Abstract
Context: Thymus alternans Klokov (Lamiaceae) is a neglected species of the genus Thymus (Sect. Serpyllum) endemic to Carpathian area, where it is used as a flavouring agent and for medicinal purposes.Objective: The aim of the work was to identify antiproliferative constituents from the flowering aerial parts of this plant.Materials and methods: Thymus alternans extracts were analyzed by HPLC-MSn and subjected to extensive chromatographic separations. The isolated compounds (phenolics and triterpenes) were structurally elucidated by MS and 1D and 2D NMR experiments. Essential oil (EO) composition was determined by GC-FID and GC-MS. Six purified triterpenes and EO were assayed for in vitro antiproliferative activity against a panel of human cancer cells, namely, breast (MDA-MB 231), colon (HCT-15 and HCT116), lung (U1810), pancreatic (BxPC3), melanoma (A375) and cervical carcinoma (A431) cells.Results: The structures of the isolated compounds were achieved on the basis of H-NMR and MS experiments. Luteolin-4′-O-β-d-glucopyranoside (P1), chrysoeriol-7-O-β-d-glucopyranoside (P2), chrysoeriol-5-O-β-d-glucopyranoside (P3), apigenin-7-O-β-d-glucopyranoside (P4), rosmarinic acid (P5), rosmarinic acid-3′-O-β-d-glucopyranoside (P6), caffeic acid-3-O-β-d-glucopyranoside (P7), 3α-hydroxy-urs-12,15-diene (T1), α-amyrin (T2), β-amyrin (T3), isoursenol (T4), epitaraxerol (T5), and oleanolic acid (T6). GC-MS analysis revealed that the EO of T. alternans was devoid of phenols and belonged to the nerolidol-chemotype, that is typical of the Sect. Serpyllum. The six purified triterpenes (T1-T6) were active with IC50 ranging from 0.5 to 5 μM being comparable or better than those of reference compounds betulinic acid and cisplatin. The EO exhibited significant effects on A375, MDA-MB 231 and HCT116 cell lines with IC50 in the range of 5–8 μg/mL.Conclusion: The reported results suggest that T. alternans can be considered as a good source of phytoconstituents with possible importance in the pharmaceutical field.
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Claims 8
Claim · model-written summary
Luteolin-4′-O-β-d-glucopyranoside, chrysoeriol-7-O-β-d-glucopyranoside and chrysoeriol-5-O-β-d-glucopyranoside were isolated from T. alternans.
- Taxon
- Thymus alternansThymus alternanst0
- Outcome
- Luteolin-4′-O-β-d-glucopyranoside (P1), chrysoeriol-7-O-β-d-glucopyranoside (P2), chrysoeriol-5-O-β-d-glucopyranoside (P3)e0
Verbatim
e0“Luteolin-4′-O-β-d-glucopyranoside (P1), chrysoeriol-7-O-β-d-glucopyranoside (P2), chrysoeriol-5-O-β-d-glucopyranoside (P3)”
t0“Thymus alternans”
Claim · model-written summary
Apigenin-7-O-glucoside, rosmarinic acid and rosmarinic acid-3′-O-glucoside were isolated from T. alternans.
- Taxon
- Thymus alternansThymus alternanst0
- Outcome
- apigenin-7-O-β-d-glucopyranoside (P4), rosmarinic acid (P5), rosmarinic acid-3′-O-β-d-glucopyranoside (P6)e0
Verbatim
e0“apigenin-7-O-β-d-glucopyranoside (P4), rosmarinic acid (P5), rosmarinic acid-3′-O-β-d-glucopyranoside (P6)”
t0“Thymus alternans”
Claim · model-written summary
Caffeic acid-3-O-β-d-glucopyranoside was isolated from T. alternans.
- Taxon
- Thymus alternansThymus alternanst0
- Outcome
- caffeic acid-3-O-β-d-glucopyranoside (P7)e0
Verbatim
e0“caffeic acid-3-O-β-d-glucopyranoside (P7)”
t0“Thymus alternans”
Claim · model-written summary
3α-hydroxy-urs-12,15-diene, α-amyrin and β-amyrin were isolated from T. alternans.
- Taxon
- Thymus alternansThymus alternanst0
- Outcome
- 3α-hydroxy-urs-12,15-diene (T1), α-amyrin (T2), β-amyrin (T3)e0
Verbatim
e0“3α-hydroxy-urs-12,15-diene (T1), α-amyrin (T2), β-amyrin (T3)”
t0“Thymus alternans”
Claim · model-written summary
Isoursenol, epitaraxerol and oleanolic acid were isolated from T. alternans.
- Taxon
- Thymus alternansThymus alternanst0
- Outcome
- isoursenol (T4), epitaraxerol (T5), and oleanolic acid (T6)e0
Verbatim
e0“isoursenol (T4), epitaraxerol (T5), and oleanolic acid (T6)”
t0“Thymus alternans”
Claim · model-written summary
GC-MS showed that the essential oil of T. alternans lacked phenols and belonged to the nerolidol chemotype.
- Taxon
- T. alternansThymus alternanse0
- Outcome
- devoid of phenols and belonged to the nerolidol-chemotypee0
Verbatim
e0“GC-MS analysis revealed that the EO of T. alternans was devoid of phenols and belonged to the nerolidol-chemotype”
Claim · model-written summary
The six purified triterpenes were active against human cancer cells with IC50 of 0.5 to 5 μM, comparable to or better than betulinic acid and cisplatin.
Verbatim
e0“The six purified triterpenes (T1-T6) were active with IC50 ranging from 0.5 to 5 μM being comparable or better than those of reference compounds betulinic acid and cisplatin”
t0“Thymus alternans”
Claim · model-written summary
The essential oil had significant antiproliferative effects on A375, MDA-MB 231 and HCT116 cell lines with IC50 of 5–8 μg/mL.
- Taxon
- Thymus alternansThymus alternanst0
- Outcome
- significant effects on A375, MDA-MB 231 and HCT116 cell linese0
- Value
- 5–8 μg/mLe0
Verbatim
e0“The EO exhibited significant effects on A375, MDA-MB 231 and HCT116 cell lines with IC50 in the range of 5–8 μg/mL”
t0“Thymus alternans”