufa phenomenon for removing the poisons in freshwater, at this point, the frequency of use of the triterpene compound can be every month
It is 1~2 time, continuous to administer at least three moon, and it can be that (dehydroeburicoic acid, dehydrogenation sulphur color are more by 200~500 μ g/mL to administer dosage
Pore fungi acid).
To confirm that triterpene compound of the present invention has the growth for inhibiting frustule really, and then can be used as to improve
The active constituent of algal tufa phenomenon carries out following tests then：
(A) extraction, purifying of triterpene compound
This experiment takes an Antrodia camphorata (Antrodia cinnamomea) sample, is crushed in advance after grain size is about 100nm,
Carrying out extraction with an ethanol water (concentration expressed in percentage by volume 95%), (the Antrodia camphorata sample of per kilogram was with 1~3 liter in 2 hours
Ethanol water extracted), it is continuous to be concentrated under reduced pressure, just extract object to obtain one.
It is continuous that the first extraction object is subjected to liquid phase-liquid phase distribution extraction after the first extraction object is dissolved in pure water, is added isometric
N-hexane, after uniformly rocking mixing, standing waits for that it is layered completely, to obtain a water layer solution, by bodies such as water layer solution mixing
Long-pending ethyl acetate, after uniformly rocking mixing, standing waits for that it is layered completely, to obtain an ethyl acetate layer solution, by the acetic acid
Methacrylate layer solution is concentrated under reduced pressure, to obtain an ethyl acetate layer extract.
After the ethyl acetate back dissolving ethyl acetate layer extract, to be adsorbed in silica gel particle, and by silica gel particle Chong
It in tubing string, using the mixed liquor of water and cyanogen methane as mobile phase, is purged with the flow velocity of 2mL/min, is wrapped respectively with obtaining
The several of the dehydrosulphurenic acid containing dehydroeburicoic acid purge with liquid, continuous to carry out washing crystallization or recrystallization by several liquid that purge with,
To obtain the dehydroeburicoic acid and dehydrosulphurenic acid of ultra-high purity.
It is continuous that the dehydroeburicoic acid and dehydrosulphurenic acid that are obtained via foregoing schemes are subjected to total ion chromatography
(total ion chromatogram, abbreviation TIC) and selective ion chromatography (selective ion monitoring, letter
Claiming SIM) result is respectively as shown in Fig. 2 a, 2b, and the mass-to-charge ratio (m/z) and delay of dehydroeburicoic acid and dehydrosulphurenic acid
Time, (retention time, abbreviation RT) was embedded in the 1st table respectively.
1st table, this test mass-to-charge ratio and the residence time of each triterpene compound.
| Triterpene compound | m/z[M+H]+ | RT (minute) |
| Dehydroeburicoic acid | 469.55 | 19.89 |
| Dehydrosulphurenic acid | 485.4 | 9.06 |
Accordingly, you can with from the Antrodia camphorata sample extraction, be purified into dehydroeburicoic acid and dehydrosulphurenic acid etc. two
Kind triterpene compound.
(B) influence of the triterpene compound to frustule survival rate
This experiment is tested with the frustule of microcystic aeruginosa (Microzystis aeruginosa), is fresh water production
Algae, have toxigenicity, therefore in hyper-proliferative formed algal tufa after, may be detrimental to health.
The dehydroeburicoic acid of various concentration, dehydrosulphurenic acid addition have been cultivated to the frustule of stationary phase respectively
In, the frustule survival rate after being observed 72 hours with flow cytometer, as a result respectively as shown in Fig. 3 a~3b.
According to result shown in Fig. 3 a~3b it is known that dehydroeburicoic acid, dehydrosulphurenic acid really can
Inhibit the growth of frustule, and is computed the IC it is known that dehydroeburicoic acid, dehydrosulphurenic acid50Numerical value is respectively
98 μ g/mL and 94 μ g/mL.
