全 文 ：天然产物研究与开发 NatProdResDev2009, 21:608-611, 592
文章编号:1001-6880(2009)04-0608-05
　
　
　ReceivedMarch20, 2008;AcceptedMay5, 2008
　FoundationItem:ThisworkwassupportedbytheNationalNaturalSci-
enceFoundationofChina(30600780).
＊CorrespondingauthorTel:86-21-50806728;E-mail:dyzhu@mail.shc-
nc.ac.cn
肾茶化学成分的研究
谭俊杰 ,谭昌恒 ,陈伊蕾 ,蒋山好 ,朱大元＊
中国科学院上海生命科学研究院上海药物研究所 新药研究国家重点实验室 , 上海 201203
摘　要:从肾茶中分离得到 11个已知化合物 , 通过 NMR及 MS数据分析 , 分别鉴定为:5-羟基-6, 7, 4′-三甲氧基
黄酮(1), 5-羟基-6, 7, 3′, 4′-四甲氧基黄烷酮(2), orthosipholF(3), siphonolB(4), 白桦酯酸(5), 2α-羟基齐墩果
酸(6), 2α, 3α-二羟基-12-烯-28-齐墩果酸(7),委陵菜酸(8),蔷薇酸(9), 熊果酸(10)和胡萝卜甙(11)。其中 ,
化合物 2 ～ 9为首次从该植物中分离得到。
关键词:肾茶;唇形科;黄酮;二萜;三萜
中图分类号:R284.1;Q946.91 文献标识码:A
ChemicalConstituentsofClerodendranthusspicatus
TANJun-jie, TANChang-heng, CHENYi-lei, JIANGShan-hao, ZHUDa-yuan＊
StateKeyLaboratoryofDrugResearch, ShanghaiInstituteofMateriaMedica, ShanghaiInstitutes
forBiologicalSciences, ChineseAcademyofSciences, Shanghai201203 , China
Abstract:ElevencompoundswereisolatedfromtheCHCl3 fractionofthe95%ethanolextractofClerodendranthusspica-
tus(Thunb.)C.Y.Wu, whichwereidentifiedtobe5-hydroxy-6, 7, 4′-trimethoxyflavone(1), 5-hydroxy-6, 7, 3′, 4′-tetra-
methoxyflavanone(2), orthosipholF(3), siphonolB(4), betulinicacid(5), maslinicacid(6), 2α, 3α-dihydroxyolean-
12-en-28-oicacid(7), tormenticacid(8), euscaphicacid(9), ursolicacid(10)anddaucosterol(11)onthebasisof
spectralanalysis.Amongthem, compounds2-9 wereobtainedfromthetitleplantforthefirsttime.
Keywords:Clerodendranthusspicatus;Labiatae;flavone;diterpene;triterpene
Introduction
Clerodendranthusspicatus(Thunb.)C.Y.Wu, known
as“renaltea” or“maoxucao”, isapopularmedicinal
herbforthetreatmentofchronicnephritis, urinarylithi-
asis, hepatitis, jaundiceandbiliarylithiasisinSouth-
eastAsia[ 1] .Previousstudiesonthiswholeplantresul-
tedintheisolationofflavonoids, polyphenolicacids
andditerpenes[ 2-4] .Inthecourseofphytochemicalin-
vestigationonthewholeplants, weobtainedeleven
knowncompounds, comprisingtwoflavonoids:5-hy-
droxy-6, 7, 4′-trimethoxyflavone(1)and5-hydroxy-6,
7, 3′, 4′-tetramethoxyflavanone(2), twohighlyoxygen-
atedisopimarane-typediterpenes:orthosipholF(3)and
siphonolB(4), sixtriterpenes:betulinicacid(5),
maslinicacid(6), 3-epimaslinicacid(7), tormentic
acid(8), euscaphicacid(9)andursolicacid(10), as
welasdaucosterol(11).Amongthem, 2-9 werefirstly
obtainedfromthetitleplant.Here, wedescribetheiso-
lationandstructureelucidationoftheabovecom-
pounds.
