CN103450319A - Separation method for erythrodiol in pittosporum leaf crude extract and new application of erythrodiol - Google Patents
Separation method for erythrodiol in pittosporum leaf crude extract and new application of erythrodiol Download PDFInfo
- Publication number
- CN103450319A CN103450319A CN2013103764188A CN201310376418A CN103450319A CN 103450319 A CN103450319 A CN 103450319A CN 2013103764188 A CN2013103764188 A CN 2013103764188A CN 201310376418 A CN201310376418 A CN 201310376418A CN 103450319 A CN103450319 A CN 103450319A
- Authority
- CN
- China
- Prior art keywords
- erythrodiol
- acetone
- extract
- column chromatography
- acetic acid
- 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.)
- Pending
Links
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the fields of chemistry and agriculture, and in particular relates to a method for separating erythrodiol from an ethyl acetate extract of an ethanol extract of pittosporum leaf dry powder. The method comprises the following steps: performing silica gel column chromatography on the ethyl acetate extract; performing gradient elution by using petroleum ether and acetone, as well as acetone and methanol in sequence to obtain 10 fractions; and further performing gradient elution on the M4 fraction with higher activity by using the petroleum ether and the acetone to obtain the erythrodiol. The invention further provides a new weeding application of the erythrodiol.
Description
Technical field
The present invention relates to chemistry and agriculture field, be to provide specifically extracting method of erythrodiol in a kind of oriental variegated coralbean leaf crude extract and uses thereof.
Background technology
Pittosporum tobira (
pittosporum tobira(Thunb.) Ait.) another name tobira, mountain alum, Root of Lindley Butterflybush, mound perfume (or spice), be Pittosporaceae tobira platymiscium.The volatile aromatic compounds such as citral, methyl aceto acetate, butanone alcohol in its branches and leaves, have stronger air purification function [Li Ling's tinkling of pieces of jade. Xibei Univ. of Agricultural & Forest Science & Technology's master thesis, 2007]; Plant can also absorb heavy metal Zn and photo-chemical smog, be a kind of good pollution resisting tree variety [Liang Shuying, Xia Shangguang, Hu Haibo. urban environment and urban ecology, 2008,21 (5): 21-24; Zhu Zhiliang, Liang Dong, Zhang Ronghua, etc. agro-environment science journal 2006,25 (3): 690-693].Its root energy dispelling, collateral-activating, blood stasis removing analgesic, leaf can detoxify, stop blooding, the puckery intestines of seed energy, controlling nocturnal emission with astringent drugs etc. [stone is of heap of stone, Wang Jinmei, Kang Wenyi. China Dispensary, 2008,19 (21): 1634-1635]; The plant extract has certain curative effect [Ju J H to obesity and diabetes, Kwak T H, Park M G. Repub. Korean Kongkae Taeho Kongbo. KR 2004016576 A 20040225,2004], also can resist thin nucleic acid virus [Van den Berghe D A, Ieven M, Mertens F, et al. Lloydia, 1978,41 (5): 463-471].Its plant powder has certain activity against snails [Abdel Gawad M M, Refahy L A, Hamed M M
.journal of Drug Research, 2000,23 (1): 1-10]; 4 kinds of opposed polarity solvent extractable matters of seed and pericarp all have restraining effect in various degree to 7 kind of plant pathogenic bacterias, and the bacteriostatic activity of seed chloroform extract the strongest [Li Ling's tinkling of pieces of jade, Zhou Wenming, big vast east wind, etc.
.northwest agricultural journal, 2007,16 (13): 274-276]; Its blade volatile matter to intestinal bacteria, White staphylococcus, subtilis and yeast have better bacteriostatic action [Liu Yunguo, Ma Tao, common vetch. the bacteriostatic action of plant volatiles. Jilin University's journal, 2004,25 (2): 39-42]; And the saponin crude extract separated from the pittosporum tobira blade also has bacteriostatic activity [Suegirev D P. Trudy Gosudarst. Nikitsk. Botan. Sada, 1959,30,36-40].The inventor finds that its blade has weeding activity [Luo little Yong first, pay bright red, Zhou Shijun. Qingdao Agricultural University's journal, 2007,24 (4): 267-270], and to the weeding activity of its ethanol extraction and different solvents extraction phase thereof measure, confirm that acetic acid ethyl ester extract has high reactivity [Wang Xia, Luo little Yong. Chinese agronomy circular, 2012,28 (25): 201-208].
