Title of Invention	"A PROCESS FOR THE ISOLATION OF UMBELLIFERONE AND APIOSYLSKIMMIN"
Abstract	A process for the isolation of umbelliferone and apiosylskimmin useful for the preparation of sun screen lotions and creams which comprises drying the said Crataeva nurvala plant material, owdering the dried plant material, sequentially extracting the dried and powdered plant material so obtained with organic solvents like hlorinated solvents such as chloroform, dichloromethane, carbon tetrachloride, ester solvents, ethyl acetate, ethyl formate, alcohols such as methanol, ethanol, n-butanol and water; at a temperature ranging 20-3 0°C and concentraqting the resultant solvent extracts to obtain a concentrate consisting of mainly umbelliferone and apiosylskimmin, allowing the concentrate top stand for crystallization followed by filtration and drying of the crystal to obtain umbelliferone and apiosylskimmin.

Title of Invention

"A PROCESS FOR THE ISOLATION OF UMBELLIFERONE AND APIOSYLSKIMMIN"

Abstract

A process for the isolation of umbelliferone and apiosylskimmin useful for the preparation of sun screen lotions and creams which comprises drying the said Crataeva nurvala plant material, owdering the dried plant material, sequentially extracting the dried and powdered plant material so obtained with organic solvents like hlorinated solvents such as chloroform, dichloromethane, carbon tetrachloride, ester solvents, ethyl acetate, ethyl formate, alcohols such as methanol, ethanol, n-butanol and water; at a temperature ranging 20-3 0°C and concentraqting the resultant solvent extracts to obtain a concentrate consisting of mainly umbelliferone and apiosylskimmin, allowing the concentrate top stand for crystallization followed by filtration and drying of the crystal to obtain umbelliferone and apiosylskimmin.

