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Based on structural elucidation of natural and hydrolyzed glycans, the general glycans profiling of D. officinale were unequivocally established for the first time as follows: The results indicated that the structure of D. officinale glycans with low degree of polymerization (DP ≤ 22) was linear α-D-1,4-glucan, whereas the structure of glycans with high degree of polymerization (DP > 24) was linear acetylated 1,4-glucomannan. The content of acetyl groups and mannose to glucose (M/G) ratio increased with the degree of polymerization of D. officinale glycans. In addition, this study showed that natural D. officinale glycans protected pancreatic β-cell damage induced by glucotoxicity through the extracellular signal-regulated kinase (ERK)1/2 pathway., Competing Interests: Declaration of competing interest The author declares no conflict of interest., (Copyright © 2024. Published by Elsevier B.V.)

Glucagon-like peptide-1 (GLP-1) as a multifunctional hormone is secreted mainly from enteroendocrine L-cells, and enhancing its endogenous secretion has potential benefits of regulating glucose homeostasis and controlling body weight gain. In the present study, a novel polysaccharide (h-DHP) with high ability to enhance plasma GLP-1 level in mice was isolated from Dendrobium huoshanense protocorm-like bodies under the guidance of activity evaluation. Structural identification showed that h-DHP was an acidic polysaccharide with the molecular weight of 1.38 × 10 5  Da, and was composed of galactose, glucose, arabinose and glucuronic acid at a molar ratio of 15.7: 11.2: 4.5: 1.0 with a backbone consisting of →5)-α-L-Araf-(1→, →3)-α-D-Galp-(1→, →6)-α-D-Galp-(1→, →3,6)-α-D-Galp-(1→, →6)-β-D-Glcp-(1→ and →4,6)-β-D-Glcp-(1→ along with branches consisting of α-L-Araf-(1→, α-D-Galp-(1→, α-D-GlcAp-(1→, β-D-Glcp-(1→ and →4)-β-D-Glcp-(1→. Animal experiments with different administration routes demonstrated that h-DHP-enhanced plasma GLP-1 level was attributed to h-DHP-promoted GLP-1 secretion in the enteroendocrine L-cells, which was supported by h-DHP-enhanced extracellular GLP-1 level in STC-1 cells. Inhibition of adenylate cyclase and phospholipase C indicated that cAMP and cAMP-triggered intracellular Ca 2+ increase participated in h-DHP-promoted GLP-1 secretion. These results suggested that h-DHP has the potential of enhancing endogenous GLP-1 level through h-DHP-promoted and cAMP-mediated GLP-1 secretion from enteroendocrine cells., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Two unusual isosativene sesquiterpene derivatives, named dendronobilol A (1) and dendronobilside A (2), and two unusual sativene sesquiterpene derivatives, named dendronobilsides B (3) and C (4), had been isolated from the stems of Dendrobium nobile. The structures of all the compounds were established using spectroscopic methods and by comparison with literature data, and their absolute configurations were confirmed via single-crystal X-ray diffraction data and electronic circular dichroism (ECD) calculations. Dendronobilol A (1) and dendronobilside A (2) possessed a unique tricyclo[4.3.0.1 2, 8 ]decan ring system, while dendronobilsides B (3) and C (4) presented a unique tricyclo[4.4.0.0 2, 8 ]decan core carbon skeleton. The above two types of sesquiterpene derivatives had been isolated and purified from plants for the first time. Compounds 1 and 2 exhibited significant effects on glucose consumption with doses of 20 and 40 μmol/L in insulin-resistant HepG2 cells, and thus improve insulin resistance., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier B.V.)

Among the diversified glycan modifications, acylation is one of the most abundant. This modification could be responsible for many of the properties of glycans, such as structural stability and specificity for biological activity. To obtain better insight into the effects of acetylation of glycans on the structure and thermostability of insulin, it is critical to investigate glycans with a high degree of acetylation. An in-depth study of three functional glycans named acetyl-mannan from Dendrobium devonianum (DDAM) was conducted herein by efficient enzymatic depolymerization, and the effect of glycosidic bonds on acetylation modification sites was studied through a molecular dynamics (MD) method, as well as its positive effect on insulin secretion, glucose uptake, and the thermal stability of tertiary structures in vitro. Further study indicated that DDAMs play a hypoglycemic role by sparking the thermostability of the insulin conformation. The hypoglycemic activity displayed a positive correlation with the degree of acetylation in DDAMs. In this work, through the MD method, we confirmed the structure characteristics of DDAMs and provided accurate data support for the structure-activity relationship analysis. Thus, these findings demonstrated that DDAMs might be an exceptional leading compound for the stability of insulin drug., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier B.V.)

