Acacienone, a terpenoid-like natural product having an unprecedented C20 framework isolated from Acacia mangium leaves.

Abstract:

:A novel C20 natural product, acacienone (1), was isolated from the leaves of Acacia mangium collected in Bangladesh. The structure of compound 1 was elucidated by spectral studies and X-ray crystallographic analysis. Acacienone (1) possesses a terpenoid-related tetracyclic framework containing 20 carbons with biogenetically unusual structural features: (i) vicinal C1-branches at the C-3 and C-4 positions in the A ring, and (ii) a cyclopentenone D ring in an androsterone-like assembly, lacking a methyl group at the C-13 position.

journal_name

J Nat Med

authors

Hara Y,Totsugi Y,Ichikawa H,Harada S,Fujii K,Ahmed F,Sadhu SK,Arai MA,Ishibashi M

doi

10.1007/s11418-020-01457-y

subject

Has Abstract

pub_date

2021-01-01 00:00:00

pages

99-104

issue

1

eissn

1340-3443

issn

1861-0293

pii

10.1007/s11418-020-01457-y

journal_volume

75

pub_type

杂志文章
  • Synergistic anticancer activities of the plant-derived sesquiterpene lactones salograviolide A and iso-seco-tanapartholide.

    abstract::We have previously shown that the two sesquiterpene lactones, salograviolide A (Sal A) and iso-seco-tanapartholide (TNP), isolated from the Middle Eastern indigenous plants Centaurea ainetensis and Achillea falcata, respectively, possess selective antitumor properties. Here, we aimed to assess the anticancer effects o...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-012-0703-6

    authors: Salla M,Fakhoury I,Saliba N,Darwiche N,Gali-Muhtasib H

    更新日期:2013-07-01 00:00:00

  • Hypolipidemic activity of Symplocos cochinchinensis S. Moore leaves in hyperlipidemic rats.

    abstract::The hypolipidemic activity of Symplocos cochinchinensis S. Moore leaves was studied in Triton WR-1339- and high fat diet-induced hyperlipidemic rats. In Triton WR-1339-induced hyperlipidemic rats, the hexane extract (250 and 500 mg/kg) exerted a significant (P < 0.01) lipid-lowering effect compared to ethyl acetate an...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-011-0548-4

    authors: Sunil C,Ignacimuthu S,Kumarappan C

    更新日期:2012-01-01 00:00:00

  • Two new xanthones from the roots of Cratoxylum cochinchinense and their cytotoxicity.

    abstract::Two new xanthones namely cratochinone A (1) and cratochinone B (2), along with 16 known xanthones, were isolated from the roots of Cratoxylum cochinchinense. Their structures were characterized by spectroscopic methods, especially 1D and 2D NMR as well as comparison with those reported in the literature for known xant...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-019-01376-7

    authors: Natrsanga P,Jongaramruong J,Rassamee K,Siripong P,Tip-Pyang S

    更新日期:2020-03-01 00:00:00

  • Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components.

    abstract::Agarwood oil and spikenard extract were examined for their sedative activity using a spontaneous vapor administration system. It was shown that inhalation of agarwood oil vapor sedated mice. The main volatile constituents of the oil were found to be benzylacetone [agarwood oil from a Hong Kong market (1)], or alpha-gu...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-007-0177-0

    authors: Takemoto H,Ito M,Shiraki T,Yagura T,Honda G

    更新日期:2008-01-01 00:00:00

  • New depsidone and dichromone from the stems of Garcinia paucinervis with antiproliferative activity.

    abstract::A new depsidone, paucinervin Q (1), a new dichromone, paucinervin R (2), and a known compound, paucinervin B (3), were isolated from the stems of Garcinia paucinervis by various chromatographic methods. Their structures were determined by analysis of spectroscopic data. The isolates were evaluated for their antiprolif...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-018-1247-1

    authors: Jia C,Xue J,Li X,Li D,Li Z,Hua H

    更新日期:2019-01-01 00:00:00

  • Pharmacological effect of carvacrol on D: -galactosamine-induced mitochondrial enzymes and DNA damage by single-cell gel electrophoresis.

