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. 2023 Jun 28;28(13):5063.
doi: 10.3390/molecules28135063.

Anti-Aging Constituents from Pinus morrisonicola Leaves

Ta-Wei Liu  1 , Sui-Wen Hsiao  2 , Chi-Ting Lin  3 , George Hsiao  4   5 , Ching-Kuo Lee  1   2   3   6
Affiliations

Anti-Aging Constituents from Pinus morrisonicola Leaves

Ta-Wei Liu et al. Molecules. .

Abstract

Pinus morrisonicola Hayata is a unique plant species found in Taiwan. Previous studies have identified its anti-hypertensive, anti-oxidative, and anti-inflammatory effects. In this study, a bioactivity-guided approach was employed to extract 20 compounds from the ethyl acetate fraction of the ethanol extract of Pinus morrisonicola Hayata's pine needles. The anti-aging effects of these compounds were investigated using HT-1080 cells. The structures of the purified compounds were confirmed through NMR and LC-MS analysis, revealing the presence of nine flavonoids, two lignans, one coumarin, one benzofuran, one phenylic acid, and six diterpenoids. Among them, PML18, PML19, and PML20 were identified as novel diterpene. Compounds 3, 4, and 5 exhibited remarkable inhibitory effects against MMP-2 and showed no significant cell toxicity at 25 μM. Although the purified compounds showed lower activity against Pro MMP-2 and Pro MMP-9 compared to the ethyl acetate fraction, we speculate that this is the result of synergistic effects.

Keywords: HT-1080 cells; Pinus morrisonicola Hayata; anti-aging; cosmetics; pinaceae.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
Activity effects of crude extract and three layers on MMP-2, Pro MMP-2 and Pro MMP-9 in HT-1080 human fibrosarcoma cell. Crude extraction (PML), Ethyl acetate layer (PMLEF), n-Butanol layer (PMLBF), and Water layer (PMLWF). p-values were derived from one-way ANOVA with Student-Newman-Keuls Tests. * p-value < 0.05, ** p-value < 0.01.
Figure 2
Figure 2
Activity effects of PMLEF fractions (Fr.2~Fr.9) on MMP-2, Pro MMP-2 and Pro MMP-9 in HT1080 human fibrosarcoma cell, and use EGCG as positive control. (a) PMLEF Fr.2~5 (b) PMLEF Fr.6~9 indicates significant differences from the vehicle. p-values were derived from one-way ANOVA with Student-Newman-Keuls Tests. * p-value < 0.05, ** p-value < 0.01.
Figure 3
Figure 3
Flow chart of isolation procedure of subfractions of PMLEF.
Figure 4
Figure 4
The structures of compounds 1–20 from the leaves of Pinus morrisonicola Hayata.
Figure 5
Figure 5
Selected 2D NMR (Chloroform-d) correlations for 18, 19, and 20. (A) 18 COSY: ―; HMBC: (H→C). (B) 19 NOESY (C) 20 COSY: ―; HMBC: → (H→C). (D) 20 NOESY.
Figure 5
Figure 5
Selected 2D NMR (Chloroform-d) correlations for 18, 19, and 20. (A) 18 COSY: ―; HMBC: (H→C). (B) 19 NOESY (C) 20 COSY: ―; HMBC: → (H→C). (D) 20 NOESY.
Figure 6
Figure 6
Activity effects of pure compounds from P. morrisonicola on MMP-2, Pro MMP-2 and Pro MMP-9 in HT1080 human fibrosarcoma cell. p-values were derived from one-way ANOVA with Student-Newman-Keuls Tests. * p-value < 0.05, ** p-value < 0.01.
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