To explore the active polysaccharides from Dendrobium devonianum, a novel O-acetylmannan (DDP-1) with molecular weight of 117 kDa was isolated from D. devonianum. The chemical and instrumental analysis indicated that the DDP-1 was a homopolysaccharide containing a backbone chain composed of →4)-β-d-Manp-(1 → (71.4%) residue with internal →4)-2-O-acetyl-β-d-Manp-(1 → (14.2%), →4)-3-O-acetyl-β-d-Manp-(1 → (7.1%), and non-reducing end β-d-Manp-(1 → (7.3%) residues. Anticancer assay in vitro revealed that DDP-1 had anticancer activity against the growth of HepG2 and MCF-7 cancer cells. Moreover, cytokine secretion assays also presented that DDP-1 can promote cytokine production of TNF-α and IL-6 in THP-1 macrophage stimulated by PMA. Finally, the effects of isolation and purification on the microstructure of DDP-1 was studied by scanning electron microscope. The morphological features of DDP-1 indicated that DDP-1 hold high potential application in hydrophilic polymer materials., (Copyright © 2022. Published by Elsevier B.V.)

A novel polysaccharide (MSP-1) was isolated from the fruiting body of Morchella sextelata and purified using DEAE-52 and Sephadex G-75. The molecular weight of MSP-1 was 1.17 × 10 4  Da, as detected by HPLC analysis. The monosaccharide composition of MSP-1 was mannose and glucose at a ratio of 1.00: 1.25. Methylation and NMR results revealed that the backbone of MSP-1 was composed of →4)-β-D-Manp-(1→, →4)-β-D-Glcp-(1→, →4)-α-D-Glcp-(1→, and →4, 6)-α-D-Glcp-(1→. SEM images of MSP-1 presented a dense network structure with porous characterizations. The immunomodulatory activities of MSP-1 were evaluated using RAW264.7 cells, and the results showed that MSP-1 promoted proliferative and phagocytic activity and increased the production of NO, TNF-α and IL-6. These results indicated that MSP-1 exhibited significant immunomodulatory activities., (Copyright © 2022. Published by Elsevier B.V.)

Ten undescribed picrotoxane-type sesquiterpenoids, dendrowardins A-J, together with two known ones, were isolated from the stems of Dendrobium wardianum Warner (Orchidaceae). Dendrowardins A-D feature the unusual 5,2-δ-lactone and additionally dendrowardins C-D are the first examples containing the 11,10-γ-lactone moiety. The structures were established using spectroscopic methods and by comparison with literature data. Further, dendrowardin E, amotin, and aduncin exhibited significant effects of promoting the proliferation on human lens epithelial cells (HLECs) induced by D-galactose., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

Two unusual dendrobine-type alkaloids, findlayines E and F (1, 2), along with five known dendrobine-type alkaloids (3-7), were isolated from the stems of Dendrobium findlayanum Par. et Rchb. f. Compound 1 is the first example of dendrobine-type alkaloids with a 2-ethoxy-2-oxoethyl group attaching to the C-2, and compound 2 is a nor-dendrobine-type alkaloid, featuring a 5-decarboxylated structure. The structures of compounds 1 and 2 were elucidated by means of extensive spectroscopic analyses, and their absolute configuration were confirmed by electronic circular dichroism (ECD) calculations. All isolates were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549 and MCF-7 human cancer cells., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier B.V. All rights reserved.)

One hitherto unknown 24-nor-13,27-cycloursane-type triterpenoid, lucumic acid A (1), one new 24-nor-ursane triterpenoid, lucumic acid B (2), along with six known triterpenoids were isolated from the ethanol extract of the leaves of Lucuma nervosa. Their structures were established on the basis of spectroscopic data interpretation. Lucumic acid A (1) is the first example of a 24-nor-triterpenoid with a 13,27-cyclopropane ring., (Copyright © 2019. Published by Elsevier B.V.)