    abstract::The present study aimed at investigating the effect of carvacrol on hepatic mitochondrial enzyme activities and DNA damage in D: -galactosamine (D: -GalN)-induced hepatotoxicity in male albino Wistar rats. The activities of hepatic mitochondrial enzymes such as isocitrate dehydrogenase, α-ketoglutarate dehydrogenase, ...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-011-0544-8

    authors: Aristatile B,Al-Numair KS,Al-Assaf AH,Pugalendi KV

    更新日期:2011-07-01 00:00:00

  • Possible attenuation of nitric oxide expression in anti-inflammatory effect of Ziziphus jujuba in rat.

    abstract::The hydroalcoholic extract of fruits of Ziziphus jujuba (ZJ) was investigated for its anti-inflammatory effect using acute and chronic models of inflammation in rat. Wistar albino rats of either sex were employed in the present study (n = 6). Acute inflammation was induced by subplantar administration of carrageenan (...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-011-0531-0

    authors: Goyal R,Sharma PL,Singh M

    更新日期:2011-07-01 00:00:00

  • Antibacterial activity of two limonoids from Swietenia mahagoni against multiple-drug-resistant (MDR) bacterial strains.

    abstract::Solvent partitioning followed by column chromatography of the MeOH extract of the seeds of Swietenia mahagoni afforded two limonoids, swietenolide (1) and 2-hydroxy-3-O-tigloylswietenolide (2). The compounds were identified by spectroscopic means. The antibacterial activity of these compounds was assessed against eigh...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-008-0287-3

    authors: Rahman AK,Chowdhury AK,Ali HA,Raihan SZ,Ali MS,Nahar L,Sarker SD

    更新日期:2009-01-01 00:00:00

  • Preventive effect of Terminalia bellirica on obesity and metabolic disorders in spontaneously obese type 2 diabetic model mice.

    abstract::Visceral obesity induces insulin resistance and is recognized as an important risk factor for metabolic syndrome (MS). Therefore, inhibition of lipid absorption from the intestine is regarded as an effective way of preventing MS. Terminalia bellirica is extensively used in Ayurvedic medicine in India and neighboring c...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-011-0606-y

    authors: Makihara H,Shimada T,Machida E,Oota M,Nagamine R,Tsubata M,Kinoshita K,Takahashi K,Aburada M

    更新日期:2012-07-01 00:00:00

  • Tareciliosides N-S: further cycloartane saponins from the leaves of Tarenna gracilipes, and cytotoxicity of saponins and triterpenes.

    abstract::Six cycloartane glycosides, named tareciliosides N-S, and a known iridoid glucoside, ixoroside, were isolated in further extensive studies on the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Tarenna gracilipes. From the EtOAc-soluble fraction, three known triterpenes were isolated. Their toxicities towar...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-012-0707-2

    authors: Zhao Z,Matsunami K,Otsuka H,Shinzato T,Takeda Y

    更新日期:2013-07-01 00:00:00

  • Pharmacokinetics and organ distribution of diarylheptanoid phytoestrogens from Curcuma comosa in rats.

    abstract::Curcuma comosa is widely used as a traditional herbal medicine for gynecological diseases in South East Asia. Previous studies reported that it has phytoestrogenic activity, and several diarylheptanoids were found to be the active constituents. In this study, the pharmacokinetics profile and organ distribution of thre...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-011-0607-x

    authors: Su J,Sripanidkulchai K,Suksamrarn A,Hu Y,Piyachuturawat P,Sripanidkulchai B

    更新日期:2012-07-01 00:00:00

  • Development of a simple and rapid method for the detection of isomiroestrol in Pueraria candollei by an immunochromatographic strip test.

