Staudtienic Acid, a Diterpene Acid from Staudtia kamerunensis

Noumbissie, B. Emakam; Kapnang, H.; Fomum, Z. Tanee; Martin, Marie‐Thérèse; Bodo, Bernard

doi:10.1021/np50079a021

Cited by 9 publications

(9 citation statements)

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“…The 'H-nmr spectrum of compound 2 (Table 1) was very similar to that of horminone [1] and the observed differ- (5,(7)(8)(9)(10)(11) and also from Staudtia kamerunensis (Myristicaceae) (6).…”

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confidence: 70%

Structure and Antimicrobial Activity of Diterpenes from the Roots of Plectranthus hereroensis

Batista¹,

Duarte²,

Nascimento³

et al. 1994

J. Nat. Prod.

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Two abietane-type diterpenoids have been isolated from the roots of Plectranthus hereroensis (Labiatae), one being the already known horminone [1] and the other a new substance, 7 alpha,12-dihydroxy-17(15-->16)-abeo-abieta-8,12,16-triene-11 ,14-dione [2], whose structure was established by spectroscopic means. Compounds 1 and 2 showed antimicrobial activity against Staphylococcus aureus, Vibrio cholerae, Candida albicans, and Pseudomonas aeruginosa.

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confidence: 70%

Structure and Antimicrobial Activity of Diterpenes from the Roots of Plectranthus hereroensis

Batista¹,

Duarte²,

Nascimento³

et al. 1994

J. Nat. Prod.

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“…His successors, the ancient Greek physicians Pedanius Dioscorides (ca. A.D. 40−90) and Soranus of Ephesus (A.D. 98−138), continued using this therapy in the first and second centuries A.D. , In addition, the topical anticancer uses of extracts from this plant , as well as from Narcissus pseudonarcissus – were recorded in the first century A.D. by the Roman natural philosopher Gaius Plinius Secundus (A.D. 23−79), better known as Pliny the Elder . Even the Bible provides multiple references to the Mediterranean Narcissus tazetta L., which has a long history of use against cancer .…”

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confidence: 99%

Chemistry, Biology, and Medicinal Potential of Narciclasine and its Congeners

2008

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Ornamental flower growers know that placing a cut daffodil (a.k.a. narcissus) in a vase with other flowers has a negative effect on the quality of those flowers and significantly shortens their vase life. Furthermore, a common horticultural practice for the cultivation of narcissus flowers involves the introduction of cuts on the bulbs before immersing them into water. The mucilage that leaches out from the cuts is constantly removed by frequent changing of water and this leads to sprouting. These observations raise speculation that specific components in the mucilage of the narcissus bulbs may have powerful growth-inhibitory effects. Historical use of narcissus flowers, as well as at least thirty other plants of the Amaryllidaceae family, in folk medicine for the management of cancer 1 speaks volumes to validate this conjecture. Indeed, powerful anticancer properties of Narcissus poeticus L. were already known to the Father of Medicine, Hippokrates of Kos (ca. B.C. 460-370), who recommended a pessary prepared from narcissus oil for the treatment of uterine tumors. 2 His successors, the ancient Greek physicians Pedanius Dioscorides (ca. A.D. 40-90) and Soranus of Ephesus (A.D. 98-138) continued using this therapy in the first and second centuries A.D.3 , 4 In addition, the topical anticancer uses of extracts from this plant5 , 6 as well as from N. pseudonarcissus7-9 were recorded in the first century A.D. by the Roman natural philosopher Gaius Plinius Secundus, (A.D. 23-79), better known as Pliny the Elder. 10 Even the Bible provides multiple references to the Mediterranean N. tazetta L., which has a long history of use against cancer. 11 The applications of narcissus oil in cancer management continued in the middle ages in Chinese, North African, Central American and Arabian medicine. 1,12 The uses of other genera of the Amaryllidaceae family were also common, e. g. Hymenocallis caribaea (L. emend Gawler) Herbert, utilized by early European medical practitioners for inflammatory tumors. 13 More recently, the plants of the Amaryllidaceae have been under intense scrutiny for the presence of the specific metabolites responsible for the medicinal properties associated with this plant family. The study began in 1877 with the isolation of alkaloid lycorine from Narcissus pseudonarcissus 14 and since then more than 100 alkaloids, exhibiting diverse biological activities, have been isolated from the Amaryllidaceae plants. Based on the present scientific evidence, it is likely that isocarbostyril constituents of the Amaryllidaceae, such as narciclasine, pancratistatin and their congeners, are the most

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“…The anticancer properties of these plants were already known in the fourth century B. C., when Hippocrates of Cos used oil from the daffodil Narcissus poeticus L. for the treatment of uterine tumors [3]. The topical anticancer uses of extracts from N. poeticus [4,5] as well as from Narcissus pseudonarcissus [6][7][8] were recorded in the first century A. D. by the Roman natural phi-losopher Pliny the Elder [9], and the applications of narcissus oil in cancer management continued in the middle ages in Chinese, North African, Central American, and Arabian medicine [2,10]. Other genera of the Amaryllidaceae family, for example, Hymenocallis caribaea, were also commonly utilized by early European medical practitioners for inflammatory tumors [11].…”

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Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design

et al. 2009

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Twenty nine Amaryllidaceae alkaloids and their derivatives belonging to five most common groups, including lycorine-, lycorenine-, tazettine-, crinine-, and narciclasine-types, were evaluated for antiproliferative, apoptosis inducing and antiinvasive activities in vitro. The antiproliferative properties of each test compound are in agreement with those reported in the literature, while the high potency of amarbellisine is reported for the first time. It was also found that with the exception of ungeremine, amarbellisine and hippeastrine, the antiproliferative effect of the potent compounds is apoptosis-mediated. Thus, apoptosis in Jurkat cells was triggered by narciclasine, narciclasine tetraacetate, C10b-R-hydroxypancratistatin, cis-dihydronarciclasine, trans-dihydronarciclasine, lycorine, 1-O-acetyllycorine, lycorine-2-one, pseudolycorine, and haemanthamine. With the exception of narciclasine, lycorine and haemanthamine, the apoptosis inducing properties of these compounds are reported for the first time. The collagen type I invasion assay revealed potent antiinvasive properties associated with N-methyllycorine iodide, hippeastrine, clivimine, buphanamine, and narciclasine tetraacetate, all of which were tested at non-toxic concentrations. The antiinvasive activity of buphanamine is particularly promising since this alkaloid is not toxic to cells even at much higher doses. This work has resulted in identification of several novel leads for anticancer drug design.

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Staudtienic Acid, a Diterpene Acid from Staudtia kamerunensis

Abstract: A new diterpene acid, staudtienic acid 111, has been isolated from Staudtia Smerunensis, and its structure has been determined from a spectroscopic study including ir, ms, and 'H and I3C nmr.

Cited by 9 publications

References 1 publication

Structure and Antimicrobial Activity of Diterpenes from the Roots of Plectranthus hereroensis

Structure and Antimicrobial Activity of Diterpenes from the Roots of Plectranthus hereroensis

Chemistry, Biology, and Medicinal Potential of Narciclasine and its Congeners

Biological Evaluation of Structurally Diverse Amaryllidaceae Alkaloids and their Synthetic Derivatives: Discovery of Novel Leads for Anticancer Drug Design

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