Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins

Matsuda, Hisashi; Morikawa, Toshio; Ando, Shinji; Oominami, Hideo; Murakami, Toshiyuki; Kimura, Ikuko; Yoshikawa, Masayuki

doi:10.1016/j.bmc.2004.03.020

Cited by 69 publications

(49 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the family of NOS, inducible NOS (iNOS) is specifically involved in pathologic aspects with the overproduction of NO and can be expressed in response to proinflammatory agents such as interleukin-1b, tumor necrosis factor-a, and LPS in various cell types including macrophages. As a part of our studies to characterize the bioactive components of natural medicines, we have investigated various NO production inhibitors, i.e., higher unsaturated fatty acids, 27) polyacetylenes, [28][29][30] coumarins, 28,30,31) flavonoids, 29,32) stilbenes, 33,34) lignans, [35][36][37] sesquiterpenes, [38][39][40][41][42][43][44][45] diterpenes, 46,47) triterpenes, [48][49][50][51] diarylheptanoids, [52][53][54] cyclic peptides, 50) alkaloids, 55,56) and phenylpropanoids. 5,6,37) Continuing of these studies, the effects of the principal constituents from E. expansa on NO production from LPS-activated macrophages were examined, and the results were summarized in Table 2.…”

Section: Inhibitory Effects On No Production In Lps-activated Mouse Pmentioning

confidence: 99%

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

Morikawa

Matsuda

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

The Convolvulaceae plant, Erycibe expansa, is widely distributed in the Southeast Asian countries and the stems of E. expansa have been used for the treatment of hepatitis, hepatic dysfunction, and hepatosis in Thailand traditional medicine.1) We have reported bioactive constituents from several natural medicines originating in Thailand such as Albizia myriophylla,2) Alpinia galanga, [3][4][5][6] Salacia chinensis, 7-9)Piper chaba, 10) and Thai Zedoary. 11) In the course of our characterization studies on the bioactive constituents from Thai natural medicines, we previously reported three new flavonoids, erycibenins A (4), B (5), and C (6), from the methanolic extract of the dried stems of E. expansa together with 17 constituents (7-23).1) As a continuing study of this natural medicine, we additionally isolated a new flavanol, erycibenin D (1), and two new flavans, erycibenins E (2) and F (3), together with 14 compounds. This paper deals with the isolation and stereostructure elucidation of three new flavonoids and the effects of principal constituents on lipopolysaccharide (LPS)-activated nitric oxide (NO) production in mouse peritoneal macrophages.The methanolic extract from the dried stems of E. expansa was partitioned into a mixture of ethyl acetate (EtOAc) and water to provide the EtOAc-soluble portion and H 2 O-soluble portion as previously described.1) The EtOAc-soluble portion was further subjected to silica gel and ODS column chromatographies and finally HPLC to give erycibenins D (1, 0.00009% from the natural medicine), E (2, 0.00026%), and F (3, 0.00027%) together with two flavans, 5,7-dimethoxy-4Ј-hydroxyflavan 12) (24, 0.00028%), 5,7,4Ј-trimethoxyfla- H COSY) experiment on 1 indicated the presence of three partial structures written in the bold lines (C-2-C-3, C-5-C-6, C-5Ј-C-6Ј) (Fig. 1). In the heteronuclear multiple bond correlations (HMBC) experiment of 1, long-range correlations were observed between the following proton and carbon pairs (H-2 and C-3, 4, 1Ј, 2Ј, 6Ј; H-3 and C-4; H-5 and C-4, 9; H-6 and C-7, 10; H-8 and C-7, 9, 10; H-2Ј and C-2, 4Ј; H-5Ј and C-3Ј; H-6Ј and C-2, 4Ј; 3Ј-OCH 3 and C-3Ј). Next, the relative stereostructure of 1 was elucidated using nuclear Overhauser enhancement spectroscopy (NOESY), which showed NOE correlations between the fol- A new flavanol, erycibenin D, and two new flavans, erycibenins E and F, were isolated from the stems of Erycibe expansa originating in Thailand. The structures of new flavonoids were elucidated on the basis of chemical and physicochemical evidence. In addition, the inhibitory activities of the isolated constituents from E. expansa on lipopolysaccharide-activated nitric oxide production in mouse peritoneal macrophages were examined. Among the principal constituents, two isoflavones, clycosin (IC 50 ‫31؍‬ m mM) and erythrinin B (18 m mM), and two rotenoids, deguelin (26 m mM) and rotenone (27 m mM), were found to show potent inhibitory activity.

show abstract

Section: Inhibitory Effects On No Production In Lps-activated Mouse Pmentioning

confidence: 99%

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

Morikawa

Matsuda

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…4 . These results suggest that compounds 42 and 61 inhibit NO production through inhibition of iNOS induction in LPS-activated macrophages 33 . Fig.…”

Section: Mechanisms Of Action: Effects Of Inos Inductionmentioning

confidence: 78%

A Review of Anti-inflammatory Terpenoids from the Incense Gum Resins Frankincense and Myrrh

2017

Self Cite

View full text Add to dashboard Cite

“…Many of these constituents showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase. [56] EtOAc extract of C. wightii showed cytotoxic due to presence of two ferulates with an unusual skeleton. It also showed moderate free radical scavenging effect against 2,2-diphenyl-1-picrylhydrazyl radicals.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Untitled

Upadhyay

2017

IJGP

View full text Add to dashboard Cite

The present review explains nutritional, therapeutic, and pharmaceutical potential of plant gum that is commonly applied to water-soluble, non-starch polysaccharides of commerce. This article also emphasizes commercial and domestic uses of important products of gum such as chicle and jelutong mainly non-elastic gums or chewing gums. These are also used in food, pharmaceutical, paper textile, and other industries. The present review also explains various biological activities such as antidiarrheic, antitumor, anti-inflammatory, anti-arthritic, antiparasitic, gastrourinary, antitumor, antiparasitic, antioxidant, chemopreventive, and gastroprotective activity of plant gums. These reduce stomach inflammation, system cleansing or to settle the intestines. Other uses for mesquite gum include treatment for lice, sore throat, cough, laryngitis, fever reduction, painful gums, and hemorrhoids and it can be used as a purgative. Gum arabic is a water-soluble dietary fiber rich in Ca , and decreases plasma phosphate concentration as well as urinary excretion of phosphate and Na + . Gums are used as adhesives, crystallization inhibitors, emulsifying agents, emulsion stabilizers, encapsulating agents, film formers, foam stabilizers, suspending agents, suspension stabilizers, or syneresis inhibitors and impart other specific properties. The gum is also used to a limited extent in polishes, contact insecticides and pesticides, photographic emulsions, and pharmaceuticals. This article suggests wider use of plant gums in generation of drug delivery system for cancer and brain tumor therapy. There is no doubt that chemical constituents of plant gums can be largely used for making therapeutic drugs because of their broadspectrum biological effectiveness.

show abstract

Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins

Cited by 69 publications

References 41 publications

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

A Review of Anti-inflammatory Terpenoids from the Incense Gum Resins Frankincense and Myrrh

Untitled

Contact Info

Product

Resources

About