Phloganthoside—a diterpene lactone glucoside from Phlogacanthus thyrsiflorus
TL;DR: In this article, a new diterpene glucoside, phloganthoside has been isolated from Phlogacanthus thyrsiflorus and its structure has been established as Phlogantholide-A-19- O -β- d -glucopyranoside.
About: This article is published in Phytochemistry.The article was published on 1987-01-28. It has received 13 citations till now. The article focuses on the topics: Diterpene & Glucoside.
Citations
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TL;DR: The structure, including the relative configuration of phlogacantholide B (1), was confirmed by X-ray crystallographic analysis of its diacetate (6) and the structure was elucidated by chemical and spectroscopic evidence.
Abstract: Two new diterpene lactones, phlogacantholides B (1) and C (2), and three new diterpene lactone glucosides, phlogacanthosides A (3), B (4), and C (5), together with lupeol, beta-sitosterol, betulin, P-daucosterol, (+)syringaresinol, and (+)-syringaresinol-4-O-beta-D-glucopyranoside, were isolated from the roots of Phlogacanthus curviflorus. Their structures were elucidated by chemical and spectroscopic evidence. The structure, including the relative configuration of phlogacantholide B (1), was confirmed by X-ray crystallographic analysis of its diacetate (6).
18 citations
TL;DR: Two new secolignans, peperomins G and H (1 and 2, resp.), were isolated from the whole plant of Peperomia dindygulensis and their structures and configurations were elucidated by spectroscopic methods including 2D‐NMR techniques.
Abstract: Two new secolignans, peperomins G and H (1 and 2, resp.), were isolated from the whole plant of Peperomia dindygulensis, together with five known secolignans, peperomin A (3), peperomin E (4), peperomin B (5), 2,3-trans-2-methyl-3-{(3-hydroxy-4,5-dimethoxyphenyl)[5-methoxy-3,4-(methylenedioxy)phenyl]methyl}butyrolactone (6), 2,3-cis-2-(hydroxymethyl)-3-{bis[5-methoxy-3,4-(methylenedioxy)phenyl]methyl}butyrolactone (7). Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR techniques. Antiangiogenic effects of all compounds were evaluated using human umbilical vein endothelial cells (HUVEC) proliferation and tube-formation tests, with compounds 4 and 5 being active in the bioassay. Compounds 4 and 5 induced obvious cell toxicity to HUVEC with IC(50) values of 1.64±0.19 and 8.44±0.4 μM, respectively. Compounds 4 and 5 also exhibited significant HUVEC tube formation-inhibiting activity with IC(50) values of 3.13±0.09 and 6.24±0.12 μM, respectively.
17 citations
Journal Article•
TL;DR: Phlogacanthus thyrsiformis (Roxb. ex Hadrw.) Mabb.
Abstract: Phlogacanthus thyrsiformis (Roxb. ex Hadrw.) Mabb., locally known as Nongmangkha is a quite popular as an ethno-botanical important plant for the meetei community in Manipur. Information presented in this paper was gathered from 68 informants using semi structure questionnaires on the utilization, taboos, folk medicine and conservation of the species. The plant forms an integral part of rites & rituals, myths, food items, taboos, medicinal, customs and traditions with the meetei community. Folk medicinal uses are cold, cough, influenza, easy deliver of child birth, abortion, irregular menstruation, diarrhea, dysentery, cholera, high blood pressure control, boils, small pox, skin problems, sprains, body ache, constipation and burns. The plant is found to be grown in every house who owns a kitchen garden. There is a superstitious belief, which is still in practiced by local people till today is not to pluck any part of the plant on Sunday.
13 citations
TL;DR: The first report on sesquiterpene and iridoid glycosides from the Phlogacanthus genus was given in this article. But their structures were not described.
Abstract: The four new diterpene and diterpene glucosides 1-4, the new bergamotene derivative 5, and the two new iridoid monoterpenoid glucosides 6 and 7, together with the eleven known compounds 8-18, were isolated from the EtOH extract of the roots of Phlogacanthus curviflorus. On the basis of chemical and spectroscopic evidence, their structures were identified as (4 alpha,5 beta,10 alpha,14 alpha)-14,19-dihydroxyabieta-8,13(15)-dieno-16,12-lactone 19-(beta-D-glucopyranoside) (=curvifloruside A; 1), (4 alpha,5 beta,10 alpha,14 alpha)-14,19-diliydroxyabieta-8,13(15)-dieno-16,12-lactone 19-[2-O-(4-hydroxy-3,5-dimethoxybenzoyl)-beta-D-glucopyranoside] (=curvifloruside B; 2), (4 alpha,5 beta,10 alpha)-19-hydroxy-14-oxoabieta-8,13(15)-dieno-16,12-lactone 19-[2-O-(4-hydroxy-3,5-dimethoxybenzoyl)-beta-D-glucopyranoside] (=curvifloruside C; 3), 19-hydroxyjolkinolide E (4), 9-oxo-alpha-bergamoten-1-yl beta-D-glucopyranoside (=curvifloruside D; 5), 6-deoxyharpagoside (=curvifloruside E; 6), and 6-epiharpagoside (=curvifloruside F; 7). This is the first report on sesquiterpene and iridoid glycosides from the Phlogacanthus genus.
8 citations
TL;DR: This photograph shows the fruit sciences department at the Central Agricultural University, Pasighat, Arunachal Pradesh, India, with a selection of fruit trees from around the country.
Abstract: Phlogacanthus (Acanthaceae) is an important group of medicinal plant found mainly in the north eastern part of India. The present article gives an account of updated information on its phytochemical and pharmacological properties and its ethno medicinal uses on account of the tale from the local people and veds. Medicinal properties of this group of plants include antipyretic, antidiabetic, coughs, colds and anti-asthma etc. Extensive research work has been done to prove its biological activities and pharmacology of its extracts. Terpenoidal glycoside, diterpene lactones and many other chemical constituents which are similar to Adathoda zeylanica have been isolated.
Key words: Phlogacanthus, nongmangkha, terpenoid, phlogacantholide.
8 citations
References
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TL;DR: Neoandrographolide (2) is shown to be the β-glucoside of ent -19-hydroxy-8(17), 13-labdadien-16,15-olide as mentioned in this paper.
44 citations
TL;DR: In this article, triterpenoid saponins from the flowers, the mature fruits and the leaves of Fatsia japonica were identified as 3- O -[β- d -glucopyranosyl(1→4)-β-d -glocopyranoyl]-hederagenin.
35 citations
TL;DR: The structure and stereochemistry of phlogantholide-A, a new diterpene lactone isolated from the leaves of Phlogacanthus thyrsiflorus has been determined as 2β,15,18-trihydroxy- ent -labd-8(17),13dien-16-oic lactone by chemical and spectroscopic means as mentioned in this paper.
17 citations
TL;DR: The assignment of the 13C NMR signals of 14-deoxy-andrographolide and its diacetate, made earlier, have now been confirmed by lanthanide shift studies on the former and also by 13C spectral studies on anhydroandrographic-grapholide diacetates.
Abstract: Carbon-13 signal assignments of the labdane diterpenoids phlogantholide-A, its diacetate and isophlogantholide-A are reported. The assignments of the 13C NMR signals of 14-deoxyandrographolide and its diacetate, made earlier, have now been confirmed by lanthanide shift studies on the former and also by 13C spectral studies on anhydroandrographolide diacetate and 14-deoxy-11,12-didehydroandrographolide diacetate.
12 citations