全 文 :2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
·综述·
*[通信作者] 耿頔,博士,讲师,研究方向:天然药物化学;E-mail:gengyiliang_ hqu@ 163. com
云实属植物的化学成分与生物活性研究进展
马轩1,耿頔1* ,易立涛1,翁连进1
(华侨大学厦门校区 化工学院,福建 厦门 361021)
[摘要] 查阅国内外相关文献,对 2005 年以来报道的云实属植物的化学成分及其生物活性进行综述。云实属
植物中含有萜类、黄酮类、甾体等多种化学成分,具有抗病毒、抗炎、抗疟疾、抗肿瘤等生物活性。
[关键词] 云实属;二萜化合物;生物活性
Advances in Research of Chemical Constituents and Biological Activity of Caesalpinia Plants
MA Xuan,GENG Di* ,YI Litao,WENG Lianjin
(College of Chemical Engineering,Huaqiao University,Xiamen 361021,China)
[Abstract] Objective:To summarize the chemical and pharmacological advances of genus Ceasalpiana
(Caesalpiniaceae)since 2005. Several classes of chemical compounds,such as flavonoids,diterpenoids,and steroids,have
been isolated from various species which were reported to show a wide range of pharmacological properties,including antiviral,
anti-inflammatory,antitumor and antimicrobial activities.
[Keywords] Caesalpinia;diterpenoids;biological activity
doi:10. 13313 / j. issn. 1673-4890. 2015. 5. 022
云实属(Caesalpinia L. )植物约有 120 ~ 150
个物种,为一多元属(polyphyletic)。东南亚是云
实亚科的一个分布中心,中国云实属植物有 20 个
物种,从热带到温带地区均有分布[1]。该属植物
有云实 Caesalpinia decapetala、苦石莲 Caesalpinia
minax Hance、苏木 Caesalpinia sappan L. 入药,多
作为民间用药,其根、皮、种子入药可用于治疗
发热、疟疾、风湿病等病症[2]。吴兆华等[2]对
2005 年之前报道的云实属化学成分及药理作用进
行综述,云实属植物部分化学成分表现出较强的
体外生物活性,具有广阔的应用前景和较大的研
究价值。本文对 2005 年以来有关云实属植物化
学成分和生物活性方面的报道进行综述,概括了
近年来云实属植物的研究概况,为其深入的研究
提供参考。
1 化学成分
目前对该属植物的研究,主要报道了二萜、黄
酮等化学成分。
1. 1 二萜类化合物
从该属得到 140 余个二萜类化合物,主要是
cassane 二萜和 norcassane 二萜。在 C. pulcherrima、
C. crista、C. sappan、C. minax 等植物中都有文献报
道[3-31],结构式如图 1 所示。
1. 2 黄酮类化合物
在 C. pulcherrima、C. millettii Hook. 、C. digyna
Rottler等植物中均发现了黄酮类化合物[32-41],结构
式如图 2 所示。
1. 3 其他
除了二萜类和黄酮类化学成分,在该属植物也发
现了其他类型的化合物[28,42-48],结构式如图 3所示。
2 生物活性
2. 1 抗炎、抗氧化活性
Min 等[35]从 C. sappan L 分离得到化学成分
protosappanin A、3-deoxysappanchalcone,以 RAW264. 7
·905·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
·015·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
·115·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
·215·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
图 1 云实属植物中的二萜类化合物
·315·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
图 2 云实属植物中的黄酮类化合物
图 3 云实属植物中的其他化合物
·415·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
巨噬细胞中脂多糖(LPS)诱导的一氧化氮(NO)产量
进行抗炎活性评价,表现出较强的抑制效果:IC50值
分别为 12. 5、8. 1 μmol·L -1。Yodsaoue Orapun等[27]
从 C. pulcherrima分离得到 pulcherrins K、L、M 等也
有潜在的抗炎活性。Hu Jun[46]研究了 C. sappan L.
