A new ent-clerodane diterpene from Detarium microcarpum Guill. & Perr. and its protective potential for osteoporosis
Copyright © 2022. Published by Elsevier B.V..
A new clerodane diterpene, named 6α-hydroxy-3,13E-clerodien-15-oic acid (1), together with a known clerodane diterpene (2), four known labdane diterpenes (3-6), a triterpenoid (7), a known steroid (8), and two benzenoid compounds (9 and 10) were isolated from Detarium microcarpum Guill. & Perr. The structures of all obtained compounds were determined by chemical properties and spectroscopic evidence, accompanied by comparisons with data in the literature. Electronic circular dichroism (ECD) was performed for compounds 1-4 to confirm the absolute configuration. Compounds 1-3 and 8-10 were evaluated for the protective effect on osteoblasts. Compound 1 was observed to increase the proliferation of dexamethasone (DEX)-treated MC3T3-E1 cells significantly at 1 μM, which was comparable with the positive control geniposide at 10 μM. The results were further confirmed by flow cytometry analysis. In addition, compound 1 increased the level of alkaline phosphatase (ALP) and mineralization in osteoblasts inhibited by DEX. Moreover, Compound 9 (vanillic acid) showed a pronounced inhibition (IC50 6.5 ± 0.6 μM) on reactive oxygen species (ROS) production, and 10 (4-O-methyl gallic acid) showed a good inhibition with IC50 as 103.3 ± 2.2 μM, compared with the standard drug ibuprofen (IC50 54.2 ± 9.2 μM). Besides, compounds 1-3 and 8-10 were non-cytotoxic against MCF-7, NCI-H460, Hela, and BJ cell lines.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2022 |
|---|---|
| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:160 |
|---|---|
| Enthalten in: |
Fitoterapia - 160(2022) vom: 03. Juli, Seite 105226 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Irshad, Rimsha [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Clerodane |
|---|
| Anmerkungen: |
Date Completed 21.06.2022 Date Revised 21.06.2022 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1016/j.fitote.2022.105226 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM34181430X |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM34181430X | ||
| 003 | DE-627 | ||
| 005 | 20231226012635.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2022 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.fitote.2022.105226 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1139.xml |
| 035 | |a (DE-627)NLM34181430X | ||
| 035 | |a (NLM)35659522 | ||
| 035 | |a (PII)S0367-326X(22)00104-6 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Irshad, Rimsha |e verfasserin |4 aut | |
| 245 | 1 | 2 | |a A new ent-clerodane diterpene from Detarium microcarpum Guill. & Perr. and its protective potential for osteoporosis |
| 264 | 1 | |c 2022 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 21.06.2022 | ||
| 500 | |a Date Revised 21.06.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2022. Published by Elsevier B.V. | ||
| 520 | |a A new clerodane diterpene, named 6α-hydroxy-3,13E-clerodien-15-oic acid (1), together with a known clerodane diterpene (2), four known labdane diterpenes (3-6), a triterpenoid (7), a known steroid (8), and two benzenoid compounds (9 and 10) were isolated from Detarium microcarpum Guill. & Perr. The structures of all obtained compounds were determined by chemical properties and spectroscopic evidence, accompanied by comparisons with data in the literature. Electronic circular dichroism (ECD) was performed for compounds 1-4 to confirm the absolute configuration. Compounds 1-3 and 8-10 were evaluated for the protective effect on osteoblasts. Compound 1 was observed to increase the proliferation of dexamethasone (DEX)-treated MC3T3-E1 cells significantly at 1 μM, which was comparable with the positive control geniposide at 10 μM. The results were further confirmed by flow cytometry analysis. In addition, compound 1 increased the level of alkaline phosphatase (ALP) and mineralization in osteoblasts inhibited by DEX. Moreover, Compound 9 (vanillic acid) showed a pronounced inhibition (IC50 6.5 ± 0.6 μM) on reactive oxygen species (ROS) production, and 10 (4-O-methyl gallic acid) showed a good inhibition with IC50 as 103.3 ± 2.2 μM, compared with the standard drug ibuprofen (IC50 54.2 ± 9.2 μM). Besides, compounds 1-3 and 8-10 were non-cytotoxic against MCF-7, NCI-H460, Hela, and BJ cell lines | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Clerodane | |
| 650 | 4 | |a Detarium microcarpum | |
| 650 | 4 | |a Diterpene | |
| 650 | 4 | |a ECD | |
| 650 | 4 | |a Labdane | |
| 650 | 4 | |a Osteoblast | |
| 650 | 7 | |a Diterpenes |2 NLM | |
| 650 | 7 | |a Diterpenes, Clerodane |2 NLM | |
| 650 | 7 | |a Reactive Oxygen Species |2 NLM | |
| 650 | 7 | |a Triterpenes |2 NLM | |
| 700 | 1 | |a Kabbashi, Ahmed Saeed Ali |e verfasserin |4 aut | |
| 700 | 1 | |a Salawu, Kayode Muritala |e verfasserin |4 aut | |
| 700 | 1 | |a Ur-Rehman, Aziz |e verfasserin |4 aut | |
| 700 | 1 | |a Cao, Yan-Gang |e verfasserin |4 aut | |
| 700 | 1 | |a Fayaz, Aneela |e verfasserin |4 aut | |
| 700 | 1 | |a Khan, Farooq-Ahmad |e verfasserin |4 aut | |
| 700 | 1 | |a Tul-Wahab, Atia |e verfasserin |4 aut | |
| 700 | 1 | |a Choudhary, M Iqbal |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Yan |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Fitoterapia |d 1948 |g 160(2022) vom: 03. Juli, Seite 105226 |w (DE-627)NLM106553100 |x 1873-6971 |7 nnns |
| 773 | 1 | 8 | |g volume:160 |g year:2022 |g day:03 |g month:07 |g pages:105226 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.fitote.2022.105226 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 160 |j 2022 |b 03 |c 07 |h 105226 | ||