The inventor further separates by the acetic acid ethyl ester extract to oriental variegated coralbean leaf dry powder ethanol extraction, therefrom be separated to first erythrodiol (Erythrodiol, have another name called Erythrodiol), and find that first it has the high herbicidal activity, thus completed the present invention.Although before this, from the Yunnan rough gentian [Zhao Lei. Yunnan University of Traditional Chinese Medicine's master thesis, 2009], four close wood [Ding Linlin. Medical University Of Tianjin's master thesis, 2010], Herba Pterocephali bretschneideri [Tian Jun, Wu Fenge, Qiu Minghua, Deng. Yunnan plant research, 1995, 17 (1): 108-110], Fructus Chaenomelis Chinesis [Gao Huiai, Wu Lijun, Deng. Chinese natural drug, 2003, l (2): 82-84] and kalimeris [Xu Wenqing, Gong little Jian, Zhou Xin, Deng. herbal medicine, 2010, 41 (7): 1056-1060] extract in the plant such as olive and separate, and it is antitumor to have reported that this compound has, anti-inflammatory, pharmacologically active [the Yang Yanjun such as anticancer cell proliferation and vasodilator, Chen Huiyun, Lin Jiehong, Deng. Traditional Chinese Medicine University Of Guangzhou's journal, 2007, 24 (2): 158-161, Feng Weixiu. foreign medical science traditional Chinese medicine fascicle, 2007,24 (2): 158-161], but there is not yet the report of relevant weeding activity aspect.And the extraction and separation method described in the present invention, be to adopt active back tracking method to explore and form step by step, the extraction that it is very suitable for this material in pittosporum tobira separates, and extracts process and the method for separating and is different from above-mentioned plant.
Summary of the invention
One of purpose of the present invention is to isolate the active substance erythrodiol from the acetic acid ethyl ester extract of oriental variegated coralbean leaf dry powder ethanol extraction.
Another object of the present invention is to provide the separation method of described compound.
Another purpose of the present invention is to provide the pesticide uses of described compound, further is to provide the weeding purpose of this compound.
Concrete, in a kind of acetic acid ethyl ester extract of oriental variegated coralbean leaf dry powder ethanol extraction, the separation method of erythrodiol, comprise the steps:
Get the acetic acid ethyl ester extract of oriental variegated coralbean leaf dry powder ethanol extraction, through silica gel column chromatography, use successively the acetone of the sherwood oil of 20:1 ~ 0:1 volume ratio and acetone mixed solvent and 50:1 ~ 2:1 volume ratio and methanol mixed solvent to carry out gradient elution and obtain A1 ~ A10 totally 10 cuts, the sherwood oil of the higher 6:1 for the A4 cut to activity ~ 0:1 volume ratio separates with the further column chromatography of acetone mixed solvent, obtains erythrodiol.
Embodiment
Compound of the present invention has following structural:
This compound is to extract from the acetic acid ethyl ester extract of oriental variegated coralbean leaf dry powder ethanol extraction.
Concrete, the acetic acid ethyl ester extract of pittosporum tobira ethanol extraction is carried out to wash-out with sherwood oil+acetone, acetone+methyl alcohol through silica gel column chromatography respectively successively, obtain A1 ~ A10 totally 10 cuts; The A4 cut higher to activity separates by the further column chromatography of sherwood oil+acetone, obtains active substance of the present invention.
Compound of the present invention has the activity of stronger inhibition plant seedling growth.The compound that the present invention separates specifically has very strong restraining effect to the growth of romaine lettuce seedling radicle and plumular axis, can be used for directly developing the plant-sourced weedicide or develops bionical weedicide as lead compound.
By embodiment and experimental example, the present invention will be described in more detail.
embodiment 1the extraction of compound erythrodiol
Get the acetic acid ethyl ester extract 65g of oriental variegated coralbean leaf dry powder ethanol extraction through silica gel column chromatography, use successively 20:1, 15:1, 10:1, 5:1, 3:1, 2:1, the sherwood oil of 1:1 and 0:1 volume ratio and acetone mixed solvent and 50:1, 20:1, 10:1, the acetone of 5:1 and 2:1 volume ratio and methanol mixed solvent carry out gradient elution and obtain A1 ~ A10 totally 10 cuts, the higher A4 cut 6:1 to activity, 5:1, 4:1, 3:1, the sherwood oil of 2:1 and 1:1 volume ratio carries out further silica gel column chromatography with acetone mixed solvent to be separated, obtain erythrodiol, for white, needle-shaped crystals.
