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Studies on the Constituents of Callicarpa Formosana Rolfe
Abstract
Two new naturally occurring flavonoids, 3,4′,5,7-tetramethoxyflavone and 3,3′,4′,5,7-pentamethoxyflavone, along with known compounds, 5-hydroxy-3,4′,7-trimethoxyflavone, 5-hydroxy-3,3′,4,7-tetramethoxyflavone, ursolic acid, 2α,3α-dihydroxyurs-12-en-28-oic acid, phytosterols, and phytosteryl glucosides, have been isolated and characterized from the fresh leaves of Callicarpa formosana Rolfe.
... (Beautyberry) locally called as 'Hnahkiah' is a small evergreen tree belongs to family Verbanaceae and is widely distributed in the Asia-Pacific regions (Shihan et al., 2015). The leaves and bark of C. arborea have been extensively used for the treatment of inflammation (Mi et al., 1984), diabetes (Junejo et al., 2017) and intestinal disorder (Chen et al., 1986). The local people of Mizoram use the leaves and bark of C. arborea as haemostatic agent and for the treatment of abdominal colic (Sharma et al., 2016) as well as in cancer treatment (Lalfakzuala, 2007). ...
The study aims to evaluate the anticancer activity of Callicarpa arborea in A549 cancer cells.Fresh non-infected leaves of Callicarpa arborea were collected from Serkawn, Lunglei District, Mizoram and various solvents were used for Soxhlet extraction at their respective boiling points. The extracts were concentrated and the anticancer activity was tested in the human lung cancerbcell line A549 using MTT and clonogenic assays. The effect of C. arborea on the antioxidant system was also assessed by measuring the levels of glutathione, glutathione s-transferases, superoxide dismutase as well as lipid peroxidation levels following standard protocols. Among the various solvent extracts of C. arborea, only chloroform extract showed significant cytotoxicity, and inhibited cell proliferation and survival against the A549 cancer cells. The chloroform extract of C. arborea induced cell death in A549 cells in a dose and time dependent manner with an IC50 of 52.8 20.4 50 μgml-1 and μgml-1 at 24 hr and 48 hr, respectively. The clonogenic assay showed that the chloroform extract was able to inhibit cell proliferation in the A549 cells and the inhibition increased with increase in dose. The chloroform extract also alleviated the levels and activities of antioxidants glutathione, glutathione-s-transferase and superoxide dismutase, while elevating the lipid peroxidation level in the A549 cells. The study shows that Callicarpa arborea possess both cytotoxic and anti-proliferative properties against the human lung cancer cell line A549. Callicarpa arborea is a potential candidate as a new anti-cancer agent and warrants further investigation.
... leaves are reported to be used in Palau and the Philippines to stupefy fish [38,39]. C. formosana Rolfe is used in Taiwanese folk medicine to treat rheumatism and disorders of the digestive tract (oral infections and unspecified stomach disorders and intestinal complaints) [15]. The bark of C. lanata L. has been used in the East Indies as a betel leaf substitute [30]. ...
About 20 species from Callicarpa have reported ethnobotanical and ethnomedical uses, and several members of this genus are well known in the traditional medical systems of China and South Asia. Ethnomedical reports indicate their use in the treatment of hepatitis, rheumatism, fever, headache, indigestion, and other ailments. Several species of Callicarpa have been reported to be used against cancer (e.g., Callicarpa americana root to treat skin cancer and Callicarpa rubella bark to treat tumors of the large intestine). Extracts from about 14 species in this genus have been evaluated for biological activity, including antibacterial, antifungal, anti-insect growth, cytotoxic, and phytotoxic activities. In addition to amino acids, benzenoids, simple carbohydrates, and lipids, numerous diterpenes, flavonoids, phenylpropanoids, phytosterols, sesquiterpenes, and triterpenes have been detected in or isolated from the genus Callicarpa. The essential oils of Callicarpa americana have recently been reported to have antialgal and phytotoxic activities, and several isolates from this species (and C. japonica) were identified as contributing to the mosquito bite-deterrent activity that was first indicated by folkloric usage. Recent bioassay-guided investigations of C. americana extracts have resulted in the isolation of several active compounds, mainly of the clerodane diterpene structural type.
