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Chemical Constituents of Pedicularis tricolor (Scrophulariaceae)

三色马先蒿的化学成分研究


从玄参科三色马先蒿( Pedicularis tricolor) 全草的乙醇提取物中分离得到17 个化合物, 采用波谱方法鉴定了它们的结构。其中化合物1 (2, 3, 5-tirmethoxy-4-hydroxy-xanthone ) 是一个新的􏷥 酮, 命名为三色马先蒿酮A (pedicutricone A); 2 ( 8α-hydroxyl-4- carboxyl-5βH, 9βH- iridoid-1α-glycoside ) 是一个新的环烯醚萜苷, 命名为三色马先蒿苷A ( pedicutricoside A); 化合物3~17 为首次从该植物中分离得到。


全 文 :三色马先蒿的化学成分研究 ?
杨利荣1 , 熊 江2 , 谭宁华2
??
, 褚洪标2 , 徐 立3 , 李明扬1
( 1 西南大学园艺园林学院 , 重庆 400716; 2 中国科学院昆明植物研究所植物化学与西部植物资源持续利用
国家重点实验室 , 云南 昆明 650204; 3 西南大学农业部蚕桑学重点实验室 , 重庆 400716)
摘要 : 从玄参科三色马先蒿 ( Pedicularis tricolor) 全草的乙醇提取物中分离得到 17 个化合物 , 采用波谱方
法鉴定了它们的结构。其中化合物 1 (2 , 3 , 5-tirmethoxy-4-hydroxy-xanthone) 是一个新的?酮 , 命名为三色
马先蒿酮 A (pedicutricone A) ; 2 ( 8α-hydroxyl-4-carboxyl-5βH, 9βH- iridoid-1α-glycoside) 是一个新的环烯醚萜
苷 , 命名为三色马先蒿苷 A ( pedicutricoside A) ; 化合物 3~17 为首次从该植物中分离得到。
关键词 : 玄参科 ; 三色马先蒿 ; 三色马先蒿酮 A ; 三色马先蒿苷 A
中图分类号 : Q 946 文献标识码 : A 文章编号 : 0253 - 2700(2006)05 - 553 - 05
Chemical Constituents of Pedicularis tricolor (Scrophulariaceae) *
YANG Li-Rong
1
, XIONG Jiang
2
, TAN Ning-Hua
2 * *
, CHU Hong-Biao
2
,
XU Li
3
, LI Ming-Yang
1
(1 College of Horticulture and Landscape Engineering, Southwest University, Chongqing 400716 , China; 2 State Key Laboratory
of Phytochemistry and Plant Resources in West China, Kunming Instituteof Botany, Chinese Academy of Sciences,
Kunming 650204 , China; 3 The Key Sericultural Laboratory of Agricultureof Ministry,
Southwest University, Chongqing 400716 , China)
Abstract: To search for new bioactive constituents from Pedicularis tricolor , a new xanthone named pedicutricone A (1)
and a new iridoid named pedicutricoside A ( 2) , along with fifteen known compounds, were isolated from theethanol ex-
tracts of the whole plants of P . tricolor for thefirst time . Their structureswereelucidated based on spectroscopic methods,
includingtwo-dimensional nuclear magnetic resonance analysis .
Key words: Scrophulariaceae; Pedicularis tricolor; Pedicutricone A ; Pedicutricoside A
Pedicularis L ., as one of the largest genera of
angiosperm, comprises about 329 species in China
( Instituteof Botany, 1979) . Some species have been
used as herbs to treat diseases for a long time (J iangsu
New Medical College, 1977 ) . Many compounds were
isolated from Pedicularis ( Chu and Tan, 2006; Wu
et al , 2002 ) , and some of them showed biological
activities of antioxidation and antitumour ( Li et al ,
1995; Yang et al , 2001 ) . Phytochemical investiga-
tion of Pedicularis tricolor H .-M .has not been per-
formed until now . In this paper, we report our study
on the chemical constituents from the whole plants of
P . tricolor . A new xanthone pedicutricone A (1 ) and
a new iridoid pedicutricoside A (2 ) , alongwith fifteen
known compounds, namely viburtinal (3) (Godeau et
al , 1977 ) , 5 , 7 , 4′-trihydroxy-flavone ( 4 ) ( Owen
et al , 2003 ) , 5, 7 , 3′, 4′-tetrahydroxy-flavone ( 5)
(Owen et al , 2003) , 5 , 7 , 4′-trihydroxy-3′-methoxy-
云 南 植 物 研 究 2006 , 28 (5) : 553~557
Acta Botanica Yunnanica

?
