A new phenanthrene dimer from <i>Dendrobium palpebrae</i>

Kyokong, Napat; Muangnoi, Chawanphat; Thaweesest, Wuttinont; Kongkatitham, Virunh; Likhitwitayawuid, Kittisak; Rojsitthisak, Pornchai; Sritularak, Boonchoo

doi:10.1080/10286020.2018.1429416

Cited by 22 publications

(14 citation statements)

References 10 publications

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“…Sonia Anti-inflammatory (NO: IC 50 27.7 μM) [ 29 ] 123 Lirioresinol A Lignans D. nobile Antioxidant (DPPH: IC 50 30.9 μM) [ 57 ] 124 Sesqui-illisimonan A Lignans Dendrobium cv. Sonia Anti-inflammatory (NO: IC 50 31.6 μM) [ 29 ] 125 Dendrocoumarin Benzocoumarins D. nobile Antibacterial ( Staphylococcus aureus : MIC 2.5 μg/mL; Micrococcus tetragenus : MIC 5.0 μg/mL) [ 36 ] 126 Itolide A Benzocoumarins D. nobile Antibacterial ( Staphylococcus aureus : MIC 2.5 μg/mL; Micrococcus tetragenus : MIC 5.0 μg/mL) [ 36 ] 127 Dendroflorin Fluorenones D. nobile Anti-inflammatory (NO: IC 50 13.4 μg/mL) and antioxidant (DPPH: IC 50 16.2 μM) [ 23 ] D. palpebrae Antioxidant [ 69 ] 128 Nobilone Fluorenones D. nobile Anti-inflammatory (NO: IC 50 38.1 μg/mL) [ 23 ] 129 3,6,9-Trihydroxy-3,4-dihydroanthracen-1-(2 H )-one Anth...…”

Section: Pharmacological Activities Of Extracts Preparations and Chemical Constituents From Dendrobium Plants For Treamentioning

confidence: 99%

“…A fluorenone, dendroflorin ( 127 ), was isolated from D. palpebrae whole plants collected from Thailand. This compound significantly decreased ROS in H 2 O 2 -stimulated RAW264.7 cells in a dose-dependent manner (12.5–50 μg/mL) [ 69 ].…”

Section: Pharmacological Activities Of Extracts Preparations and Chemical Constituents From Dendrobium Plants For Treamentioning

confidence: 99%

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Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review

Wang

2021

Nat. Prod. Bioprospect.

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Dendrobium Sw. is one of the largest genera in the orchidaceous family and includes 900–2000 species. Among them, more than 80 Dendrobium species have been reported in China. However, there are only six Dendrobium species, namely, D. bigibbum var. superbum (syn. D. phalaenopsis), D. chrysanthum, D. fimbriatum, D. loddigesii, D. nobile, and D. officinale (syn. D. candidum), listed in the New Inventory of Existing Cosmetic Ingredients in China Launched. Artificial planting of Dendrobium species has been a great success in China. To better utilize Dendrobium resources for medicinal and cosmetic purposes, we summarize their traditional uses and pharmacologically active compounds for treating dermatological disorders in this review. “Orchidaceae”, “Dendrobium”, “traditional use”, “ethnobotany”, “dermatological disorder”, and “skin disease” were used as search terms to screen the literature. Cited references were collected between 1970 and 2020 from the Web of Science, China National Knowledge Internet (CNKI), SciFinder, Google Scholar, and Chinese books. From the search, it was found that there are 22 Dendrobium species with traditional uses in dermatological disorders, and 131 compounds from Dendrobium plants have been reported to possess anti-inflammatory, antimicrobial, antioxidant, antiaging, anti-psoriasis, and tyrosinase-inhibitory activities, implying that Dendrobium plants are important resources for the discovery of active compounds and the development of new drugs and cosmetics. D. crepidatum, D. denneanum, D. loddigesii, D. nobile, and D. officinale have been extensively studied. More research on other Dendrobium species is needed. The major active compounds found in Dendrobium species are phenanthrenes, alkaloids, flavonoids, phenylpropanoids, and lignans. Several compounds, such as loddigesiinol A, (S)-5-methoxy-2,4,7,9-tetrahydroxy-9,10-dihydrophenanthrene, (S)-4-methoxy-2,5,7,9-tetrahydroxy-9,10-dihydrophenanthrene, 2,5-dihydroxy-4-methoxy-phenanthrene 2-O-β-d-glucopyranoside, (9R)-1,2,5,9-tetrahydroxy-9,10-dihydrophenanthrene 5-O-β-d-glucopyranoside, (+)-homocrepidine A, and vicenin 2, have significant anti-inflammatory activities and inhibit nitric oxide (NO) production with IC50 values less than 5 μM, and these compounds are worthy of further study. Graphic Abstract

