Arucadiol

Reassessing the molecular structures of some previously isolated abietane diterpenoids with a naphthalene moiety and the structure-activity relationship (SAR) of quinone diterpenoids.[Pubmed:36115387]

Phytochemistry. 2022 Dec;204:113433.

Crystals of previously described para-naphthoquinone abietane diterpenoids 12,16-dideoxy-aegyptinone B and 12-deoxy-salvipisone were obtained from Zhumeria majdae Rech.f. & Wendelbo. However, single-crystal X-ray diffraction analysis followed by reinterpretation of their NMR data revealed that their structures require revision, and they should be revised to the two ortho-naphthoquinones, zhumerianone C and aethiopinone, respectively. Interestingly, a further search through literature revealed that there were more of such cases, in which differentiation between the ortho-/para-orientation had not been carried out correctly in the structure elucidation of naphthalene containing abietane diterpenoids. Therefore, in the current study, we pointed out some 1D and 2D NMR generalizations that would help the unambiguous deduction of the ortho-/para-orientation of naphthalene containing abietanes and revised the structure of some previously described compounds accordingly. Based on these generalizations, structures of sibiriquinones A and B, sahandinone, and sahandone were revised to the known structures 1,2-didehydromiltirone, miltirone, saprorthoquinone, and sahandone B, respectivelyand tebesinone B, Arucadiol, and sahandol II were revised to three undescribed structures. It was also proposed that structures of palmitoyl Arucadiol and compounds with the salvifolane skeleton need revision. Furthermore, these structure revisions shed light on the structure-activity relationship of the quinone diterpenoids, approving that the ortho-quinone is the critical structural component for cytotoxicity in these compounds.

Construction and Screening of Fractional Library of Salviae Miltiorrhizae Radix et Rhizoma for the Rapid Identification of Active Compounds against Prostate Cancer.[Pubmed:35251179]

J Oncol. 2022 Feb 24;2022:9955834.

Efficient screening of anticancer agents is in urgent need to develop new drugs that combat malignant tumors and drug resistance. In this study, a combined strategy composed by solvent partition and HPLC fractionation was developed to generate an herbal fraction library of Salviae Miltiorrhizae Radix et Rhizoma to quickly and efficiently screen anticancer agents. All library entries are directed into 96 well plates which are well mapped with HPLC chromatograms. The cell proliferation assay revealed seven active subfractions. Then, the major active ten peaks in these subfractions were prepared and isolated by semipreparative HPLC, and their inhibitory activities against prostate cancer cells were then tested at the same concentration level, leading to the identification of several active compounds. In addition, the structures of compounds Arucadiol (2), 15,16-dihydrotanshinone I (4), methyl tanshinonate (5), cryptanshinone (7), 1,2-dihydrotanshinquinone I (9), and tanshinone IIA (10) were characterized by mass spectrometry and X-ray crystallographic analysis, and they were confirmed to be active in suppressing prostate cancer cell proliferation at 7.5 or 15 mug/mL, among which, the minor compounds 2, 4, and 5 showed higher activities than 9 and 10. This study provided a rapid strategy of identifying new anticancer agents in Salviae Miltiorrhizae Radix et Rhizoma, which can be applied in other herbal medicines.

Identification of phytochemicals and antioxidant activity of Premna microphylla Turcz. stem through UPLC-LTQ-Orbitrap-MS.[Pubmed:34731817]

Food Chem. 2022 Mar 30;373(Pt B):131482.

Premna microphylla Turcz. is a commonly used traditional Chinese medicine totreatdysentery and appendicitis. Present study is focused to explore antioxidants and other compounds in the Premna microphylla Turcz. stem. Assessment of chemical composition was done with high sensitivity UPLC-LTQ-Orbitrap-MS and for Separation Thermo Hypersil Gold (100 mm x 2.1 mm, 1.9 microm) was used while electrospray ionization (ESI) was used for the mass spectrometry. 18 compounds were identified including Vitexin (1), Schaftoside (2), Vicenin-2 (3), Apigenin-6, 8-di-C-arabinoside (4), Apigenin-7-O-beta-d-glucoside (5), Carnosic acid (6), Apigenin-8-C-beta-d-xylopyranoside (7), Prostratin (8), Aurantio-obtusin-beta-d-glucoside (9), Royleanone (10), 5-hydroxy-7,3',4'-Trimethoxy flavonols (11), 6-Hydroxy-5,6-dehydrosugiol (12), 14-deoxycoleon (13), Arucadiol (14), Obtusinone-B (15), Trehalose (16), Citric acid (17) and Betaine (18). Among these, 6 compounds including (6), (8), (9), (16), (17) and (18) were identified first time within this genus and plant. Study highlights the importance of Premna microphylla Turcz. stem extract for strong therapeutic potential against oxidation-related diseases.

Selective in vitro and in silico butyrylcholinesterase inhibitory activity of diterpenes and rosmarinic acid isolated from Perovskia atriplicifolia Benth. and Salvia glutinosa L.[Pubmed:27817931]

Phytochemistry. 2017 Jan;133:33-44.