干燥 心 材 95% 乙 醇 提 取 液,从 中 分 离 得 到
protosappanin A、B 和 brazilein,在体外均有较好的
抗氧化活性。
2. 2 抗肿瘤活性
Caesalpinolide A-E 均从热带云实豆中得到。
Caesalpinolide A和 B是差向异构体,抑制 MCF-7 乳
腺癌细胞系细胞增殖的半数抑制浓度(IC50)值分别
为 12. 8、6. 1 μmol·L -1,同时伴有抑制子宫内膜癌
和宫 颈 癌 细 胞 系 细 胞 增 殖 的 作 用。此 外,
Caesalpinolide D在对抗宫颈癌、前列腺癌和乳腺癌
细胞系细胞增殖方面也表现出较好的活性[10,13]。
Ma Guoxu 等[8] 从苦石莲种子中分离得到
Caesalpin A-H,Caesalpin A 表现出较强的抗恶性细
胞增生的活性:对 HepG-2 细胞的 IC50值为 4. 7 μmol
·L -1,对 MCF-7 细胞的 IC50值为 2. 1 μmol·L
-1。
2. 3 抗疟疾活性
Bonducellpins E-G 是从热带云实豆(C. bonduc)
种子乙酸乙酯溶性部位分离得到的。对耐多药菌株
K1 恶性疟原虫生长表现出较好的抑制活性,IC50值
分别为 1. 6、5. 8、3. 8 μmol·L -1[22]。
3 结论
云实属植物具有较好的生物活性,近些年主要
的研究方向集中在二萜类化合物上,并且报道了很
多具有较强生物活性的化学成分。需要继续深入进
行云实属植物化学成分的研究,探讨其抗肿瘤、抗
氧化、抗炎等方面的生物活性,提高云实属植物资
源的综合利用价值。
参考文献
[1] 李世晋,张奠湘,陈忠毅. 中国云实属植物分类学修订
[J].广西植物,2006,26(1) :8-12.
[2] 吴兆华,王立波,高慧媛,等. 云实属植物化学成分及药
理活性研究进展[J].中国现代中药,2007,9(2) :25-30.
[3] Roach J S,McLean S,Reynolds W F,et al. Cassane and
norcassane diterpenoids of Caesalpinia bonduc [J].
Heterocycles,2007,71(5) :1067-1073.
[4] Zhao P,Chen H Q,Wang H,et al. Four new cassane
diterpenes from the seeds of Caesalpinia minax[J].
Phytochemistry Letters,2013,6(4) :606-609.
[5] Kalauni S K,Awale S,Tezuka Y,et al. Methyl migrated
cassane-type furanoditerpenes of Caesalpinia crista from
Myanmar[J]. Chem Pharm Bull,2005,53 (10 ) :
1300-1304.
[6] Awale S,Linn T Z,Tezuka Y,et al. Constituents of
Caesalpinia crista from Indonesia[J]. Chem Pharm Bull,
2006,54(2) :213-218.
[7] Dickson R A,Houghton PJ,Hylands PJ,et al. Antibacterial
and antioxidant cassane diterpenoids from Caesalpinia
benthamiana [J]. Phytochemistry,2007,68 (10 ) :
1436-1441.
[8] Ma G X,Yuan J Q,Wu H F,et al. Caesalpins A-H,Bioactive
Cassane-Type Diterpenes from the Seeds of Caesalpinia
minax[J]. J Nat Prod,2013,76(6):1025-1031.
[9] Zhang J Y,Wu F H,Qu W,et al. Two new cassane
diterpenoids from the seeds of Caesalpinia sappan Linn[J].
Zhongguo Tianran Yaowu,2012,10(3) :218-221.
[10]Yadav P P,Arora A,Bid H K,et al. New cassane butenolide
hemiketal diterpenes from the marine creeper Caesalpinia
bonduc and their antiproliferative activity[J]. Tetrahedron
Lett,2007,48(40) :7194-7198.
[11]Yodsaoue O,Cheenpracha S,Karalai C,et al. Phanginin A-
K,diterpenoids from the seeds of Caesalpinia sappan Linn
[J]. Phytochemistry,69(5) :1242-1249.
[12]Ma G X,Xu X D,Cao L,et al. Cassane-type diterpenes from
the seeds of Caesalpinia minax with their antineoplastic
activity[J]. Planta Med,2012,78(12) :1363-1369.
