Homalolides C-D, two new sesquiterpenoids from the rhizomes of Homalomena pendula.

Two new sesquiterpenoids, homalolides C - D (1‒2), were co-isolated from the rhizomes of Homalomena pendula (Blume) Bakh.f collected in Vietnam with five known ones, aromadendrane-4α,10α-diol (3), bullatantriol (4), 1ß,4ß,6α-trihydroxy-eudesmane (5), 1ß,4ß,6ß-trihydroxyeudesmane (6), and 1ß,4ß,7α-trihydroxy-eudesmane (7). The structures and relative configuration of new compounds were elucidated by 1 D-/2D-NMR, IR, UV and HRESIMS analyses, and by comparisons to the reported data in the literature. Homalolide C presented an unprecedented skeleton with the 4/8 bicyclic system. All isolates did not exhibit appreciable inhibitory effects on LPS-induced NO production in the RAW 264.7 macrophage cell line and on the growth of human lung cancer cell line (SK-LU-1).

Structure revision and absolute configuration of 5,7-diepi-2α-hydroxyoplopanone and anti-osteoporotic activities of sesquiterpenoids from the rhizomes of Homalomena pendula.

Five sesquiterpenoids including 2α-hydroxyoplopanone (1), oplopanone (2), 1ß,4ß,6α-trihydroxy-eudesmane (3), 1ß,4ß,7α-trihydroxy-eudesmane (4) and bullatantriol (5) were isolated from Homalomena pendula. The structure of the previously reported compound, 5,7-diepi-2α-hydroxyoplopanone (1a), has been revised to 1 by the spectroscopic evidences (1D-/2D-NMR, IR, UV and HRESIMS) and by comparison between experimental and theoretical NMR data using DP4+ protocol. Furthermore, the absolute configuration of 1 was unambiguously assigned by ECD experiments. Compounds 2 and 4 displayed a potent ability to stimulate osteogenic differentiation of MC3T3-E1 cells at 4 µg/mL (by 123.74% and 131.07%, respectively) and 20 µg/mL (by 112.45% and 126.41%, respectively) whilst 3 and 5 did not show any activities. At 20 µg/mL, 4 and 5 significantly promoted the mineralization of MC3T3-E1 cells with values of 112.95% and 116.37%, respectively, whereas 2 and 3 were inactive. The results indicated that 4 could be an excellent component for anti-osteoporosis studies from the rhizomes of H. pendula.

Sesquiterpenoids from the rhizomes of Homalomena pendula and their anti-inflammatory activities.

Sixteen sesquiterpenoids including two new ones, homalolides A - B (1‒2), were firstly isolated from the methanolic extract of the rhizomes of Homalomena pendula collected in Vietnam. The structures and relative stereochemistry of new compounds were elucidated by 1D-/2D-NMR, IR, UV and HRESIMS analyses. The GCMS experiment demonstrated that homalolide A (1) is an artifact due to the methylation during methanolic extraction process. All isolates (1‒16) were tested for their inhibitory activities against lipopolysaccharide-induced nitric oxide production in the RAW 264.7 macrophage cell line. Compounds 1, 3, 6‒8, 10‒12 displayed moderate inhibitory effect on NO production with IC50 values ranging from 35.41 to 64.06 µM.

Chemically characterized nanoencapsulated Homalomena aromatica Schott. essential oil as green preservative against fungal and aflatoxin B1 contamination of stored spices based on in vitro and in situ efficacy and favorable safety profile on mice.

Present study deals with the efficacy of nanoencapsulated Homalomena aromatica essential oil (HAEO) as a potent green preservative against toxigenic Aspergillus flavus strain (AF-LHP-NS 7), storage fungi, AFB1, and free radical-mediated deterioration of stored spices. GC-MS analysis revealed linalool (68.51%) as the major component of HAEO. HAEO was encapsulated into chitosan nanomatrix (CS-HAEO-Ne) and characterized through SEM, FTIR, and XRD. CS-HAEO-Ne completely inhibited A. flavus growth and AFB1 biosynthesis at 1.25 µL/mL and 1.0 µL/mL, respectively in comparison to unencapsulated HAEO (1.75 µL/mL and 1.25 µL/mL, respectively). CS-HAEO-Ne caused significant reduction in ergosterol content in treated A. flavus and provoked leakage of cellular ions (Ca+2, Mg+2, and K+) as well as 260 nm and 280 nm absorbing materials. Depletion of methylglyoxal level in treated A. flavus cells illustrated the novel antiaflatoxigenic efficacy of CS-HAEO-Ne. CS-HAEO-Ne exhibited superior antioxidant efficacy (IC50 (DPPH) = 4.5 µL/mL) over unencapsulated HAEO (IC50 (DPPH) = 15.9 µL/mL) and phenolic content. CS-HAEO-Ne depicted excellent in situ efficacy by inhibiting fungal infestation, AFB1 contamination, lipid peroxidation, and mineral loss with acceptable sensorial profile. Moreover, broad safety paradigm (LD50 value = 7150.11 mg/kg) of CS-HAEO-Ne also suggests its application as novel green preservative to enhance shelf life of stored spices.