Experimental
General
OpticalrotationsweremeasuredusingaPerkin-Elmer
341 polarimeter.UVspectrumwasconductedwithAgi-
lent1100 serieswithDADdetector.ESI-MSdatawere
obtainedwithaLCQ-Decamassspectrometer.NMR
spectrawererecordedonaVarianMercuryplus300or
BrukerDRX400 spectrometers, inwhichthechemical
shiftvalueswerereportedinppm(δ)andcouplingcon-
stants(J)weregiveninHz.ODS-Agel(Greenherbs
Science＆ TechnologyDevelopmentCo., Ltd., Bei-
jing, China), SephadexLH-20(PharmaciaBiotechAB,
Uppsala, Sweden)andSilicagel(200-300, 400 mesh)
wereusedforcolumnchromatography(CC)andprecoated
DOI :10.16333/j.1001-6880.2009.04.033
platesofsilicagel(HSGF254)(QingdaoHaiyangChem-
icalGroupCo., Qingdao)forTLC.
Plantmaterial
ThewholeplantsofC.spicatuswerecolectedinthe
southofYunnanProvince, China, inOctober2006, and
identifiedbyDr.JiHuangofourinstitute.Avoucher
specimen(No.06-10-05)wasdepositedinourlaborato-
ry.
Extractionandisolation
ThedriedandpowderedwholeplantsofC.spicatus(5
kg)wereextractedthricewith95% EtOH(40 L×3)at
roomtemperature.Theconcentratedextractwassus-
pendedinH2O(3 L)andpartitionedsuccessivelywith
petroleumether(PE, 60-90 ℃), CHCl3 , EtOAcandn-
BuOH(each3L×3).TheCHCl3 fraction(26.6g)was
repeatedlyisolatedoversilicagel(gradientPE-Me2CO,
CHCl3-Me2COandCHCl3 -MeOH), SephadexLH-20
(CHCl3 /MeOH 1∶3)andODS-A(CH3CN/MeOH/
H2O25∶25∶50※ 40∶40∶20)columnstogivecom-
pounds1(36 mg), 2(15 mg), 3(242 mg), 4(181
mg), 5(52 mg), 6(80 mg), 7(43 mg), 8(54 mg), 9
(33mg), 10(735mg)and11(61 mg).
Identification
5-Hydroxy-6 , 7, 4′-trimethoxyflavone(1)　C18 H16
O6 , yelowishpowder;UVλmaxnm:276, 330;1HNMR
(CDCl3 , 300 MHz)δ:12.78(1H, s, OH-5), 7.84
(2H, d, J=8.8 Hz, H-2′, 6′), 7.01(2H, d, J=8.8
Hz, H-3′, 5′), 6.58(1H, s, H-8), 6.54(1H, s, H-3),
3.97, 3.93, 3.90(each3H, s, MeO-6, 7, 4′).ESI-MS
(pos.)m/z:329.1([ M+H] +), 679.2([ 2M+Na] +)
.Thesedatawereidenticaltothosereported[ 5].
5-Hydroxy-6 , 7, 3′, 4′-tetramethoxyflavanone(2)　
C19H20O7 , lightyelowishpowder;[ α] 20D -33°(c0.135,
CHCl3);UVλmaxnm:296, 346;1HNMR(CDCl3 , 300
MHz)δ:11.87(1H, s, OH-5), 6.98(2H, m, H-2′,
6′), 6.90(1H, d, J=8.8 Hz, H-5′), 6.11(1H, s, H-
8), 5.35(1H, dd, J=13.3 , 3.0 Hz, H-2), 3.92,
3.90, 3.87, 3.84(each3H, s, MeO-6, 7, 3′, 4′), 3.11
(1H, dd, J=17.3, 13.3 Hz, H-3α), 2.79(1H, dd, J
=17.3, 3.0 Hz, H-3β).ESI-MSm/z:361.1([ M+
H] +), 743.2([ 2M+Na] +)(pos.), 359.0([ M-
H] -)(neg.)Thedataabovewereinagreementwith
theliterature[ 6] .
