JOURNAL OF SCIENCE OF HNUE Natural Sci. 2017, Vol 62, No. 3, pp. 42-50 Tins paper is available online al hUp;//stdb.hnue edu.vn
DOI 10.18173/2354-!059.2017-0006
N G H I E N c u t T A C H C H I E T N H O M CAU T U T ^ O H U O N G VA XAC filNH H O A T T i N H S I N H H Q C CUA C H U N G T R O N G T I N H DAU V O Q U A Q U Y T LANG SON
N g u y e n V a n Lgi
Trucmg Dai hoc Cdng nghiep Hd Ndi. Minh Khai. Hd Ndi
Tom tat. Su dung phircrng phap sac ki col. he dung moi nia giai /i-hexan/dietyl etc vdi ti le
=1/1 tir 4 niLlinh dau voquyt Lang Son d3 lach chiet dirge 0.25 mL dich sanh dac mau vang dam, CO mill Iham dac tmng (phan doan 2). BJLng phuang phap GC-MS da xac djnh duoc 10 cau tii chinh lir phan doan nay nhu. octanal, cilronellal, decanal, neral, linalyl acetale, dodccanal, gcranial, a-sinensal, y7-sinensal va geranyl acetate. K6l hap vai phuang phap danh gia cam quan A khong A da khang dinh rang day chinh la nhom cau lii tao hirong trong tinh dau vo qua quyl Lang San. Ben canh do cung da xac dinh diroc mgi so hoat [mh smh hoc ciia nhom cau tir lao huang trong phan doan ,2, kha nang quet g6c tu do DPPH (38,17 ± 0,22%) va kha nang khang 4 chung vi smh val kt^m dinh: Staphylococcus aureus.
Bacillus ceretis. Escherichia coll va Salmonella typhi.
Tir khda-. Nhom cau Lii tao huong, ho^t tinh .sinh hoc, lach chiet, lmh dau vo qua quyt Ming Son.
1. Mo-dau
Cay quyl co ten khoa hpc la Citrus reticulata Blanco var. tangerine. CJ Viet Nam quyt diroc trong a nhieu nai, co nhieu giong lot eho nang suat cao va chat lugng lot. Cay quyl thich nghi vdi dieu kien nhiet d a i , no it bi sau benh hon cam. Cay quyt truac day ciu dugc trong g huyen Bac Sgn, tinh Lang San, hien nay dugc trong a tat ca cac huyen ciia tinh Lang Son. Loai quyt nay thuang cho nang suat cao, qua chin co mau vang, miii chua nhieu nudc va co vi ngpt. Vo quyt t h u a n g mong, eo chua nii tinh dau, miii thom de chiu. Trong tinh dau vo qua quyt co chua nhieu cau tu thupc nhom tecpen va dan xual chua oxi ciia lecpen, co vai tro quan trpng trong cong nghiep Ihuc pham va m j pham [1]. Tuy nluen chi eo mgt vai cau tu chinh co gia tri va lao miii thgm dac trung cho tinh dau vo qua quyt. 0 Viet Nam hien nay co rat it cong trinh nghien cim va xac dinh cac cau tu t^o miii thgm dac trung trong tinh dau vo qua quyt. Trong khi do nhu cau ve thong tin, dU lieu cac cau t u tao miii dac Inrng trong tinh dau vo qua quyt sii dung eho inuc dich huong lieu thuc pham vit my pham la rat can ihiel. Nghien cuu nay d l dua ra quy trinh tach chiet va xac djnh hogt tinli sinh hpc ciia nhom cac cau lu lao miii thom dac trung trong tinh dau vo qua quyl Lang Son, lam phong phu them nguon tu lieu ve qua quyl a nude la.
Ngay nhan bai: 18/11/2016. Ngay nhan dang: 8/3/2017.
Tac gia lien h?, Nguyen Van Lgi, dja chi e-mail, [oichebien@yahoo,com
Nghien c-iiv lach chiet nhom cdu td tqa huang vd xdc dinh hoat tinh sinh hpc ciia chimg trong tmh ddu..
