(<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids

The leaves of <i>Ginkgo biloba</i> have been used in treating freckles and effectively reducing cough and sputum in folk medicines. Recently, investigations into the correlation between ginkgo leaves and the proliferative activity of osteogenic differentiation have been conducted. Howeve...

Full description

Saved in:
Bibliographic Details
Main Authors: Se Yun Jeong, Kwang Ho Lee, Seon Hee Kim, Min Hye Yang, Gakyung Lee, Ki Hyun Kim
Format: Article
Language:English
Published: MDPI AG 2025-01-01
Series:Plants
Subjects:
Online Access:https://www.mdpi.com/2223-7747/14/2/261
Tags: Add Tag
No Tags, Be the first to tag this record!
_version_ 1832587620595531776
author Se Yun Jeong
Kwang Ho Lee
Seon Hee Kim
Min Hye Yang
Gakyung Lee
Ki Hyun Kim
author_facet Se Yun Jeong
Kwang Ho Lee
Seon Hee Kim
Min Hye Yang
Gakyung Lee
Ki Hyun Kim
author_sort Se Yun Jeong
collection DOAJ
description The leaves of <i>Ginkgo biloba</i> have been used in treating freckles and effectively reducing cough and sputum in folk medicines. Recently, investigations into the correlation between ginkgo leaves and the proliferative activity of osteogenic differentiation have been conducted. However, bioactive compounds that enhance osteogenesis or exhibit osteoporosis prevention from <i>G. biloba</i> have not been fully identified. Phytochemical investigation of the MeOH extract of <i>G. biloba</i> leaves led to the isolation and identification of a new biflavonoid glycoside, (<i>aS</i>)-glucosciadopitysin (<b>1</b>), along with five flavonoids (<b>2</b>–<b>6</b>), through LC/MS-guided isolation approach. The structure of the new compound <b>1</b> was elucidated by the spectroscopic methods, including 1D and 2D NMR analysis, as well as HR-ESIMS. The absolute configuration of sugar moiety was established through acid hydrolysis, followed by chemical derivatization reaction and the axial chirality arising from the biaryl system with substituents was determined by electronic circular dichroism (ECD) calculations. The isolated flavonoids (<b>1</b>–<b>6</b>) were tested for their effects on mesenchymal stem cell (MSC) differentiation at 20 μM using Oil Red O and alkaline phosphatase (ALP) staining. Ginkgetin (<b>2</b>) was further evaluated for osteogenic activity on C3H10T1/2 cells at concentrations of 1, 2.5, 5, and 10 μM for 10 days. ALP staining and RT-PCR assessed the gene expression of osteogenic markers ALP and osteopontin (OPN). Ginkgetin (<b>2</b>) demonstrated the strongest osteogenic activity, significantly increasing the expression of ALP (12.5-fold) and OPN (4.0-fold) at 10 μM, comparable to the positive control, oryzativol A. Ginkgetin (<b>2</b>) shows potential as a therapeutic agent for osteopenia by promoting osteogenesis in MSCs, suggesting its promising role in treating osteoporosis.
format Article
id doaj-art-073f20584b654342b45e31b659fafc4b
institution Kabale University
issn 2223-7747
language English
publishDate 2025-01-01
publisher MDPI AG
record_format Article
series Plants
spelling doaj-art-073f20584b654342b45e31b659fafc4b2025-01-24T13:46:59ZengMDPI AGPlants2223-77472025-01-0114226110.3390/plants14020261(<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of BioflavonoidsSe Yun Jeong0Kwang Ho Lee1Seon Hee Kim2Min Hye Yang3Gakyung Lee4Ki Hyun Kim5School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaResearch Institute, Sungkyun Biotech Co., Ltd., Anyang 14118, Republic of KoreaDepartment of Pharmacy, College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan 46241, Republic of KoreaDepartment of Integrative Biological Sciences and Industry, Sejong University, Seoul 05006, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaThe leaves of <i>Ginkgo biloba</i> have been used in treating freckles and