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Phylogenetic relationships between Clerodendrum (Lamiaceae) and other Ajugoid genera inferred from nuclear and chloroplast DNA sequence data.

Over the last two centuries the circumscription of the large, pan-tropical genus Clerodendrum (Lamiaceae) has changed frequently, as different authorities have added or removed taxa on the basis of various morphological characters. With the development of molecular methods for systematic research the process of circumscribing taxa has become increasingly analytical. When morphology signals the possibility that taxa are closely related, molecular methods can be used to test the hypothesis objectively. Aegiphila, Amasonia, Huxleya, and Kalaharia are similar morphologically to Clerodendrum. In this paper we use nuclear ribosomal ITS and chloroplast ndhF sequence data to clarify the positions of these four genera relative to Clerodendrum. We show that the Australian monotypic genus Huxleya evolved from within Clerodendrum. Accordingly, we sink Huxleya into Clerodendrum and make a new combination, Clerodendrum linifolium.

Cell Nucleus↗

Molecular characterization of a new emaravirus infecting Clerodendrum thomsoniae plants.

High-throughput sequencing revealed a new emaravirus named clerodendrum yellow blotch virus (ClYBV), infecting Clerodendrum thomsoniae plants in São Paulo State, Brazil. Four genomic RNA segments (RNA1, RNA3, RNA4, and RNA5) were recovered, whereas RNA2 remained undetected. Phylogenetic analysis and pairwise comparisons based on amino acid sequences showed ClYBV is most closely related to redbud yellow ringspot-associated virus (RYRaV, Emaravirus cercidis). No ClYBV particles were observed by transmission electron microscopy in leaf tissues from infected plants. These results support the identification of ClYBV as a new Emaravirus member, though the undetectable RNA2 suggests the isolate may be defective, lacking this segment and unable to produce virus particles. The binomial species name "Emaravirus clerodendri" is proposed.

Phylogeny↗

Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum.

Three pheophorbide-related compounds (1-3) were isolated from the leaves and stems of Clerodendrum calamitosum. The methyl ester of 3 (6) and the known (10S)-hydroxypheophytin a (7) also were isolated from leaves of the related plant Clerodendrum cyrtophyllum. Compounds 1 and 6 were isolated for the first time as naturally occurring products from a plant source. All structures were elucidated by detailed spectroscopic analysis. Biological evaluation showed that 1 and 2 exhibited strong cytotoxicity against human lung carcinoma (A549), ileocecal carcinoma (HCT-8), kidney carcinoma (CAKI-1), breast adenocarcinoma (MCF-7), malignant melanoma (SK-MEL-2), ovarian carcinoma (1A9), and epidermoid carcinoma of the nasopharynx (KB), and its etoposide- (KB-7d), vincristine- (KB-VCR), and camptothecin-resistant (KB-CPT) subclones. Compound 3 was less cytotoxic than 1 and 2. Compounds 4-6, the methyl esters of 1-3, showed strongly increased cytotoxicity compared with the parent acids. Interestingly, 6 was the most active derivative among these compounds. Compound 7 was inactive.

Adenocarcinoma↗

Ubiquitin Conjugation to Protein Increases following Chilling of Clerodendrum Leaves.

The protein content of clerodendrum (Clerodendrum speciosum) leaves declines following chilling (48 h, 3 degrees C). Using western and dot blots and fluorescence immunoassays, we found that isolated leaf proteins had more conjugated ubiquitin following chilling. In contrast, the amount of free ubiquitin declined by almost 90% after chilling. The increase in ubiquitin conjugation was greater in the membrane fraction than in the soluble fraction.

Journal Article↗

[Studies on the antitumor effect of Clerodendrum bungei Steud or C. foetidum Bge].

Clerodendrum B(I) at dosage of 100g/kg ip or sc for 7 days was shown to have antitumor effect on hepatic carcinoma and sarcoma 180 in mice. In the mean time, 100g/kg sc of (I) interrupted 3H-TdR incorporation into DNA of sarcoma 180 cells in mice, 100, 10g/kg sc of (I) could suppress the phagocytic activity of the peritoneal macrophage against the CRBC (chicken red blood cells) in mice, 100g/kg sc of (I) also made the production of serum hemolysin less than one half of that of the control in mice immunized with SRBC. Clerodendrum C at 100g/kg could inhibit the growth of hepatic carcinoma in mice.

Animals↗

Neo-clerodane diterpenoids from Clerodendrum inerme.

