Constituents of the Vietnamese Medicinal Plant Orthosiphon stamineus.

Abstract

From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxygenated staminane-type diterpenes [staminolactones A (8) and B (9) and norstaminol A (10)1 were isolated. Moreover, staminolactone A (8) is 8,14-secostaminane-type and staminolactone B (9) is 13,14-secostaminane-type, while norstaminol A (10) is 14-norstaminen-type. Together with these new diterpenes, sixteen known compounds were also isolated and identified to be: 7,3',4'-tri-O-methylluteolin (11), eupatorin (12), sinensetin (13), 5-hydroxy-6,7,3',4'-tetramethoxyflavone (14), salvigenin (15), ladanein (16), tetramethylscutellarein (17), 6-hydroxy-5,7,4'-trimethoxyflavone (18), vomifoliol (19), aurantiamide acetate (20), rosmarinic acid (21), caffeic acid (22), oleanolic acid (23), ursolic acid (24), betulinic acid (25), and beta-sitosterol (26). All the isolated compounds were tested for their cytotoxicity towards highly liver metastatic murine colon 26-L5 carcinoma cells, and the new diterpenes, except for 4, and flavonoids (11, 12, 16, 18) showed cytotoxicity with an ED50 value between 10 and 90 microg/ml.

Highly-Oxygenated Isopimarane-Type Diterpenes from Orthosiphon stamineus of Indonesia and Their Nitric Oxide Inhibitory Activity.

“…The 1 H-and 13 C-NMR spectra of compound 3 also closely resembled those of orthosiphol I (20) obtained from Vietnamese O. stamineus, 13) 3 2.20 s pound 3 was assumed to be 3-O-deacetylorthosiphol I, which was confirmed by the COSY, HMQC, HMBC, and ROESY spectra. The absolute stereochemistry of 3 was determined by comparing its CD spectrum ( Fig.…”

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

“…Because it appears that flavonoid 7-O-methylation is a prerequisite for 6-hydroxylation in these two mint species, the first question is whether this route is common in the Lamiaceae and whether it is shared by non-mints producing identical or very similar flavones, such as Alnus (48), Rubus (49), and Eupatorium (50), all of which are reported to accumulate SALV. In the Lamiaceae, phytochemical data for some groups, such as Thymus (51,52), Origanum (53), and Orthosiphon (54), indicate that they only accumulate 6-substituted flavonoids possessing 7-O-methylated hydroxyl moieties and therefore could well follow the same pattern. Likewise, the discovery of the flavonoid 7-O-demethylation prompts an investigation into the frequency of demethylation in flavonoid metabolism.…”

SENYAWA INHIBITOR Α-Glukosidase DAN ANTIOKSIDAN DARI KUMIS KUCING DENGAN PENDEKATAN METABOLOMIK BERBASIS FTIR

“…Pada spektrum aktif fraksi kloroform dapat diamati gugus fungsi aktif penanda diterpen yaitu hidroksil pada bilangan gelombang 3396-3420 cm -1 dan ester karbonil pada bilangan gelombang 1113-1284 cm -1 . Berdasarkan hasil identifikasi gugus fungsi penanda senyawa penghambat aktivitas enzim α-glukosidase mengindikasikan senyawa dari kelompok diterpen tipe isopimaran yaitu ortosifol F-J (Tezuka et al, 2000), ortoarisin A, ortoarisin B, ortoarisin C, ortoarisin D, ortoarisin E, ortoarisin F, ortoarisin G (Di et al, 2013) (Xia et al, 2015). enyawa penghambat aktivitas enzim α-glukosidase juga diidentifikasi dari kelompok diterpen tipe isopimaran teroksigenasi yaitu ortosifol O, ortosifol P, ortosifol Q, dan noortosifonolida A (Awale et al, 2002), kelompok diterpen tipe isopimaran teroksigenasi tinggi ortosifol A, ortosifol B, ortosifol U, ortosifol V, ortosifol W, ortosifol X, ortosifol Y dan ortosifol Z (Masuda et al, 1992;Awale et al, 2003), kelompok diterpen tipe isopimaran termigrasi yaitu neoortosifol A dan neoortosifol B (Ohashi et al, 2000), dan senyawa ortoarisin H dari kelompok diterpen tipe sekoisopimaran (Di et al, 2013).…”

“…Diterpen tipe sekoisopimaran dari Salvia cinnabarina diketahui memiliki aktivitas antipasmodik (Capasso et al, 2004) dan mutagenik (Di Sotto et al, 2009) akan tetapi aktivitas penghambatan terhadap enzim α-glukosidase belum pernah dilaporkan. Senyawa penghambat aktivitas enzim α-glukosidase diidentifikasi dari kelompok diterpen tipe staminan adalah staminol A, staminol B, staminolakton A, staminolakton B, norstaminol A (Tezuka et al, 2000) dan ortoarisin I (Di et al, 2013).…”