2. Noi dung nghien cmi
2.1. Thyc nghiem 2.1.1. Doi tu-ong nghien cihi
Tinh dau vo qua quyl Lang San dugc khai thac bang phuong phap trich li bSng elanol 95%
vaduoc lam khan bing Na2S04 khan. Dung moi su dung de tach chiSt ciu tii tao huang la w-hexan va dietyl ete. Mau tinh dau chuan dugc ep ca hpc trong moi truang lanh, ly tam 2500 vong/phiit trong 5 phiit, lam khan phan linh dSu bang NajSOj khan [4].
2.1.2. Phmmg phap nghien cii-u
- Phucmg phdp tdch chiet nhdm cdu tic tao huang
Tach chiet nhom eau tu tao huang bang phuang phap sac ky col dugc lien hanh vai chat hkp phu la silicagel Merck 60, ca hat 100 - 160 mesh, dugc boat hoa a nhiet dp 105 "C. thai gian 24 gig, dung moi nra giai la n-hexan va dietyl ete [2]
- Phuang phdp xac dmh nhdm cdu lu tao hucmg
Cac cau tu lao huong trong tinh dau vo qua quyt Lang San dugc xac djnh theo phuang phap GS-MS. bang may sic ky khi GC6890-MS5898, cot mao quan HT-5MS. vai chuang Irinh thuc hien nhu sau: nhiet do cot 80 - 150 "C, t6c do tang nhiel 3 "C/phiil, giiJ a 5 phut va 150 - 220 "C toe dp tang nhiet 8"C/phut, giir a 5 phiit. Dieu kien MS: ion hoa mau a the ion hoa 70 eV, nhiel do duy tri 250 "C, khi mang la heli, toe do dong 0,5 mL/phiit, toe dp chia dong 1:50 [2, 3].
- Phuang phdp ddnh gid cdm quan nhdm cdu lu lao huong
Su dung phep thii A khong A, hgi dong danh gia cam quan dugc lua chpn la 12 nguai, moi nguai duge lam quen vdi mau A la mau tinh dau vo qua quyt Lang San dugc tach chiet bang phu'ong phap ep lanh goi la mau chuan. Mau khong A la mau phan doan 1, phan doan 2 va phan doan 3. Moi thanh vien hpi dong nhan dugc cac cap mau da dugc ma hoa, trong moi cap do co 1 mau A va 1 mau khong A [4]
- Phuong phdp xdc dinh khd ndng quel gdc ludo DPPH
Dya tren nguyen tac 1 .l-diphenyl-2-picryihydrazyl (DPPH) co kha nang tao ra goc lu do ben trong dung dich elanol bao hoa. Mau thi nghiem gom co 0,1 mL dich chiia cac cau tu tao huong, 2 mL etyl axetat. 1,9 mL melanol va I mL DPPH. Hon hgp sau khi phoi trpn lac nhe va de yen trong bong loi 6 nhiel do phong 30 phut, do dp hap Ihu a buac song 517 nm [5. 6] Kha nang quet goc ly do ciia mau dugc linh bang cong ihuc % DPPH = [(An- (A-A|,))/Ao] ^ 100 %, trong do Aoi mau kiem chiing. A: mau thi nghiem, A|,: mau irang.
-Xdc dinh khd ndng khdng khudn bdng phucmg phdp khuech tdn thach
Moi truang canh thang thuang, ki lueu MPA, gom (g/L) Cao Ihit (3,0), eao nam men (5,0), peplon (10,0), muoi an, (5,0), pha trong 1000 mL nuac, pH = 6,5- 6,8. Sau khi thanh trung, moi truang MPA duac lam nguoi 45 - 48''C. bo sung vi sinh vat kiem dinh vdi ti le 150|jl dich chung trong 30 mL moi truang MPA xop. lac deu va do vao dia pertri VOL chieu day thach la 5mm. Diing klioan nut due 16 tren dTa (9 = 5mm). Diing micropipet nho vao moi 16 80fil mau (nong dp 50 mg/mL), sau do dat cac dTa da nho mau vao tii lanh a 4 "C. de trong vong 3 gio cha khuech tan dich. Tiep Iheo chuyen dTa vao hi am 32 "C, dgc ket qua sau thai gian 24 gia. Kha nang khang khudn dugc xac dinh bang cong thuc. D - d = BK trong do D: duang kinh vong khang khuan (cm), d: duong kinh 16 khoan thach (cm), BK. ban kinh vong vo khuan (em) [7-9].
