Eudesmane and Eremophilane Sesquiterpenes from the Fruits of Alpinia oxyphylla with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells

Abstract

Alpinia oxyphylla Miquel (Zingiberaceae) has been reported to show antioxidant, anti-inflammatory, and neuroprotective effects. In this study, two new eudesmane sesquiterpenes, 7α-hydroperoxy eudesma-3,11-diene-2-one (1) and 7β-hydroperoxy eudesma-3,11-diene-2-one (2), and a new eremophilane sesquiterpene, 3α-hydroxynootkatone (3), were isolated from the MeOH extract of dried fruits of A. oxyphylla along with eleven known sesquiterpenes (4–14). The structures were elucidated by the analysis of 1D/2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and optical rotation data. Compounds (1–3, 5–14) were evaluated for their protective effects against tert-butyl hydroperoxide (tBHP)-induced oxidative stress in adipose-derived mesenchymal stem cells (ADMSCs). As a result, treatment with isolated compounds, especially compounds 11 and 12, effectively reverted the damage of tBHP on ADMSCs in a dose-dependent manner. In particular, 11 and 12 at 50 µM improved the viability of tBHP-toxified ADMSCs by 1.69 ± 0.05-fold and 1.61 ± 0.03-fold, respectively.

Hyperhubeins A–I, Bioactive Sesquiterpenes with Diverse Skeletons from Hypericum hubeiense

“…22,25,32 This compound inhibited LPS-induced NO production and protected against oxidative stress-induced adipose-derived mesenchymal stem cells. 33,34 A possible mechanism of action has not been proposed. In the present study, Western blotting and molecular docking indicated that compound 12 exerted anti-neuroinflammatory activity probably via regulation of TLR-4/NF-κB signaling, and so it has the potential to be developed as a possible therapeutic agent to treat NDDs.…”

“…Compared with LPS-treated cells, preincubation with 12 suppressed LPS-induced expression of TLR-4, iNOS, and cyclooxygenase-2 (COX-2) and reduced the p-NF-κB/NF-κB ratio (Figure ). Compound 12 was previously reported in phytochemical studies on grapefruit juice and the fruits of Alpinia oxyphylla . ,, This compound inhibited LPS-induced NO production and protected against oxidative stress-induced adipose-derived mesenchymal stem cells. , A possible mechanism of action has not been proposed. In the present study, Western blotting and molecular docking indicated that compound 12 exerted anti-neuroinflammatory activity probably via regulation of TLR-4/NF-κB signaling, and so it has the potential to be developed as a possible therapeutic agent to treat NDDs.…”

Eremophilane and cadinane sesquiterpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities

“…2 Additionally, the dried fruits of A. oxyphylla have been traditionally used as a Chinese medicine and are recorded in the Pharmacopoeia of the People's Republic of China for their tonic, aphrodisiac, and anti-polyuria effects. 3 Previous phytochemical studies have identified various compounds in A. oxyphylla, including volatile oil, 4 terpenes, 5 diarylheptanes 6 and flavonoids. 6 Among these constituents, sesquiterpenoids are considered the characteristic and main bioactive constituents.…”

“…15 As part of our ongoing investigation of more novel effective anti-inflammatory sesquiterpenoids from A. oxyphylla, a total of 38 structurally diverse sesquiterpenoids (Fig. 1), including six previously undescribed eremophilane sesquiterpenoids (1)(2)(3)(4)(5)(6), six new cadinane sesquiterpenoids (23)(24)(26)(27)(28)(29), and 26 known analogues (7-22, 25 and 31-38) were isolated and identified. Among the isolates, compound 1 possesses an unusual rearranged eremophilane skeleton, 28 and 29 are unusual rearranged cadinane sesquiterpenoids, featuring rare spiro [5.6] carbon skeletons, while 23, 24, 26, and 27 are rare nor-cadinane sesquiterpenoids.…”

“…Previous phytochemical studies have identified various compounds in A. oxyphylla , including volatile oil, 4 terpenes, 5 diarylheptanes 6 and flavonoids. 6 Among these constituents, sesquiterpenoids are considered the characteristic and main bioactive constituents.…”