Full Text	This invention relates to a orocess for the isolation or umbel1iferone and aoiosvlskimmin useful -for the preparation or suncreen lotions and creams. The oresent invention oarticular 1 y relates to a process for the isolation of umbeliifsrone and aoiosvl sk i men in fron a new source.Crataeva nurva1 a. The umbelliferone and apiosy1skirmmin isolated according to the process of the present, invention are a o hen o lie compound anc. its qlvcoside. In the drawings accompanving this specification Umbel 1 iferone is represented bv formula 1 and apiosyIskimmin is represented as formula 2 having the structure umbel 1 iferone B-D-aDiosyl-(1->6>-B-D-glucopyranoside. Umbel 1 iferone is used in sunscreen lotions and creams. The aoiosylskimmin may be used direct.lv as suncreen comnounti or as an intermediate to provide umbel 1 if erone. Umbel 1 iferone of formula 1 is a well known compound and apiosylskimmin of formula 2 has also been reoorted in the literature, the reference may tae made to D. Gantimur. A.I, Svrchina, A.A. Semenov, Khim prir. Soedin, (1986). (.U, 36 and M. Takata, S,. Shibata, T. Okuyama, PI ant a Med „ (1990). 56. ( .1. > . 133. The isolation of apiosyIskimmin from the olant PhioJodicarous sibiricus and Peucedanum pracruptorum has Peer reported mainly for its chemical characterisation. In these two references of Khim. Prir. Soedin (1986), (1). 36 only. the structure elucidation of apiosyIskimmin has been described and no details of isolation procedure have been reported. In Plant? I Med. (1990), 56 C 1 ) , 135 it was reported that the n-butanol soluble fraction of roots of Peucedanum praeruptorum was purified by chromatography on silica gel and'Sephadex LH-20 column and HPLC (OD3) to yield furanocoumarine glycosides and the coumarine derivatives. Evidently this lengthy procedure is unlikely to be exploited for large scale isolation of umbelliterone anc apiosy1skimm in as it involves time consuming chroma tog r a phv anc! use of costly reagents. The main object of the present invention is to provide a process for the isolation of umbelliferane ans apiosylkimmin useful for the preparation of sunscreen lotions and creams. Another embodiment of the present invention is to provide a process for the isolation of umbelliferone and apiosylskimmin from a new source, Crataeva nurvala. Still another object of the present invention is to provide a simple and economical process for the isolation of umbelliferone and apiosylskimmin. Yet another object of the present injvetion is to provide a process for the isolation of umbelliferone and apiosylskimmin without using time consuming chromatographic procedure and costly chemicals. Accordingly the present invention provides a process for the isolation of umbelliferone and apiosylskimmin useful for the preparation of sun screen lotions and creams which comprises drying the said Crataeva nurvala plant material, powdering the dried plant material, sequentially extracting the dried and powdered plant material so obtained with organic solvents like chlorinated solvents such as chloroform, dichloromethane, carbon tetrachloride, ester solvents, ethyl acetate, ethyl formate, alcohols such as methanol, ethanol, n-butanol and water; at a temperature ranging 20-3 0°C and concentraqting the resultant solvent extracts to obtain a concentrate consisting of mainly umbelliferone and apiosylskimmin, allowing the concentrate top stand for crystallization followed by filtration and drying of the crystal to obtain umbelliferone and apiosylskimmin. In an embodiment of the present invention the drying of the plant material may be effected using known methods such as air drying. In yet another embodiment of the present invention the powdering of the dried and powdered plant material is effected using organic solvents like chlorinated solvents such as chloroform, dichloromethane, carbon tetrachloride, ester solvents such as ethylacetate, ethyl formate, alcohols such as perchloration, soxhelt extraction for a period in the range of 12 to 96 hours. In yet awnother embodiment of the present invention the concentrate is allowed to stand for a period of 1 to 15 days at room temperature or 1-48 hrs at a temperature in the range of-5°to35°C. In another embodiment of the present invention the drying of umbelliferone and In an embodiment of the present invention the drying of the plant material may be effected using known methods such as air drying. In another embodiment the powedering of the dried plant material may be done using conventional methods. In yet another embodiment the extraction of the dried and powdered plant material is effected using organ-ic solvents like chlorinated solvents such as chloroform, dichloromethane, carbontetrachloride, ester solvents such as ethylacetate, ethyl formate, alcohols such as ethanol, methanol, n-butanol and water. In still another embodiment the extraction may be effected using known methods such as percolation, soxhlet extraction for a period in the range of 12 to 96 hours. In yet another embodiment the concentrate is allowed to stand for a period of 1 to 15 days at room temperature o or 1 to 48 hours at a temperature in the range of -5 to o 35 C. In another embodiment the drying of umbelliferone and aplsylskimmin is effected using a desicator containinc dehvdratina aqent. such as fused calcium chlcr3.de phosphorous pentodide. under vaccum at a pressure in the range of 0.1 to 25 mm, The extraction of oowedered 0.1, ant. material was cone in a Dercolator The air dried sowdered material of Crataeva nurvala was extracted with ch1oriated solvents 1i e chlorQform . Dichloramethane, carbontetrachloride etc, ester solvent such as ethy1acetate , ethvi formate etc. a1cohols such as ethano1 . methanol . n-butsnal etc and water. The oercalation period nav be varied from 12 to 96 hrs, The extract was concentrated and allowed to stand overnight to a few days to crystallise out the solid and drving the? solid in a vaccum desicator to vield umbel 1 i f erone from chloroform and ap.iosylakimmin from methane', ex tract. - The following examples are given by way of illustration of the process of the present invention and should not. bo construec to limit the scope of the present invention, 1 Example 1 A total of 1 ka of dried and powdered bark of Crataeva Qurvale, was successively extracted in a percolator with chloroform (1,,5 1 x, 3) and then with methanol (21 x 3) for 30 hrs each. The chloroform extract was concentrated to 3.(210 ml and allowed to stand overnight. The solid which crystallized out filtered and dried in vac.cum desicator to yield umbel 1 if erone The methanol extract was concentrated to 150 ml and allowed to stand for 3 days to separate out crystals of apiosvlskimmin in room temperature. The mother liquor was again concentrated and allowed to stand as before to get further crops of crystals. A ^ot.a.l of 36 cj of 'Soiosv I sk .vmroin was obtained. Example 2 The dried powdered bark of Crataeva nurvale, (1 kg) was percolated succissively with ethylacetate and ethanol (48 hrs). The ethylacetate extract was concentrated and allowed to stand overnight. Solid so formed filtered and dried in vaccum to yield crystals of umbel1iferone (1.2 g). The ethanol extract was concentrated to 100 ml and allowed to stand for 1 day in a refrigerator. The solid was filtered and dried in a vaccum to yeild apiosylskimmi38 g). The main advantages of the process of the present invention are , 1. time consuming chromatographic methods have been excluded 2. costly chemicals and sophisticated instruments are not used 3. the process is simple and cost effective Claim: 1. A process for the isolation of umbelliferone and apiosylskimmin useful for the preparation of sun screen lotions and creams which comprises drying the said Crataeva nurvala plant material, powdering the dried plant material, sequentially extracting the dried and powdered plant material so obtained with organic solvents like chlorinated solvents such as chloroform, dichloromethane, carbon tetrachloride, ester solvents, ethyl acetate, ethyl formate, alcohols such as methanol, ethanol, n-butanol and water; at a temperature ranging 20-3 0°C and concentraqting the resultant solvent extracts to obtain a concentrate consisting of mainly umbelliferone and apiosylskimmin, allowing the concentrate top stand for crystallization followed by filtration and drying of the crystal to obtain umbelliferone and apiosylskimmin. 2. A process as claimed in claim 1, wherein the concentrate was allowed to stand for a period of 1 to 15 days at room temperature or 1-48 hrs at a temperature in the rangeof-5°to350C. 3. A process as claimed in claim 1, wherein the drying of umbelliferone and apiosylskimmin is effected using a dessicator containing dehydrating agent such as fused calcium chloride, phosphorus pentaoxide under vacuum at a pressure in the range of 0.1 mm to 25 mm. 4. A process for the isolation of umbelliferone and apiosylskimmin useful for the preparation of sun screen lotions and creams substaqntiawlly as herein dewscribed with reference to the examples.