2.2. Ket qua va thao luan 2.2.1. Tach nhom cau tir tao huoTig
Can 40 g silicagel de nhoi cot, hiit 4 mL linh dau vo qua quyl Lang San dua len col. Phan
doan 1 duge nia giai vai 340 mL dung moi n-hexan thi lap trong suot dugc tach ra Phan doan 2
43Nguyin Van Lgi
nia giai vai 320 mL dung moi «-hexan va dietyl ete ty le la «-hexane: dietyl ete = 1:1 thi lop mau vang dam d u g c tach ra khoi cot. Phan doan 3 nja giai voi 350 mL dung moi dietyl ete thi lgp mau vang nhat d u a c lach ra klioi cot. Phan doan 1, eo quay 52 phiit thi thu dugc 1,96 mL djch trong suot, khong co miii tham Phan doan 2. eo quay 15 phiit thi thu dugc 0.25 mL dich sanh dae mau vang dam, co mui tham dac trung ciia linh diu vo qua quyt. Phan doan 3. co quay 14 phut thi thu d u a c 0.35 mL dich mau vang nhat, co miii tham nhe. Quy trinh tach c h i a nhom cac cau tu tao huong dugc mo ta tren Hinh 1.
Rua giai bang dung moi n hex an (340 mL)
Riia giai bang he dung moi rt-hexan/dielyl ele
= 1/1 (320 mL) Riia giai bang dung moi
dielyl ele (350 mL)
Hinh L Sa do quy trinh tdch chiet nhom cdc cau tu tgo huffng - Phdn doan 1:
+ Xac dinh cac cau tii trong phan doan I:
Bang p h u a n g phap GC-MS da xac dinh dugc 16 cau t u trong phan doan tinh dau vo qua quyt Lang San lach chiet vai dung moi fi-hexan (phan doan 1), ket qua duge irinh bay a Bang 1.
Bang 1 cho thay cae cau tu trong phan doan tinh dau vo qua quyt Lang San tach ehiet bang dung moi n-hexan, khong eo mau va trong suot, thanh chu yeu la hidrocacbon. Trong cac eau tii nay nhom monotecpen co 11 cau tu chiem 74,42% (dac biet la mpt so cau tu chiem ly le cao n h u limonene: 15,06%, p-eymene: 12,14%, /?-pinene: 10,54%, rf-5-carene: 7.89%...) va nhom sesquitecpen eo 4 cau tii chiem 24,76%. trong do co mgt so cau tir chiem ty le cao nhu «- farnesene: 7,87%, valencene: 4,96%.
Hinh 2. Sac ki dd cdc cau tti-trong phan doan I
Nghien cuu tdch chiet nhom cdu tu tgo huong vd .xdc dinh hogt tinh sinh hpc ciia chmg trong tinh ddu..
Bdng I. Cdc cau tu trong phan dogn I stt
1 2 3 4 5 6 7 8 9 10
n
12 13 14 15 16
Ten cac cau tir nonane
a-pinene camphene
^-pinene sabinene (5-i-carene myrcene a-phellandrene a-terpinene p-cymene limonene a-cubebene 5-elemene
^-bhsabolene valencene a-famesene
Tho'i gian luu (phiit) 2,269 6,846 7,118 7,653 7,841 8,056 9,923 12,127 13,943 14.905 15.237 15,617 15,765 15,893 17.627 18,338
Ti le (%) 6,06 2.92 3,73 10,54 2,83 7.89 2.96 3,82 6,47 12,14 15,06 3,05 4.02 4,86 4,96 7,87 Ghi chu Ti le (%) tinh theo dien tieh pie sdc ki + Xac dinh miii ciia phan doan 1:
DS xac dinh min ciia phan doan I, xel cac cap mau theo phuang phap A khong A, ket qua Bang 2. Tong hpp ket quo
MSU gioi thi|u
A Khong A
T6ng
trd Iffi ciia nhom ngu&i thii tren mdu phdn doan I Ngirdi thii" lira chon
A Gia tri quan sat
3 8 U
Gia tri li thuyet
5.5 5,5 11
Khong A Gia trj Gia tri quan sat li thuySt
9 4 13
6,5 6,5 13
Tong
12 12 24 X. = 2 . « ^ = 4,19
Gia trj X^tinh toan dugc nay ldn hon gia tn X',h= 3,84 a miic y nghTa a la 5%. Dieu do ket
luan ring nguai thu dS phan biet dugc hai mau A va khong A Co nghTa la phan doan 1
(tach chiet bing dung moi n-hexan) khong co miu giong miii cua linh dau vo qua quyt
45
Lang San tach ehiet bang phuang phap ep lanh. Nhu vay phan doan 1 khong co mui tham cua tinh dau.
