• Nghien CIFU - Ky thuat
Tong quan ve nhom hop chit allianpolyenylbenzen phan lap dtftfc tir chi Piper L., ho Ho tieu (Piperaceae)
Hoang Viet Dung'*, Do Quyen^ Nguyin Minh Chinh' 'HQC vien Qudny
^Tnrdng Dgi hgc Dirac Hd NQI E-mail: [email protected] Summary
A review on natural compounds of alkanpolyenylbenzene group isolated from Piper L. genus is presented. The compounds of this group are divided into 3 subgroups, including: propenylbenzen (34 compounds), polyprenylbenzen (42 compounds) and alkenylbenzen (14 compounds). Of them, many compounds possess interesting bioactivities, such as antiplatelet, antifungality, antioxidanee, cytotoxicity... Therefore, this group still remains promisingly potential in recovery of new pharmaceutical compounds and active structures in the coming future.
Keywords: Alkanpolyenylbenzene, propenylbenzene, polyprenylbenzene, alkenylbenzene. Piper L
0 $ t van dePiper L. Id chi Idn nhat trong sd cac chi thuge hg Ho tieu vd ia mOt trong nhi>ng ehi Idn nhat eua ngdnh thuc vdt hat kin. Chi ndy ed sd lugng khodng tren 1000 lodi va phdn bd rfing khap d khu vuc khi hgu nhigt ddi vd can nhigt ddi '^•^^.
Nh&ng khu vgc tren the gidi cfi sg phdn bd da dgng eua ehi Piper L. gdm cd: Nam My, Trung My, chau A. Theo kinh nghiem ddn gian, chi Piper L. dugc su dyng de Idm thude ehOa mgt sd benh nhu: viem dudng tifiu hfia, day byng khfi tifiu, vifim hgng, sdt, giam dau, bfinh thdp khdp, adu ehinh mifin dich... '^^, Theo thdng kfi, da cd khoang gan 100 lodi Piper L. dugc nghien cdu vd thdnh phan hda hgc vd tae dung duge ly. Ve hoa hgc, cdc nhdm hgp chat chinh trong chi nay gdm cd: amid, alkanpolyenylbenzen (APB), flavonoid, lignan, neolignan, terpen... vd cung da mgt bdi bdo tdng quan ve hda hgc dd cgp ddn mgt nhdm nhd cua nhfim hgp chat
^pgii9j J^Jy nhien, tdi tieu^^^' da xudt ban each day 17 nam, ke tir do den nay, da ed them nhieu efing trinh nghifin cdu vfi hda hgc chi Piper L.
dugc thuc hi$n. Bfin cgnh dfi, theo each phdn logi trong tdi ll§u'^^, nhdm propenylphenol chi la mOt nhfim nhfi trong nhdm APB ma chung tfii tdng quan d day. Vi vgy, ehung tfii thgc hifin n^i dung nay nhdm d p nhdt thfing tin de ed edi nhin
day du han ve nhdm hgp chat APB, mOt trong nhQ'ng nhdm hgp chdt chinh cOa ehi Piper L.
Nhom hgp chat alkanpolyenylbenzen
Tfin cua nhdm hgp ehat nay bdt ngudn tu cong thuc eau tgo eua nfi gdm cd phan nhdm the alkanpolyenyl gdn vdi nhdn thorn. Cdc ehdt thudc nhdm nay dugc ehia thanh 3 nhdm dudi ddy.
Nhom hgp chat co cdu t^o khung propenylbenzen
Nhdm hgp chat propenylbenzen duge chia thanh 2 nhdm nhd Id nhdm allylbenzen vd nhfim prop-1-en-1-yl-benzen. Cong thdc cdu tgo Chung cua 2 nhdm chi khac nhau d vj tri ndi dfii eua nhdm the propenyl. Qua tdng hgp tdi ligu, da ed 34 chdt thuge nhdm ndy dugc bao edo phan ldp td ehi Piper L. Trong dd, ed 24 ehdt thufic nhdm allylbenzen vd 10 chdt thuge nhfim
prop-1-en-1-ylbenzen E^2.I6,I9]Nhom hop chdt allylbenzen
Hinh 1: Ciu t^o khung allylbenzen
• Nghien C I J U - Ky thuat
Dge diem chung cOa cdc chat thude nhdm ndy Id:
- Nhdm thd R i , R2 vd R5 thudng Id -H, mfit sd it ede ehdt cfi R2 = R5 Id nhdm -OCH3.
