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鸡蛋花中化学成分及生物活性研究进展



全 文 :天然产物研究与开发 Nat Prod Res Dev 2011,23:565-570,589
文章编号:1001-6880(2011)03-0565-07
收稿日期:2009-12-08 接受日期:2010-05-20
* 通讯作者 Tel:86-013870886467;E-mail:luyzsu@ hotmail. com
鸡蛋花中化学成分及生物活性研究进展
洪 挺1,余 勃2,陆 豫2* ,邱声祥3
1南昌大学药学系,南昌 330006;2 南昌大学中德联合研究院,南昌 330047;3 中国科学院华南植物园,广州 510650
摘 要:本文对鸡蛋花植物的化学成分和生物活性进行综述,为该植物的进一步开发和利用提供科学依据。
关键词:鸡蛋花;化学成分;生物活性
中图分类号:Q946. 91;R284. 2 文献标识码:A
Advances in Studies on Chemical Compositions and
Biological Activities of Plumeria rubra
HONG Ting1,YU Bo2,LU Yu2* ,QIU Sheng-xiang3
1Department of Pharmacy of Nanchang University,Nanchang 330006,China;2Sino-German Joint Research Institute of
Nanchang University,Nanchang 330047,China;3Chinese Academy of Sciences South China Botanical Garden,Guangzhou 510650,China
Abstract:This review summarized the chemical constituents and biological activities for plant of Plumeria rubra,in order
to provide science evidence for further development and utilization of this plant.
Key words:Plumeria rubra;chemical constituents;biological activities
鸡蛋花(Plumeria rubra L. cv. Acutifolia)为夹竹
桃科的落叶小乔木,又名缅栀子,因其花瓣洁白,花
心淡黄,极似蛋白包裹着蛋黄因此得名。原产地在
南美洲,200 多年前就已经引入中国,主要在广东,
福建,广西,云南等地有栽培。夹竹桃科植物一般都
有毒性,但鸡蛋花提取液对大鼠无致畸作用[1],而
且干燥的花常用于入药,治湿热下疮,咳嗽等症,亦
能清热,润肺解毒,鲜花浸膏则可做食品香精和化妆
品,鸡蛋花还有延缓衰老和抗氧化作用[2-5]。在广东
等地区常炒食或泡茶,“五花茶”具有很好的治疗
“奇热”症,其中就含有鸡蛋花[6],鸡蛋花还可以制
作凉茶治疗妇科病[7]。本研究对其化学成分和生
物活性等方面的研究成果做系统概述,为开发和利
用该植物资源提供科学依据。
1 化学成分
鸡蛋花中含有多种化学成分,迄今从中已分离
并获得的有环烯醚萜类、三萜类、黄酮醇类、醇类、醛
类、脂肪酸类等成分。现结合中外文献对鸡蛋花植
物中的化学成分进行总结。
1. 1 环烯醚萜类成分
Brigitta E和 Karsten K等[8]从干燥的鸡蛋花树
皮中分离出鸡蛋花素 plumericin(1) ,异鸡蛋花素
Isoplumericin(2) ,并鉴定出其结构和立体构型(1S,
5R,8R,9R,10R) ,纠正了以前 Marinete SS 等错误的
鸡蛋花素(1a) ,异鸡蛋花素(2a)立体构型。Leonar-
dus BSK,Soefjan T等[9]从干燥的鸡蛋花树皮分离到
黄蝉花素 allamcin(3) ,黄蝉花定 allamandin(4) ,α-
allamcidin(5) ,β-allamcidin(6) ,香豆素鸡蛋花苷 13-
O-trans-p-coumaroylplumieride(7) ,15-去甲基鸡蛋花
苷 15-demethylplumieride(8)。关晔等[10]从鸡蛋花
的花中分离到两个新环烯醚帖类化合物(9,10) ,鸡
蛋花苷 plumieride(11)。Bina SS[11]等从鸡蛋花叶
中分离出 1α-鸡蛋花苷(1α-plumieride)。
1. 2 三萜类成分
Bina SS[12]等从鸡蛋花叶中分离到 3β-27-di-
hydroxy-urs-12-ene (12) ,3β-hydroxy-urs-30-p-E-hy-
droxy-cinnamoyl-12-en-28-oic acid (13 ) ,27-E-4-
hydroxycinnamoyloxybetulinic acid[13](14) ,熊果酸
ursolic acid(15) ,白桦脂酸 betulinic acid[14](16)和
β-香树脂素 β-amyrin[15](17)。Bina SS[11]等从鸡蛋
花的叶和茎中提取分离到 dammara-12,20(22)-Z-
dien-3-one(18) ,dammara-12,20(22)Z-dien-3β-ol
(19) ,olean-12-en-3β,27-diol(20) ,27-hydroxyolean-
urs-12-en-3-one(21) ,3β-hydroxy-27-Z-feruloyloxy-28-