Ten previously undescribed stilbenoids, including six bibenzyls (bleochrins A-F, 1-6), three phenanthrenes derivatives (bleochrins G-J, 7-10) along with eleven known compounds were isolated from the rhizomes of Bletilla ochracea Schltr. The structural characterizations of 1-21 were accomplished by spectroscopic data, while the absolute stereostructure of 6 was confirmed by electronic circular dichroism (ECD) data analyses. All isolated metabolites except 7 were evaluated for cytotoxic activity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480). Four isolates exhibited significant inhibitory ability against HL-60, SMMC-7721, and MCF-7 cell lines, with IC 50 values ranging from 0.79 to 6.57 μM. The isolates were tested further for inhibitory effects on the NO production of the liposaccharide (LPS)-induced RAW264.7 macrophages and showed activity with IC 50 values at 15.29-24.02 μM., (Copyright © 2018 Elsevier B.V. All rights reserved.)

Four new dihydrophenanthrenofuran, bleochranols A-D (1-4), along with 21 known compounds including phenanthrenes (5-14) and bibenzyls (15-25) were isolated and elucidated from the rhizomes of Bletilla ochracea. Combination of 1D/2D NMR techniques and the Electronic Circular Dichroism (ECD) spectroscopy based on the empirical helicity rules, chemical structure of those isolates were determined. All the compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7 and SW480 human cancer cell lines by MTS assay and anti-inflammatory activity by nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. Among the 25 tested compounds, bleochranol A (1) showed remarkable cytotoxic activity against HL-60, A-549, and MCF-7 with IC 50 values of 0.24 ± 0.03, 3.51 ± 0.09 and 3.30 ± 0.99 μM respectively. The anti-inflammatory assay showed that compound 12 exhibited most potential activity against NO production in RAW 264.7 macrophages with IC 50 2.86 ± 0.17 μM. The results indicated that the main chemical constituents of B. ochracea were phenanthrene and bibenzyl and similar to that of B. striata., (Copyright © 2018 Elsevier B.V. All rights reserved.)

A novel arabinogalactan (MOP-1) was isolated from leaves of Moringa oleifera and was purified by macro-porous resin, DEAE-52 Cellulose and Sepharose 6B gel filtration chromatography. High performance gel permeation chromatography (HPGPC) analysis showed that the molecular weight of MOP-1 was 7.65 × 10 7  Da. Monosaccharide composition analysis indicated that sugar composition is Rha: Ara: Gal in a molar ratio of 1:7.32:12.12. Structural analysis indicated that MOP-1 has a backbone of →1)-β-d-Galp-(3,4→ with highly branched chains at O-4 position. The branches were composed of →1)-β-d-Galp-(4→, →1)-α-d-Galp-(2→, Araf-(1→, Galp-(1→. Its antioxidant activities were evaluated by DPPH radical scavenging capacity, 2,2'-Azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS) radical cation scavenging capacity, and ferric-reducing antioxidant power (FRAP). The results indicated MOP-1 exhibited significant antioxidant activities., (Copyright © 2018 Elsevier B.V. All rights reserved.)

A new bibenzyl derivative, dendrocandin V (1) and a new sesquiterpene amino ether, wardianumine A (2), together with eleven known compounds, including phenanthrenes (denbinobin (3), 9,10-dihydro-denbinobin (4), mostatin (5), loddigesiinols A (6)), bibenzyls (moscatilin (7), 5-hydroxy-3,4'-dimethoxybibenzyl (8), 3,4-dihydroxy-5,4'-dimethoxy bibenzyl (9), dendrocandin A (10), gigantol (11), dendrocandin U (12)) and an alkaloids (dihydroshihunine, 13) were isolated from the EtOH extraction of stems of Dendrobium wardianum Warner. Isolation of the new compound 2 indicated that N,N-dimethylethanolamine as the key adduction in the synthesis of dendroxine and its analogs in Dendrobium species. The hypothetical biosynthetic pathway of 2 was then postulated. Inspired by literature and traditional usage of the herbal medicine, some compounds were sent for cytotoxic activity and the results indicated that compounds 1, 3, 4, 5 showed cytotoxic activities against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480) with IC50 from 2.33-38.48μM. Among those compounds, 3 and 4 showed cell line selectivity with strong activity comparable to DDP., (Copyright © 2017. Published by Elsevier B.V.)