... The fractions with muscarinic receptor binding activities were separated further to obtain pure compounds. The compounds characterized by NMR and MS were six polymethoxyflavones [3,5,6,7,8pentamethoxy-3 0 ,4 0-methylenedioxyflavone (1) (Fauvel et al., 1981;Jong and Wu, 1989;Ritchie et al., 1965); 3,5,6,7-tetramethoxy-3 0 ,4 0-methylenedioxyflavone (3) ( Jong and Wu, 1989;Ritchie et al., 1965); 3,3 0 ,4 0 ,5,7-pentamethoxyflavone (4) ( Chen et al., 1986;de la Torre et al., 2004;Dong et al., 1999;Herunsalee et al., 1987); 3,5-dimethoxy-3 0 ,4 0 ,6,7bismethylenedioxyflavone (5) ( Fauvel et al., 1981;Higa et al., 1987;Jong and Wu, 1989;Ritchie et al., 1965); 3,5,8-trimethoxy-3 0 ,4 0 ,6,7-bismethylenedioxyflavone (6) ( Fauvel et al., 1981;Higa et al., 1987;Jong and Wu, 1989); and 3,5,7-trimethoxy-3 0 ,4 0-methylenedioxyflavone (7) ( Higa et al., 1987;Ho et al., 2003)] and one furanocoumarin [5-methoxy-8-geranyloxypsoralen (2) ( Franke et al., 2001;Sokolova et al., 1976)]. Compounds 2 and 6 were isolated for the first time from M. subunifoliolata. ...
The bark extract of Melicope subunifoliolata (Stapf) T.G. Hartley showed competitive muscarinic receptor binding activity. Six polymethoxyflavones [melibentin (1); melisimplexin (3); 3,3',4',5,7-pentamethoxyflavone (4); meliternatin (5); 3,5,8-trimethoxy-3',4',6,7-bismethylenedioxyflavone (6); and isokanugin (7)] and one furanocoumarin [5-methoxy-8-geranyloxypsoralen (2)] were isolated from the bark extract. Compounds 2 and 6 were isolated for the first time from M. subunifoliolata. The methoxyflavones (compounds 1, 3, 4, 5, 6, and 7) show moderate inhibition in a muscarinic receptor binding assay, while the furanocoumarin (compound 2) is inactive. The potency of the methoxyflavones to inhibit [(3)H]NMS-muscarinic receptor binding is influenced by the position and number of methoxy substitution. The results suggest these compounds are probably muscarinic modulators, agonists or partial agonists/antagonists.
Callicarpa arborea (CA) (English - Beautyberry) locally called as ‘Hnahkiah’ is a small evergreen tree of the family Verbanaceae. The study aims to evaluate the effects of Callicarpa arborea on the level of various antioxidants and reproductive integrity in type II Human lung adenocarcinoma (A549). Treatment of A549 cells with different doses of Callicarpa arborea extracts resulted in alleviation of antioxidants (GSH, GST and SOD) and the elevation of lipid peroxidation. The clonogenic assay demonstrated that treatment of A549 cells with different doses of extracts of Callicarpa arborea resulted in a decline in the number of colonies of A549 cells.
Es stehen viele neue Angaben zur Verbreitung und zum Chemismus von Iridoiden, Polyphenolen, etherischen Ölen, Chinonen, Diterpenen und Triterpenen zur Verfügung.
This review focuses on the occurrence and structural elucidation of neo-clerodane type diterpenes from Verbenaceae (no matter if recently reclassified based on phylogenetic research) and the semisynthetic compounds of closely related structure obtained. Biological activities of crude extracts and isolated diterpenes will be briefly discussed.
The root and aerial parts of Rosa taiwanensis Nakai contain the chemical constituents phenols, unsaturated acids, loliolide, abscisic acid, flavones, sterols, lupeol, betulin, betulinic acid, oleanolic acid and ursolic acid derivatives. Among them, 2α,3α‐dihydroxyurs‐12,19‐dien‐28‐oic acid and its C‐3 epimer are new compounds.
The first total synthesis of (+)-pentandranoic acid A (1) was accomplished in 14 steps, starting from alcohol 3. Our synthesis features several key transformations, such as an ozonolysis-aldol cyclization-dehydration ring contraction sequence and a selective 1,4-diol oxidation, and provides an efficient synthetic route to this rare clerodane diterpenoid.
Ethnopharmacological relevance:
Callicarpa L. (Verbenaceae) has been used for centuries in Traditional Chinese Medicine (TCM) for the prevention and treatment of a wide number of health disorders such as inflammation, rheumatism, hematuria, fracture, hematemesis, menoxenia, gastrointestinal bleeding, scrofula, etc.
Aims of the review:
To assess the scientific evidence for therapeutic Callicarpa in TCM and to identify future research needs.
Methods:
The available information on the ethnopharmacological uses in Chinese medicine, phytochemistry, pharmacology and clinical practice of Callicarpa species was collected via a library and electronic search (PubMed, ScienceDirect, Google Scholar and CNKI).
Results:
A variety of ethnomedical use of Callicarpa has been recorded in many ancient Chinese books. Phytochemical investigation of this genus has resulted in identification of more than 200 chemical constituents, among which diterpenes, triterpenoids and flavonoids are the predominant groups. The isolates and crude extract have exhibited a wide spectrum of in vitro and in vivo pharmacological effects involving anti-inflammatory, hemostatic, neuroprotective, anti-amnesic, antitubercular, antioxidant, antimicrobial and analgesic activities. Preparations containing Callicarpa species exerted good efficacy on clinical applications of gynecological inflammation, internal and external hemorrhage as well as acne vulgaris and chronic pharyngitis, etc. From the toxicity perspective, only three Callicarpa species have been assessed.