[13] Yadav PP,Maurya R,Sarkar J,et al. Cassane Diterpenes
from Caesalpinia bonduc[J]. Phytochemistry,2009,70(2) :
256-261.
[14]Yan C,Ma L Y,Miao J H,et al. A new cassane diterpenoid
lactone from the seed of Caesalpinia minax[J]. Chin Chem
Lett,2009,20(4) :444-446.
[15]Li D M,Ma L,Liu G M,et al. Cassane diterpene-lactones
from the seed of Caesalpinia minax[J]. Chem Biodiversity,
2006,3(11) :1260-1265.
[16]Pranihanchai W,Karalai C,Pinglimanont C,et al. Cassane
diterpenoids from the stem of Caesalpinia pulcherrima[J].
Phytochemistry,2009,70(2) :300-304.
[17]Yin Y,Ma L,Hu L H,et al. Cassane-type diterpenoids from
the seeds of Caesalpinia magnifoliolata[J]. Helv Chim
Acta,2008,91(5) :972-977.
[18] Kiem PV,Minh C V,Huong H T,et al. Caesaldecan,a
cassane diterpenoid from the leaves of Caesalpinia
decapetala[J]. Chem Pharm Bull,2005,53(4) :428-430.
[19]Das B,Srinivas Y,Sudhakar C,et al. New diterpenoids from
Caesalpinia species and their cytotoxic activity[J]. Bioorg
Med Chem Lett,2010,20(9) :2847-2850.
[20]Yodsaoue O,Karalai C,Ponglimanont C,et al. Pulcherrins
D-R,potential anti-inflammatory diterpenoids from the roots
·515·
2015 年 5 月 第 17 卷 第 5 期 中国现代中药 Modern Chinese Medicine May 2015 Vol. 17 No. 5
of Caesalpinia pulcherrima[J]. Tetrahedron,2011,67(36) :
6838-6846.
[21]Cheenpracha S,Karalai C,Ponglimanont C,et al. Cassane-
type diterpenes from the seeds of Caesalpinia crista[J].
Helv Chim Acta,2006,89(5) :1062-1066.
[22]Pudhom K,Sommit D,Suwankitti N,et al. Cassane
Furanoditerpenoids from the Seed Kernels of Caesalpinia
bonduc from Thailand[J]. J Nat Prod,2007,70 (9) :
1542-1544.
[23]Wu Z H,Wang L,Gao H,et al. Neocaesalpin L1,a new
diterpenoid compound from Caesalpinia minax [J].
Zhongguo Zhongyao Zazhi,2008,33(10) :1145-1147.
[24] Cheng J,Roach J S.,McLean S,et al. Three new cassane
diterpenes from Caesalpinia pulcherrima [J]. Natural
Product Communications,2008,3(11) :1751-1754.
[25]Cota B B,Menezes O D,Pessoa de S E,et al. New cassane
diterpenes from Caesalpinia echinata[J]. Fitoterapia,2011,
82(7) :969-975.
[26]Cheenpracha S,Srisuwan R,Karalai C,et al. New
diterpenoids from stems and roots of Caesalpinia crista[J].
Tetrahedron,2005,61(36) :8656-8662.
[27]Yodsaoue O,Karalai C,Ponglimanont C,et al. Potential anti-
inflammatory diterpenoids from the roots of Caesalpinia
mimosoides Lamk[J]. Phytochemistry,2010,71(14-15) :
1756-1764.
[28]Ochieng C O,Manguro L A O,et al. Voulkensin C-E,new
11-oxocassane-type diterpenoids and a steroid glycoside
from Caesalpinia volkensii stem bark and their
antiplasmodial activities [J]. Bioorganic & Medicinal
Chemistry Letters,2013,23(10) :2088-3095.
[29]Zheng Y,Zhang S W,Cong H J,et al. Caesalminaxins A-L,
Cassane Diterpenoids from the Seeds of Caesalpinia minax
[J]. J Nat Med,2013,76:2210-2218.
