A cytotoxic diarylheptanoid from Viscum cruciatum

Martı́n-Cordero, Carmen; López‐Lázaro, Miguel; Agudo, Marı́a Angeles; Navarro, Eduardo; Trujillo, Juan Manuel; Ayuso, Marı́a Jesús

doi:10.1016/s0031-9422(01)00293-x

Cited by 25 publications

(12 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 3 was previously isolated from Viscum cruciatum (Viscaceae), 4) 4 from Alnus rubra (Betulaceae), 5) and 5 from Alnus japonica. 6) They showed 1 H-and 13 C-NMR spectroscopic data which agreed well with the values reported in the literature.…”

mentioning

confidence: 99%

See 1 more Smart Citation

New Diarylheptanoids from Amomum muricarpum ELMER

Giang

Sơn²,

Matsunami

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Amomum muricarpum ELMER (Zingiberaceae) is a medicinal plant 2-3 m tall which is distributed in dense forests in Guangdong and Guangxi provinces (China) at 300-1000 m above sea level.1) The plant is also distributed in the Philippines and recently was found in Vietnam by a group of botanic taxonomists of the Vietnam Academy of Science and Technology. The lack of phytochemical reports on A. muricarpum prompted us to investigate the species that grows in Vietnam. We succeeded in the isolation of the two new diarylheptanoids 1 and 2 together with the three known compounds 3-5, of which the isolation and structure determination are described in this paper.The extraction of the oven-dried rhizomes of A. muricarpum with MeOH and sequential fractionation using solvents of increasing polarities gave n-hexane-, CH 2 Cl 2 -, EtOAc-, and 1-BuOH-soluble fractions. The isolation of compounds 1-5 ( Fig. 1) . The locations of the carbonyl group at C-3 and methoxyl group at C-5 were unambiguously determined with the 1 H-1 H correlated spectroscopy (COSY) and heteronuclear multiple bond correlation (HMBC) spectra of 1 (Fig. 2). The absolute stereochemistry of the methoxyl group was determined to be 5R on the basis of the negative sign of the optical rotation and positive Cotton effect associated with the carbonyl n→p* transition at 350 nm (De ϩ0.57) in the circular dichroism (CD) spectrum of 1 in comparison with those of a series of analogous compounds.2) Thus the structure of 1 was determined to be (5R)-5-methoxy-1,7-bis(3,4-dihydroxyphenyl)-3-heptanone, which was given the trivial name muricarpone A.Compound 2 was obtained as a syrup. Its molecular formula was determined to be C 19 H 22 O 5 based on the results of negative-ion HR-FAB-MS. The IR spectrum exhibited a hydroxyl absorption band at 3286 and a ketone band at 1696 cm Ϫ1. The 1 H-, 13 C-NMR (Table 1), and DEPT spectra of 2 disclosed the presence of seven carbons of the heptane chain including the isolated carbonyl group [d C 213.7 (s), 45.3 (t), 43.6 (t), 35.9 (t), 32.1 (t), 30.4 (t), 24.3 (t)] and two identical 3,4-dihydroxyphenyl moieties. The asymmetrical nature of the heptane chain was evident from the appearance of all seven carbons in the 13 C-NMR spectrum. The carbonyl group was located at C-3 by comparing the 13 C chemical shifts of 2 with those of yakuchinone A.3) This assignment was further confirmed in the HMBC experiment (Fig. 3). A and B, together with three known diarylheptanoids, 1,7-di-(3,4-dihydroxyphenyl)-4-hepten-3-one, 1-(3,4-dihydroxyphenyl)-7-(4؆-hydroxyphenyl)-4-hepten-3-one, and 1,7-bis(p-hydroxyphenyl)-4-hepten-3-one, were isolated from the rhizomes of Amomum muricarpum ELMER (Zingiberaceae). Their structures were determined using spectroscopic analyses.

show abstract

mentioning

confidence: 99%

“…6) They showed 1 H-and 13 C-NMR spectroscopic data which agreed well with the values reported in the literature. [4][5][6] Very few reports on diarylheptanoids from the genus Amomum (Zingiberaceae) have appeared in recent years, 7,8) although they may receive renewed scrutiny as a future source of new diarylheptanoids from nature.…”

mentioning

confidence: 99%

New Diarylheptanoids from Amomum muricarpum ELMER

Giang

Sơn²,

Matsunami

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…Diarylheptanoids have been isolated previously from Aceraceae, Betulaceae, Zingiberaceae, Leguminosae [9], Dioscorea spongiosa [10], and Viscum cruciatum [11]. These compounds exhibited wide range of biological activities [9], especially cytotoxic [11] and antiosteoporotic [10] actions.…”