Conclusions:
Pharmacological results have validated the use of Callicarpa species in the traditional medicine. As literature demonstrated, terpenoids and flavonoids are perhaps responsible for most of the activities shown by the plants of this genus. However, the detailed active compounds and the underlying mechanisms remain a work in progress. In addition, more attention should be paid to C. nudiflora as well as the domain of rheumatism.
The three new lignanoids 1-3 and the five new phyllocladane diterpenoids 7-11 were isolated from the leaves of Callicarpa furfuraceae, together with two known lignanoids, lariciresinol (4) and (+)-sesamin (5), and five known diterpenoids, 17-norphyllocladane-3,16-dion (6), calliterpenone (12), calliterpenone 17-acetate (13), (3 beta,16 alpha)-phyllociadane-3,16,17-triol (14), and (3 beta,16 alpha)-phyllocladane-3,16,17-triol 17-acetate (15). Their structures were established by spectral-data interpretation.
The presence of several types of allelochemicals has been reported from Ajuga, a Labiatae genus comprising more than 40 species of wide distribution in extratropical regions of both hemispheres. The
genus is of great medicinal and economic importance and among the biological properties of the secondary metabolites, the
antifeedant activity against pest insects appears to be related to the presence of neo-clerodane type diterpenes. This review focuses on the isolation and structural elucidation of this type of compounds from
Ajuga species and the hemisynthetic compounds of closely related structure obtained. The reported biological activity of crude
extracts and isolated diterpenes will be briefly commented.
Leaf extracts of Callicarpa pentandra provided four new clerodane-type diterpenoids (1-4), of which 1, 2, and 4 have ring-A-contracted structures. Their structures and stereochemistry were established by spectral data interpretation, and for 3 also by single-crystal X-ray diffraction.
The methanol spectra of flavones and flavonols exhibit two major absorption peaks in the region 240 – 400 nm¹. These two peaks are commonly referred to as Band I (usually 300 – 380 nm, Table V-1 records the λmaxvalues for Band I for all flavones and flavonols examined in the present investigation), and Band II (usually 240 – 280 nm). Band I is considered to be associated with absorption due to the B-ring cinnamoyl system, and Band II with absorption involving the A-ring benzoyl system (see III) [1].
From the petrol extract of the aerial parts of Callicarpa macrophylla Vahl (Fam: Verbenaceae) two new tetracyclic diterpenes viz. calliterpenone and calliterpenone monoacetate were isolated and their structures and stereochemistry were established as I and II respectively from a careful analysis of their spectroscopic data and chemical evidences and also by their conversions to (−)-17-norkaurane.
The quantitative shift reagent behavior of polymethoxylated flavones in the presence of Pr(fod)3 shows that for structural elucidation of these molecules the degree of substitution in the neighborhood of the carbonyl group can be determined from the number of signals that are strongly shifted and broadened. The induced shifts of the remaining signals are of complementary help and even the resonances of individual methoxyl groups can be ascribed.
Three rare naturally occurring flavonol 3-methyl ethers have been isolated from stems of Aframomum giganteum: kaempferol 3,7,4′-trimethyl ether, quercetin 3,7,4′-trimethyl ether (ayanin) and quercetin 3,7,3′,4′-tetramethyl ether (retusine). The following compounds have also been isolated: chrysophanol, physcion, 2,6-dimethoxybenzoquinone and β-sitosterol. Phytochemical aspects of the flavonoids occurring in the Zingiberaceae are discussed.
The mass spectra of some simple flavones, flavonols, and their permethyl ethers have been examined. A new fragmentation pathway of 6-methoxyflavones is discussed, and the formation of (M—H)+ and (M—H3O)+ ions is discussed. It is shown that significant structural information can be obtained from the mass spectra of polyhydroxyflavones and their ethers.
Nobiletin and irigenin were identified as inhibitors of cyclic AMP phosphodiesterase, which were contained in peels of immature fruits of Citrus reticulata BLANCO (Japanese name “Seihi”) and in rhizomes of Iris florentina L. The structure activity relationships of 33 flavonoids were studied and polymethoxy flavonoids were generally more inhibitory against cAMP phosphodiesterase than corresponding polyhydroxy flavonoids. Nobiletin, irigenin and pentamethyl quercetin showed inhibitory effect on barium sulphate transport in the small intestine of mice. Further pharmacological investigations have revealed that these flavonoids have cholinergic activity.
Asia-Pacific Symposium on Natural Product Chemistry
- Y.P. Chen
- C.C. Chen
- H.T. Chen
- H.Y. Hsu