New Indole Glycosides from Aesculus chinensis var. chekiangensis and Their Neuroprotective Activities

The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glyc...

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Published inMolecules (Basel, Switzerland) Vol. 24; no. 22; p. 4063
Main Authors Zhang, Nan, Cao, Shijie, Huang, Weixing, Li, Pan, Kang, Ning, Ding, Liqin, Qiu, Feng
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 09.11.2019
MDPI
Subjects
Acids
Aesculus - chemistry
aesculus chinensis bge. var. chekiangensis (hu et fang) fang
Cell Line, Tumor
Cytotoxicity
Glucose
Glycosides - pharmacology
HCT116 Cells
Hep G2 Cells
Humans
Indoles - pharmacology
Medicine, Chinese Traditional - methods
n-glucosylated indoles
neuroprotective activity
Neuroprotective Agents - pharmacology
Nitrogen
Plant Extracts - pharmacology
Traditional Chinese medicine
United States > US
N-glucosylated indoles
neuroprotective activity
Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang
Online AccessGet full text
ISSN1420-3049
1420-3049
DOI10.3390/molecules24224063

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Abstract The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides (1–6) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus. Structures of the new compounds (1–6) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1–5 and 9–10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1–10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC50 > 50 μM).
AbstractList The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called "Suo Luo Zi", have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides (1-6) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus. Structures of the new compounds (1-6) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1-5 and 9-10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1-10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC50 > 50 μM).The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called "Suo Luo Zi", have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides (1-6) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus. Structures of the new compounds (1-6) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1-5 and 9-10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1-10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC50 > 50 μM).
The dried seeds of Bge. var. (Hu et Fang) Fang, called "Suo Luo Zi", have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides ( - ) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of . Structures of the new compounds ( - ) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds - and - exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates - on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC > 50 μM).
The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides (1–6) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus. Structures of the new compounds (1–6) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1–5 and 9–10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1–10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC50 > 50 μM).
The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides ( 1 – 6 ) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus . Structures of the new compounds ( 1 – 6 ) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1 – 5 and 9 – 10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1 – 10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC 50 > 50 μM).
The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called "Suo Luo Zi", have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides (1−6) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus. Structures of the new compounds (1−6) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1−5 and 9−10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1−10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC50 > 50 μM).
Author Cao, Shijie
Kang, Ning
Zhang, Nan
Huang, Weixing
Ding, Liqin
Qiu, Feng
Li, Pan
AuthorAffiliation 2 Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; caoshijie@tjutcm.edu.cn
1 School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; 13373750625@163.com (N.Z.); satellitehuang@163.com (W.H.); a_pan_18@126.com (P.L.); kangndd@163.com (N.K.)
AuthorAffiliation_xml – name: 2 Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; caoshijie@tjutcm.edu.cn
– name: 1 School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; 13373750625@163.com (N.Z.); satellitehuang@163.com (W.H.); a_pan_18@126.com (P.L.); kangndd@163.com (N.K.)
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Keywords N-glucosylated indoles
neuroprotective activity
Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang
Language English
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Snippet The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine....
The dried seeds of Bge. var. (Hu et Fang) Fang, called "Suo Luo Zi", have been used in traditional Chinese medicine. Nevertheless, most studies have been...
The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called "Suo Luo Zi", have been used in traditional Chinese medicine....
The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine....
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StartPage 4063
SubjectTerms Acids
Aesculus - chemistry
aesculus chinensis bge. var. chekiangensis (hu et fang) fang
Cell Line, Tumor
Cytotoxicity
Glucose
Glycosides - pharmacology
HCT116 Cells
Hep G2 Cells
Humans
Indoles - pharmacology
Medicine, Chinese Traditional - methods
n-glucosylated indoles
neuroprotective activity
Neuroprotective Agents - pharmacology
Nitrogen
Plant Extracts - pharmacology
Traditional Chinese medicine
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Title New Indole Glycosides from Aesculus chinensis var. chekiangensis and Their Neuroprotective Activities
URI https://www.ncbi.nlm.nih.gov/pubmed/31717579
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Volume 24
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