Three new triterpenoids, patrinolides B-D (1-3), and two new iridoids, patriscabioins K-L (9-10), together with five known compounds (4-8) were isolated from the extract of the whole plants of Patrinia scabiosaefolia. Compounds 1, 9, and 10 contained the unique substituents in Valerianaceae family, such as isovalery and 3-methylcrotonyl. Compound 2 was a 24-nor-ursane triterpenoid. Their structures were established on the basis of extensive spectroscopic analysis (UV, IR, MS, 1D and 2D NMR). The inhibitory activities against nitric oxide synthase (NOS) of all triterpenoids were tested. The results showed that compound 4 had moderate inhibitory activity with IC 50 of 10.1μM. Furthermore, it also showed strongest inhibitory activities on AChE with IC 50 values of 10.0μM., (Copyright © 2017. Published by Elsevier B.V.)

Four new cycloartane triterpenoids, 1α,3β-dihydroxy-16-keto-24(31)-en-cycloartane (1), 31-methoxyl-passifloic acid (2), cyclopassifloside XIV (3), and cyclopassifloside XV (4), together with six known compounds (5-10) were isolated from Passiflora edulis Sims. Their structures were elucidated on the basis of extensive spectroscopic analysis. All the compounds were evaluated for protective effects against damage of PC12 cell induced by glutamate according to traditional usage of the herbal medicine, and the results indicated that cycloartane triterpenoids maybe one of the active compositions of P. edulis Sims for the treatment of neurodegenerative disease., (Copyright © 2016. Published by Elsevier B.V.)

Five new oleanane-type triterpene saponins including steganogenin 3-O-β-D-glucopyranoside (1), steganogenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (2), steganogenin 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3), chichipegenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (4) and chichipegenin 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (5), along with four known oleanane-type triterpenes and triterpene saponins (6-9) were isolated from EtOH extract of the whole plant of Hydrocotyle nepalensis. To the best of our knowledge, oleanane-type triterpenes possessing skeleton with 17, 22-seco-backbone (1-3) are not common in natural products. Compound 8 was isolated as a new natural product. The structures of new compounds were elucidated by extensive spectroscopic methods and chemical evidence. Moreover, the cytotoxic activity of all the isolates against five selected human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) was evaluated and the results indicated that compounds 6 and 7 show stronger cytotoxic activity., (Copyright © 2016 Elsevier B.V. All rights reserved.)

Volvalerine A (1), a novel N-containing bisesquiterpenoid derivative with a dihydroisoxazole ring, and its possible biosynthetic precursor, 1-hydroxy-1,11,11-trimethyldecahydrocyclopropane azulene-10-one (2), were isolated from the roots of Valeriana officinalis var. latifolia. Their structures and relative configurations were identified using spectroscopic data and X-ray crystallography. A plausible biosynthetic pathway for 1 is also presented., (Copyright © 2016 Elsevier B.V. All rights reserved.)

A neutral heteropolysaccharide (DOP-1-1) consisted by mannose and glucose (5.9:1) with an average molecular weight at about 1.78×10(5) Da was purified from Dendrobium officinale. Based on Fourier transform infrared spectrum (FT-IR) and nuclear magnetic resonance (NMR) spectra, it suggested that partial structure of DOP-1-1 is an O-acetylated glucomannan with β-d configuration in pyranose sugar forms. The immunomodulatory activity of DOP-1-1 was evaluated by secretion level of cytokine (interleukin (IL)-1β and IL-10) and tumor necrosis factor (TNF)-α in vitro. Our results suggested that DOP-1-1 could stimulate cytokine production (TNF-α, IL-1β) in cells. These findings demonstrated that the purified polysaccharide from D. officinale presented significant immune-modulating activities. Furthermore, by Western-blot we can found that the signaling pathways of DOP-1-1 induced immune activities involving ERK1/2 and NF-кB. As to antioxidant activity, DOP-1-1 hadn't showed remarkable scavenging capacity of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) in contrast with other studies of polysaccharides from D. officinale., (Copyright © 2015 Elsevier B.V. All rights reserved.)