- Phdn dogn 2-
+ Xac dinh cac cau tu trong phan doan 2:
Sii dung phuang phap GC-MS, xac dinh dugc 10 cau lu trong phan doan nay, kel qua dupe the hien a Bang 3
Bdng 3. Cdc cdu td-trong phdn dogn 2 stt
1 2 3 4 5 6 7 8 9 10
Ten cac cau tir octanal
cilronellal decanal neral linalyl acetate dodecanal geranial n-sinensat j5-sinensal geranyl acetate
Thtri gian liru (phiit) 2,785 5,610 7,341 9.266 10,357 11.628 12.754 15.342 16,129 16,573
Ti le (%) 3,79 20,62 14.53 11.75 7.06 7,12 9,18 11,69 9,04 4,16
L,L
Hinh 3, Sdc ki do cdc cau tu- trong phdn doan 2
Phan doan tinh dSu vo qua quyt Lang San tach chiet vol he dung moi «-hexan va dietyl ete CO mau vang dam, mui thom dac tnmg, trong do CO 8 cau tu thuoc nhom andehil chiem 87,72%, dac biet la c6 mot s6 c5u tu chilm ty le cao nhu citronellal- 20,62%, decanal; 14,53%, neral- 1 i ,47% va n-sinensal: 11,69%. Nhom este co 2 ciu tii chi6m 11,22% (linalyl acetate: 7,()6% va geranyl acetate: 4,16%). Theo tac gia Le Thanh VSn va cong su [11] cho rang cau trac to hop huong gom 2 thanh phan chinh la Ihanh phSn tao huong (chat mui chu thi chit khuech tan va chit h6 tro) va thanh phin c6 djnh huong. Thanh phan c6 djnh huong. thuong la nhthig thanh phin CO kh6i luong phan tii Ion, nhiet do soi cao, kho bay hoi trong khong khi, cr dang set, co do nhoi cao hoac kit tinh rjn, ching han nhu^-cyclodextrin, maltodexirin. Tac giaChoi H.S va cong su [12], khi nghien ciiu cac ciu tii trong tinh diu ciia qua thugc ho citrus cho rang, cac cau tu co nhom c'hirc andehit dong vai tto la chit tao mui chu lh6 va cac ciu tii co nhom chiic este dong vai tro la chat khuech tan.
+ Xac dinh mui ciia phan doan 2: . DS khing dinh phan doan 2 co phai la phan doan tao mui thom dac trong cho tinh dau v6
qua quyt Lang Son hay khong, sii dung phep thu A-khong A, nhim xac dinh mui ciia phan dop
tinh diu vo quyt Lang Son tach chiet bing dung moi n-hexan va dietyl ete voi mui ciia tmh dau
vd qua quyt Lang Son duoc tach chiet bing phuang phap ep lanh Ket qua thu duoc, trinh bay a
Bang 4.
Nghien cuu tdch chiet nhom cdu id tao huong vd xdc dinh hogt linh sinh hpc ciia chiing trong tmh ddu..
Bdng 4. Tdng hap kit qud trd ldi cua nhom ngudi thii- tren mdu phan dogn 2 IVIau gioi
thieu
A Khong A
Tong
Nguoi thu lu-a chon A
Gia tri quan sat
6 8 14
Gia tri li thuyet 7 7 14
Khong Gii tri quan sat
6 4 10
A Gia tri li thuyet 5 5 10
Tong
12 12 24
: Q -
Gia tri X tinh toan dugc nho han gia tri X^|,= 3,84 a mue y nghTa a la 5%. Dieu nay kel luan rang nguori thii d a khong phan biet dugc miii ciia phan doan tinh d i u vo quyt Lang Son tach chiet b a n g dung moi n-hexan va dietyl ete vai miii ciia tinh d i u vo qua quyt Lang S a n duae tach chifit b&ng p h u a n g phap ep lanh (tinh dau vd qua quyt d u g c tach chigt bSng p h u a n g phap ep lanh gpi la mau chuan. vi p h u a n g phap nay duoc ep c a hgc trong moi truang lanh. do do giu dugc miii diic trung ciia tinh dau vo qua quyt Lang San). Phan doan tinh d t u tach chiet b i n g dung moi H-hexan va dietyl ele eo mui giong mui cua tinh dau vo qua quyl Lang San tach chiSt bang p h u a n g phap ep lanii.