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Section: Pharmacological Activities Of Extracts Preparations and Chemical Constituents From Dendrobium Plants For Treamentioning

confidence: 99%

Section: Pharmacological Activities Of Extracts Preparations and Chemical Constituents From Dendrobium Plants For Treamentioning

confidence: 99%

Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review

Wang

2021

Nat. Prod. Bioprospect.

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“…These have been used as traditional folk remedies for the treatment of various diseases, such as chronic atrophic gastritis, diabetes, and cardiovascular disease [ 3 ]. Previous phytochemical studies on the Dendrobium species have resulted in the isolation of diverse types of compounds, such as alkaloids [ 4 , 5 , 6 , 7 , 8 , 9 , 10 ], bibenzyls [ 9 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ], phenanthrenes [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ], fluorenones [ 18 , 31 ], sesquiterpenoids [ 6 , 32 , 33 ], lignans [ 21 , 34 ], flavonoids [ 35 , 36 ], and polysaccharides [ 37 , 38 , 39 ]. These compounds have been reported as exhibiting neuroprotective [ 4 , 5 ], anticancer [ 6 , 10 , 11 , 12 , 13 , 14 , 15 ,…”

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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“…The chemical structure of 4 was proposed as a dimer of a phenanthrene derivative based on the analysis of its HR-ESI-MS and NMR data. 19 First, we determined 1 H NMR in acetone-d 6 , but H-9 and H-10 of the phenanthrene skeleton displayed as a sharp singlet signal at δ H 8.06 (2H). Therefore, we changed the solvent to CDCl 3 , and the phenanthrene structure was confirmed by the presence of two pairs of ortho-coupled doublet protons at δ 3).…”

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confidence: 99%

Immunomodulatory Effects of New Phenanthrene Derivatives from Dendrobium crumenatum

et al. 2023

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Three new phenanthrene derivatives (1, 2, 4), one new fluorenone (3), and four known compounds (5–8) were isolated from the ethyl acetate extract of Dendrobium crumenatum Sw. stems using column chromatography. The chemical structures were elucidated by analysis of spectroscopic data. The absolute configuration of 4 was determined by electronic circular dichroism calculation. We also evaluated the immunomodulatory effects of compounds isolated from D. crumenatum in human peripheral blood mononuclear cells from healthy individuals and those from patients with multiple sclerosis in vitro. Dendrocrumenol B (2) and dendrocrumenol D (4) showed strong immunomodulatory effects on both CD3+ T cells and CD14+ monocytes. Compounds 2 and 4 could reduce IL-2 and TNF production in T cells and monocytes that were treated with phorbol-12-myristate-13-acetate and ionomycin (PMA/Iono). Deep immune profiling using high-dimensional single-cell mass cytometry could confirm immunomodulatory effects of 4, quantified by the reduction of activated T cell population under PMA/Iono stimulation, in comparison to the stimulated T cells without treatment.

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A new phenanthrene dimer from Dendrobium palpebrae

Cited by 22 publications

References 10 publications

Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review

Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review

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

Immunomodulatory Effects of New Phenanthrene Derivatives from Dendrobium crumenatum

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