- Nhfim the R3 va R4 thudng la nhfim -OH, - OCH3 hoge -OCOCH3.
- Mgt vdi chat thuge nhdm ndy ed R2 + R3 hoge R3 + R4 = -OCH2O-.
Mgt vdi v i du ve nhO-ng chat thufic nhdm nay d u g e gidl thifiu d bang 1.
Nam 2013, tde gid S. Chen va cgng s g da phdn lgp t u lodi P. taiwanense Lin & Lu 3 hgp chdt dimer mdi vdi ede monomer gidng nhau vd cd cau tgo id allylbenzen'^^. V i du: ehdt diallylcateehol (1) ed cdng thdc cau tgo nhu sau:
Nhom hg'p chat prop-1-en-1-yl-benzen
Hinh 2: Cau tao eua khung f^op-1-en-1-ylt}enzen Dge a d m chung cixa cdc chat thufic nhom nay Id:
- Nhfim thd Ri, R4 vd R5 thudng Id -H.
- Nhdm the R2 vd Ra cfi the la -H hoac - OCH3, mdt vdi chat eo Rz + R3 = -OCHzO-.
Mgt vdi v i dy ve nhung chat thuge nhdm nay d u g c gidi thigu d bang 2.
Cfi 3 hgp ehat thuge nhom ndy ed edng thue cdu tgo khdc so vdi ede chat eon lgl d vj tri nhdm the Rz vd R3, v i dy: chat (7S,8R)~4- hydroxy-4',7-epoxy-8,3'-neolignan-7'[E]-en (2) phdn l | p d u g e t u lodi P. regnelli (Miq.) C. DC.
cfi cau tgo nhu sau'^^':
Nhom hgp chat co ciu tao khung polyprenylbenzen
Hinh 3; Ciu tao cua khung polyprenylbenzen Da CO 42 hgp chat thuOc nhfim ndy d u g c bdo cao phan lap t u ehi Piper L. ^^''' ^°' ^'^' ^^'.
Nhung hgp chdt nay cd sd gdc prenyl thay ddi t u 1 dfin 4. Cae gdc prenyl ndi vdi nhau tao thanh maeh thdng vd d m^t sd chdt mgeh ndy d u g c gan thfim cdc nhdm the '^^'^^. Nhom thd gan vdi nhan tham thudng ggp nhat Id -OH vd - COOH, ddi khi la nhom -OCH3 vd hifim ggp mdt sd nhdm thd khdc nhu -COOCH3.
Mgt vdi vi dy ve nhiing chat thudc nhdm ndy d u g c gidl thifiu d bang 3.
Nhdm hgp chat alkenylbenzen khac Tir chi Piper L., da cd 14 ehat thuge nhom alkenylbenzen d u g c phdn ldp '^' ^' ^.
Hinh 4: Ciu tao eua khung alkenylbenzen Dde diem ehung ve cau tao hfia hgc cua nhom ndy Id cd nhdm the aikenyl thudng dgng mgeh thang vdi sd carbon thay ddi t u 5 ddn 14.
Mflt sd it cde ehat trong nhdm cfi cdu tgo nhom the aikenyl id gdc 2-methyl-but-1-en- 4-yl. Cdc nhdm thd edn lgi eua nhdn thom cd thd Id nhdm -OH, -OCH3, -COOH hogc-COOCHa.
Mgt vdi v i dy ve nhung ehdt thuge nhdm ndy d u g c gidi thi$u d bang 3.
TAP CHf DirOC HOC - 07/2013 (S6 447 NAM 53)
• Nghien CIFU - Ky thuat
Bang 1 : A/fgf sd hgp ehat ed cii
Ma Tin hgp chit 3 Chevibetol 4 Apiol 5 Myristicin R<
-H -H -H
1 tao khung allylbenzen Cau tnic Ri Rs R<
-H -OCH3 -OH -OCH3 -OCH2O-
-OCH2O- -OCH3 Rs H -OCH3
-H
Loai P. bettie L.
P. schmidtii Hook. f.
P. nigrum L [31 [11]
[19]
Bang 2: l^gt sd hop ehit ed ciu tao khung prop-1-en-1-yl-benzen
6 7 8
Ten hop chdt Pipermargin Isoelemicin Sarisan
R.
