Sesquiterpenoids are comprised of three C₅ units and derived from farnesyl diphosphate. In these C₁₅ family of terpenoids, drimane-type sesquiterpenoids are unique as their chemical structure of decahydronaphthalene along with the methyl group decorations resemble the A/B rings of labdane derived diterpenoids and the eastern part of many meroterpenoids. In the past decades, based on their chemical structural features and diverse bioactivities, great efforts have been made to perform chemical and biological research on this family of natural products, leading to the characterization of a large of new compounds and a few biosynthetic pathways. In this review, we collected 164 new drimane-type sesquiterpenoids from fungi between January 2004 and October 2021 and classified them into three major subfamilies, so as to highlight their diverse chemical structures, biological activities, and biosynthetic pathways,.
Polycyclic Sesquiterpenes ; Sesquiterpenes/chemistry* ; Fungi ; Terpenes/chemistry* ; Diterpenes

To study the chemical constituents in the non-alkaloid part of stems of Dendrobium nobile. The macroporous adsorption resin, MCI, silica gel, RP-C_(18), and Sephadex LH-20 gel, preparative thin layer chromatography, and preparative high-performance liquid chromatography(HPLC) were used to isolate and purify the compounds. The structures of the compound were determined according to the spectra data, physicochemical properties, and relevant references. A total of 8 compounds were isolated from D. nobile, which were soltorvum F(1), p-hydroxyphenylpropionic acid(2), vanillic acid(3), p-hydroxybenzoic acid(4), N-trans-cinnamic acid acyl-p-hydroxybenzene ethylamine(5),(+)-(1R,2S,3R,4S,5R,6S,9R)-2,11,12-trihydroxypicrotoxane-3(15)-lactone(6), dendronobilin H(7), soltorvum E(8). Compound 1 was a novel compound, named as soltorvum F. Compound 8 was isolated from Dendrobium species for the first time.
Dendrobium/chemistry* ; Molecular Structure ; Sesquiterpenes, Guaiane ; Sesquiterpenes/chemistry*

OBJECTIVETo study the chemical constituents roots of Saussurea lappa C. B. Clarke.

METHODIsolation and purification were carried out by silica gel, Sephadex LH-20 and RP-18 column chromatography. The chemical structures of constituents were elucidated on the basis of spectral data.

RESULTEight compounds were isolated and identified as: 1beta-hydroxycolartin (1), 5alpha-hydroxy-beta-costic acid (2), 11alpha,13-dihydroxydehidrocostuslactone (3),11,13-dihydro-7,11-dehydro-13-hydroxy-3-desoxyzaluzanin C (4), 8alpha-hydroxyl-11betaH-11,13-dihydrodehydrocostuslactone (5), Soulangianolide A (6), Syringaresinol (7), Scopoletin (8).

CONCLUSIONCompounds 1-4, 6-8 were isolated from the genus Saussurea for the first time, and compound 5 was isolated from this plant for the first time.

Plant Roots ; chemistry ; Saussurea ; chemistry ; Sesquiterpenes ; chemistry

OBJECTIVETo study chemical constituents from the roots of Saussurea lappa.

METHODChemical constituents were separated and purified by various techniques such as silica gel column chromatography, Sephadex LH-20 and reversed phase RP-18 column chromatography. Their structures were identified on the basis of spectral data.

RESULTSeventeen compounds were separated and identified as ascleposide E(1), (+)-1-hydroxypinoresinol-4"-O-methyl ester-4'-beta-D-glucopyranoside (2), (+)-1 -hydroxypinoresinol-4"-O-beta-D-glucopyranoside(3), (+)-1-hydroxypinoresinol-1-O-P-D-glucopyranoside (4), phenyl-beta-D-glucopyranoside (5), benzyl-beta-D-glucopyranoside (6), n-butyl-beta-D-glucopyranoside (7), ilicic alcohol (8), beta-cyclocostunolide (9), reynosin (10), 11beta, 13-dihydroreynosin (11), arbusculin A(12), 1beta-hydroxy-arbusculin A (13), santamarin (14), dehydrocostuslactone (15), 11beta, 13-dihydro-3-epizaluzanin C(16)and costunolide (17).

CONCLUSIONCompounds 1-2 were separated from this genus for the first time,and compounds 3,5-7 were separated from this plant for the first time.

Ethanol ; chemistry ; Glucosides ; chemistry ; Lactones ; chemistry ; Plant Roots ; chemistry ; Saussurea ; chemistry ; Sesquiterpenes ; chemistry ; Sesquiterpenes, Eudesmane ; chemistry

To study the chemical constituents of the inflorescences of Coreopsis tinctoria from Xinjiang, isolation and purification of constituents were carried out by column chromatography on macroporous resin (D101) , MCI gel, MDS gel, silica gel, Sephadex LH-20 and semi-preparative HPLC. The structures of the compounds were identified by physicchemical properties and spectral data analysis. Fourteen compounds were isolated and identified as coretinterpenoid A (1), coretinphenol (2), quercetin (3), quercetin-3-O-β-glucopyranoside (4), luteolin (5), taxifolin (6), 7, 3', 5'-trihydroxyflavanone (7), isookanin (8), isookanin-7-O-β-D-glucopyranoside (9), 5, 7, 3', 5'-tetrahydroxyflavanone-7-O-β-D-glucopyranoside (10), butein (11), okanin (12), sulfuretin (13), and linocinnamarin (14). Compound 1 was a new isabolane-type sesquiterpenoid and compounds 4, 10 and 13 were isolated from this plant for the first time.
Coreopsis ; chemistry ; Sesquiterpenes ; chemistry ; isolation & purification

The medicinal Lindera aggregata(Lindera, Lauraceae) boasts abundant resources, which is widely used in clinical settings. It has been found that the main chemical constituents of this medicinal species are sesquiterpenoids, alkaloids, sesquiterpenoid dimers, flavonoids, and phenolic acids. Some unreported novel structures, including lindenane-type sesquiterpene dimers and trimers, have been discovered from L. aggregata in recent years. The extracts and active components of L. aggregata have anti-tumor, anti-inflammatory, antalgic, liver-protecting, antioxidant, lipid-lowering, and glucose-lowering activities, and their mechanisms of action have been comprehensively investigated. This study summarizes the research on the chemical constituents and bioactivities of L. aggregata over the past decade, which is expected to serve as a reference for the future research and utilization of L. aggregata.
Lindera/chemistry* ; Alkaloids ; Flavonoids ; Antioxidants ; Sesquiterpenes/chemistry*

Guaiane-type sesquiterpenoids are a class of terpenoids with [5,7] ring-fused system as the basic skeletal structure composed of three isoprene units, which are substituted by 4,10-dimethyl-7-isopropyl. According to the difference in functional groups and degree of polymerization, they can be divided into simple guaiane-type sesquiterpenoids, sesquiterpene lactones, sesquiterpene dimers, and sesquiterpene trimers. Natural guaiane-type sesquiterpenoids are widely distributed in plants, fungi, and marine organisms, especially in families such as Compositae, Zingiberaceae, Thymelaeaceae, Lamiaceae, and Alismataceae. Guaiane-type sesquiterpenoids have good antibacterial, anti-inflammatory, anticancer, and neuroprotective effects. In this paper, the novel guaiane-type sesquiterpenoids isolated and identified in recent 10 years(2013-2022) and their biological activities were reviewed in order to provide refe-rences for the research and development of guaiane-type sesquiterpenoids.
Humans ; Molecular Structure ; Sesquiterpenes, Guaiane ; Asteraceae/chemistry* ; Sesquiterpenes

OBJECTIVETo study sesquiterpenoids of Coniogramme maxima.

METHODChemical constituents were separated by chromatography and their structures were identified according to physicochemical property and spectrum data.

RESULTFifteen compounds were separated by chromatography technique. Their structures were determined by spectral data, including 10 sesquiterpenoids as (3S)-pteroside D (1), epi-pterosin L (2), pterosin D (3), onitin (4), pterosin Z (5), onitisin (6), onitisin-glucopyranoside (7), onitin-15-O-beta-D-glucopyranoside (8), (2S,3R)-pterosin-L-2'-O-beta-D-glucopyranoside (9) and (3R)-peterosin D-3-O-beta-D-glucopyranoside (10). The other compounds were uracil (11), 3,4-dihydroxybenzaldehyde (12), 5-hydroxymethyl-2-furancarboxaldehyde (13), beta-sitosterol (14) and daucosterol (15).

CONCLUSIONThe above 15 compounds are separated from C. maxima for the first time, including 9 compounds being first separated from genus Coniogramme.

Ferns ; chemistry ; Indans ; chemistry ; Indenes ; chemistry ; Sesquiterpenes ; chemistry ; Sitosterols ; chemistry

OBJECTIVETo reveal the factors that affect the contents of volatile oil and beta-elemene in oil in Sarcandrae and to provide scientific basis for Sarcandrae's reasonable exploitation and quality assessment.

METHODA GC method was established and the contents of volatile oil and beta-elemene were determined in Sarcandrae from different length of time to grow, different medicament portions, different collection periods and different length of time to dry.

RESULTThe length of time to grow had no significant effect and the collection periods had effect on the volatile oil yield and content of beta-elemene. The volatile oil yield and content of beta-elemene were the highest in Sarcandrae harvested in December. The yield of volatile oil in different medicament portions descended in an order of roots, leaves and stems. The content of beta-elemene was the highest in leaves and the lowest in stems. With the increasing of the length of time to dry, the volatile oil yield and content of beta-elemene decreased calculated on an anhydrous basis.

CONCLUSIONThe established method is simple, accurate and repeatable. It can be used for the quality control of beta-elemene in Sarcandrae. The study provides a valuable basis for the quality assessment, the development and utilization of Sarcandrae.

Magnoliopsida ; chemistry ; Oils, Volatile ; chemistry ; Plant Leaves ; chemistry ; Sesquiterpenes ; chemistry

Halogenated sesquiterpenes are important derivatives of sesquiterpenes, referring to chemical components of sesquiterpenes that contain halogens such as chlorine, bromine, and iodine. Halogenated sesquiterpenes have attracted attention from researchers in China and abroad because of their diverse structures, unique halogen elements, and extensive pharmacological activities. Studies have shown that halogenated sesquiterpenes exhibit significant antimicrobial, anti-inflammatory, anticancer, insecticidal, hypoglycemic, and enzyme inhibitory activities. In order to better explore the potential pharmaceutical value of halogenated sesquiterpenes, this paper reviewed the structural characteristics and pharmacological activities of halogenated sesquiterpenes in the past two decades, aiming to provide references for further research and development of this class of compounds.
Sesquiterpenes/chemistry* ; Anti-Inflammatory Agents/pharmacology* ; China