OrthosipholF(3)　C38H44O11 , whitepowder;[ α] 20D -
147°(c0.28, CHCl3);1HNMR(CDCl3 , 300 MHz)δ:
7.57(2H, dd, J=8.0, 1.0 Hz, H-2′, 6′), 7.47(2H,
dd, J=8.0, 1.0 Hz, H-2″, 6″), 7.44(1H, t, J=8.0,
1.0 Hz, H-4′), 7.31(1H, t, J=8.0, 1.0 Hz, H-4″),
7.20(2H, t, J=8.0 Hz, H-3′, 5′), 6.98(2H, t, J=
8.0 Hz, H-3″, 5″), 5.77(1H, dd, J=17.6, 11.0 Hz,
H-15), 5.63(1H, m, H-11), 5.53(1H, t-like, J=3.0
Hz, H-2), 5.28(1H, d, J=3.0 Hz, H-1), 4.98(1H,
d, J=3.0 Hz, H-3), 4.87(1H, d, J=17.6 Hz, H-
16), 4.70(1H, d, J=11.0 Hz, H-16), 4.23(1H, m,
H-7), 3.02(1H, d, J=3.0 Hz, H-9), 2.75(1H, dd, J
=15.2, 4.0 Hz, H-12), 2.68(1H, dd, J=13.0, 2.5
Hz, H-5), 2.22(1H, dd, J=15.2, 2.0 Hz, H-12),
2.03 and1.89(each1H, m, H-6), 1.82(3H, s, 2-
OCOMe), 1.50(3H, s, 3-OCOMe), 1.47(3H, s, H-
20), 1.25(3H, s, H-17), 1.12(3H, s, H-19), 0.99
(3H, s, H-18);13 CNMR(DEPT)(CDCl3 , 100 MHz)
δ:214.0(s, C-14), 170.7(s, 3-OCOMe), 170.1(s, 2-
OCOMe), 165.7(s, C-7″), 164.5(s, C-7′), 141.9(d,
C-15), 132.4(d, C-4′), 132.0(d, C-4″), 130.2(s, C-
1′), 130.0(s, C-1″), 129.6(2C, d, C-2′, 6′), 129.4
(2C, d, C-2″, 6″), 127.9(2C, d, C-3′, 5′), 127.6(2C,
609Vol.21 　　　　　　TANJun-jie, etal:ChemicalConstituentsofClerodendranthusspicatus　
Table1　 13CNMRdataof5-9(Pyridine-d5 , 100MHz)
5 6 7 8 9
1 39.3(t) 47.8(t) 42.8(t) 47.9(t) 42.9(t)
2 28.3(t) 68.6(d) 66.1(d) 68.6(d) 66.1(d)
3 78.1(d) 83.8(d) 79.3(d) 83.8(d) 79.4(d)
4 39.5(s) 39.8(s) 38.8(s) 39.8(s) 38.8(s)
5 55.9(d) 55.9(d) 48.8(d) 55.9(d) 48.8(d)
6 18.8(t) 18.9(t) 18.5(t) 19.0(t) 18.6(t)
7 34.8(t) 33.2(t) 33.2(t) 33.5(t) 33.5(t)
8 41.1(s) 39.8(s) 40.0(s) 40.4(s) 40.6(s)
9 51.0(d) 48.2(d) 48.0(d) 47.8(d) 47.6(d)
10 37.5(s) 38.5(s) 38.7(s) 38.5(s) 38.7(s)
11 21.2(t) 23.9(t) 23.9(t) 24.1(t) 24.1(t)
12 26.1(t) 122.5(d) 122.5(d) 127.8(d) 128.0(d)
13 38.6(d) 144.9(s) 144.8(s) 140.1(s) 139.9(s)
14 42.8(s) 42.2(s) 42.2(s) 42.1(s) 42.2(s)
15 30.3(t) 28.3(t) 28.3(t) 29.3(t) 29.2(t)
16 32.9(t) 23.7(t) 23.7(t) 26.4(t) 26.4(t)
17 56.6(s) 46.6(s) 46.6(s) 48.3(s) 48.3(s)
18 49.8(d) 42.0(d) 42.0(d) 54.6(d) 54.6(d)
19 47.8(d) 46.4(t) 46.4(t) 72.7(s) 72.7(s)
20 151.3(s) 31.0(s) 30.9(s) 42.4(d) 42.4(d)
21 31.2(t) 34.2(t) 34.2(t) 27.0(t) 26.9(t)
22 37.6(t) 33.2(t) 33.2(t) 38.5(t) 38.5(t)
23 28.7(q) 29.3(q) 29.5(q) 29.3(q) 29.4(q)
24 16.3(q) 16.9(q) 22.3(q) 17.7(q) 22.3(q)
25 16.4(q) 17.5(q) 16.6(q) 16.9(q) 16.6(q)
26 16.4(q) 17.7(q) 17.5(q) 17.3(q) 17.3(q)
27 14.9(q) 26.2(q) 26.1(q) 24.7(q) 24.6(q)
28 178.8(s) 180.1(s) 180.2(s) 181.0(s) 180.6(s)
29 109.9(t) 33.2(q) 33.2(q) 27.1(q) 27.1(q)
30 19.5(q) 23.7(q) 23.7(q) 16.8(q) 16.8(q)
d, C-3″, 5″), 113.1(t, C-16), 77.9(s, C-8), 76.1(d,
C-3), 71.7(d, C-1), 69.0(2C, d, C-7, C-11), 66.2
(d, C-2), 47.8(s, C-13), 43.9(s, C-10), 42.5(d, C-
9), 38.9(t, C-12), 37.4(s, C-4), 35.5(d, C-5),
27.9(q, C-18), 27.6(q, C-17), 23.3(t, C-6), 22.0
(q, C-19), 20.7(q, 2-OCOMe), 20.5(q, 3-OCOMe),
17.1(q, C-20);ESI-MS(pos.)m/z:699.3([ M+
Na] +)1375.6([ 2M+Na] +).Thesedatawerein
consistentwiththosereportedfororthosipholF[ 7] .