Three neo-clerodane diterpenoids, inermes A, B and 14,15-dihydro-15 beta-methoxy-3-epicaryoptin, have been isolated from the hexane extract of the leaves of Clerodendrum inerme in addition to an epimeric mixture of 14,15-dihydro-15-hydroxy-3-epicaryoptin. Structures of these compounds have been elucidated on the basis of spectral studies.

Clerodendrum↗

Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (Lamiaceae).

The cyanogenic diglycoside lucumin ((R)-mandelonitrile-beta-D-primeveroside) and monoglucoside prunasin ((R)-mandelonitrile-beta-D-glucoside) were isolated from the foliage of the rare Australian rainforest tree species Clerodendrum grayi (Lamiaceae). This is the first reported isolation of the diglycoside lucumin from vegetative tissue (foliage), and the first reported co-occurrence of lucumin and prunasin. Furthermore, unusually, the diglycoside lucumin was the most abundant cyanogen accounting for approximately 60% of total cyanide in a leaf tissue.

Acetonitriles↗

4alpha-methyl-24beta-ethyl-5alpha-cholesta-14,25-dien-3beta-ol and 24beta-ethylcholesta-5, 9(11), 22E-trien-3beta-ol, sterols from Clerodendrum inerme.

From the aerial parts of Clerodendrum inerme, two new sterols (4alpha-methyl-24beta-ethyl-5alpha-cholesta-14, 25-dien-3beta-ol and 24beta-ethylcholesta-5, 9(11), 22E-trien-3beta-ol) and a new aliphatic ketone (11-pentacosanone) were isolated together with another known aliphatic ketone (6-nonacosanone) and a diterpene (clerodermic acid). The structure elucidations were based on analyses of physical and spectroscopic data.

Cholestanes↗

Anti-inflammatory and antipyretic properties of Clerodendrum petasites S. Moore.

The methanol extract from Clerodendrum petasites S. Moore (CP extract) was assessed for anti-inflammatory and antipyretic activities on the experimental animal models. It was found that CP extract possessed moderate inhibitory activity on acute phase of inflammation in a dose-related manner as seen in ethyl phenylpropiolate-induced ear edema (ED(50)=2.34 mg/ear) as well as carrageenin-induced hind paw edema (ED(30)=420.41 mg/kg) in rats. However, CP extract did not elicit any inhibitory effect on arachidonic acid-induced hind paw edema in rats. In subchronic inflammatory model, CP extract provoked a significant reduction of transudation but had no effect on proliferative phase when tested in cotton pellet-induced granuloma model. CP extract also reduced the alkaline phosphatase activity in serum of rats in this animal model. Moreover, CP extract possessed an excellent antipyretic effect when tested in yeast-induced hyperthermic rats. It is postulated that the anti-inflammatory and antipyretic effects of CP extract are caused by the inhibition of the prostaglandin synthesis. Anyhow, CP extract did not possess any analgesic activity in acetic acid-induced writhing response in mice. The results obtained show that C. petasites has beneficial properties since it possesses potent antipyretic and moderate anti-inflammatory activities without ulcerogenic effect.

Administration, Cutaneous↗

Constituents of Clerodendrum bungei.

Two new compounds, 5-O-ethylcleroindicin D (1) and bungein A (2), together with 12 known compounds (3-14), were isolated from the aerial parts of the medicinal plant Clerodendrum bungei. The structures of 1 and 2 were elucidated as a perhydrobenzofuran derivative and a peroxide dimer by spectral and chemical evidence. Compounds 3-14 have been obtained from this species for the first time.

Clerodendrum↗

A new iridoid diglycoside from Clerodendrum chinense.

A new iridoid diglucoside, 5-O-beta-glucopyranosyl-harpagide, has been isolated from the aerial part of Clerodendrum chinense together with three known iridoid glucosides and six known cyclohexylethanoids. Their structures have been determined by analyses of spectroscopic data.

Clerodendrum↗

[Studies on chemical constituents of Clerodendrum bungei].

OBJECTIVE: To study the constituents from Clerodendrum bungei. METHOD: The constituents were isolated and purified with chromatographic methods, and identified by NMR, MS and IR. RESULT: Five compounds were isolated, beta-sitosterol (1), taraxerol (2), glochidone (3), glochidonol (4), glochidiol (5). CONCLUSION: Compounds (3), (4) and (5) were isolated for the first time from C. bungei.

Clerodendrum↗

Micropropagation of Clerodendrum aculeatum through adventitious shoot induction and production of consistent amount of virus resistance inducing protein.