Twenty-one compounds (nine iridoids and twelve sesquiterpenoids), including ten previously unknown (five iridoids and five sesquiterpenoids) were isolated from whole dried material of Valeriana stenoptera. Structures were established on the basis of extensive spectroscopic analysis and the relative stereochemistry of 13-hydroxypatchoulol A was further confirmed by X-ray crystallographic data. All isolates were evaluated for their effects on nerve growth factor (NGF)-mediated neurite outgrowth in pheochromocytoma (PC12) cells and seven compounds showed potent promoting effects., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Three new iridoids, jatamanvaltrates R-S (1-2) and jatamanin Q (3), as well as three new sesquiterpenoids, valeriananoids D-E (4, 5) and clovane-2β-isovaleroxy-9α-ol (6), together with nine known compounds were isolated from the roots of Valeriana jatamansi Jones. Compound 2 was the first reported iridoid with fatty acid esters in the Valerianaceae family. The structures of new compounds were established on the basis of extensive spectroscopic analysis. Moreover, all the isolates were evaluated for inhibitory activity on acetylcholinesterase (AChE)., (Copyright © 2015 Elsevier B.V. All rights reserved.)

One new phenanthrene, aphyllone A (1) and four new bibenzyl derivatives, aphyllone B (2) and aphyllals C-D (3-5), together with nine known compounds (6-14), were isolated from the stems of Dendrobium aphyllum (Roxb.) C. E. Fischer. The structures of these new compounds were elucidated by means of extensive spectroscopic analyses, and the absolute configuration of compound 1 was determined by single crystal X-ray diffraction and quantum calculations. Compounds 6, 8 and 14 inhibited NO production at the concentration of 25 μM in LPS-stimulated RAW264.7 cells with the inhibition (%) of 32.48, 35.68, and 38.50. Compound 2 possessed significant DPPH radical scavenging activity with scavenging percentage of 87.97% at the concentration of 100 μg/mL., (Copyright © 2014. Published by Elsevier B.V.)

Three tigliane-type diterpenoids named excoecafolins A-C and two daphnane-type diterpenoids named excoecafolins D and E, together with 13 known compounds, were isolated from the EtOAc extract of Excoecaria acerifolia Didr. Their structures were elucidated through the analysis of the spectroscopic data. The anti-HIV-1 activity evaluation of five of these compounds showed that four possessed moderate anti-HIV-1 activities with EC50 0.258, 0.036, 0.046, and 0.978 μM, SI >1,836.9, 431.1, 298.7, and >503.7, respectively. Additionally, the chemotaxonomic issue of the affinity correlation between Thymelaeceae and Euphorbiaceae is discussed based on the isolates., (Copyright © 2014 Elsevier B.V. All rights reserved.)

Gastrodia elata (tianma) is a traditional Chinese herbal medicine (TCM) often used for the treatment of cerebrovascular diseases. In this study, we investigated the effects of tianma on the brain protein metabolism by quantitative proteomics to gain evidence for a direct relationship between tianma treatment and brain functions. One-year-old rats were treated with tianma (~2.5 g/kg/day) for 3months and the brain tissue proteome was analyzed by using the iTRAQ (isobaric tag for relative and absolute quantification) technology. According to our results, the long-term treatment with tianma could modulate the brain protein metabolism at the proteome level by down-regulating the expressions of various proteins, such as Gnao1 and Dctn2, which are related to neuronal growth cone control and synaptic activities. In addition, tianma treatment also induced the up-regulation of molecular chaperons and proteins related to the misfolded protein response, like Anxa5, and also other proteins involved in Huntington's disease (HD) (e.g. Pacsin1 and Arf3). Concluding, tianma could eventually contribute to activities related to synaptic plasticity and neuro-restorative processes and thus might be a novel candidate agent for the treatment of neurodegenerative diseases by regulating the brain proteome., (Copyright © 2012 Elsevier B.V. All rights reserved.)

Seven previously unreported daphnane-type diterpene esters named acutilobins A-G, together with 12 known ones, were isolated from EtOAc extract of Daphne acutiloba Rehd. Their structures were elucidated based on the spectroscopic data. The cytotoxic and anti-HIV-1 activities of these daphnane-type diterpene esters were evaluated through bioassays. Fourteen of these isolates exhibited definite cytotoxic activities against the five human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480. Additionally, anti-HIV-1 activities were observed in 13 daphnane-type diterpene esters, among which acutilobins A-G exhibited significant anti-HIV-1 activities with EC₅₀ below 1.5 nM and SI over 10,000. Particularly, genkwanineVIII showed the strongest activity with EC₅₀ 0.17 nM and SI 187,010., (Copyright © 2011 Elsevier Ltd. All rights reserved.)