DOI:10.16333/j.1001-6880.2011.03.039
表 1 鸡蛋花提取物抗肿瘤作用
Table 1 The anti-tumor of extractions of Plumeria rubra
化合物
Compound
ED50 /μg·mL-1
纤维肉瘤 黑色素瘤 乳癌 肺癌 结肠癌 KB细胞 小鼠白血病 P338
黄鸡蛋花 3. 4 0. 7 3. 5 3. 0 1. 3 4. 6 2. 5
黄蝉花素 3. 1 0. 9 0. 1 1. 2 0. 3 0. 3 0. 2
黄蝉花定 0. 8 0. 3 0. 4 0. 7 0. 3 0. 4 0. 2
2,5-二甲氧基苯醌 3. 4 2. 7 5. 2 1. 3 1. 4 3. 8 2. 5
鸡蛋花素 0. 2 2. 8 0. 4 0. 2 0. 1 0. 3 1. 2
鹅掌楸碱 8. 9 19 30 6. 0 16 6. 0 2. 4
2. 2 抑制 HIV病毒
在 2001 年,Kavita V和 Sanjay G[34]发现鸡蛋花
中的黄鸡蛋花素对 HIV 病毒逆转录过程有抑制作
用。后来 Ghee TT 和 Sangkook L 等[35]发现鸡蛋花
提取物黄鸡蛋花素对 HIV病毒有抑制作用[对 HIV-
1,IC50 = 98 μg·mL
-1(400 μM) ;HIV-2,IC50 = 87 μg
·mL-1(375 μM) ,其作用机理是抑制 HIV逆转录酶
即 DNA合成酶。以前化疗的药物都是针对 DNA的
机制,很少针对 DNA 合成酶,这样就使得化疗效果
不好。因为 DNA合成酶会使受损的 DNA又恢复正
常,而黄鸡蛋花素就是针对 DNA 合成酶的。DNA
合成酶具有修复受损 DNA 作用,其机理机理为:
DNA合成酶(Ligase)+ ATPligase-AMP + PPi,Lig-
ase-AMP + nicked DNA (or other substrates) lig-
ase-AMP-DNAsealed DNA + AMP + ligase
从中可知,如果 DNA 合成酶受阻,则可以加快
肿瘤细胞死亡。
2. 3 抗真菌作用
Egwaikhide PA[36]等发现鸡蛋花的花和叶的甲
醇提取物对化脓棒杆菌、粪链球菌、芽孢杆菌属等都
有很强的抑制作用。其鸡蛋花甲醇提取物见表 2。
表 2 鸡蛋花花和叶的甲醇提取物
Table 2 Methanol extracts of Plumeria rubra flower and leaf
部位
Part
提取率
Yield
单宁
Tannins
缩合单宁
phloba-
tannins
皂苷
Saponins
黄酮
Flavonoids
甾体
Streoids
三萜
Terpenoids
还原糖
Reducing
sugar
Carborry 生物碱Alkaloids
花 1. 5% + - - + - + + - +
叶 3. 16% + + + + + + + + +
+ = present - = absent
Mullika TC[37]等也发现鸡蛋花能治疗奈瑟菌引
起的淋病。Shokeen P等[38]也发现鸡蛋花叶的提取
物能治疗炎症、感染、皮肤病、发热和性传播疾病。
有关治疗淋病奈瑟菌情况见表 3,表 4,表 5。
表 3 受各种抗生素敏感的从临床分离的和世界卫生组织的淋病奈瑟球菌菌株
Table 3 Susceptibility of clinical isolates and WHO strains of Neisseria gonorrhoeae to various antibiotics
WHO strain /
clinical isolate
β-Lactamase
test PEN CFX SPM
TET
CDS test
NCCLS
method CIP NAL
WHO A -ve S S R Not TRNG S S S
WHO B -ve LS S S Not TRNG S S S
WHO C -ve LS S S Not TRNG R S S
WHO G -ve LS S S TRNG TRNG LS R
WHO K -ve R LS S Not TRNG R R R
WHO L -ve R LS S Not TRNG I R R
WHO O + ve R S R Not TRNG R LS
865 天然产物研究与开发 Vol. 23
1 -ve LS S S Not TRNG S R R
2 + ve R S S TRNG TRNG R R
3 -ve LS S S Not TRNG S LS R
4 -ve LS S S Not TRNG S R R
5 -ve LS S S TRNG TRNG R R
6 -ve LS S S Not TRNG S LS R
7 + ve R S S Not TRNG S R R
8 -ve LS S S Not TRNG LS R R
9 + ve R S S Not TRNG S R R
10 -ve S S S TRNG TRNG R R
11 -ve LS S S Not TRNG S R R
PEN,青霉素;CFX,头孢曲松;SPM,大观霉素;TET,四环素;CIP,环丙沙星;NAL,萘啶酸;CDS,calibrated dichotomous sensitivity;NCCLS,Na-
tional Committee for Clinical Laboratory Standards;S,sensitive;R,resistant;LS,less sensitive;I,intermediate;TRNG,tetracycline-resistant N. Gonorrhoe-
ae.