Chemical composition and antibacterial activities of essential oils from rhizomes and aerial parts of Homalomena cochinchinensis (Araceae).

In this study, the phytochemical composition and antibacterial activity of the essential oils isolated from the rhizomes and the aerial parts of Homalomena cochinchinensis were analysed for the first time using gas chromatography-mass spectrometry (GC-MS) and disk diffusion method. Consequently, 36 constituents were reported from H. cochinchinensis rhizomes, including linalool (57.4%), terpinen-4-ol (10.6%), α-sabinene (4.2%) as major compounds. Meanwhile, 30 compounds have been identified in the essential oil of the aerial parts of H. cochinchinensis, which myrcene (41.1%), sabinene (8.2%), D-limonene (9.1%) were the main constituents. Furthermore, the antibacterial activity of the essential oil from the rhizomes of the studied species could inhibit the growth of all six tested bacterial strains, including Bacillus cereus, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Salmonella typhimurium whereas the essential oil from the aerial parts was proved to be able to inhibit the growth of five bacterial strains except S. enteritidis.

Characterization of the complete chloroplast genome of Homalomena occulta (Lour.) Schott.

Homalomena occulta (Lour.) Schott (H. occulta) is a traditional Chinese medicine. However, the chloroplast genome has not been reported. Here, we assembled and analyzed the complete chloroplast (CP) genome of H. occulta. We found that the CP genome of H. occulta is 165,398 bp in length and contains a large single-copy (LSC) region of 92,861 bp, a small single-copy (SSC) region of 20,943 bp and an inverted repeat (IR) region of 25,797 bp. The genome contains 130 genes including 85 protein-coding genes, 8 rRNA and 37 tRNA. Phylogenetic analysis indicated that H. occulta is close to Philodendron lanceolatum. This study provides useful data for the development of molecular markers and identification of H. occulta.

Further sesquiterpenoids from the rhizomes of Homalomena occulta and their anti-inflammatory activity.

The rhizomes of Homalomena occulta are called Qian-nian-jian in Traditional Chinese Medicine (TCM), which is widely consumed in China owing to its health benefits for the treatment of rheumatoid arthritis and for strengthening tendons and bones. A phytochemical investigation on this famous TCM yielded 19 sesquiterpenoids (1-19) with various carbocyclic skeletons including isodaucane (2, 8, and 9), guaiane (3), eudesmane (4 and 10-15), oppositane (5, 16, and 17), and aromadendrane (18 and 19) types. The structures of new compounds, Homalomenins A-E (1-5), were determined by diverse spectroscopic data. Compound 1 possessed a rare sesquiterpenoid skeleton and compound 5 represented the first example of 1,4-oxa-oppositane sesquiterpenoid. These isolates were evaluated for their inhibitory effects on COX-2 mRNA, COX-2 protein expression, and prostaglandin E2 (PGE2) production in Raw264.7 cells, which demonstrated that compounds 5, 18, 19 showed potent anti-inflammatory activity by suppressing LPS-induced COX-2 expression and PGE2 production in a dose-dependent manner.

New insights on the phylogenetic relationships among the traditional Philodendron subgenera and the other groups of the Homalomena clade (Araceae).

Philodendron (Araceae) is one of the largest Neotropical plant genera, with approximately 500 species and at least 1000 species predicted. There is a considerable ecological diversity in the group, although most species occur in the humid forests of tropical America. Despite being relatively well-studied in taxonomic analyses, the relationships among the traditional morphological groups of the genus are not well-established, mainly regarding the three traditional subgenera, referred here as Philodendron sensu lato (s.l.), P. subg. Pteromischum, P. subg. Philodendron and P. subg. Meconostigma, which was recently recognized as a separate genus, Thaumatophyllum. Therefore, the present work evaluates the phylogenetic position and the monophyly of Philodendron s.l. and its three main subdivisions, and the sister groups within the Homalomena clade, which also includes the Neotropical genus Adelonema, the two Asian genera Homalomena and Furtadoa, and the two African genera Cercestis and Culcasia, by means of molecular phylogenetic approaches including chloroplast DNA (atpF-atpH, rpl32-trnL, trnQ-5'-rps16 and trnV-ndhC) and nuclear (ITS2) markers. The monophyly of Philodendron s.l. and its three lineages is confirmed and our analyses corroborate previous morphologic data indicating Thaumatophyllum as sister to the clade formed by P. subg. Pteromischum and P. subg. Philodendron.