Full Text

This invention relates to a orocess for the isolation or umbel1iferone and aoiosvlskimmin useful -for the preparation or suncreen lotions and creams.
The oresent invention oarticular 1 y relates to a process for the isolation of umbeliifsrone and aoiosvl sk i men in fron a new source.Crataeva nurva1 a.
The umbelliferone and apiosy1skirmmin isolated according to the process of the present, invention are a o hen o lie compound anc. its qlvcoside. In the drawings accompanving this specification Umbel 1 iferone is represented bv formula 1 and apiosyIskimmin is represented as formula 2 having the structure umbel 1 iferone B-D-aDiosyl-(1->6>-B-D-glucopyranoside.
Umbel 1 iferone is used in sunscreen lotions and creams. The aoiosylskimmin may be used direct.lv as suncreen comnounti or as an intermediate to provide umbel 1 if erone.
Umbel 1 iferone of formula 1 is a well known compound and apiosylskimmin of formula 2 has also been reoorted in the literature, the reference may tae made to D. Gantimur. A.I, Svrchina, A.A. Semenov, Khim prir. Soedin, (1986). (.U, 36 and M. Takata, S,. Shibata, T. Okuyama, PI ant a Med „ (1990). 56. ( .1. > . 133. The isolation of apiosyIskimmin from the olant PhioJodicarous sibiricus and Peucedanum pracruptorum has Peer reported mainly for its chemical characterisation. In these two references of Khim. Prir. Soedin (1986), (1). 36 only. the structure elucidation of apiosyIskimmin has been described and no
details of isolation procedure have been reported. In Plant?
I Med. (1990), 56 C 1 ) , 135 it was reported that the n-butanol
soluble fraction of roots of Peucedanum praeruptorum was purified by chromatography on silica gel and'Sephadex LH-20 column and HPLC (OD3) to yield furanocoumarine glycosides and the coumarine derivatives.
Evidently this lengthy procedure is unlikely to be exploited for large scale isolation of umbelliterone anc apiosy1skimm in as it involves time consuming chroma tog r a phv anc! use of costly reagents.
The main object of the present invention is to provide a process for the isolation of umbelliferane ans apiosylkimmin useful for the preparation of sunscreen lotions and creams.