- Phdn dogn 3.
-+ Xac dinh cac cau t u trong phan doan 3 :
Bdng 5. Cdc cdu tu trong phdn dogn 3
stt
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ten cac can tir octanol terpinene-4-ol a-terpineiol decanol
^-citronellol geraniol nerol periUyl alcohol cedrenol nonanoic acid cM-geranio!
/ranj-geraniol thylmol piperitone men thone
Thoi gian liru (phiit) 3.024 4,863 6,847 7,118 7,652 7,843 8,377 9,928 12,127 13,942 14,541 14,897 14,985 16,786 17,125
Ti 11 (%) 15,06 5,42 6,53 6.68 13,12
1,08 9,87 5,56 7,34 3,84 1,89 3,81 5,47 5,72 5,26
Nguyen Van Loi
Bang phuang phap GC-MS da xac dmh duge 15 cau lu trong phan doan tinh dau vo qua quyt Lang San tach ehiet bang dung moi dietyl ete (phan doan 3). Phan doan nay eo mau vang nhat va trong suot. kel qua dugc trinh bay a Bang 5.
..L-.,IilLl_..l .liJi
Hinh 4. Sac ki dd cdc cdu tu trong phdn dogn 3
Ket qua nghien ciiu trong Bang 5 cho thay dS xac dinh dugc 15 ciu tii trong phan doan 3, trong do nhom ancol co 12 cau tii chiem 81,83%, nhom axit co 1 cau tu chiem 3,84% va nhdm xeton CO 2 cau tir chiem 10,98%.
+ Xac dinh miii ciia phan doan 3:
De xac dinh miii ciia phan doan 3, xet cac cap mau theo phuang phap A khong A, ket qua dugc the Men a Bang 6.
Bdng 6. Tdng hop ket qua trd ldi cua nhdm nguai thu tren mau phan dogn 3 Mau gioi
thieu
AKhong A
Tong
Nguoi thu Iva ch^n Gia tri
quan sat
10 4 14A Gia tri li thuyet
7 7 14
Kh Gia tri quan sat
2 8 10
jngA Gia trj li thuyet
5 5 10Tong
12 12 24
' (Q-T)^
Gia tri X" tinh loan dugc Ion han gia tri X^;,= 3,84 a mire y nghTa a la 5%, Dilu do ket lu^n rang nguai thir da phan bipt dugc hai mau A va khong A. Co nghTa la phan doan 3 (tach chiet bang dung moi dielyl ele) khong co miii giSng miii ciia tinh dau vd qua quyt L^ng Son tach chiet bang phugng phap ep lanh.
2.2.2. Xac dinh hoat tinh sinh hoc ciia nhom cSu tii' tao huang
- Xdc dinh khd nang quel gdc tu do DPPH eda nhdm cdu tu tao huang
Kha nang quel goc ly do DPPH cua nhom cau Hi tao huang Irong phan doan 2 ciia linh dau vd qua quyt Lang Son duge thue hien lai phong thi nghiem Truang Dai hpc Cong nghiep Ha Npi.
Ket qua dugc trinh bay d Bang 7
Nghien ciiu tdch chiet nhom cdu td tao huang vd xdc dinh hoat tinh sinh hpc cua chiing trong linh ddu..
stt 1 2
Bdng 7. Khd ndng quel gdc tu do DPPH ciia nhom cdu tit tqo hu-ffng trong linh ddu vii qud quyt Lgng Son
IMau thi nghi£m Nhom cau ni lao huong Vitamin C
Khdi luong (mL) 0,1 0,1
% quet goc tu do DPPH 38,17 ±0,22 39,34 ±0,19
Ket qua nghien cuu trong Bang 7 cho thay nhom cau tii tao h u a n g trong tmh d i u vo qua quyt CO kha nang quel goc t u do DPPH nho hom vitamin C.Xdc dinh khd ndng khdng khudn cita nhdm cau tu tgo huang
X a c dinh kha nang k h a n g khuan cua nhom cau tii tao h u a n g trong linh diiu vo qua quyt Lang Son, tren cac chung vi sinh val kiem chung n h u sau: Staphylococcus aureus, Escherichia coli. Salmonella typhi va Bacillus cereus.