HPLC fingerprint of Homalomena occulta / 中草药

Objective: To establish an HPLC method for the fingerprint analysis of Homalomena occulta and evaluate the quality though similarity calculation. Methods: Waters e2695 was applied to analyze ten batches of H. occulta. Phenomenex Gemini 110A C18 column was performed (250 mm × 4.6 mm, 5 μm) with acetonitrile and 0.01% phosphoric acid in agradient mode at a flow rate of 1.0 mL/min at 290 nm and the separation was performed at 30 ℃. The similarity was analyzed with Similarity Evaluation System for Chromatographic Fingerprint of Chinese Materia Medica 2004A. Results: The HPLC characteristic fingerprint of H. occulta with 11 commons peaks, and one of them were identified by comparing with reference subslances. The values of similarity was higher than 0.887. The HPLC method showed better results of stability, precision, and repeatability. Conclusion: It is the first time to establish the HPLC fingerprint of H. occulta. Those described can not only provides an identification method for fingerprint, but also provides the foundation of quality control.

Sesquiterpenoids from the Rhizomes of Homalomena occulta.

Naturally occurring oplopanane sesquiterpenoids are rarely reported. A phytochemical investigation on the rhizomes of Homalomena occulta (Lours) has resulted in the discovery of six oplopanane sesquiterpenoids (1-6), including four new (1-4) and one 3,5-seco-oplopanane (6), together with three previously reported sesquiterpenoids (7-9). In addition three new oplopananes (2a-4a) were also obtained by chemical transformation. All structures of these sesquiterpenoids were established based on the comprehensive spectroscopic analyses, including NMR, MS, and IR, and comparing with the literatures.

New sesquiterpenes from the rhizomes of homalomena occulta.

Six new sesquiterpenes (1-6), along with eight known ones (7-14) were isolated from the rhizomes of Homalomena occulta. Structure elucidation of the new compounds was achieved through 1D NMR, 2D NMR spectroscopic techniques and HRESIMS, while the absolute configurations of compounds 1, 2 and 5 were confirmed by X-ray crystallographic analysis. All of the isolates were evaluated for their activity against LPS-induced production of nitrogen oxide (NO) in macrophage cells, and compounds 1 and 5 showed inhibitory effect on NO production with the IC50 values of 21.2 and 15.4 µM, respectively.

[Sesquiterpenoids from rhizome of Homalomena occulta].

Twelve compounds were isolated from alcohol extracts of the rhizome of Homalomena occulta by using various chromatographic techniques including column chromatography onsilica gel and C18 reverse-phase silica gel, and semi-preparative HPLC. Their structures were identified by physico-chemical properties and spectroscopic data analysis as 3α, 7α-dihydroxy-cadin-4-ene (1), 3-oxofabiaimbricatan (2), 3ß, 4α-dihydroxy-7-epi-eudesm-11(13)-ene (3), integrifonol A(4), 1ß, 6ß-dihydroxy-7-epi-eudesm-11(13)-ene (5), 4ß, 7ß, 11-enantioeudesmantriol (6), epi-guaidiol (7), oplopanone(8), (-)-1ß, 4ß, 6α-trihydroxy-eudesmane (9),2α-hydroxyhomalomenol(10), (-)-T-muurolol (11) and hamalomenol A(12). Compounds 1-7 were obtained from the genus Homalomena for the first time and 11-12 were firstly reported from the species. Additionally, compounds 3, 5 and 8 displayed inhibitory effects against the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage RAW264.7 cells with IC50 values of 6.51, 3.25, 7.78 µmol•L⁻¹, respectively.

Sesquiterpenoids from rhizome of Homalomena occulta / 中国中药杂志

Twelve compounds were isolated from alcohol extracts of the rhizome of Homalomena occulta by using various chromatographic techniques including column chromatography onsilica gel and C₁₈ reverse-phase silica gel, and semi-preparative HPLC. Their structures were identified by physico-chemical properties and spectroscopic data analysis as 3α, 7α-dihydroxy-cadin-4-ene (1), 3-oxofabiaimbricatan (2), 3β, 4α-dihydroxy-7-epi-eudesm-11(13)-ene (3), integrifonol A(4), 1β, 6β-dihydroxy-7-epi-eudesm-11(13)-ene (5), 4β, 7β, 11-enantioeudesmantriol (6), epi-guaidiol (7), oplopanone(8), (-)-1β, 4β, 6α-trihydroxy-eudesmane (9),2α-hydroxyhomalomenol(10), (-)-T-muurolol (11) and hamalomenol A(12). Compounds 1-7 were obtained from the genus Homalomena for the first time and 11-12 were firstly reported from the species. Additionally, compounds 3, 5 and 8 displayed inhibitory effects against the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophage RAW264.7 cells with IC₅₀ values of 6.51, 3.25, 7.78 μmol•L⁻¹, respectively.