?? ?Author for correspondence . Tel : 0871 - 5223800; Fax: 0871 - 5223800; E - mail : nhtan@mail .kib. ac. cn
Received date: 2006 - 04 - 07 , Accepted date: 2006 - 04 - 30
作者简介 : 杨利荣 (1974 - ) 女 , 博士研究生 , 主要从事植物生物工程及植物化学研究。 ?
Foundation item: This work was supported by the Foundation of ChineseAcademy of Sciences ( West Light Program) and theNational Natural Sci-
ence Foundation of China ( 30572258 )
flavone (6) (Wagner andChari , 1976) , 5 , 7 , 4′-tri-
hydroxy-3′, 5′-dimethoxy-flavone ( 7 ) ( Chung et al ,
2005) , 3 , 5 , 4′-trihydroxy-3′, 5′-dimethoxy-flavone-
7-O-β-D-glucopyranoside ( 8) ( Wu et al , 1997 ) , 3 ,
5, 4′, 5′-trtrahydroxy-3′-methoxy-flavone-7-O-β-D-glu-
copyranoside ( 9 ) ( Cioffi et al , 2002 ) , 3 , 5, 3′,
4′-trtrahydroxy-flavone-7-O-β-D-glucopyranoside ( 10 )
(Flamini et al , 1997; Yu and Yang, 2002 ) , 3β,
19α-dihydroxy-12-ursen-28-oic acid ( 11 ) ( Huang et
al , 1998 ) , actoside ( 12 ) ( Ers?z et al , 2002 ) ,
martynoside (13 ) (Wang and Jia, 1996) , methyl 3 ,
4-dihydroxybenzoate ( 14) (Luo et al , 2001) , benzyl
2-O-β-D-glucopyranosyl-β-D-glucopyranoside ( 15 )
(Okamura et al , 1981 ) , daucosterol (16) (Yang et
al , 1998 ) and β-sitosterol ( 17 ) ( Zhang et al ,
2002) , were isolated using several chromatographic
purificationsteps, includingSi gel , SephadexLH-20 ,
MCI , Rp18 column chromatography and preparation
HPLC on Rp18 fromthe ethanol extracts of whole pla-
nts of P . tricolor (Fig . 1) .
Fig . 1 Structureof compounds 1 - 13
Result and Discussion
Compound 1 was isolated as a yellow powder .
The molecular formula was established as C16 H14 O6 by
HR + TOF-MS ( m?z 303.0871 [M + H] + , calcd .
455 云 南 植 物 研 究 28 卷
303 .0868 ) , and which could be supported by evi-
dences from the DEPT experiment . The
1
H-NMR
spectrum showed existence of one hydroxyl group (δ
12 .77 , 1H , s ) , one 1 , 2 , 3-trisubstitution
benzene ring (δ7 .83 , 1H, d, J = 8 .1 Hz; 7 . 32 ,
1H, t, J = 8 .0 Hz; δ 7 .25 , 1H, d, J = 7 .8
Hz) , one isolated aromatic proton (δ6 .64 , 1H, s) ,
and three methoxyl groups (δ 4 .04 , 3 .98 , 3 .94 ) .
