New Tetranortriterpenoids from Swietenia humilis

Segura-Correa, Rosabel; Mata, Rachel; Anaya, Ana Luisa; Hernández‐Bautista, Blanca E.; Villena, R.; Soriano-Garcı́a, Manuel; Bye, Robert; Linares, Edelmira

doi:10.1021/np50099a016

Cited by 37 publications

(30 citation statements)

References 8 publications

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“…Fraction FIII, eluted with EtOAc : MeOH 7 : 3, was further rechromatographed on Si gel using hexane-EtOAc (mixtures of increasing polarity) and this process allowed the isolation of humilinolide A. Purification to homogeneity was achieved by preparative TLC on Si gel using benzene : EtOAc (1 : 1) as the eluent. IR, MP, and NMR data of the isolated humilinolide A were identical to those of an authentic sample (Segura-Correa et al, 1993;Jiménez et al, 1997).…”

Section: Methodsmentioning

confidence: 54%

“…Previous phytochemical analysis conducted with the seeds led to the isolation and characterization of seven limonoids, including humilinolide A ( Fig. 1) (Okorie and Taylor, 1971;Segura-Correa et al, 1993). The limonoids produced by this species, possess insect and plant growth regulating properties (Segura-Correa et al, 1993;Jiménez et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

“…1) (Okorie and Taylor, 1971;Segura-Correa et al, 1993). The limonoids produced by this species, possess insect and plant growth regulating properties (Segura-Correa et al, 1993;Jiménez et al, 1997). However, the pharmacological potential of these compounds has not been yet explored, particularly the effects related to the use of the plant for the treatment of gastrointestinal malaises.…”

Section: Introductionmentioning

confidence: 99%

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Contractile response induced by a limonoid (humilinolide A) on spontaneous activity of isolated smooth muscle

Perusquı́a¹,

Herńndez²,

Jiménez³

et al. 1997

Phytother. Res.

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The in vitro effect of the limonoid humilinolide A, isolated from Swietenia humilis (Meliaceae), on spontaneous contractions of guinea-pig ileum, and uterus from oestrus, dioestrus, ovariectomized and oestrogen-primed rats was studied. Humilinolide A caused a concentration dependent and non-reversible excitatory effect on intestinal and uterine smooth muscle, distinguished as spasmogenic and uterotonic action respectively. However, the potency of this compound to induce contraction was different in the distinct preparations assayed: in ileal musculature of male guinea-pigs, as well as in uterine muscle of dioestrus and ovariectomized rats, a slight excitatory effect was observed; in contrast to an intense excitatory effect displayed in rat uterus with high oestrogen levels (oestrus and oestrogenized). These data suggest that the contractile response induced by humilinolide A could be mediated by oestrogens, probably by occupancy of some receptors in myometrial plasma membranes to induce uterotonic response, which may be oestrogen-dependent.

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Section: Methodsmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Contractile response induced by a limonoid (humilinolide A) on spontaneous activity of isolated smooth muscle

Perusquı́a¹,

Herńndez²,

Jiménez³

et al. 1997

Phytother. Res.

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“…S. humilis has recently been listed as an endangered species in need of protection. Segura-Correa et al (45) isolated from the seeds of this species four new tetranortriterpenoids with the same limonoid type skeleton: humilinolides A, B, C, and D ( Figure 10). Limonoids possess a wide range of biological activities, including insect antifeedant and growth regulating properties, a variety of medicinal effects in animals and humans, and antifungal, bacteriocidal, and antiviral activity.…”

Section: Swietenia Humilis and Limonoidsmentioning

confidence: 99%

Allelopathy in Mexican Plants

Anaya

Hernández‐Bautista

Pelayo-Benavides

et al. 1994

ACS Symposium Series

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Research on allelopathy in Mexico has focused on plant species with ecological importance, some of them with medicinal use. Seeds, fungi and insects have been used in bioassays directed to assess activity of plant extracts and isolates. Allelochemicals can modify cellular structure and activities including respiration and division. Research priorities are based on the vast diversity of Mexican flora, its potential as a source of useful natural products, and the lack of knowledge in these areas.Researchers of different disciplines have found allelopathy increasingly interesting because of potential application of allelopathic compounds as herbicides, pesticides or growth regulators. Allelopathy may also be used to further manage biotic resources.The physiological effects of compounds with phytotoxic activity (allelochemicals, and/or herbicides) vary widely. Almost all of these compounds act with specificity on different groups of organisms. This characteristic renders them attractive in the search for new bio-active compounds (1).We are currently conducting studies on different species of Mexican plants with ecological or medicinal importance. Traditional knowledge, so rich in Mexico, has frequently suggested where to look for active compounds. Knowing that allelochemicals may affect different life organization levels -communities, organisms, tissues, cells, organelles and metabolic processes-plant extracts and isolated compounds have been evaluated using seeds, phytopathogenic fungi and insects as bioassays. Germination, growth, development, reproduction and survival are first determined, followed by the evaluation of the possible modes of action of tested compounds on processes such as respiration, cell division, enzymatic activities, and structural arrangements of tissues and cells.

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“…Tetranortriterpenoids are diverse and abundant in members of the family Meliaceae. Many papers about tetranortriterpenoids isolated from the family Meliaceae have discussed their roles in antifeeding (1-3), cytotoxicity (4)(5)(6), ichthyotoxicity (7), insect growth inhibition (8), inhibition of cell adhesion (9,10), and larval growth (11). The genus Munronia Wight (Meliaceae), comprising 13-15 species, is naturally distributed in China, Sri Lanka, India, Indonesia, and The Philippines.…”

Section: Introductionmentioning

confidence: 99%

Insect Antifeedants from Munronia henryi: Structure of Munroniamide

Wu²,

Chen³

et al. 2003

J. Agric. Food Chem.

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A novel A,B-seco-tetranortriterpenoid lactam, named munroniamide (1), along with three known ceramides (2-4), was isolated from the methanolic extract of the whole bodies of Munronia henryi. The structure of 1 was established using spectroscopic methods. Compound 2 exhibited significant antifeeding activity, and 1 exhibited moderate activity, whereas 3 and 4 showed negative activity against Pieris brassicae L.

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New Tetranortriterpenoids from Swietenia humilis

Cited by 37 publications

References 8 publications

Contractile response induced by a limonoid (humilinolide A) on spontaneous activity of isolated smooth muscle

Contractile response induced by a limonoid (humilinolide A) on spontaneous activity of isolated smooth muscle

Allelopathy in Mexican Plants

Insect Antifeedants from Munronia henryi: Structure of Munroniamide

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