In summary, triterpene compound of the invention is to improve the purposes of algal tufa phenomenon, by with the triterpenes
Object is closed as to inhibit the active constituent of frustule hyper-proliferative, to prevent the risk of drinking water pollution caused by algal tufa phenomenon from asking
Topic, reaches the effect of safeguarding health.
The foregoing is merely a prefered embodiment of the invention, is not able to this and limits the protection domain that the present invention is implemented, therefore all ginsengs
Simple equivalent changes and modifications made by the description of the present invention are examined, protection scope of the present invention is still belonged to.
Claims (3)
1. a kind of triterpene compound is improving the purposes of algal tufa phenomenon, which is characterized in that the triterpene compound is thrown in one
A poisons in freshwater, to inhibit the hyper-proliferative of frustule in the poisons in freshwater；
Wherein, which is selected from dehydroeburicoic acid or dehydrosulphurenic acid.
2. triterpene compound as described in claim 1 is improving the purposes of algal tufa phenomenon, which is characterized in that wherein, should
Triterpene compound is dehydroeburicoic acid, and with monthly, the administering dosage of 30~500 μ g/mL administers the fresh water every time
Water body.
3. triterpene compound as described in claim 1 is improving the purposes of algal tufa phenomenon, which is characterized in that wherein, should
Triterpene compound is dehydrosulphurenic acid, and with monthly, the administering dosage of 30~500 μ g/mL administers every time
The poisons in freshwater.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW104106525 | 2015-03-02 | ||
| TW104106525A TWI532432B (en) | 2015-03-02 | 2015-03-02 | A use of triterpenes for improving algal bloom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105935054A CN105935054A (en) | 2016-09-14 |
| CN105935054B true CN105935054B (en) | 2018-07-27 |
Family
ID=56509220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510479078.0A Expired - Fee Related CN105935054B (en) | 2015-03-02 | 2015-08-07 | Use of triterpenes for improving algal bloom |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN105935054B (en) |
| TW (1) | TWI532432B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101214238A (en) * | 2007-01-05 | 2008-07-09 | 国鼎生物科技股份有限公司 | Application of 'niuzhangzhi' extract for inhibiting tumor cell growth |
| US20090318400A1 (en) * | 2008-06-18 | 2009-12-24 | Mackay Memorial Hospital | Method for inhibiting tumor growth with dehydrosulphurenic acid extracted from antrodia cinnamomea |
| CN102614195A (en) * | 2011-01-26 | 2012-08-01 | 高雄医学大学 | Triterpenoid composition of antrodia cinnamomea fruiting body, preparation and analysis method |
-
2015
- 2015-03-02 TW TW104106525A patent/TWI532432B/en not_active IP Right Cessation
- 2015-08-07 CN CN201510479078.0A patent/CN105935054B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101214238A (en) * | 2007-01-05 | 2008-07-09 | 国鼎生物科技股份有限公司 | Application of 'niuzhangzhi' extract for inhibiting tumor cell growth |
| US20090318400A1 (en) * | 2008-06-18 | 2009-12-24 | Mackay Memorial Hospital | Method for inhibiting tumor growth with dehydrosulphurenic acid extracted from antrodia cinnamomea |
| CN102614195A (en) * | 2011-01-26 | 2012-08-01 | 高雄医学大学 | Triterpenoid composition of antrodia cinnamomea fruiting body, preparation and analysis method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105935054A (en) | 2016-09-14 |
| TWI532432B (en) | 2016-05-11 |
| TW201632069A (en) | 2016-09-16 |
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Effective date of registration: 20200728 Address after: 13th Floor, 168 Dingzhong Road, Sanmin District, Kaohsiung City, Taiwan, China Patentee after: Yan Hongkai Address before: No. 23 Pingguang Road, Neipu Township, Pingtong County, Taiwan, China Patentee before: MEIHO University OF SCIENCE AND TECHNOLOGY |
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