Deducting threemethoxyl groups in the13 C-NMR spec-
trum, one carbonyl group (δ 181 .1 ) and 12 carbon
atoms were left, which indicated that 1 was possessed
of the characteristic structure of C6 -C1 -C6 of xanthone
(Kijjoa et al , 2000 ) . In the HMBC spectrum, the
correlationsof H - 1 (δ 6 .64 , 1H, s) and H - 8 (δ
7 .83 , 1H, d, 8 . 0 ) with the carbonyl group (δ
181 .1 ) indicated that bothof C - 1 (δ90 .9 ) andC - 8
(δ116 .5) were unsubstituted . C - 2 , 3 , 4 , 5 must
be substituted by OMeor OH . Locations of these sub-
stituents were confirmed by the HMBC and ROESY ex-
periments . The cross - peaks of H - 1 (δH 6 .64) with
C - 2 (δC 160 .0) and C - 3 (δC 132 .0) , 2-OCH3 (δH
3 .98) with C - 2 , 3-OCH3 (δH 3 .94) with C - 3 , 5-
OCH3 (δH 4 .04) with C - 5 (δC 148 .2) in the HMBC
spectrum, and H - 1 with 2-OCH3 , H - 6 (δH 7 .25)
with 5-OCH3 in the ROESY spectrum revealed thatδC
56 .3 , 60 .8 and 56 .3 must be located at C - 2 , C - 3
and C - 5 , respectively . Therefore, hydroxyl group
must be at C - 4 . Based on above spectral analysis,
structure of 1 was assigned as 2 , 3 , 5-tirmethoxy-4-
hydroxy-xanthone, named pedicutriconeA , which is a
new compound .
Compound 2 was isolated as a brown sticky solid .
The molecular formula was established as C16 H24 O10 by
HR-TOF-MS ( m?z 375 .1292 [ M-H ] + , calcd .
375 .1291 ) . The1 H-NMR and 13 C-NMR spectrumda-
ta for 2 were typical for iridoid glycosides, and very
similar to those reported for mussaenosidic acid (Koba-
yashi et al , 1985 ) . The ROESY experiment dis-
played different relative configuration from mussaeno-
sidic acid . The correlations of H - 1 (δ 5 .44 , 1H,
d, J = 3 .6 Hz) with H - 9 (δ2 .21, 1H , m) and H
- 10 (δ1 .31 , 3H, s) , and H - 9 with H - 5 (δ3 .13
- 3 .39 , 1H, m) , suggested that H - 1 , H - 5 , H
- 9 and H - 10 were in the sameorientation (Fig . 1 ) .
According to the literature ( Chu and Tan, 2006) , the
chemical shift of C - 1 will be less than 100 if H - 5 is
inβ-orientation; but if H - 5 is inα-orientation, the
chemical shift of C - 1 will be over 100 . Hence, H -
1 , H - 5 , H - 9 and H - 10 are inβ-orientation be-
cause the chemical shift of C - 1 in 2 is 95 .2 . Thus,
2 was determined to be 8α-hydroxyl-4-carboxyl-5βH,
9βH-iridoid-1α-glycoside, named pedicutricoside A ,
which is a new compound .
Experimental
General Experimental Procedures Optical rotationswere
determined on a Horbia SEAP-300 polarimeter . IR spectra were
recorded onaBio-Rad FTS-135 spectrophotometer with KBr pelle-
ts . UV spectra were obtained on a Shimadzu 2401PC spectropho-
tometer . NMR experiments were performed on a Bruker AM-400
and aDRX-500 spectrometer . TMS was used as the internal stan-
dard . MS was recorded on a VG Auto Spec-3000 spectrometer .
Silica platefor TLC and silica gel ( 200 - 300 mesh) for column
chromatography were obtained from Qingdao Marine Chemical
Corporation (Qingdao, China) and Sepheadaex LH-20 (25 - 100
μm) fromPharmacia Fine Chemical Co ., Ltd ., Sweden) .
Plant materials Pedicularis tricolor H .-M .was collected
in Zhong Dian, Yunnan Province of China in August 2003 and
identified by Professor Wang Hong (Kunming Instituteof Botany,
Chinese Academy of Sciences) . The voucher specimen was de-
posited in theherbariumof KunmingInstituteof Botany, Chinese
Academy of Sciences .
Extraction and Isolation The dried whole plants ( 7 .4
kg) of P . tricolor were powdered and extracted with 95% EtOH
for four times (each oneweek) at roomtemperature . After evap-
oration to dryness under reduced pressure, 1 . 8 kg residue was
obtained, which was suspended in water andthen extracted suc-
cessivelywith petroleum ether ( 60 - 90℃ , 18 L ) and EtOAc
(25 L) . The EtOAc-soluble part (1 .0 kg) was chromatographed
on silicagel (5 . 0 kg) , elutedwith agradient CHCl3 -MeOH ( 20
∶1; 15∶1 ; 9∶1; 7∶3; 1∶1; each 8 L ) mixture to obtain 20
fractions (2 L each) . These fractions were combined into nine
major fractions (A1-A9) based onTLC behaviors . Each fraction
was chromatographed repeadlyover a silicagel ( 200 - 300 mesh)
column, Sephedax Sephadex LH-20 to yield 1 ( 6 mg) , 2 ( 13
mg) , 3 (17 mg) , 4 ( 13 mg) , 5 (12 mg) , 6 (9 mg) , 7 ( 25
5555 期 YANG Li-Rong et al: Chemical Constituents of Pedicularis tricolor
mg) , 8 (5 mg) , 9 ( 6 mg) , 10 ( 9 mg) , 11 (11 mg) , 12
(317 mg) , 13 (417 mg) , 14 (18 mg) , 15 ( 88 mg) , 16 ( 21
mg) . The petroleum ether-soluble part ( 164 g) was chromato-
graphed on silica gel ( 1 .5 kg) , eluting with a petroleum ether-
acetone ( 100∶0 ; 7∶3 ; 1∶1; 3∶7; 0∶100 ; each 8 L) mixture
to obtain5 fractions ( B1-B5 ) . B2 andB3 were separatedfurther
by CC on silica gel to yield 17 (407 mg) .
Compound 1 , C16 H14 O6 , yellow powder , [α]26D + 1.25°
( c 0 .59 , CHCl3 ) ; UVλmax ( CHCl3 ) nm: 204 , 254 , 273 ,
307 , 363 ; IR (KBr) νmax cm- 1 : 3425 , 2941 , 1659 , 1612 ,
1585 , 1497 , 1452 , 1433 , 1361 , 1318 , 1278 , 1232 ,
1198 , 1147 , 1107 , 993 , 901 , 792; 1 H-NMR and 13 C-NMR
spectral data see Table 1 ; HR + TOF-MS m?z: 303 .0871 [M
+ H ] + , calcd . 303 .0868 ; EI-MS m?z ( % ) : 302 [M ] +
(81) , 287 ( 100 ) , 273 ( 17) , 259 ( 83 ) , 244 ( 17 ) , 216
(32 ) , 188 (16) , 122 (24) , 107 (16) .
Table 1 13 C and 1 H-NMR spectral dataof compound 1
Carbon No .
HMQC
δC δH
1 ?H-1 H COSY HMBC ROESY
1 ?90 .9d 6 .64 (s) 2 [-OMe
2 ?160 .0s H-1 R, 2-OMe
3 ?132 .0s H-1 R, 3-OMe
4 ?153 .9s
4 ?a 153 .2s H-1
4b 146 ?. 0s H-6 , 8
5 ?148 .2s H-7 R, 5-OMe
6 ?115 .6d 7 v. 25 ( d, 7 . 8 ) H-7 H-8 5 [-OMe
7 ?123 .6d 7 ~. 32 ( t, 8 . 0 ) H-6 s, 8
8 ?116 .5d 7 v. 83 ( d, 8 . 0 ) H-7 H-6
8 ?a 121 .0s H-7
8b 104 ?. 2s H-1
9 ?181 .1s H-1 , 8
5 ?-OMe 56 .3q 4 .04 (s)
2 ?-OMe 56 .3q 3 .98 (s)
3 ?-OMe 60 .8q 3 .94 (s)
4 ?-OH 12 .77 (s)
Note: in CDCl3 , 500 MHz forδH & 125 MHz forδC ; δin ppm, J in Hz; TMS
Table 2 13 C and 1 H-NMR spectral dataof compound 2
Carbon No .
