TY - JOUR
T1 - (+)-Erythro-∆80-7S,8R-Dihydroxy-3,30,50-Trimethoxy-8-O-40-Neolignan, an Anti-Acne Component in Degreasing Myristica fragrans Houtt
AU - Lee, Chia Jung
AU - Huang, Chun Wei
AU - Chen, Lih Geeng
AU - Wang, Ching Chiung
N1 - Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/10
Y1 - 2020/10
N2 - Acne is a common skin condition observed in adolescents. Nutmeg (Myristica fragrans Houtt) (MF) is a well-known traditional Chinese medicine; its major toxic components, safrole and myristicin, are rich in essential oils. Essential oils of MF (MFO) were extracted by hydrodistillation; the residue was extracted using 50% methanol (MFE-M). The minimum inhibitory concentration (MIC) of MFE-M against Cutibacterium acnes and Staphylococcus aureus was 0.64 mg. Four compounds were obtained from MFE-M: myristicin (1), (+)-erythro-∆80-7S,8Rdihydroxy-3,3,50-trimethoxy-8-O-40-neolignan (2), (+)-erythro-∆8’-7-hydroxy-3,4,3’,5’-tetramethoxy 8-O-4-neolignan (3), and erythro-∆80-7-acetoxy-3,4,30,50-tetramethoxy-8-O-40-neolignan (4). Compound 2 exerted the strongest antimicrobial activity, with MICs of 6.25 and 3.12 µg/mL against C. acnes and S. aureus, respectively. Moreover, 2 inhibited NO, PGE2, iNOS, and COX-2 levels in RAW 264.7 cells induced by LPS or heat-killed C. acnes; NO production at 50% inhibitory concentrations (IC50) was 11.07 and 11.53 µg/mL, respectively. Myristicin and safrole content was higher in MFO than in MFE-M. MFO and MFE-M caused no skin irritation after a single topical application in Wistar rats. MFE-M, with low safrole and myristicin content, did not cause skin irritation and exhibited an anti-acne effect; moreover, 2 was identified as the active substance. Therefore, MFE-M could be employed to develop anti-acne compounds for use in cosmetics.
AB - Acne is a common skin condition observed in adolescents. Nutmeg (Myristica fragrans Houtt) (MF) is a well-known traditional Chinese medicine; its major toxic components, safrole and myristicin, are rich in essential oils. Essential oils of MF (MFO) were extracted by hydrodistillation; the residue was extracted using 50% methanol (MFE-M). The minimum inhibitory concentration (MIC) of MFE-M against Cutibacterium acnes and Staphylococcus aureus was 0.64 mg. Four compounds were obtained from MFE-M: myristicin (1), (+)-erythro-∆80-7S,8Rdihydroxy-3,3,50-trimethoxy-8-O-40-neolignan (2), (+)-erythro-∆8’-7-hydroxy-3,4,3’,5’-tetramethoxy 8-O-4-neolignan (3), and erythro-∆80-7-acetoxy-3,4,30,50-tetramethoxy-8-O-40-neolignan (4). Compound 2 exerted the strongest antimicrobial activity, with MICs of 6.25 and 3.12 µg/mL against C. acnes and S. aureus, respectively. Moreover, 2 inhibited NO, PGE2, iNOS, and COX-2 levels in RAW 264.7 cells induced by LPS or heat-killed C. acnes; NO production at 50% inhibitory concentrations (IC50) was 11.07 and 11.53 µg/mL, respectively. Myristicin and safrole content was higher in MFO than in MFE-M. MFO and MFE-M caused no skin irritation after a single topical application in Wistar rats. MFE-M, with low safrole and myristicin content, did not cause skin irritation and exhibited an anti-acne effect; moreover, 2 was identified as the active substance. Therefore, MFE-M could be employed to develop anti-acne compounds for use in cosmetics.
KW - Anti-acne effect
KW - Anti-inflammatory effect
KW - Cutibacterium acnes
KW - Myristica fragrans Houtt
KW - Skin irritation
KW - Staphylococcus aureus
UR - http://www.scopus.com/inward/record.url?scp=85092752528&partnerID=8YFLogxK
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U2 - 10.3390/molecules25194563
DO - 10.3390/molecules25194563
M3 - Article
C2 - 33036279
AN - SCOPUS:85092752528
SN - 1420-3049
VL - 25
JO - Molecules
JF - Molecules
IS - 19
M1 - 4563
ER -