SiphonolB(4)　C38 H44 O12 , whitepowder;[ α] 20D -
141°(c0.155, CHCl3);1HNMR(CDCl3 , 300 MHz)
δ:7.63(2H, dd, J=8.0, 1.0 Hz, H-2′, 6′), 7.40
(2H, dd, J=8.0, 1.0 Hz, H-2″, 6″), 7.35(1H, t, J=
8.0, 1.0Hz, H-4′), 7.25(1H, t, J=8.0, 1.0 Hz, H-
4″), 7.11(2H, t, J=8.0 Hz, H-3′, 5′), 6.96(2H, t, J
=8.0 Hz, H-3″, 5″), 5.86(1H, dd, J=17.6, 10.6
Hz, H-15), 5.83(1H, t, J=2.8 Hz, H-11), 5.77
(1H, d, J=3.0 Hz, H-1), 5.54(1H, t, J=3.0 Hz, H-
610 NatProdResDev　　　　　　　　　　　　　　　　　　　　 　Vol.21
2), 5.05(1H, d, J=3.0 Hz, H-3), 4.86(1H, d, J=
17.6Hz, H-16), 4.58(1H, d, J=10.6 Hz, H-16),
4.35(1H, br.s, H-7), 4.35(1H, m, H-20), 4.21
(1H, dd, J=11.9, 4.0 Hz, H-20), 3.27(1H, d, J=
2.7 Hz, H-9), 2.91(1H, dd, J=15.7, 2.8 Hz, H-
12), 2.82(1H, dd, J=13.2, 2.2 Hz, H-5), 2.42
(1H, dd, J=15.7, 2.8 Hz, H-12), 2.24(1H, m, H-
6), 1.91(1H, m, H-6), 1.86(3H, s, 2-OCOMe), 1.58
(3H, s, 3-OCOMe), 1.39(3H, s, H-17), 1.10(3H, s,
H-19), 1.04 (3H, s, H-18);13 C NMR(DEPT)
(CDCl3 , 100 MHz)δ:215.4(s, C-14), 170.8(s, 2-
OCOMe), 170.6(s, 3-OCOMe), 165.9(s, C-7″),
165.2(s, C-7′), 142.5(d, C-15), 132.7(d, C-4′),
132.1(d, C-4″), 129.6(2C, d, C-2′, 6′), 129.4(2C,
s, C-1′, 1″), 129.3(2C, d, C-2″, 6″), 128.0(2C, d, C-
3′, 5′), 127.5(2C, d, C-3″, 5″), 112.7(t, C-16), 76.6
(s, C-8), 75.6(d, C-3), 70.3(d, C-11), 69.3(d, C-
1), 68.5(d, C-7), 67.3(d, C-2), 62.5(t, C-20),
49.1(s, C-10), 47.3(s, C-13), 44.6(d, C-9), 37.5
(s, C-4), 37.2(t, C-12), 36.3(d, C-5), 29.2(q, C-
17), 27.5(q, C-18), 23.5(t, C-6), 21.8(q, C-19),
20.7(q, 2-OCOMe), 20.6(q, 3-OCOMe);ESI-MSm/
z:715.3([ M +Na] +)1407.7([ 2M +Na] +)
(pos.), 691.6([ M-H] -)(neg.)Thedataabovewere
inagreementwiththeliterature[ 8] .