HMQC
δC δH
1 ?H-1 H COSY HMBC ROESY
1 n95 4. 2d 5 ?. 44 (1H , d, 3 . 6 ) H-9 H-3 r, 5 , 9 , 1′ H-6 sb , 7 , 9 , 10 , 1′
3 n151 G. 8d 7 ?. 39 (1H , s) H-1 r, 5
4 n113 K. 8s H-3 r, 5 , 6a, 6b, 9
5 n32 4. 0d 3 ?. 13-3 q. 39 (1H , m) H-6a, 6b, 9 H-1 r, 3 , 6 , 7 , 9 H-6 sa, 9
a: 2 7. 27 (1H , m) H-5 ?, 6b, 7 H-6 sb , 7
6 n30 <. 7t H-5 r
b: 1 ;. 47 (1H , m) H-5 ?, 6a, 7 H-6 sa
7 n40 <. 7t 1 ?. 71 (2H , t, 6 . 8 ) H-6a, 6b H-5 r, 6 , 9 , 10 H-1 s, 6a, 9 , 10
8 n80 9. 5s H-1 o, 5 , 6a, 6b, 7 , 9 , 10
9 n52 4. 3d 2 ?. 21 (1H , m) H-1 , 5 H-5 r, 6a, 6b, 7 , 10 H-1 s, 5
10 ?24 4. 6q 1 .31 (3H , s) H-7 r, 9 H-1 s, 7
11 ?171 K. 0s H-3 r, 5
1 a′ 99 4. 6d 4 ?. 67 (1H , d, 7 . 8 ) H-1 r
2 a′ 74 4. 7d 3 ?. 13-3 q. 39 (1H , m)
3 a′ 78 4. 2d 3 ?. 13-3 q. 39 (1H , m)
4 a′ 71 4. 6d 3 ?. 13-3 q. 39 (1H , m)
5 a′ 77 4. 9d 3 ?. 13-3 q. 39 (1H , m)
a: 3 7. 89 (1H , d, 11 i. 4)
6 a′ 62 <. 9t
b: 3 ;. 64 (1H , dd, 6 m. 1 , 11 S. 7 )
Note: in CD3 OD, 400 MHz forδH & 100 MHz forδC ; δ in ppm, J in Hz; TMS
Compound 2 , C16 H24 O10 , brown sticky solid; [α] 26D -
69 .9°( c 0 .29 , MeOH ) ; UVλmax (MeOH ) nm: 201 , 230;
IR (KBr) νmax cm- 1 : 3425 , 1680 , 1640 , 1384 , 1075; 1 H-
NMR and 13 C-NMR spectral data seeTable 2; HR-TOF-MS m?
655 云 南 植 物 研 究 28 卷
z: 375 .1292 [M-H ] + , calcd . 375 .1291 ; FAB-MS ( nega-
tive) m?z ( % ) : 375 [ M-H ] + ( 100 ) , 311 ( 12 ) , 219
(24 ) , 154 (18) , 127 (42) .
Acknowledgements: The authors are grateful to the members of
the analytical group in StateKey Laboratoryof Phytochemistry and
Plant Resources in West China, Kunming Institute of Botany,
Chinese Academy of Sciences, for the spectral measurements .
References:
于德 4泉 , 杨峻山 , 2002 . 分析化学手册 - 第七分册 ( 核磁共振
波谱分析 ) [M ] . 北京 : 化学工业出版社 , 838
中国 4科学院植物研究所 , 1979 . 中国植物志 [ M ] . 北京 : 科学
出版社 , 348
江苏 4新医学院 , 1977 . 中药大词典 [M ] . 上海 : 上海人民出版
社 , 286
Chu #HB , Tan NH , 2006 . Iridoid glycosides from Pedicularis dolicho-
cymba H .-M .[ J ] . Journal of Integrative Plant Biology, in press
Chun /g IM, HahnSJ , AhmadA , 2005 . Confirmation of potential herbi-
cidal agents in hulls of rice, Oryza sativa [ J ] . J Chem Ecol , 31
(6 ) : 1339—1352
Ciof ?fi G, D’Auria M, Braca A , et al , 2002 . Antioxidant and free-
radical scavenging activity of constituents of the leaves of Tachigalia
paniculata [ J ] . J Nat Prod, 65 (11 ) : 1526—1529
Ers? z T , Berkman MZ, Tasdemir D, et al , 2002 . Iriodid and pheny-
lethanoid glycosides from Euphrasia pectinata [ J ] . Turk J Chem,
26 : 179—188
Flam &ini G, Braca A , Cioni PL , et al , 1997 . Three new flavonoids
and other constituents from Lonicera implexa [ J ] . J Nat Prod,
60 : 449—452
Gode +au RP, Rossi JC , Fouraste I , 1977 . Methyl-4-formyl-7 cyclopenta
( c) pyrane isole apres hydrolyse acide de Viburnum tinus [ J ] .
