Isolation and Identification of Chemical Constituents from

LIU Xi; WANG Yong; KUANG Xiao-dong; REN Gang; HE Xiao-ru; FENG Li-hua; WANG Bin; ZHOU Zhi-wang

doi:10.13422/j.cnki.syfjx.2018040056

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Isolation and Identification of Chemical Constituents from

更新时间：2024-01-04

- Isolation and Identification of Chemical Constituents from
- Chinese Journal of Experimental Traditional Medical Formulae Vol. 24, Issue 4, Pages: 56-65(2018)
- 作者机构：
- 作者简介：
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- DOI：10.13422/j.cnki.syfjx.2018040056
  CLC： R284.1
- Published：2018
- 稿件说明：
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LIU Xi, WANG Yong, KUANG Xiao-dong, et al. Isolation and Identification of Chemical Constituents from [J]. Chinese journal of experimental traditional medical formulae, 2018, 24(4): 56-65.
DOI：

LIU Xi, WANG Yong, KUANG Xiao-dong, et al. Isolation and Identification of Chemical Constituents from [J]. Chinese journal of experimental traditional medical formulae, 2018, 24(4): 56-65. DOI： 10.13422/j.cnki.syfjx.2018040056.

摘要

目的：研究波罗蜜属植物牛李Artocarpus nigrifolius枝条的化学成分。方法：采用硅胶，小孔树脂（MCI gel），LH-20羟丙基葡聚糖凝胶（Sephadex LH-20），ODS，HPLC等柱色谱分离手段，对牛李干燥枝条的95%乙醇提取物进行了系统的化学成分研究，根据化合物的理化性质及光谱数据鉴定其结构。结果：共分离了26个化合物，大部分为三萜类成分。包括16个三萜，2个降三萜，6个甾醇，1个苯甲醛衍生物和1个小分子胺类化合物。分别鉴定为20-hydroxy-4α，4β，14α-trimethyl-9β，19-cyclopregnane-3-one（1），1-（N-叔丁基）氨基丙酮（2），24-methylenecycloartanone（3），cyclolaudenone（4），24-methylenecycloartanol（5），4-羟基-3，5-二甲氧基苯甲醛（6），环桉烯醇（7），cycloart-23-ene-3β，25-diol（8），β-谷甾醇（9），3β，24，25-trihydroxycycloartane（10），（23E）-27-nor-3α-hydroxycycloart-23-en-25-one（11），3β-hydroxy-22，23，24，25，26，27-hexanordammarane-20-one（12），12-en-3β-hydroxy-olean-11-one（13），（24S）-cycloartane-24，25-diol-3-one（14），桦木酸（15），羽扇豆醇（16），α-香树脂醇（17），（22E）-25，26，27-trinor-3β-hydroxycycloart-22-en-24-al（18），3β-hydroxy-urs-11-en-13β，28-olide（19），11α-hydroxy-α-amyrin（20），3β-羟基豆甾-5，22-二烯-7-酮（21），7-ketositosterol（22），β-香树脂醇（23），（24S）-麦角甾-5-烯-3β，7α，二醇（24），7α-hydroxysitosterol（25）和7β-hydroxysitosterol（26）。结论：化合物1为新的环阿屯烷型C24降三萜，化合物2为首次以天然产物的形式从自然界中获得，化合物6，8，11，15~17，20，22和23均为首次从波罗蜜属植物中分离得到，其余化合物均为首次从桑科植物中分离得到。三萜类成分可能为牛李的抗肿瘤活性物质基础，值得进一步深入研究。

Abstract

Objective: To study the chemical constituents of Artocarpus nigrifolius of Artocarpus genus (Moraceae). Method: Compounds were isolated and purified by the normal phase silica gel

MCI gel

Sephadex LH-20

ODS

HPLC and other column chromatography separation methods. Their structures were identified by spectrascopic methods based on physicochemical properties. Result: Twenty-six compounds

including 16 triterpenoids

2 nortriterpenoids

6 steroids

1 benzaldehyde derivative and 1 amino compound

were isolated from the ethyl acetate fraction in 95% ethanol extract of Artocarpus nigrifolius. All of the above isolates were identified as 20-hydroxy-4α

4β

14α-trimethyl-9β

19-cyclopregnane-3-one (1)

1-(tert-butylamino)propan-2-one (2)

24-methylenecycloartanone (3)

cyclolaudenone (4)

24-methylenecycloartanol (5)

4-hydroxy-3

5-dimethxybenzaldehyde (6)

cycloeucalenol (7)

cycloart-23-ene-3β

25-diol (8)

β-sitosterol (9)

3β

25-trihydroxycycloartane (10)

(23E)-27-nor-3α-hydroxycycloart-23-en-25-one (11)

3β-hydroxy-22

27-hexanordammarane-20-one (12)

12-en-3β-hydroxy-olean-11-one (13)

(24S)-cycloartane-24

25-diol-3-one (14)

betulinic acid (15)

lupeol (16)

α-amyrin (17)

(22E)-25

27-trinor-3β-hydroxycycloart-22-en-24-al (18)

3β-hydroxy-urs-11-en-13β

28-olide (19)

11α-hydroxy-α-amyrin (20)

(22E)-3β-hydroxystigmasta-5

22-dien-7-one (21)

7-ketositosterol (22)

β-amyrin (23)

(24S)-methyl-5-cholestene-3β

7α-diol (24)

7α-hydroxysitosterol (25) and 7β-hydroxysitosterol (26)

respectively. Conclusion: Compound 1 is a novel cycloartane C24 nortriterpenoid

and compound 2 is reported as a naturally occurring compound for the first time. Compounds 6

15-17

22 and 23 are isolated from Artocarpus genus for the first time. Besides

all of the other compounds were isolated from Artocarpus genus for the first time. Triterpenoids may be the antitumor active components of A. nigrifolius

and is worth further study.

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