Another embodiment of the present invention is to provide a process for the isolation of
umbelliferone and apiosylskimmin from a new source, Crataeva nurvala.
Still another object of the present invention is to provide a simple and economical process
for the isolation of umbelliferone and apiosylskimmin.
Yet another object of the present injvetion is to provide a process for the isolation of
umbelliferone and apiosylskimmin without using time consuming chromatographic
procedure and costly chemicals.
Accordingly the present invention provides a process for the isolation of umbelliferone
and apiosylskimmin useful for the preparation of sun screen lotions and creams which
comprises drying the said Crataeva nurvala plant material, powdering the dried plant
material, sequentially extracting the dried and powdered plant material so obtained with
organic solvents like chlorinated solvents such as chloroform, dichloromethane, carbon
tetrachloride, ester solvents, ethyl acetate, ethyl formate, alcohols such as methanol,
ethanol, n-butanol and water; at a temperature ranging 20-3 0°C and concentraqting the
resultant solvent extracts to obtain a concentrate consisting of mainly umbelliferone and
apiosylskimmin, allowing the concentrate top stand for crystallization followed by
filtration and drying of the crystal to obtain umbelliferone and apiosylskimmin.
In an embodiment of the present invention the drying of the plant material may be
effected using known methods such as air drying.
In yet another embodiment of the present invention the powdering of the dried and
powdered plant material is effected using organic solvents like chlorinated solvents such
as chloroform, dichloromethane, carbon tetrachloride, ester solvents such as ethylacetate,
ethyl formate, alcohols such as perchloration, soxhelt extraction for a period in the range
of 12 to 96 hours.
In yet awnother embodiment of the present invention the concentrate is allowed to stand
for a period of 1 to 15 days at room temperature or 1-48 hrs at a temperature in the range
of-5°to35°C.
In another embodiment of the present invention the drying of umbelliferone and
In an embodiment of the present invention the drying of the plant material may be effected using known methods such as air drying.
In another embodiment the powedering of the dried plant material may be done using conventional methods.
In yet another embodiment the extraction of the dried and powdered plant material is effected using organ-ic solvents like chlorinated solvents such as chloroform, dichloromethane, carbontetrachloride, ester solvents such as ethylacetate, ethyl formate, alcohols such as ethanol, methanol, n-butanol and water.
In still another embodiment the extraction may be effected using known methods such as percolation, soxhlet extraction for a period in the range of 12 to 96 hours.
In yet another embodiment the concentrate is allowed
to stand for a period of 1 to 15 days at room temperature
o or 1 to 48 hours at a temperature in the range of -5 to
o 35 C.
In another embodiment the drying of umbelliferone and
aplsylskimmin is effected using a desicator containinc
dehvdratina aqent. such as fused calcium chlcr3.de phosphorous pentodide. under vaccum at a pressure in the range of 0.1 to 25 mm,
The extraction of oowedered 0.1, ant. material was cone in a Dercolator The air dried sowdered material of Crataeva nurvala was extracted with ch1oriated solvents 1i e chlorQform . Dichloramethane, carbontetrachloride etc, ester solvent such as ethy1acetate , ethvi formate etc. a1cohols such as ethano1 . methanol . n-butsnal etc and water. The oercalation period nav be varied from 12 to 96 hrs, The extract was concentrated and allowed to stand overnight to a few days to crystallise out the solid and drving the? solid in a vaccum desicator to vield umbel 1 i f erone from chloroform and ap.iosylakimmin from methane', ex tract. -
The following examples are given by way of illustration of the process of the present invention and should not. bo construec to limit the scope of the present invention,
1 Example 1
A total of 1 ka of dried and powdered bark of Crataeva Qurvale, was successively extracted in a percolator with chloroform (1,,5 1 x, 3) and then with methanol (21 x 3) for 30 hrs each. The chloroform extract was concentrated to 3.(210 ml and allowed to stand overnight. The solid which crystallized out filtered and dried in vac.cum desicator to yield umbel 1 if erone The methanol extract was concentrated to 150 ml and allowed to stand for 3 days to separate out crystals of apiosvlskimmin in room temperature. The mother liquor was again concentrated and allowed to stand as before to get further crops of crystals. A ^ot.a.l of 36 cj of 'Soiosv I sk .vmroin was obtained.
Example 2
The dried powdered bark of Crataeva nurvale, (1 kg) was percolated succissively with ethylacetate and ethanol (48 hrs). The ethylacetate extract was concentrated and allowed to stand
overnight. Solid so formed filtered and dried in vaccum to yield crystals of umbel1iferone (1.2 g).
The ethanol extract was concentrated to 100 ml and allowed to stand for 1 day in a refrigerator. The solid was filtered and dried in a vaccum to yeild apiosylskimmi38 g).
The main advantages of the process of the present invention are ,
1. time consuming chromatographic methods have been excluded
2. costly chemicals and sophisticated instruments are not used
3. the process is simple and cost effective