Phytochemistry, 16 ( 5) : 604—606
Huan 2g CG ( 黄成 钢 ) , Chen YZ ( 陈 耀 祖 ) , Fan CS ( 范 春 升 ) ,
1998 . 13 C-NMR analysis of two natural pentacyclic triterpenic acids
[ J ] . J Zhejiang Univ ( Natural Sciences) ( 浙江大学学报 自然
科学版 ) , 32 (4) : 406—410
Kijj ?oa A , Gonzalez MJ , Pinto MMM, 2000 . Xanthones from Calophyl-
lum teysmannii var. inophylloide [ J ] . Phytochemistry, 55 ( 7 ) :
833—836
Koba ?yashi H , Karasawa H , Miyase T, et al , 1985 . Studies on the
constituents of Cistanchis herba . VI . Isolation and structure of a
new iridoid glycoside, 6-deoxycatalpol [ J ] . Chem Pharm Bull ,
33 ( 9) : 3645—3650
Li J ?( 李忌 ) , Zheng Y (郑云 ) , Zheng RL (郑荣梁 ) , et al , 1995 .
Antitumour effects of phenylpropanoid glycosides [ J ] . Chin Pharm
J (中国药学杂志 ) , 30 : 269—270
Luo ?XD ( 罗晓东 ) , Wu SH (吴少华 ) , Ma YB ( 马云保 ) , et al ,
2001 . Chemical constituents from Dysoxylumhainanense [ J ] . Acta
Bot Yunnan ( 云南植物研究 ) , 23 (3) : 368—372
Okam ?uraN , Yagi A , Nishioka I , 1981 . Studies on the constituents of
Zizyphi fructus . V . Structures of glycosides of benzyl alcohol ,
vomifoliol and naringenin [ J ] . Chem Pharm Bull , 29 ( 12 ) :
3507—3514
Owen ?RW, Haubner R , Mier W, et al , 2003 . Isolation, structure
elucidation and antioxidant potential of the major phenolic and fla-
vonoid compounds in brined olive drupes [ J ] . Food Chem Toxi-
col , 41 (5 ) : 703—717
Wagn ?er H , Chari VM, 1976 . 13 C-NMR-spektren natürlich vorkom-
mender flavonoide [ J ] . Tetra Lett, 21 : 1799—1802
Wang ?CZ ( 王长增 ) , J ia ZJ ( 贾 忠建 ) , 1996 . Iridoid, lignan and
phenylpropanoid glycosides from Pedicularis chinenesis [ J ] . J
LanzhouUniv ( Natural Sciences ) ( 兰 州 大 学学 报 自 然科 学
版 ) , 32 (2) : 64—68
Wu J B, Cheng YD, Su LL , 1997 . A flavonol c-glycoside from
Moghania macrophylla [ J ] . Phytochemistry, 45 ( 8 ) : 1727—
1728
Wu Z ?( 吴 臻 ) , Li FR ( 李 发 荣 ) , Yang JX ( 杨 建 雄 ) , 2002 .
Rsearches in Pedicularis L [ J ] . Lishizhen Medicine and Materia
Medica Research ( 时珍国医国药 ) , 13 : 305—307
Yang ?DJ (杨大坚 ) , Liu HY ( 刘红亚 ) , Li XZ ( 李新中 ) , et al ,
1998 . The constituents of Tetrastigma hemsleyanum Diels et Gilg
[ J ] . China J Chin Materia Med ( 中国中 药杂志 ) , 23 ( 7 ) :
419—420
Yang ?JX (杨建雄 ) , Tian JW ( 田京伟 ) , Li FR (李发荣 ) , 2001 .
Influence on antioxidative ability of Taibaishen in mice [ J ] .
Northwest Pharm J (西北药学杂志 ) , 16 : 209—211
Zhan ?gY (张艺 ) , Li WJ ( 李文军 ) , Meng XL ( 孟宪丽 ) , et al ,
2002 . The constituents of Pterocephalus hookeri ( C . B . Clarke)
Hoeck [ J ] . Journal of Chengdu University of Traditional Chinese
Medicine ( 成都中医药大学学报 ) , 25 (3 ) : 41—42
7555 期 YANG Li-Rong et al: Chemical Constituents of Pedicularis tricolor
〔上接 534 页〕
J( desiccation sensitive) seeds may be related to habitat . Seed Science Research, 6 : 175 - 182 .
