Identification of Two New Phenanthrenes from Dendrobii Herba and Their Cytotoxicity towards Human Hypopharynx Squamous Carcinoma Cell (FaDu)

Nam, Bomi; Ryu, Seung Mok; Lee, Dong‐Ho; Jung, Chan-Hun; Jin, Chang Hyun; Kim, Jin Baek; Lee, Ik Soo; Han, Ah Reum

doi:10.3390/molecules24122339

Cited by 11 publications

(11 citation statements)

References 37 publications

(57 reference statements)

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“…Batatasin III (3) is also a well-known component of Dendrobium species. 20 Although 1 and 2 did not show cytotoxic activities on the human pharynx squamous carcinoma (FaDu) cell line in our previous study, 19 it has been reported that compound 1 has cytotoxic activity against several other cancer cell lines 21 and has a hypotensive effect 22 ; compound 2 shows diverse biological properties, such as anti-inflammatory, anticancer, antiosmotic, and antioxidant activities. [23][24][25] Batatasin III (3) has been reported to have anticancer and α-glucosidase inhibitory activities.…”

mentioning

confidence: 71%

“…Denthyrsinin (1) and gigantol (2) were isolated from dried stems of Dendrobii Herba, as described in the previous study. 19 Batatasin III (3) was purchased from Wuhan ChemFaces Biochemical Co., Ltd., Hubei, China. All the microorganisms were obtained from the Korean Collection for Type Cultures (KCTC).…”

Section: Materials and Microorganismsmentioning

confidence: 99%

“…Recently, we have isolated a series of phenanthrenes and bibenzyls from Dendrobii Herba. 19 Among them, denthyrsinin (1) and gigantol (2) were isolated as major compounds. Batatasin III (3) is also a well-known component of Dendrobium species.…”

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confidence: 99%

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Microbial Glycosylation of Phenanthrene and Bibenzyls by Mucor hiemalis

Nam

Han

Lee

2020

Natural Product Communications

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Microbial transformation of denthyrsinin (1), gigantol (2), and batatasin III (3), the major constituents of Dendrobium species (Orchidaceae), was performed using the filamentous fungus Mucor hiemalis KCTC 26779. Three glycosylated metabolites were obtained in the biotransformation of 1-3, and their structures were identified as denthyrsinin-6- O-β-d-glucoside (4), gigantol-5- O-β-d-glucoside (5), and batatasin III-3- O-β-d-glucoside (6) by analyzing 1-dimensional and 2-dimensional-nuclear magnetic resonance spectra, as well as high-resolution electrospray ionization mass spectral data. Among them, metabolite 4 has not been previously reported. Mucor hiemalis was revealed to catalyze enzymatically glucosylation of the hydroxyl group of phenanthrenes and bibenzyls. This research provides an efficient approach for the glycosylation of phenanthrenes and bibenzyls and can expand the library of available phenanthrene and bibenzyl derivatives for further biological evaluations.

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confidence: 71%

Section: Materials and Microorganismsmentioning

confidence: 99%

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Microbial Glycosylation of Phenanthrene and Bibenzyls by Mucor hiemalis

Nam

Han

Lee

2020

Natural Product Communications

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“…Thus, it was subjected to bioassay-guided fractionation, which led to the isolation of 13 compounds. Among the isolates, moscatilin exhibited significant cytotoxicity against the FaDu cell line [14]. Several studies have reported that moscatilin exerted potent effects on numerous cancer cell lines [15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Moscatilin Induces Apoptosis in Human Head and Neck Squamous Cell Carcinoma Cells via JNK Signaling Pathway