Compound erythrodiol to above-mentioned separation carries out Structural Identification, and the gained spectral data is as follows:
The ESI-MS spectrogram shows [M+H]
+be 443;
1h-NMR (CDCl
3, 500MHz) spectrogram shows δ: 5 .19 (1H, t,
j=3.5 Hz, H-12), 3.56 (1H, d,
j=11.0 Hz, H-3), 3.20 (2H, d,
j=10.5Hz, H-28), each 3 H of 1.16,0.99,0.94,0.83,0.88,0.87,0.79(, s, 7 CH
3);
13c-NMR (CDCl
3, 125MHz) spectrogram shows δ: 38.6(C-1), 27.3(C-2), 79.0(C-3), 38.8(C-4), 55.2(C-5), 18.4(C-6), 32.6(C-7), 39.8(C-8), 47.6(C-9), 36.9(C-10), 23.6(C-11), 122.4(C-12), 144.2(C-13), 41.8(C-14), 25.6(C-15), 22.0(C-16), 36.9(C-17), 42.4(C-18), 46.5(C-19), 31.0(C-20), 34.1(C-21), 31.1(C-22), 28.1(C-23), 15.6(C-24), 15.6(C-25), 16.8(C-26), 25.9(C-27), 69.8(C-28), 33.2(C-29), 23.6(C-30).
experimental example 2ethyl acetate each cut of phase of oriental variegated coralbean leaf dry powder ethanol extraction and the weeding activity of erythrodiol thereof
1) experiment material
Romaine lettuce
2) experimental technique
Agar method: by the romaine lettuce seed after 0.2% chlorine bleach liquor soaks 15min, rinse for several times and soak water suction 3 ~ 5h left and right under juxtaposition flowing water with tap water, with distilled water wash for several times then, evenly be placed on the thieving paper in square plate with cover, drip distilled water not floating to seed, shading is placed in complete intelligent growth cabinet (HP1000GS-B type, Wuhan auspicious magnificent plant and instrument limited liability company) in, germinate, migrate to until radicle (or seminal root) 0.5% agar gel that is mixed with each stage extract while reaching 3 ~ 5mm and (prepare in advance 100mL, and in even dispensing to 3 small beaker) on, the medicinal extract of each extract needs in advance respectively with being added to the toxic matrix of preparation in agar-agar soln after the 0.5ml acetone solution again, each processes acetone maximum concentration in (containing blank) is 0.5%, and after solidifying, processed again in agar after configuration, growth to recipient plant under this concentration does not have detrimentally affect.0.5% agar gel (containing 0.5% acetone) that does not contain extract of take is blank.First with sharp mouth tweezers, at the agar surface solidified, insert 5 apertures during transplanting, distinguish afterwards the basically identical pre-sprouting recipient plant seed of gripping radicle length, radicle (or seminal root) is vertically implanted in agar gel gently by osculum.5, every beaker, repeat 3 times.For preventing the impact of illumination on compound and Young Plant root growth, each beaker is put into to the growth cabinet shading and cultivate 2 ~ 3d.Growth cabinet is set to the automated cycle of 14h (25 ℃) and 10h (20 ℃), and in case, relative humidity is 60%.After pending end, measure respectively the length of recipient plant seedling radicle and plumular axis with the electronics vernier callipers, with the actual increment of radicle and plumular axis, calculate inhibiting rate.
3) experimental result
Each cut of ethyl acetate extraction phase of oriental variegated coralbean leaf dry powder ethanol extraction and erythrodiol to the inhibition activity of romaine lettuce growth of seedling in Table 1 ~ 2.In 10 cuts of ethyl acetate phase, the highest with the activity of A4 and A9, because the amount of A9 fails further to separate (table 1) less.Separate and obtain erythrodiol through the further column chromatography to the A4 cut, under 5.0g/L concentration is processed to the inhibiting rate of romaine lettuce seedling radicle and plumular axis growth up to 89.8% and 72.8%(table 2).
The ethyl acetate of table 1 oriental variegated coralbean leaf dry powder ethanol extraction is the restraining effect (2.0g/L) of each cut to the romaine lettuce growth of seedling mutually
The restraining effect of table 2 erythrodiol to the romaine lettuce growth of seedling
Conclusion: this extract has good restraining effect to the growth of recipient plant seedling as seen, can be used for directly developing the plant-sourced weedicide or develops bionical weedicide as lead compound.
Claims (5)
1. the separation method of erythrodiol in an oriental variegated coralbean leaf crude extract, is characterized in that comprising the steps:
Get the acetic acid ethyl ester extract of oriental variegated coralbean leaf dry powder ethanol extraction through silica gel column chromatography, use successively the acetone of the sherwood oil of 20:1 ~ 0:1 volume ratio and acetone mixed solvent and 50:1 ~ 2:1 volume ratio and methanol mixed solvent to carry out gradient elution and obtain A1 ~ A10 totally 10 cuts, the sherwood oil of the higher 6:1 for the A4 cut to activity ~ 1:1 volume ratio separates with the further column chromatography of acetone mixed solvent, obtains erythrodiol.
2. the method for claim 1, is characterized in that acetic acid ethyl ester extract is carried out to the separation of two-stage column chromatography.