Claim:
1. A process for the isolation of umbelliferone and apiosylskimmin useful for the
preparation of sun screen lotions and creams which comprises drying the said
Crataeva nurvala plant material, powdering the dried plant material, sequentially
extracting the dried and powdered plant material so obtained with organic
solvents like chlorinated solvents such as chloroform, dichloromethane, carbon
tetrachloride, ester solvents, ethyl acetate, ethyl formate, alcohols such as
methanol, ethanol, n-butanol and water; at a temperature ranging 20-3 0°C and
concentraqting the resultant solvent extracts to obtain a concentrate consisting of
mainly umbelliferone and apiosylskimmin, allowing the concentrate top stand for
crystallization followed by filtration and drying of the crystal to obtain
umbelliferone and apiosylskimmin.
2. A process as claimed in claim 1, wherein the concentrate was allowed to stand for
a period of 1 to 15 days at room temperature or 1-48 hrs at a temperature in the
rangeof-5°to350C.
3. A process as claimed in claim 1, wherein the drying of umbelliferone and
apiosylskimmin is effected using a dessicator containing dehydrating agent such
as fused calcium chloride, phosphorus pentaoxide under vacuum at a pressure in
the range of 0.1 mm to 25 mm.
4. A process for the isolation of umbelliferone and apiosylskimmin useful for the
preparation of sun screen lotions and creams substaqntiawlly as herein dewscribed
with reference to the examples.

Documents:

755-del-1998-abstract.pdf

755-del-1998-claims.pdf

755-del-1998-correspondence-others.pdf

755-del-1998-correspondence-po.pdf

755-del-1998-description (complete).pdf

755-del-1998-drawings.pdf

755-del-1998-form-1.pdf

755-del-1998-form-19.pdf

755-del-1998-form-2.pdf

755-del-1998-form-3.pdf

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Patent Number

217908

Indian Patent Application Number

755/DEL/1998

PG Journal Number

17/2008

Publication Date

25-Apr-2008

Grant Date

29-Mar-2008

Date of Filing

24-Mar-1998

Name of Patentee

COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

Applicant Address

RAFI MARG, NEW DELHI-110001, INDIA.

Inventors:

#	Inventor's Name	Inventor's Address
1	BIKAS CHANDRA PAL	CHEMICAL BIOLOGY, 4, RAJA S.C. MULLICK ROAD, JADAVPUR, CALCUTTA 700032,

PCT International Classification Number

A61K 7/26

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA