Diterpene lactones and iridoid glycosides of plants of the genusLagochilus

Zainutdinova, U. N.; Pulatova, M. P.; Badalbaeva, T. A.; Umarova, R. U.; Mavlyankulova, Z. I.; Pulatova, T. P.; Aslanova, Kh. A.

doi:10.1007/bf00638413

Cited by 6 publications

(4 citation statements)

References 2 publications

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“…Lagochilin ( 1 ) is the main component of the total extractive substances of many species of the genus. Lagochilin ( 1 ) identified in L. inebrians, L. setulosus, L. gypsaceus [ 37 ], L. hirsutissimus [ 33 ], L. proskorjacovii [ 61 ], and L. pubescens [ 62 ]. L. inebrians gathered in Samarkand province contained 2.3% lagochilin, L. setulosus gathered in Chimkent province 1.1%, and L. gypsaceus gathered in Kashkadar’ya province 2.1% [ 66 ].…”

Section: Phytochemical Studiesmentioning

confidence: 99%

The Genus Lagochilus (Lamiaceae): A Review of Its Diversity, Ethnobotany, Phytochemistry, and Pharmacology

Mamadalieva

Akramov

Wessjohann

et al. 2021

Plants

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The genus Lagochilus (Lamiaceae) is native to Central, South-Central, and Eastern Asia. It comprises 44 species, which have been commonly used as herbal medicines for the treatments of various ailments for thousands of years, especially in Asian countries. This review aims to summarize the chemical constituents and pharmacological activities of species from the genus Lagochilus to unveil opportunities for future research. In addition, we provide some information about their traditional uses, botany, and diversity. More than 150 secondary metabolites have been reported from Lagochilus, including diterpenes, flavonoids, phenolic compounds, triterpenoids, iridoid glycosides, lignans, steroids, alkaloids, polysaccharides, volatile, non-volatile and aromatic compounds, lipids, carbohydrates, minerals, vitamins, and other secondary metabolites. In vitro and in vivo pharmacological studies on the crude extracts, fractions, and isolated compounds from Lagochilus species showed hemostatic, antibacterial, anti-inflammatory, anti-allergic, cytotoxic, enzyme inhibitory, antispasmodic, hypotensive, sedative, psychoactive, and other activities.

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Section: Phytochemical Studiesmentioning

confidence: 99%

The Genus Lagochilus (Lamiaceae): A Review of Its Diversity, Ethnobotany, Phytochemistry, and Pharmacology

Mamadalieva

Akramov

Wessjohann

et al. 2021

Plants

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“…The preparation and physicochemical properties of lagochirsine have been published [2]. Single crystals of lagochirsine were grown from acetone solution at room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…The crystallographic investigations were conducted on an automated four-circle STOE/STAD14 diffractometer at room temperature. The crystals were trigonal, space group P3 2 Key words: lagochilin, lagochirsine, crystal structure, x-ray structure analysis.…”

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confidence: 99%

X-ray structure of lagochirsine

et al. 2004

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The molecular structure of the lagochilin diterpenoid lagochirsine was determined by x-ray structure analysis. The crystallographic investigations were conducted on an automated four-circle STOE/STAD14 diffractometer at room temperature. The crystals were trigonal, space group P3 2 (No. 145), C 20 H 32 O 5 , a = b = 14.289(2) Å, c = 8.2320(16) Å, V = 1455.6(4) Å 3 , Z = 3, D calc = 1.206 g/cm 3 , R = 0.065 (R w = 0.1368).Diterpenoids isolated from plants of the Lagochilus genus are highly physiologically active. They can be used as starting materials for preparing highly effective medicinal preparations [1]. In particular, the medicinal preparation "Lagoden," which is used for various hemorrhages, is based on the lactone lagochirsine, which is isolated from L. hirsutissimus, L. setulosus, and L. gypsaceus. The structure of lagochirsine was established by chemical transformations and PMR spectroscopy. However, its confirmational structure was not elucidated. The present article reports results of an x-ray structure analysis of lagochirsine. Figure 1 shows the molecular conformation and atomic numbering. Asymmetry parameters that characterize the degree of deviation of this conformation from the ideal one were calculated using the RING program [3] in order to define more accurately the conformation of all rings. The six-membered cyclohexane lagochirsine rings A and B of starting lagochilin [4,5] and lagochilin derivatives [6, 7] have a slightly distorted chair conformation [for ring A: ∆C s = 2.8° (C2), ∆C 2 = 1.9° (C2-C3); for ring B: ∆C s = 0.9° (C8), ∆C 2 = 0.8° (C7-C8)]. Atoms C4 and C1 deviate from the plane of C2-C3-C5-C10 by 0.68 and 0.65 Å, respectively; atoms C6 and C9 from that of C7-C8-C10-C5, by 0.70 and 0.71 Å, respectively.The conformation of five-membered rings C and D is an envelope [∆C s (C12) = 4.4° and ∆C s (C13) = 2.5°, respectively]. Atoms C11, C9, O5, and C13 in ring C are planar with a maximum least-squares deviation of 0.02 Å. Atom C12 deviates by 0.46 Å. Atoms C14, C16, O3, and C15 of ring D are planar with a maximum least-squares deviation of 0.01 Å. Atom C13 deviates by 0.45 Å. Rings A and B are trans-fused.Methyls on C4 and C10 are axial; that on C8, equatorial. Fig. 1. Conformation of lagochirsine and atomic numbering.

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“…We studied the mass spectra and spectra of metastable ions of lagochiline (1) [2], 3,18-O-isopropylidene lagochiline (2) [3], 3,18,15,16-di-O-isopropylidene lagochiline (3) [3], acetyl derivatives of lagochiline (4-13) [4], anhydrolagochiline (14) [5], lagochirsine (15) [6], isolagochirsine (16) [5], lagochirsidine (17) [5], dehydration products of lagochiline 11,12-dehydrolagochiline (18) [6], 9,13-epoxy-3,18,16-trihydroxy-15-norlabdane (19) [7], acid-hydrolysis products of lagoden 6,7-dehydrolagochirsine (20) [6], and a mixture of acetyl derivatives from acetylation of lagochiline by acetic anhydride [8].…”

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confidence: 99%