3. described method as arbitrary as claim 1-2, is characterized in that the acetic acid ethyl ester extract that material therefor is oriental variegated coralbean leaf dry powder ethanol extraction.
4. the weeding purpose of erythrodiol.
5. purposes as claimed in claim 4, is characterized in that described erythrodiol separates by the arbitrary described method of claim 1-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013103764188A CN103450319A (en) | 2013-08-27 | 2013-08-27 | Separation method for erythrodiol in pittosporum leaf crude extract and new application of erythrodiol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013103764188A CN103450319A (en) | 2013-08-27 | 2013-08-27 | Separation method for erythrodiol in pittosporum leaf crude extract and new application of erythrodiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103450319A true CN103450319A (en) | 2013-12-18 |
Family
ID=49733197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2013103764188A Pending CN103450319A (en) | 2013-08-27 | 2013-08-27 | Separation method for erythrodiol in pittosporum leaf crude extract and new application of erythrodiol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103450319A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977359A (en) * | 2017-05-03 | 2017-07-25 | 淮海工学院 | A kind of preparation method and purposes of pittosporum tobira fruit extract |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1871251A (en) * | 2003-09-26 | 2006-11-29 | 帕纳克斯医药公司 | Novel triterpene derivatives, preparation thereof and use thereof |
-
2013
- 2013-08-27 CN CN2013103764188A patent/CN103450319A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1871251A (en) * | 2003-09-26 | 2006-11-29 | 帕纳克斯医药公司 | Novel triterpene derivatives, preparation thereof and use thereof |
Non-Patent Citations (1)
| Title |
|---|
| DAVID TORRES-ROMERO，ET AL.，: "Friedelane Triterpenes from Celastrus vulcanicola as Photosynthetic Inhibitors", 《J. AGRIC. FOOD CHEM.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977359A (en) * | 2017-05-03 | 2017-07-25 | 淮海工学院 | A kind of preparation method and purposes of pittosporum tobira fruit extract |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Biradar et al. | Extraction of some secondary metabolites & thin layer chromatography from different parts of Centella asiatica L.(URB) | |
| Fu et al. | Extraction optimization of oleanolic and ursolic acids from pomegranate (Punica granatum L.) flowers | |
| CN107522680B (en) | Anti-tumor extract of south American wedelia chinensis and preparation method and application thereof | |
| Segneanu et al. | Bioactive molecules profile from natural compounds | |
| Yang et al. | Analysis of Hydroxy Fatty Acids from the Pollen of Brassica campestris L. var. oleifera DC. by UPLC-MS/MS | |
| CN104817432B (en) | A kind of anticancer usage of diterpene-kind compound | |
| CN101824067A (en) | Barrigenol-type triterpenoid saponins compound, preparation method and application thereof | |
| Jash et al. | Phytochemical investigation of the hexane extract of stem bark of Peltophorum pterocarpum (DC.) | |
| Ndunda et al. | Diterpenoid derivatives of Kenyan Croton sylvaticus | |
| Yeo et al. | Isolation of wound healing compounds from Heliotropium indicum | |
| Biskup et al. | Composition and biological activity of Rhaponticum carthamoides extracts obtained from plants collected in Poland and Russia | |
| Verardo et al. | New triterpenic acids produced in callus culture from fruit pulp of Acca sellowiana (O. Berg) Burret | |
| Sikder et al. | Secondary metabolites from seed extracts of Syzygium cumini (L.) | |
| CN103450319A (en) | Separation method for erythrodiol in pittosporum leaf crude extract and new application of erythrodiol | |
| CN105061545B (en) | Triterpene saponin componds and its preparation method and application in shiny-leaved yellowhorn | |
| CN101190259A (en) | Southern magnolia total lactone extract and preparation method and application thereof | |
| CN102911236A (en) | Method for extracting beta-sitosterol from Coreopsis grandiflora leaf and new application thereof | |
| Uddin et al. | Cytotoxic activity of extracts/fractions of various parts of Pistacia integerrima stewart | |
| CN107880084A (en) | The method that middle extraction preparation high-purity acteoside is spent from platymiscium of reaching the clouds | |
| Parikh et al. | Extraction and Phytochemical Evaluation of LitseaGlutinosa Bark Methanolic Extract | |
| CN103570795A (en) | Preparation method of tripterine | |
| CN110204589B (en) | Effective component of feather cockscomb seed, extraction method and application thereof in preparing neuroprotective medicament | |
| CN104140391A (en) | Method for separating and purifying highly pure Euphorbia factor from moleplant seed | |
| Chou et al. | Hydrophobic metabolites from Rhododendron formosanum and their allelopathic activities | |
| CN103450023A (en) | Extraction method of ethyl gallate in peony leaves and new application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20131218 |