表 4 与青霉素比较抑制临床分离和世界卫生组织的淋病奈瑟球菌菌株
Table 4 Inhibition of various clinical isolates and WHO strains of Neisseria gonorrhoeae in comparison with penicillin
Plant part Less sensitiveb Sensitivec Highly sensitived
Plumeria rubra leaves
Clinical isolates 8 ,10,11 1 ,3,5,6 2,4 ,7 ,9
WHO strains A,B,C G K,L,O
P. rubra stem
Clinical isolates 3,6,8,10,11 1,4,5,9 2,7
WHO strains A,B,C G K,L,O
P. rubra stem bark
Clinical isolates 8,10,11 1,3,4,5,6,9 2,7
WHO strains A,B,G C K,L,O
b 1 ~ 50% inhibition,c 51 ~ 99% inhibition,d ≥100% inhibition.
表 5 与环丙沙星比较抑制临床分离和世界卫生组织的淋病奈瑟球菌菌株
Table 5 Inhibition of various clinical isolates and WHO strains of Neisseria gonorrhoeae in comparison with ciprofloxacin
Plant part Less sensitiveb Sensitivec Highly sensitived
Plumeria rubra leaves
Clinical isolates 无 1 ,3,6,7,8,9,11 2,4 ,5,10
WHO strains A,B,C,G,O 无 K,L
P. rubra stem
Clinical isolates 3,6,8,10,11 1,4,8,9,11 2,5,10
WHO strains A,B,C. G,O 无 K,L,
P. rubra stem bark
Clinical isolates 8,10,11 1,3,4,5,6,9 2,4,5,10
WHO strains A,B,C,G,O 无 K,L
b 1 ~ 50% inhibition,c 51 ~ 99% inhibition,d ≥100% inhibition.
2. 4 其它方面
鸡蛋花性甘平,具有治湿下痢,里急后重,又能
润肺解毒、止咳,预防防中暑等功效[2]。Ryan JC
等[39]发现鸡蛋花有治疗肺结核的作用。Elfahmi
等[32]发现它有抗疟疾,抗寄生虫,抗炎,镇痛等方面
的作用。
965Vol. 23 洪 挺等:鸡蛋花中化学成分及生物活性研究进展
3 展望
鸡蛋花由于其具有广泛的药理作用,因而具有
很大的潜在药用价值,这些年研究较多但在我国起
步比较晚。其所含有的环烯醚萜类化合物由于具有
很强的抗真菌和肿瘤活性作用而受到广泛关注,最
近又发现鸡蛋花具有治疗 HIV 作用。为促进其研
究还可以从以下几方面进行深入研究: (1)加大种
植面积,进行优良品质的筛选和培育,尽可能提高其
有效成分含量;(2)其化合物结构复杂,提取分离难
度大,所以提取分离方法还有待改进; (3)其化学合
成主要是手性难以保持,所以寻找新的化学合成方
法和路径很有必要; (4)其有效化学成分结构和药
物靶点之间的构效关系有待研究等。总之,这些问
题的解决对鸡蛋花的研究发展和利用有重大意义。
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985Vol. 23 李 勇等:海洋毒素研究进展