et al. 2020

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Dendrobii Herba is an herbal medicine that uses the stems of Dendrobium species (Orchidacea). It has been traditionally used to treat fever, hydrodipsomania, stomach disorders, and amyotrophia. In our previous study, a bibenzyl compound, moscatilin, which is isolated from Dendrobii Herba, showed potent cytotoxicity against a FaDu human pharyngeal squamous carcinoma cell line. Prompted by this finding, we performed additional studies in FaDu cells to investigate the mechanism of action. Moscatilin induced FaDu cell death by using 5 μM of concentration and by mediating apoptosis, whereas cell proliferation following treatment with 1 μM of moscatilin was not suppressed to the same levels as by the anti-cancer agent, cisplatin. Apoptosis-related protein expression (cleaved caspase-8, cleaved caspase-7, cytochrome c, cleaved caspase-9, cleaved caspase-3, and poly (ADP-ribose) polymerase (PARP) was increased by treating with 5 μM of moscatilin. This suggests that moscatilin-mediated apoptosis is associated with the extrinsic and intrinsic apoptotic signaling pathways. In addition, moscatilin-induced apoptosis was mediated by the c-Jun N-terminal kinase (JNK) signaling pathway. Overall, this study identified additional biological activity of moscatilin derived from natural products and suggested its potential application as a chemotherapeutic agent for the management of head and neck squamous cell carcinoma.

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“…In our previous study, nine phenanthrenes, three bibenzyls, and a lignan were isolated from the ethyl acetate fraction of Dendrobii Herba, which were examined for their cytotoxicity against FaDu human hypopharynx squamous carcinoma cells [ 40 ]. Among them, densiflorol B, 6,7-dimethoxyphenanthrene-2,5-diol, dehydroorchinol, 1,5,7-trimethoxy-2-phenanthrenol, ephemeranthol A, and 3-[(1 E )-2-(3-hydroxyphenyl)ethenyl]-5-methoxyphenol exhibited cytotoxicity, and together with moscatilin, exhibited remarkable activity (IC 50 , 2.55 μg/mL).…”

Section: Introductionmentioning

confidence: 99%

Chemical and Biological Profiles of Dendrobium in Two Different Species, Their Hybrid, and Gamma-Irradiated Mutant Lines of the Hybrid Based on LC-QToF MS and Cytotoxicity Analysis

Nam

Jang

Han

et al. 2021

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The Dendrobium species (Orchidaceae) has been cultivated as an ornamental plant as well as used in traditional medicines. In this study, the chemical profiles of Dendrobii Herba, used as herbal medicine, Dendrobium in two different species, their hybrid, and the gamma-irradiated mutant lines of the hybrid, were systematically investigated via ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QToF MS). Among the numerous peaks detected, 17 peaks were unambiguously identified. Gigantol (1), (1R,2R)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1H)-one (2), tristin (3), (−)-syringaresinol (4), lusianthridin (5), 2,7-dihydroxy-phenanthrene-1,4-dione (6), densiflorol B (7), denthyrsinin (8), moscatilin (9), lusianthridin dimer (10), batatasin III (11), ephemeranthol A (12), thunalbene (13), dehydroorchinol (14), dendrobine (15), shihunine (16), and 1,5,7-trimethoxy-2-phenanthrenol (17), were detected in Dendrobii Herba, while 1, 2, and 16 were detected in D. candidum, 1, 11, and 16 in D. nobile, and 1, 2, and 16 in the hybrid, D. nobile × candidum. The methanol extract taken of them was also examined for cytotoxicity against FaDu human hypopharynx squamous carcinoma cells, where Dendrobii Herba showed the greatest cytotoxicity. In the untargeted metabolite analysis of 436 mutant lines of the hybrid, using UPLC-QToF MS and cytotoxicity measurements combined with multivariate analysis, two tentative flavonoids (M1 and M2) were evaluated as key markers among the analyzed metabolites, contributing to the distinction between active and inactive mutant lines.

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Identification of Two New Phenanthrenes from Dendrobii Herba and Their Cytotoxicity towards Human Hypopharynx Squamous Carcinoma Cell (FaDu)

Cited by 11 publications

References 37 publications

Microbial Glycosylation of Phenanthrene and Bibenzyls by Mucor hiemalis

Microbial Glycosylation of Phenanthrene and Bibenzyls by Mucor hiemalis

Moscatilin Induces Apoptosis in Human Head and Neck Squamous Cell Carcinoma Cells via JNK Signaling Pathway

Chemical and Biological Profiles of Dendrobium in Two Different Species, Their Hybrid, and Gamma-Irradiated Mutant Lines of the Hybrid Based on LC-QToF MS and Cytotoxicity Analysis

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