Bdng 8. Khd nang khdng khuan ciia nhdm cdu tu tgo huang trong tinh dau vo qud quyt Lgng San
Stt
1 2 3 4
Chiing vi sinh vat Staphylococcus aureus Escherichia coli Salmonella typhi Bacillus cereus
Duomg kinh vong khang khuan (cm) 3,4
2,8 2,6 3,2
Ket qua trong Bang 8 cho thay nhom eau tu lao h u a n g trong tinh dau vd qua quyl Lang Son CO kha nang khang khuan tren cac chiing vi sinh vat kiem dinh. Theo tac gia Friedman M va cpng sir [10] eho rang d u a n g kinh vong Iron khang kliuan > 3,0 cm tlii dugc coi la khang khuan manh va d u o n g kinh vong tron khang khuan tir 2,0 - 2,9 cm thi dugc coi la khang khuan trung binh. Vay kha nang k h a n g k h u a n manh nhat ciia n h o m cau tii tao h u a n g trong tinh dau vo qua quyt L a n g S a n la doi vai chiing Staphylococcus aureus va Bacillus cereus.
3. Ket luan
Sii dpng p h u a n g phap sac ki col, he dung moi rua giai n-hexan/dietyl ele voi ti le the lich
=1/1 tir 4 mL linh dau vo quyl Lang S a n da tach chiet dugc 0,25 mL dich sanh dac mau vang dam. CO mill Iham dac trung (phan doan 2). Bang p h u a n g phap GC-MS da xac dinh d u g e 10 eau tiJr trong phan doan nay. trong do co 8 cau t u Ihupc nhom andehit (octanal, citronellal, decanal, neral, dodecanal, geranial, a-sinensal, ^-sinensal) chiem 87,72% va 2 eau tir thupc nhom este (linalyl acetate, geranyl acetate) chiem 11.22%. Kel hgp vdi p h u a n g phap danh gia cam quan A khong A da khSng dinh rang trong 3 phan doan thi phan doan 2 lach chiet bang he dung moi n- hexan va dietyl ele la phan doan co chua cac cau tir lao miii tham dac trung cua linh dau vo qua quyl L?ing Son. Ben canh do cung da xac djnh dtrgc mpt so hoat tinh sinh hpc ciia nhom cau Hi t^o hucmg trong'phan doan 2 nhu kha nang quel goc lu do DPPH (38,17 ± 0,22%) va kha nang khang khuan tren 4 chiing vi smh val kiem dinh: Staphylococcus aureus. Bacillus cereus.
Escherichia coli va Salmonella typhi.
Nguyen Van Loi
TAI LIEU THAM KHAO
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ABSTRACT
Extraction and biological activity of the group of flavoring constituents in Lang Son tangerine peel oil
N g u y e n Van Loi Hanoi University of Industry, Mmh Khai. Hanoi The Lang Son tangerine peel oil (4 mL) was subjected to column chromatography over silica gel, eluted with n-hexane-dielhyl ether solution (ratio 1:1. v/v) to afford 0.25 m L o f a dark yellow tangerine-odour fraction 2. By GC-MS method was obtained thai this fraction contains len main constituents.'including octanal. citronellal. decanal, neral, linalyl acetate, dodecanal. geranial, a- sinensal, y?-sincnsal and geranyl acetate. They are identified as flavoring constituenls by "A-nol-A"
sensory analysis method. This group of components obtained a free radical scavenging activity DPPH (inhibited activity of 38.17 ± 0.22%) and a good resistance to 4 bacterial strains (Staphylococcus aureus. Bacillus cereus. Escherichia coli and Salmonella typhi).
Keywords: Biological activity, extraction, group of flavoring constituents, Lang Son langerme peel oil.
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