-H -H -H
Cau true Ri Rl
•O0H3 -OCH3 -H -OCH3
-OCHaO- R, -OCH3
-H -H
Rs -H -H -OCHs
Loai P. marginatum Jacq.
P. solmsianum C. DC.
P. guineense Th. & Sch.
TLTK [4] [13]
[191
Bang 3: l\/ldt sd hgp chat eo ciu tao khung polyprenylbenzen ,._ T- L ..-'.. Cau true
n R, Ri Rl R, 3-(3',7'-dimethyl-2',6--octadienyl)-
' 4-methoxy-benzoic acid ^ '"^"^ " " " " • ' ^ ° ° "
R, -H
Loar
P. aduncum L.
TLTK
[6] Methyl 4-hydroxy-3-(3'-methyl-2'
butenyl) benzoat -H -H -COOCH3 -H P. [14]
COOH COOCH;
Bang 4: Mpf sd hgp chat ed eau tao khung alkenylbenzen
TSn hop chat Ciu trdc
Aikenyl R, Gibbilimbol C
(±)-4-Hydroxy-3,5- bis(2-hydroxy-3- methyl-3-butenyl)
benzoic acid
-H P. gibbillmbum C. DC.
-C5H9O -OH -C5H9O -COOH - n P. glabratum Kunth
TAP CHi DirpCHQC - 07/2013 (S6 447 NAM 53>
% Nghien CCFU ~ Ky thuat
Ket lu|in
Kdt qud cCia nhij-ng nghifin euu ve thdnh phdn hfia hge ehi Piper L. cho thay mgt sg da dgng ve cdu tgo hda hgc eua cac nhdm hgp chat ehinh nfii ehung vd eua nhfim hgp chat APB ndi rieng. Da ed 90 chdt thuge nhdm hgp ehdt APB dugc phdn ldp, bao edo vd dugc chia thdnh 3 nhfim nhd gdm: nhdm propenylbenzen cd 34 chdt, nhdm polyprenylbenzen cd 42 ehat va nhom hgp chat alkenylbenzen khdc cd 14 ehat, CCing vdi nhfim hgp ehdt amid, nhdm hgp chat APB cung sd hi>u nhieu tde dung sinh hgc ddng quan tdm nhu: uc chd kdt tgp tieu cdu, khang nam, ehdng oxy hda... Vi vgy, nhdm hgp chdt ndy van an ehua nhidu tiem ndng trong qud trinh tim kidm hgp chdt eo hogt tinh sinh hgc cung nhu qud trinh tim kiem nhung khung cau tnic dan dudng dd tdng hgp thudc mdi, dge bigt khi tidn hdnh nghien euu vdi nhung loai mdi.
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"PhenylalkalCHds from Piper marginatum".
Phytochemistry. Vol. 38, No. 4,1381 - 1384.
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13. Roberto CO. Martins, Leandro R. Laton-e, Patricia Sartorelii, Massuo J. Kato (2000),
"Phenylpropanoids and tetrahydrofuran lignans from Piper solmsianum", Phytochemistry, 55, 843 - 846.
14. Rogelio Pereda-Miranda, Claude B. Bemard, Tony Durst, John Thor Amason et al (1997), "Methyl 4-Hydroxy-3-(3'-methyl-2'-butenyl) benzoate. Major Insecticidal Principle from Piper guanacastensis", J.
Nat. Prod., 60. 262-204.
15. Rosa Martha Perez Gutierrez, Adriana Maria Neira Gonzalez, Carlos Hoyo-Vadillo (2013),
"Alkaloids from Piper: A review of its phytochemistry and pharmacology", Mini-Reviews in Medicinal Chemistry, 13,163-193,
16. Si Chen, Hung-Yi Huang, Ming-Jen Cheng et al (2013), "Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities", Phytochemistry, 1 - 7.
17. Terrence P. Green, Edward M. Treadwell, David F. Wiemer (1999), "/Vrieianal, a prenylated benzoic add from Pper arieianum", J. Nat Prod-, 62, 367 - 368.
18. T. Ruegg, A l . Calderon, E, F. Queiroz (2006), "3- Famesyl-2-hydrD)qt)enzoic add is a new anti- He/co/jacterpyto/f compound from Piper mul^inen/ium", Joumal of Ethnophanriacology, 103,461 -467.
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unf ^ annnti ^cA AAH ^ X M 53)