[30]Wu J,Chen G,Xu X T,et al. Seven new cassane
furanoditerpenes from the seeds of Caesalpinia minax[J].
Fitoterapia,2014,92:168-176.
[31]Ma R J,Hu J M,Yang X Y,et al. Three New Cassane-Type
Diterpenes from Caesalpinia minax[J]. Helvetica Chimica
Acta,2012,97:1009.
[32]Cuong T D,Hung T M,Kim J C,et al. Phenolic compounds
from Caesalpinia sappan heartwood and their anti-
inflammatory activity[J]. J Nat Prod,2012,75 (12) :
2069-2075.
[33] Ata A,Gale E M,Samarasekera R. Bioactive chemical
constituents of Caesalpinia bonduc (Fabaceae) [J].
Phytochem Lett,2009,2(3) :106-109.
[34] Maheswara M,Siddaiah V,Venkata R C. Two new
homoisoflavonoids from Caesalpinia pulcherrima[J]. Chem
Pharm Bull,2006,54(8) :1193-1195.
[35]Min B S,Cuong T D,Huang T M,et al. Compounds from the
heartwood of Caesalpinia sappan and their anti-inflammatory
activity[J]. Bioorg Med Chem Lett,2012,22 (24) :
7436-7439.
[36]Das B,Thirupathi P,Rabikanth B,et al. Isolation,synthesis,
and bioactivity of homoisoflavonoids from Caesalpinia
pulcherrima[J]. Chem Pharm Bull,2009,57 (10):
1139-1141.
[37]Zhao H X,Bai H,Wang Y S,et al. A new homoisoflavan
from Caesalpinia sappan[J]. J Nat Med,2008,62(3) :
325-327.
[38] Chen P,Yang J. Flavonol galactoside caffeiate ester and
homoisoflavones from Caesalpinia millettii Hook.[J]. Chem
Pharm Bull,2007,55(4) :655-657.
[39]Fu L C,Huang X A,Lai Z Y,et al. A new 3-benzylchroman
derivative from Sappan Lignum(Caesalpinia sappan) [J].
Molecules,2008,13(8) :1923-1930.
[40]Roy S K,Agrahari U C,Gautam R,et al. Isointricatinol,a
new antioxidant homoisoflavonoid from the roots of
Caesalpinia digyna Rottler[J]. Nat Prod Res,2012,26(8) :
690-695.
[41]Xu N,Xu X D,Ma L Y,et al. A new homoflavonoid from the
seed of Caesalpinia minax Hance[J]. Chin Chem Let,
2010,21(6) :696-698.
[42]Wu Z H,Wang L B,Gao H Y,et al. New diterpene from the
seeds of Caesalpinia minax Hance[J]. Shenyang Yaoke
Daxue Xuebao,2008,25(12) :964-966.
[43]Zhang Q,Liu X T,Liang J Y,et al. Chemical constituents
from the stem of Caesalpinia decapetala[J]. Zhongguo
Tianran Yaowu,2008,6(3) :168-171.
[44]Nozaki H,Hayashi K I,Kido M,et al. Pauferrol A,a novel
chalcone trimer with a cyclobutane ring from Caesalpinia
ferrea Mart exhibiting DNA topoisomerase II inhibition and
apoptosis-inducing activity[J]. Tetrahedron Lett,2007,48
(47) :8290-8292.
[45]Shu S I,Deng A J,Li Z H,et al. Two novel biphenyl dimers
from the heartwood of Caesalpinia sappan[J]. Fitoterapia,
2011,82(5) :762-766.
[46]Hu J,Yan X L,Wang W,et al. Antioxidant activity in vitro
of three constituents from Caesalpinia sappan L. [J].
Tsinghua Science and Technology,2008,13(4) :474-479.
[47]Wang Z,Sun J Bo,Qu W,et al. Caesappin A and B,two
novel protosappanins from Caesalpinia sappan L. [J].
Fitoterapia,2014,92:280-284.
[48]Zhao M B,Li J,Shi S P,et al. Two New Phenolic Compounds
from the Heartwood of Caesalpinia sappan L. [J].
Molecules,2014,19:1-8.
(收稿日期 2014-09-21)
·615·