effectively reducing cough and sputum in folk medicines. Recently, investigations into the correlation between ginkgo leaves and the proliferative activity of osteogenic differentiation have been conducted. However, bioactive compounds that enhance osteogenesis or exhibit osteoporosis prevention from <i>G. biloba</i> have not been fully identified. Phytochemical investigation of the MeOH extract of <i>G. biloba</i> leaves led to the isolation and identification of a new biflavonoid glycoside, (<i>aS</i>)-glucosciadopitysin (<b>1</b>), along with five flavonoids (<b>2</b>–<b>6</b>), through LC/MS-guided isolation approach. The structure of the new compound <b>1</b> was elucidated by the spectroscopic methods, including 1D and 2D NMR analysis, as well as HR-ESIMS. The absolute configuration of sugar moiety was established through acid hydrolysis, followed by chemical derivatization reaction and the axial chirality arising from the biaryl system with substituents was determined by electronic circular dichroism (ECD) calculations. The isolated flavonoids (<b>1</b>–<b>6</b>) were tested for their effects on mesenchymal stem cell (MSC) differentiation at 20 μM using Oil Red O and alkaline phosphatase (ALP) staining. Ginkgetin (<b>2</b>) was further evaluated for osteogenic activity on C3H10T1/2 cells at concentrations of 1, 2.5, 5, and 10 μM for 10 days. ALP staining and RT-PCR assessed the gene expression of osteogenic markers ALP and osteopontin (OPN). Ginkgetin (<b>2</b>) demonstrated the strongest osteogenic activity, significantly increasing the expression of ALP (12.5-fold) and OPN (4.0-fold) at 10 μM, comparable to the positive control, oryzativol A. Ginkgetin (<b>2</b>) shows potential as a therapeutic agent for osteopenia by promoting osteogenesis in MSCs, suggesting its promising role in treating osteoporosis.https://www.mdpi.com/2223-7747/14/2/261<i>Ginkgo biloba</i>NMR analysiselectronic circular dichroism (ECD) calculationsmesenchymal stem cellalkaline phosphatase
spellingShingle Se Yun Jeong
Kwang Ho Lee
Seon Hee Kim
Min Hye Yang
Gakyung Lee
Ki Hyun Kim
(<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids
Plants
<i>Ginkgo biloba</i>
NMR analysis
electronic circular dichroism (ECD) calculations
mesenchymal stem cell
alkaline phosphatase
title (<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids
title_full (<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids
title_fullStr (<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids
title_full_unstemmed (<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids
title_short (<i>aS</i>)-Glucosciadopitysin, a New Biflavonoid Glycoside from the Leaves of <i>Ginkgo biloba</i> and Osteogenic Activity of Bioflavonoids
title_sort i as i glucosciadopitysin a new biflavonoid glycoside from the leaves of i ginkgo biloba i and osteogenic activity of bioflavonoids
topic <i>Ginkgo biloba</i>
NMR analysis
electronic circular dichroism (ECD) calculations
mesenchymal stem cell
alkaline phosphatase
url https://www.mdpi.com/2223-7747/14/2/261
work_keys_str_mv AT seyunjeong iasiglucosciadopitysinanewbiflavonoidglycosidefromtheleavesofiginkgobilobaiandosteogenicactivityofbioflavonoids
AT kwangholee iasiglucosciadopitysinanewbiflavonoidglycosidefromtheleavesofiginkgobilobaiandosteogenicactivityofbioflavonoids
AT seonheekim iasiglucosciadopitysinanewbiflavonoidglycosidefromtheleavesofiginkgobilobaiandosteogenicactivityofbioflavonoids
AT minhyeyang iasiglucosciadopitysinanewbiflavonoidglycosidefromtheleavesofiginkgobilobaiandosteogenicactivityofbioflavonoids
AT gakyunglee iasiglucosciadopitysinanewbiflavonoidglycosidefromtheleavesofiginkgobilobaiandosteogenicactivityofbioflavonoids
AT kihyunkim iasiglucosciadopitysinanewbiflavonoidglycosidefromtheleavesofiginkgobilobaiandosteogenicactivityofbioflavonoids