12 . BFinchSavageWE , Blake PS, Clay HA , 1996 . Desiccation stressin recalcitrant Quercus robur L . seeds results in lipid peroxida-
tion and increased synthesis of jasmonates and abscisic acid . Journal of Experimental Botany, 47 (298) : 661 - 667 .
13 . @FinchsavageWE , Pramanik SK , Bewley JD, 1994 . The Expression of Dehydrin Proteins in Desiccation-Sensitive (Recalcitrant)
Seeds of TemperateTrees . Planta, 193 (4 ) : 478 - 485 .
14 . AFu JR , ZhangBZ, WangXP, et al ., 1990 . Physiological-Studies on Desiccation, Wet Storage and Cryopreservation of Recal-
citrant Seeds of 3 Fruit Species andTheir Excised Embryonic Axes . Seed Science and Technology, 18 (3 ) : 743 - 754 .
15 . @Kim HH, Yoon JW , Park SU , et al ., 2005 . Assessment of desiccation sensitivityof tea embryos for cryopreservation . CryoLe-
tters, 26 (4) : 269 - 276 .
16 . 9Leprince O, Buitink J , Hoekstra FA , 1999 . Axes and cotyledons of recalcitrant seeds of Castanea sativa Mill . exhibit contrasting
responses of respiration to drying in relation to desiccation sensitivity . Journal of Experimental Botany, 50 (338) : 1515 - 1524 .
17 . @Liang Y , Sun WQ, 2000 . Desiccation tolerance of recalcitrant Theobroma cacao embryonic axes: theoptimal drying rate and its
physiological basis . Journal of Experimental Botany, 51
18 . ?Li CR , Sun WQ, 1999 . Desiccation sensitivity and activities of free radical-scavenging enzymes in recalcitrant Theobroma cacao
seeds . Seed Science Research, 9 (3) : 209 - 217 .
19 . ?Obroucheva NV , Antipova OV , 2004 . The role of water uptake in the transition of recalcitrant seeds from dormancy to germina-
tion . Russian J ournal of Plant Physiology, 51 (6 ) : 848 - 856 .
20 . APammenter NW, Vertucci CW, Berjak P , 1991 . Homeohydrous (Recalcitrant) SeedsDehydration, TheState Of Water And Vi-
ability Characteristics In Landolphia-Kirkii . Plant Physiology, 96 (4 )
21 . seeds of Ekebergia capensis . Seed ScienceResearch, 8 (4 )
22 . @Pritchard HW , 1991 . Water Potential and Embryonic AxisViability in Recalcitrant Seeds of Quercus Rubra . Annals of Botany,
67 (1) : 43 - 49 .
23 . @Roberts EH, 1973 . Predicting the storage life of seeds . Seed Science and Technology, 1 : 499 - 514 .
24 . >Song SQ, Berjak P , Pammenter NW , et al ., 2003 . Seed recalcitrance: a Current Assessment . Acta Botanica Sinica, 45
(6) : 638 - 643 .
25 . 105 (2 ) : 193 - 198 .
26 . @Wesley Smith, J . Pammenter NW , Berjak P , et al . , 2001 . The effects of two dryingrates on the desiccation tolerance of em-
bryonic axes of recalcitrant jackfruit ( Artocarpus heterophyllus Lamk .) seeds . Annals of Botany, 88 : 653 - 664 .
相关网站 :
Ecological Flora Database: http:?www.york. ac.uk?res?ecoflora?cfm?ecofl?index. cfm
International society for seed science: http:?www. SeedSciSoc.org
International Seed Testing Association ( ISTA) : http:?www. seedtest.org?
MillenniumSeed Bank Project: http:??www. rbgkew.org.uk?msbp?index.html
Plant Micromorphology Bibliographic Database: http:??www. rbgkew.org.uk?data?kbd-redirect. html
Seed Information Database: http:?www. rbgkew. org.uk?data?sid?
Seedquest: http:??www.seedquest. com?
Seed Oil fOFA : http:??www.bagkf. de?sofa?
The American Society of Plant Physiologists: http:?www. aspb.org?
The seed biology palace: http:?www.seedbiology.de?
The seed site: http:?theseedsite. co.uk?
The Seed Biology Electronic MailingList: http:?www. css. cornell . edu?seedbio?seedbio. html
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