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Tung, Nguyen Thanh; Hung, Nguyen Quang; Luyen, Nguyen Thi; Dat, Nguyen Tien; Pussa, Tonu; Rusalepp, Linda; Ilisson, Mihkel; Raal, Ain
Proceedings of the Estonian Academy of Sciences, 03/2021, Volume: 70, Issue: 1Journal Article
The chemical composition and biological activities of Balanophora fungosa var. globosa (BFG) were studied for the first time. Also, the chemical composition of some other Balanophora species was established for comparison. Phenolic compounds isolariciresinol, gallic acid, pinoresinol, methyl caffeate, and epipinoresinol-4-O-beta-D-glucopyranoside were isolated from Balanophora fungosa var. globosa collected in Vietnam and identified by the NMR analysis. Some in vitro biological activities of the isolated compounds, including the inhibitory effect on NO production and cytotoxic effects, were evaluated. The chromatographic methods were developed to determine the chemical fingerprints of BFG and its very close taxon subsp. indica (Arn.) B. Hansen (BFI), also of the two new species recently recorded for the flora of Vietnam Balanophora tobiracola Makino (BT) and Balanophora subcupularis P.C. Tam (BS). Among the isolated compounds, isolariciresinol showed a moderate inhibitory effect on NO production (I% = 56.02 at concentration of 100 microg/mL), while gallic acid at concentration of 100 microg/mL demonstrated moderate cytotoxicity against cancer cell lines MCF-7 (human breast carcinoma) and PC3 (human prostate gland carcinoma). The HPTLC analysis showed similarities in the chemical compositions of BFG and BFI, as well as the difference between their compositions and these of BT and BS. O-caffeoyl-O-galloyl-glucoside I, caffeic acid glucoside, O-caffeoyl-di-galloyl-beta-D-glucoside V, and 1-O-caffeoyl-3-O-galloyl-4,6-HHDP-beta-D-glucoside as principal compounds were identified among 31 phenolic substances of BFI and BFG by using HPLC-MS/MS. Key words: anti-cancer activity, anti-inflammatory activity, Balanophora fungosa subsp. indica, Balanophora subcupularis, Balanophora tobiracola, isolation. Vietnamis kasvava taime Balanophora fungosa varietas globosa keemilist koostist ja bioloogilist aktiivsust uuriti selles töös esmakordselt. Samuti võrreldi mõnede Balanophora perekonna liikide keemilist koostist. Fenoolsed ühendid isolaritsiresinool (1), gallushape (2), pinoresinool (3), metüülkafeaat (4) ja epipinoresinool-4-O-beta-D-glukopüranosiid (5) isoleeriti ning identifitseeriti NMR-analüüsi tulemusel Vietnamist kogutud B. fungosa varietas globosa droogiproovi põhjal. Isoleeritud koostisainete mõned toimed, nagu NO produktsiooni inhibeeriv ja rakutoksiline efekt, tehti kindlaks in vitro. Töötati välja kromatograafilised meetodid B. fungosa varietas globosa ja sellele väga lähedase taksoni B. fungosa subsp. indica (Arn.) B. Hansen, aga ka Vietnamist hiljuti avastatud kahe uue liigi Balanophora tobiracola Makino ja Balanophora subcupularis P.C. Tam (BS) omavaheliseks eristamiseks. Isoleeritud komponentidest näitas isolarit-siresinool keskmise tasemega NO produktsioon I inhibeerivat efekti (I% = 56,02 kontsentratsioonil 100 microg/mL), samas oli gallushappel kontsentratsiooni 100 microg/mL korral keskmine rakutoksiline aktiivsus inimese rinnakartsinoomi rakkudesse (MCF-7) ja eesnäärmekartsinoomi rakkudesse (PC3). HPTLC-analüüs näitas sarnasust B. fungosa varietas globosa ja B. fungosa subsp. indica keemilise koostise vahel, mis aga oli erinev B. tobiracola ja B. subcupularis'e fütokeemilise profiili puhul. Kahes sarnase koostisega taksonis identifitseeriti HPLC-MS/MS-meetodil 31 fenoolset ühendit, millest peamised on O-kafeoüül-O-galloüülglükosiid I, kohvhappeglükosiid, O-kafeoüüldigalloüül-beta-D-glükosiid V ja 1-O-kafeoüül-3-O-galloüül-4,6-HHDP-beta-D-glükosiid.
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