    abstract::Pueraria candollei (P. candollei) is a traditional Thai herb widely used for estrogen replacement therapy because it contains many unique chromenes that possess potent estrogenic activity, one of which is known as isomiroestrol. Since isomiroestrol is a promising compound that is solely present in P. candollei, it can...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-019-01307-6

    authors: Chaingam J,Kitisripanya T,Krittanai S,Sakamoto S,Tanaka H,Putalun W

    更新日期:2019-06-01 00:00:00

  • Effect of altitude on picroside content in core collections of Picrorhiza kurrooa from the north western Himalayas.

    abstract::Picrorhiza kurrooa Royle ex Benth (Scrophulariaceae), commonly known as Kutki, is a major ingredient of many ayurvedic preparations prescribed in the treatment of various diseases. Picrosides I and II are the active agents responsible for the medicinal effects of Kutki, and the variation in content of these compounds ...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-010-0491-9

    authors: Katoch M,Fazli IS,Suri KA,Ahuja A,Qazi GN

    更新日期:2011-07-01 00:00:00

  • Four new Amaryllidaceae alkaloids from Zephyranthes candida.

    abstract::Four new Amaryllidaceae alkaloids (1-4) possessing a homolycorine-type or a crinine-type skeleton have been isolated from the aerial part of Zephyranthes candida, and their structures were elucidated on the basis of spectroscopic data. The stereochemistry was elucidated by combination of NOESY correlations and CD anal...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-014-0819-y

    authors: Shitara N,Hirasawa Y,Hasumi S,Sasaki T,Matsumoto M,Wong CP,Kaneda T,Asakawa Y,Morita H

    更新日期:2014-07-01 00:00:00

  • Determination of (E)-ferulic acid content in the root of Angelica acutiloba: a simple chemical evaluation method for crude drug quality control.

    abstract::The root of Angelica acutiloba Kitagawa is an important crude drug in Kampo medicines (traditional Japanese medicine). Chemical evaluation of crude drugs is crucial to ensuring the safety and efficacy of herbal medicine; however, there is currently no chemical standard for the A. acutiloba crude drug in Japanese pharm...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-018-1190-1

    authors: Shinjyo N,Fuchino H,Kawahara N,Hishida A

    更新日期:2018-06-01 00:00:00

  • Satureja khuzestanica attenuates apoptosis in hyperglycemic PC12 cells and spinal cord of diabetic rats.

    abstract::Several studies have indicated the involvement of oxidative stress and high glucose-induced cell death in the development of diabetic neuropathy. Satureja khuzestanica has been recommended in the literature as a remedy for the treatment of diabetes, and also contains antioxidant agents. Here, we investigated the possi...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-012-0646-y

    authors: Kaeidi A,Esmaeili-Mahani S,Abbasnejad M,Sheibani V,Rasoulian B,Hajializadeh Z,Pasban-Aliabadi H

    更新日期:2013-01-01 00:00:00

  • Hirtionosides A-C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta.

    abstract::From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A-C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-012-0692-5

    authors: Nomoto Y,Sugimoto S,Matsunami K,Otsuka H

    更新日期:2013-04-01 00:00:00

  • Preliminary phytochemical investigation of Lychnis flos-cuculi herbs.

    abstract::Five polyphenolic compounds were identified from the diethyl ether and ethyl acetate extracts of the herb of ragged robin, Lychnis flos-cuculi L. (Caryophyllaceae). The identified and isolated compounds were established as a caffeic acid, luteolin, apigenin, apigenin 8-C-beta-D-glucopyranoside (vitexin) and luteolin 8...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-008-0261-0

    authors: Tomczyk M

    更新日期:2008-10-01 00:00:00

  • Non-alkaloidal composition of Ephedra Herb is influenced by differences in habitats.

    abstract::Ephedra Herb is a crude drug defined as the terrestrial stem of Ephedra sinica, E. intermedia, or E. equisetina. It is often used to treat headaches, bronchial asthma, nasal inflammation, and the common cold. In this study, we isolated characteristic non-alkaloidal constituents from the extracts and identified them in...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-018-1265-z

    authors: Oshima N,Yamashita T,Uchiyama N,Hyuga S,Hyuga M,Yang J,Hakamatsuka T,Hanawa T,Goda Y