Rapid micropropagation through adventitious shoot induction from in vitro raised leaf explants of Clerodendrum aculeatum (Verbenaceae), was successfully achieved for the first time. Basal portion of the leaves showed highest regeneration potential when grown on MS medium supplemented with BA (5.0 mg/l) and NAA and IBA (0.5 mg/l of each). Shoots after elongation in growth regulator-free medium, were rooted in MS medium containing 0.5 mg/l of NAA and IBA. Aqueous leaf extract of in vitro raised plants, induced high degree of resistance against viruses in susceptible healthy hosts when applied prior to virus inoculation. Upon purification from leaves of cultured plants, the resistance inducing protein, showed molecular mass of 34 kDa. Amount of resistance inducing protein obtained from leaves of cultured plants, was consistent throughout the year, as compared to the protein isolated from leaves of field grown plants, which showed marked seasonal fluctuation. The purified 34 kDa protein from in vitro raised plants, was serologically related to field grown plants and possessed similar characteristics. The micropropagated plants were successfully established in earthen pots under greenhouse conditions.

Botany↗

A new phenylethanoid glycoside from Clerodendrum inerme.

A new phenylethanoid glycoside, 2-(3-methoxy-4-hydroxylphenyl) ethyl-O-2",3"-diacetyl-alpha-L-rhamnopyranosyl-(1-->3)-4-O-(E)-feruloyl-beta-D-glucopyranoside, was isolated from the aerial parts of Clerodendrum inerme (L.) Gaertn, together with monomelittoside, melittoside, inerminoside A1, verbascoside, isoverbascoside, campneoside I. Their structures were determined by spectroscopic methods.

Clerodendrum↗

A systemic antiviral resistance-inducing protein isolated from Clerodendrum inerme Gaertn. is a polynucleotide:adenosine glycosidase (ribosome-inactivating protein).

Two systemic antiviral resistance-inducing proteins, CIP-29 and CIP-34, isolated from Clerodendrum inerme Gaertn. leaves, were tested for ribosome-inactivating properties. It was found that CIP-29 has the characteristics of a polynucleotide:adenosine glycosidase (ribosome-inactivating protein), in that it inhibits protein synthesis both in cell-free systems and, at higher concentrations, in cells, and releases adenine from ribosomes, RNA, poly(A) and DNA. As compared with other known RIPs, CIP-29 deadenylates DNA at a high rate, and induces systemic antiviral resistance in susceptible plants.

Adenine↗

Sterols of some Clerodendrum species (Verbenaceae): occurrence of the 24 alpha- and 24 beta-epimers of 24-ethylsterols lacking a delta 25-bond.

The configurations at C-24 of 24-alkylsterols of six samples of Clerodendrum species (Verbenaceae) - the aerial parts of C. fragrans, C. inerme, C. infortunatum, C. scandens, and C. siphonanthus, and the seeds of C. infortunatum - were examined by NMR. All samples contained 24 beta-ethylsterols possessing a delta 25-bond, clerosterol and 22-dehydroclerosterol, as the dominant sterol components. The other 24-ethylsterols lacking a delta 25-bond, 24-ethyl-22-dehydrocholestanol, 24-ethylcholesterol, and 24-ethyl-22-dehydrocholesterol, which were present as minor components, were shown to be mixtures of the 24 alpha- and 24 beta-epimers, with the 24 alpha-epimers predominating in all cases. Four minor 24-methyl-sterols, 24-methylcholestanol, 24-methylcholesterol, 24-methyl-22-dehydrocholesterol, and 24-methyllathosterol, were shown to be C-24 epimeric mixtures, whereas two others, 24-methyl-22,25-bisdehydrocholesterol and 24-methyl-22-dehydrolathosterol, were found to be present only as the 24 beta-epimers. This is the first report of the occurrence of 24 beta-ethyl-22-dehydrocholestanol in higher plants.

Chemical Phenomena↗

Inerminosides A1, C and D, three iridoid glycosides from Clerodendrum inerme.

Three new iridoid biglycosides, inerminosides A1, C and D were isolated from the leaves of Clerodendrum inerme and their structures were established as 2'-O-(beta-D-apiofuranosyl)-mussaenosidic acid, 2'-O-[5"-O-(8-hydroxy-2,6- dimethyl-2(E)-octenoyl)-beta-D-apiofuranosyl]-gardoside and 2'-O-[5"-O-(p-hydroxy-benzoyl)-beta-D-apiofuranosyl]-mussaenosi dic acid, respectively.

Carbohydrate Sequence↗

Megastigmane and iridoid glucosides from Clerodendrum inerme.

From the aerial parts of Clerodendrum inerme, two megastigmane glucosides (sammangaosides A and B) and a iridoid glucoside (sammangaoside C) were isolated together with 15 known compounds. The structural elucidations were based on analyses of physical and spectroscopic data.

Cyclohexanones↗