Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities
Phytochemical investigation of the leaf extract of Uvaria grandiflora Roxb. ex Hornem led to the isolation and identification of two new highly oxygenated cyclohexenes, uvariagrandols A (1) and B (2), together with seven known compounds (3–9). Their structures were elucidated by spectroscopic method...
Saved in:
| Main Authors: | , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2025-01-01
|
| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844024173574 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1841526215937097728 |
|---|---|
| author | Virayu Suthiphasilp Moses Egoh Betangah Passakorn Teerapongpisan Narawadee Rujanapun Boonyanoot Chaiyosang Sarawut Tontapha Pakit Kumboonma Brian O. Patrick Raymond J. Andersen Rawiwan Charoensup Thidarat Duangyod Phunrawie Promnart Tharakorn Maneerat Surat Laphookhieo |
| author_facet | Virayu Suthiphasilp Moses Egoh Betangah Passakorn Teerapongpisan Narawadee Rujanapun Boonyanoot Chaiyosang Sarawut Tontapha Pakit Kumboonma Brian O. Patrick Raymond J. Andersen Rawiwan Charoensup Thidarat Duangyod Phunrawie Promnart Tharakorn Maneerat Surat Laphookhieo |
| author_sort | Virayu Suthiphasilp |
| collection | DOAJ |
| description | Phytochemical investigation of the leaf extract of Uvaria grandiflora Roxb. ex Hornem led to the isolation and identification of two new highly oxygenated cyclohexenes, uvariagrandols A (1) and B (2), together with seven known compounds (3–9). Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. The (1S,2S,3R,6S) absolute configuration of uvariagrandols A and B was established by the comparison of the experimental and calculated electronic circular dichroism (ECD). (+)-Grandifloracin (9) displayed cytotoxicity against SW480 and K562 cell lines with IC50 values of 154.9 and 60.9 μM, respectively. 6-Methoxyzeylenol (5) had α-glucosidase inhibitory activity with the IC50 value of 34.1 μM. |
| format | Article |
| id | doaj-art-a0ec3a7a38824985a677fd5f1d919f90 |
| institution | Kabale University |
| issn | 2405-8440 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj-art-a0ec3a7a38824985a677fd5f1d919f902025-01-17T04:50:55ZengElsevierHeliyon2405-84402025-01-01111e41326Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activitiesVirayu Suthiphasilp0Moses Egoh Betangah1Passakorn Teerapongpisan2Narawadee Rujanapun3Boonyanoot Chaiyosang4Sarawut Tontapha5Pakit Kumboonma6Brian O. Patrick7Raymond J. Andersen8Rawiwan Charoensup9Thidarat Duangyod10Phunrawie Promnart11Tharakorn Maneerat12Surat Laphookhieo13Department of Industrial Technology and Innovation Management, Faculty of Science and Technology, Pathumwan Institute of Technology, Bangkok, 10330, ThailandCenter of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, ThailandFuturistic Science Research Center, School of Science, Walailak University, Nakhon Si Thammarat, 80160, Thailand; Center of Excellence for Advanced Research in Future-Oriented Sciences (CEAR-FOS), Walailak University, Nakhon Si Thammarat, 80160, ThailandMedicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, ThailandNatural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, ThailandInstitute of Nanomaterials Research and Innovation for Energy, Khon Kaen University, Khon Kaen, 40002, ThailandDepartment of Applied Chemistry, Faculty of Science and Liberal Arts, Rajamangala University of Technology Isan, Nakhon Ratchasima, 30000, ThailandDepartments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, CanadaDepartments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, CanadaMedicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, ThailandMedicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, ThailandSchool of Science, Mae Fah Luang University, Chiang Rai, 57100, ThailandCenter of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, ThailandCenter of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; Corresponding author. Center of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.Phytochemical investigation of the leaf extract of Uvaria grandiflora Roxb. ex Hornem led to the isolation and identification of two new highly oxygenated cyclohexenes, uvariagrandols A (1) and B (2), together with seven known compounds (3–9). Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. The (1S,2S,3R,6S) absolute configuration of uvariagrandols A and B was established by the comparison of the experimental and calculated electronic circular dichroism (ECD). (+)-Grandifloracin (9) displayed cytotoxicity against SW480 and K562 cell lines with IC50 values of 154.9 and 60.9 μM, respectively. 6-Methoxyzeylenol (5) had α-glucosidase inhibitory activity with the IC50 value of 34.1 μM.http://www.sciencedirect.com/science/article/pii/S2405844024173574Uvaria grandifloraAnnonaceaeHighly oxygenated cyclohexenesα-Glucosidase inhibitory activityCytotoxicity |
| spellingShingle | Virayu Suthiphasilp Moses Egoh Betangah Passakorn Teerapongpisan Narawadee Rujanapun Boonyanoot Chaiyosang Sarawut Tontapha Pakit Kumboonma Brian O. Patrick Raymond J. Andersen Rawiwan Charoensup Thidarat Duangyod Phunrawie Promnart Tharakorn Maneerat Surat Laphookhieo Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities Heliyon Uvaria grandiflora Annonaceae Highly oxygenated cyclohexenes α-Glucosidase inhibitory activity Cytotoxicity |
| title | Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities |
| title_full | Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities |
| title_fullStr | Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities |
| title_full_unstemmed | Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities |
| title_short | Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities |
| title_sort | highly oxygenated cyclohexenes from the leaves of uvaria grandiflora roxb ex hornem and their cytotoxic and α glucosidase inhibitory activities |
| topic | Uvaria grandiflora Annonaceae Highly oxygenated cyclohexenes α-Glucosidase inhibitory activity Cytotoxicity |
| url | http://www.sciencedirect.com/science/article/pii/S2405844024173574 |
| work_keys_str_mv | AT virayusuthiphasilp highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT mosesegohbetangah highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT passakornteerapongpisan highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT narawadeerujanapun highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT boonyanootchaiyosang highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT sarawuttontapha highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT pakitkumboonma highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT brianopatrick highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT raymondjandersen highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT rawiwancharoensup highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT thidaratduangyod highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT phunrawiepromnart highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT tharakornmaneerat highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities AT suratlaphookhieo highlyoxygenatedcyclohexenesfromtheleavesofuvariagrandifloraroxbexhornemandtheircytotoxicandaglucosidaseinhibitoryactivities |