    更新日期:2019-01-01 00:00:00

  • Effect of eurycomanone on cytochrome P450 isoforms CYP1A2, CYP2A6, CYP2C8, CYP2C9, CYP2C19, CYP2E1 and CYP3A4 in vitro.

    abstract::Eurycomanone, an active constituent isolated from Eurycoma longifolia Jack, was examined for modulatory effects on cytochrome P450 (CYP) isoforms CYP1A2, CYP2A6, CYP2C8, CYP2C9, CYP2C19, CYP2E1 and CYP3A4 using in vitro assays. The IC50 value was determined to assess the potencies of modulation for each CYP isoform. O...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-013-0794-8

    authors: Pan Y,Tiong KH,Abd-Rashid BA,Ismail Z,Ismail R,Mak JW,Ong CE

    更新日期:2014-04-01 00:00:00

  • Pharmacokinetics study of asperosaponin VI and its metabolites cauloside A, HN saponin F and hederagenin.

    abstract::This experiment's with aim was to study the pharmacokinetics of asperosaponin VI and its three metabolites (cauloside A, HN saponin F and hederagenin) via a sensitive high performance liquid chromatography connected with electrospray ionization triple quadrupole mass spectrum (HPLC-ESI-MS/MS). Chromatographic separati...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-014-0821-4

    authors: Liu EW,Wang JL,Han LF,Chang YX,Wang T,Huo Y,Wang L,Gao XM

    更新日期:2014-07-01 00:00:00

  • Antitumor effect of the seashell protein Haishengsu on Ehrlich ascites tumor: an experimental study.

    abstract::The aim of the study was to investigate the in vivo effect of the seashell protein Haishengsu (HSS) on Ehrlich ascites tumor. Mice were inoculated with Ehrlich ascites tumor cells and randomly divided into three HSS groups and a control group. The survival times in the three HSS-treated groups was longer than in the c...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-009-0346-4

    authors: Liu JZ,Chen SG,Bin Z,Wang CB,Li GY,Wang LX

    更新日期:2009-10-01 00:00:00

  • Bastadins, cyclic tetramers of brominated-tyrosine derivatives, selectively inhibit the proliferation of endothelial cells.

    abstract::Eight bastadins, tetramers of brominated-tyrosine derivatives, were isolated from the marine sponge Ianthella basta, and their anti-proliferative activities against endothelial cells were examined. A structure-activity relationship study of these compounds revealed that a macrocyclic structure was crucial, and a basta...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-006-0045-3

    authors: Aoki S,Cho SH,Hiramatsu A,Kotoku N,Kobayashi M

    更新日期:2006-07-01 00:00:00

  • Two new monoterpenes from Sibiraea angustata.

    abstract::Two novel monoterpenes, sibiscolacton (1) and sibiraic acid (2), were isolated from the aerial part of Sibiraea angustata RCHD: . along with seven known compounds, namely three phenylpropanoids (3-5), two flavonoids (6,7), one glucityl ferulate (8, sibirate), and a monoterpene glucoside (9, sibiskoside). The structure...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-009-0362-4

    authors: Li B,Lee JB,Hayashi K,Ito Y,Sun WJ,Wang X,Kano Y,Hayashi T

    更新日期:2010-01-01 00:00:00

  • BBB-permeable aporphine-type alkaloids in Nelumbo nucifera flowers with accelerative effects on neurite outgrowth in PC-12 cells.