Betulinicacid(5)　C30H48O3 , whitepowder;[ α] 20D +
9°(c0.15, CHCl3);1HNMR(Pyridine-d5 , 300 MHz)
δ:4.96(1H, s, H-29α), 4.78(1H, s, H-29β), 3.53
(1H, m, H-19), 3.46(1H, m, H-3), 2.75(1H, m, H-
13), 2.64(1H, m, H-16β), 1.81(3H, s, H-30), 1.24
(3H, s, H-23), 1.08(3H, s, H-27), 1.07(3H, s, H-
26), 1.02(3H, s, H-24), 0.84(3H, s, H-25);13 C
NMR(DEPT)seeTable1;ESI-MSm/z:479.3([ M+
Na] +), 935.6([ 2M+Na] +)(pos.);455.4([ M-
H] -)(neg.).Thesedatawereidenticaltothoserepor-
ted[ 9] .
Maslinicacid(6)　C30H48O4 , whitepowder;[ α] 20D +
53°(c0.11 , pyridine);1H NMR(Pyridine-d5 , 300
MHz)δ:5.46(1H, br.s, H-12), 4.09(1H, m, H-2β),
3.39(1H, d, J=9.4 Hz, H-3α), 3.29(1H, dd, J=
13.5, 3.8 Hz), 1.27, 1.25, 1.07, 1.01, 0.99, 0.98,
0.93(each3H, s, H-23 toH-30);13CNMR(DEPT)
seeTable1;ESI-MSm/z:495.4([ M+Na] +), 967.8
([ 2M+Na] +)(pos.), 471.3([ M-H] -)(neg.)The
dataabovewereinagreementwiththeliterature[ 10] .
2α, 3α-Dihydroxyolean-12-en-28-oicacid(7)　C30
H48 O4 , whitepowder;[ α] 20D +71°(c0.13, pyri-
dine);1HNMR(Pyridine-d5 , 300 MHz)δ:5.49(1H,
br.s, H-12), 4.34(1H, m, H-2β), 3.80(1H, d, J=
2.2 Hz, H-3α), 3.31(1H, dd, J=13.8, 4.0 Hz),
1.30, 1.21, 1.05, 1.02, 1.00, 0.95, 0.93(each3H, s,
H-23toH-30);13CNMR(DEPT)seeTable1;ESI-MSm/
z:967.8([ 2M+Na] +)(pos.), 471.5([ M-H] -)(neg.)
Thesedatawereidenticaltothosereported[ 11, 12] .
Tormenticacid(8)　C30H48O5 , whitepowder;[ α] 20D -
16°(c0.13, pyridine);1HNMR(Pyridine-d5 , 300
MHz)δ:5.55(1H, br.s, H-12), 4.09(1H, m, H-2β),
3.37(1H, d, J=9.2Hz, H-3α), 3.03(1H, s, H-18),
1.69(3H, s, H-27), 1.41(3H, s, H-29), 1.24(3H, s,
H-23), 1.09(3H, d, J=6.1 Hz, H-30), 1.07(3H, s,
H-26), 1.06(3H, s, H-24), 0.98(3H, s, H-25);13 C
NMR(DEPT)seeTable1;ESI-MSm/z:511.4([ M+
Na] +), 999.8([ 2M+Na] +)(pos.), 487.8([ M-
H] -)(neg.)Thedataabovewereinconsistentwith
thosereportedfortormenticacid[ 10, 13].
Euscaphicacid(9)　C30H48O5 , whitepowder;[ α] 20D -
3°(c0.12, pyridine);1H NMR(Pyridine-d5 , 300
MHz)δ:5.56(1H, br.s, H-12), 4.29(1H, d, J=10.6
Hz, H-2β), 3.75(1H, br.s, H-3β), 3.02(1H, s, H-
18), 1.62(3H, s, H-27), 1.40(3H, s, H-29), 1.25
(3H, s, H-23), 1.09(3H, d, J=6.0 Hz, H-30), 1.09
(3H, s, H-26), 0.96(3H, s, H-24), 0.88(3H, s, H-
25);13 CNMR(DEPT)seeTable1;ESI-MSm/z:
511.4([ M+Na] +), 999.9([ 2M+Na] +)(pos.);
487.5([ M-H] -)(neg.)Thesedatawereidenticalto
thosereportedforeuscaphicacid[ 13] .
Ursolicacid(10)anddaucosterol(11)　Ursolicacid
(10)anddaucosterol(11)wereidentifiedbycomparing
theirspectraldata(including1HNMRandLC-ESI-
MS)withthoseofauthenticsamples.
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592 天然产物研究与开发　　　　　　　　　　　　　　　　　　　　 　Vol.21