Section: Discussionmentioning

confidence: 99%

“…These compounds exhibited wide range of biological activities [9], especially cytotoxic [11] and antiosteoporotic [10] actions. Except for diosponin A and B, two antiosteoporotic components from Dioscorea spongiosa [10], which displayed a 1-ketone structure, all other known diarylheptanoids belonged to the 3-ketone or 3,5-diketone types.…”

Section: Discussionmentioning

confidence: 99%

Mistletonone, a Novel Antioxidative Diarylheptanoid from the Branches and Leaves of Viscum coloratum

Zhou

et al. 2007

Molecules

View full text Add to dashboard Cite

Mistletonone, a novel diarylheptanoid, was isolated from the branches and leaves of Viscum coloratum (Kom.) Nakai (Loranthaceae). It was identified as 1,7-di-(phydroxyphenyl)-5-hydroxyl-cis-2,3-epoxy-1-one on the basis of spectral evidence. The compound showed significant scavenging effects on hydroxyl radicals and superoxide anion radicals in the direct assay using the electron spin resonance (ESR) technique.

show abstract

“…In a systematic review, Kienle et al found that quality of life (QOL) and tolerability of chemotherapy, radiotherapy or surgery were improved in patients receiving mistletoe in 21 of 24 clinical studies (15 randomized, 9 non-randomized) conducted with breast and gynecological cancer patients (Kienle et al [2009]). In the arena of basic science breast cancer research, mistletoe effects included prevention of surgery-induced suppression of granulocyte function (Büssing et al [2005]), DNA repair in damaged peripheral blood mononuclear cells (Kovacs [2002]), cytotoxic effect (Martín-Cordero et al [2001]), and effects in different breast cancer cell lines on immune defense and stress response genes, as well as on cell-cell adhesion and cytoskeleton pathways (Eggenschwiler et al [2006]).…”

Section: Introductionmentioning

confidence: 99%

Barriers and challenges in integration of anthroposophic medicine in supportive breast cancer care

et al. 2013

View full text Add to dashboard Cite

In the last decade, more and more oncology centers are challenged with complementary medicine (CM) integration within supportive breast cancer care. Quality of life (QOL) improvement and attenuation of oncology treatment side effects are the core objectives of integrative CM programs in cancer care. Yet, limited research is available on the use of specific CM modalities in an integrative setting and on cancer patients’ compliance with CM consultation. Studies are especially warranted to view the clinical application of researched CM modalities, such as anthroposophic medicine (AM), a unique CM modality oriented to cancer supportive care. Our objective was to characterize consultation patterns provided by physicians trained in CM following oncology health-care practitioners’ referral of patients receiving chemotherapy. We aimed to identify characteristics of patients who consulted with AM and to explore patients’ compliance to AM treatment. Of the 341 patients consulted with integrative physicians, 138 were diagnosed with breast cancer. Following integrative physician consultation, 56 patients were advised about AM treatment and 285 about other CM modalities. Logistic multivariate regression model found that, compared with patients receiving non-anthroposophic CM, the AM group had significantly greater rates of previous CM use [EXP(B) = 3.25, 95% C.I. 1.64-6.29, p = 0.001] and higher rates of cancer recurrence at baseline (p = 0.038). Most AM users (71.4%) used a single AM modality, such as mistletoe (viscum album) injections, oral AM supplements, or music therapy. Compliance with AM modalities following physician recommendation ranged from 44% to 71% of patients. We conclude that AM treatment provided within the integrative oncology setting is feasible based on compliance assessment. Other studies are warranted to explore the effectiveness of AM in improving patients’ QOL during chemotherapy.

show abstract

A cytotoxic diarylheptanoid from Viscum cruciatum

Cited by 25 publications

References 11 publications

New Diarylheptanoids from Amomum muricarpum ELMER

New Diarylheptanoids from Amomum muricarpum ELMER

Mistletonone, a Novel Antioxidative Diarylheptanoid from the Branches and Leaves of Viscum coloratum

Barriers and challenges in integration of anthroposophic medicine in supportive breast cancer care

Contact Info

Product

Resources

About