Pharmacodynamic Effects of Volatile Oil from Homalomena occulta on Adjuvant-induced Arthritis Model Rats and Its Mechanism Study / 中国药房

OBJECTIVE:To study the pharmacodynamic effects of volatile oil from Homalomena occulta on adjuvant-induced arthritis(AA)model rats and its mechanism. METHODS:60 rats were randomly divided into normal control group(0.5%polysor-bate 80),model control group (0.5% polysorbate 80),positive control group (Tripterygium glycosides tablets,10 mg/kg), high-dose,middle-dose and low-dose(0.08,0.04 and 0.02 ml/kg)groups of volatile oil from H. occulta. Except for normal control group,other groups were given complete Freund's adjuvant subcutaneously via right rear foot plantar to induce AA model,and giv-en relevant medicine intragastrically for 25 days,once a day,since modeling. The articular swelling degree,immune organ (thy-mus gland and spleen) index,pathological change,the contents of IL-1β and TNF-α in serum were detected. RESULTS:Com-pared with normal control group,the primary and secondary articular swelling degree and thymus gland index of rats and the serum contents of IL-1β and TNF-α increased in model control group,while spleen index decreased(P<0.05 or P<0.01);obvious tissue swelling,large amount of neutrophile granulocyte,leukomonocyte and macrophage infiltrating joint surrounding tissue,the prolifer-ation of synovial cells and obvious osteoarthritic lesion were observed in podarthrum. Compared with model control group,the pri-mary and secondary articular swelling degree and the serum content of IL-1β decreased in the volatile oil from H. occulta groups;thymus gland index increased in middle-dose and low-dose groups of the volatile oil from H. occulta;the content of TNF-α de-creased in high-dose group of the volatile oil from H. occulta(P<0.05 or P<0.01). The inflammatory cell infiltration of joint sur-rounding tissue relieved in treatment groups,synovial cells proliferation was not obvious and synovial cells morphology was im-proved. CONCLUSIONS:The volatile oil from H. occulta has the pharmacodynamic effects on AA in rat,and its mechanism might be related to the serum content reduction of IL-1β and TNF-α.

A new sesquiterpenoid from the rhizomes of Homalomena occulta.

Chemical constituents of EtOAc extract from the rhizomes of traditional Chinese medicine Qian-nian-jian (Homalomena occulta) have been studied, a new sesquiterpenoid, named euadesma-4-ene-1ß,15-diol (1), and four related known compounds, polydactin B (2), oplodiol (3), 1ß,4ß,7α-trihydroxyeudesmane (4), and (-)1ß,4ß,6α-trihydroxy-eudesmane (5), were isolated. Their structures were elucidated using spectroscopic methods including 1D and 2D NMR techniques and mass spectrometry. All the isolates were tested against the human lung adenocarcinoma A549 using MTT assay method. Oplodiol (3) and (-)1ß,4ß,6α-trihydroxy-eudesmane (5) were found to show moderate cytotoxic effects on A549 with IC50 values at 25.5 and 15.0 µg/mL, respectively.

In vitro propagation of Homalomena aromatica Schott., an endangered aromatic medicinal herb of Northeast India.

A successful report on the in vitro propagation of Homalomena aromatica via rhizome axillary bud multiplication is presented. Rhizome bud explants were cultured on Murashige and Skoog medium supplemented with various concentrations of cytokinins to induce multiple shoot formation for micropropagation. The highest number of shoots was achieved in MS medium supplemented with 2.0 mg l(-1) 6-benzylaminopurine. The regenerated shoots rooted most efficiently on half-strength MS medium supplemented with 0.5 mg l(-1) α-naphthalene acetic acid. The regenerated plantlets showed no morphological differences from the parent plant. This protocol takes approximately 6 months to reach the acclimatization stage from the initiation stage and facilitates commercial and rapid propagation of H. aromatica.

Studies on homalomeneae (araceae) of borneo v: a new species and new supergroup record, of homalomena from sabah, malaysian borneo.

Homalomena galbana Baharuddin S. & P.C. Boyce is described from the Maliau Basin Conservation Area, Sabah, representing the first species of the Homalomena Supergroup to be recorded from Sabah, and the first mesophytic species of the Supergroup to be described from Borneo. The species is illustrated and a brief discussion on the pollination role of interpistillar staminodes is presented.