    abstract::Blood-brain barrier (BBB)-permeable components in the methanolic extract of Nelumbo nucifera flowers showed accelerative effects on neurite outgrowth in PC-12 cells. Among the constituents isolated from N. nucifera flowers in our previous study, aporphine-type alkaloids, lirinidine, asimilobine, N-methylasimilobine, a...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-019-01368-7

    authors: Yano M,Nakashima S,Oda Y,Nakamura S,Matsuda H

    更新日期:2020-01-01 00:00:00

  • Confirmation of the antispasmodic effect of shakuyaku-kanzo-to (TJ-68), a Chinese herbal medicine, on the duodenal wall by direct spraying during endoscopic retrograde cholangiopancreatography.

    abstract::The purpose of the study was to evaluate the suppressive effect of TJ-68 on duodenal spasms during endoscopic retrograde cholangiopancreatography (ERCP). At the point when the duodenal papilla was confirmed after insertion of the endoscope during ERCP, 5.0 g TJ-68 (Tsumura Co., Tokyo, Japan) was dissolved in 50 ml of ...

    journal_title:Journal of natural medicines

    pub_type: 临床试验,杂志文章

    doi:10.1007/s11418-008-0304-6

    authors: Sakai Y,Tsuyuguchi T,Ishihara T,Kato K,Tsuboi M,Ooka Y,Katsuura K,Ohara T,Takayama S,Kimura M,Kasanuki J,Ai M,Yokosuka O

    更新日期:2009-04-01 00:00:00

  • Sanjecumins A and B: new limonoids from Sandoricum koetjape.

    abstract::Two new limonoids, sanjecumins A (1) and B (2), have been isolated from the leaves of Sandoricum koetjape, together with sandoripins A (3) and B (4). Their structures and absolute configurations were elucidated on the basis of NMR and CD data. Sandoripins A (3) and B (4) moderately inhibited nitric oxide production in...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-012-0677-4

    authors: Nagakura Y,Nugroho AE,Hirasawa Y,Hosoya T,Rahman A,Kusumawati I,Zaini NC,Morita H

    更新日期:2013-04-01 00:00:00

  • Polyphenolic compounds isolated from the leaves of Myrtus communis.

    abstract::Four hydrolyzable tannins [oenothein B (1), eugeniflorin D(2) (2), and tellimagrandins I (3) and II (4)], two related polyphenolic compounds [gallic acid (5) and quinic acid 3,5-di-O-gallate (6)], and four myricetin glycosides [myricetins 3-O-beta-D-xyloside (7), 3-O-beta-D-galactoside (8), 3-O-beta-D-galactoside 6''-...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-008-0251-2

    authors: Yoshimura M,Amakura Y,Tokuhara M,Yoshida T

    更新日期:2008-07-01 00:00:00

  • Effects of shakuyakukanzoto and its absorbed components on twitch contractions induced by physiological Ca2+ release in rat skeletal muscle.

    abstract::Shakuyakukanzoto (SKT) is a kampo medicine composed of equal proportions of Glycyrrhizae radix (G. radix) and Paeoniae radix (P. radix). A double-blind study reported that SKT significantly ameliorated painful muscle cramp in cirrhosis patients without the typical severe side effects of muscle weakness and central ner...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-015-0890-z

    authors: Kaifuchi N,Omiya Y,Kushida H,Fukutake M,Nishimura H,Kase Y

    更新日期:2015-07-01 00:00:00

  • Phytochemical constituents of Mongolian traditional medicinal plants, Chamaerhodos erecta and C. altaica, and its constituents prevents the extracellular matrix degradation factors.

    abstract::Activity-guided isolation of the n-butanol fraction of Chamaerhodos erecta and water soluble fraction of C. altaica resulted in the isolation of 39 compounds, including new compounds identified as 4,5-dihydroxybenzaldehyde-3-O-β-D-glucopyranoside (1) from C. erecta and quercetin-3-O-β-D-glucuronopyranosyl-4'-O-β-D-glu...

    journal_title:Journal of natural medicines

    pub_type: 杂志文章

    doi:10.1007/s11418-013-0748-1

    authors: Selenge E,Odontuya G,Murata T,Sasaki K,Kobayashi K,Batkhuu J,Yoshizaki F

    更新日期:2013-10-01 00:00:00