Cholinesterase inhibition is one of the most treatment strategies against Alzheimer's disease (AD) where metal accumulation is also strongly associated with pathology of the disease. In the current study, we assessed inhibitory effect against acetyl- (AChE) and butyrylcholinesterase (BChE) and metal-chelating capacity of twelve diterpenes: Arucadiol, miltirone, tanshinone IIa, 1-oxomiltirone, cryptotanshinone, 1,2-didehydromiltirone, 1,2-didehydrotanshinone IIa, 1beta-hydroxycryptotanshinone, 15,16-dihydrotanshinone, tanshinone I, isotanshinone II, 1(S)-hydroxytanshinone IIa, and rosmarinic acid, isolated from Perovskia atriplicifolia and Salvia glutinosa. The compounds were tested at 10 mug/mL using ELISA microtiter assays against AChE and BChE. QSAR and molecular docking studies have been also performed on the active compounds. All of the compounds showed higher [e.g., IC(50) = 1.12 +/- 0.07 mug/mL for 1,2-didehydromiltirone, IC(50) = 1.15 +/- 0.07 mug/mL for cryptotanshinone, IC(50) = 1.20 +/- 0.03 mug/mL for Arucadiol, etc.)] or closer [1,2-didehydrotanshinone IIa (IC(50) = 5.98 +/- 0.49 mug/mL) and 1(S)-hydroxytanshinone IIa (IC(50) = 5.71 +/- 0.27 mug/mL)] inhibition against BChE as compared to that of galanthamine (IC(50) = 12.56 +/- 0.37 mug/mL), whereas only 15,16-dihydrotanshinone moderately inhibited AChE (65.17 +/- 1.39%). 1,2-Didehydrotanshinone IIa (48.94 +/- 0.26%) and 1(S)-hydroxytanshinone IIa (47.18 +/- 5.10%) possessed the highest metal-chelation capacity. The present study affords an evidence for the fact that selective BChE inhibitors should be further investigated as promising candidate molecules for AD therapy.

Isolation and Fast Selective Determination of Nor-abietanoid Diterpenoids from Perovskia atriplicifolia Roots Using LC-ESI-MS/MS with Multiple Reaction Monitoring.[Pubmed:26410997]

Nat Prod Commun. 2015 Jul;10(7):1149-52.

In the first part of this study we extracted, isolated, and identified the main diterpenoid constituents from the roots of a Central Asian medicinal and ornamental plant--Perovskia atriplicifolia Benth. Eight major nor-abietanoid pigments were obtained using NP silica gel column chromatography and preparative RP-HPLC: cryptotanshinone, 1-hydroxycryptotanhinone, miltirone, 1-oxomiltirone, tanshinone IIa, 1,2 didehydrotanshinone IIa, 1,2 didehydromiltirone, the non-quinone diterpenoid - Arucadiol, as well as rosmarinic acid as a main phenolic compound. Secondly, we used the obtained compounds for fast and selective determination of the main diterpenes present in P. atriplicifolia root extract. After extraction with n-hexane, the quantitative analysis was carried out by LC-MS/MS with a triple quadrupole (qQq) mass detector without any prior clean-up step. Identification of the diterpenes was confirmed by multiple reaction monitoring (MRM) using the most representative transitions from the precursor ions, while the most sensitive transitions were used for quantification in a 19-minute run. Most of the isolated and analyzed compounds had not been previously reported from this species. This easily cultivated plant is a promising source of several pharmacologically valuable abietanoid diterpenoids.

[Chemical constituents from Salvia przewalskii Maxim].[Pubmed:22010351]

Yao Xue Xue Bao. 2011 Jul;46(7):818-21.

The investigation on Salvia przewalskii Maxim was carried out to find the relationship of the constituents and their pharmacological activities. The isolation and purification were performed by various chromatographies such as silica gel, Sephadex LH-20, RP-C18 column chromatography, etc. Further investigation on the fraction of the 95% ethanol extract of Salvia przewalskii Maxim yielded przewalskin Y-1 (1), anhydride of tanshinone-II A (2), sugiol (3), epicryptoacetalide (4), cryptoacetalide (5), Arucadiol (6), 1-dehydromiltirone (7), miltirone (8), cryptotanshinone (9), tanshinone II A (10) and isotanshinone-I (11). Their structures were elucidated by the spectral analysis such as NMR (Nuclear Magnetic Resonance) and MS (Mass Spectrometry). Compound 1 is a new compound. Compounds 4 and 5 are mirror isomers (1 : 3). Compounds 4, 5, 6, 8, 11 were isolated from Salvia przewalskii Maxim for the first time.

New orthoquinones from the roots of Salvia lanigera.[Pubmed:17253304]

Planta Med. 1998 Oct;64(7):632-4.

A chloroform extract of the roots of the Egyptian Salvia lanigera Poir. afforded two new orthoquinones, lanigerone (8-hydroxy-3-isopropyl-7-methyl-1,2-naphthoquinone) and salvigerone (methyl 1,10-seco-5(10),6,8,13-abietatetraene-11,12-dion-1-oate) together with two known diterpenoids, Arucadiol and pisiferal. Structural assignments of the new compounds were based on spectroscopic methods (UV, IR, MS, ID- and 2D-NMR).

Diterpenoids from Salvia prionitis.[Pubmed:17265309]

Planta Med. 1988 Oct;54(5):443-5.

Seven diterpenoids, 3-ketosapriparaquinone ( 1), salvilenone, 3-hydroxysalvilenone ( 2), Arucadiol, royleanone, sugiol, and ferruginol were isolated from the root of SALVIA PRIONITIS Hance (Labiatae); Compounds 1 and 2 are new natural products. The structure of 1 was established through the interpretation of spectral data.